Leap Academy with Ilana Golan

We’re bringing back one of our favorite conversations from the Leap Academy podcast with digital marketing expert and entrepreneur Neil Patel. Neil’s story shows how hard work, persistence, and learning from failure lead to success. As a teenager, he started businesses, including building websites, but struggled with ineffective marketing agencies. This pushed him to learn digital marketing, and by 16, he helped a client make $20M, marking the start of his career. After facing challenges with his earlier ventures, he shifted from starting businesses to acquiring and turning underperforming ones into successes. Now, as the founder of NP Digital, he runs a global marketing company that helps businesses grow. In this episode, Neil talks with Ilana about his journey, the strategies behind his success, and how businesses can overcome challenges and scale in today’s competitive market. Neil Patel is a New York Times bestselling author, digital marketing expert, and the founder of one of the top 100 most brilliant companies, according to Entrepreneur Magazine. With over 15 years of experience, Neil has been instrumental in helping businesses grow their online presence and revenue. In this episode, Ilana and Neil will discuss: (00:00) Introduction (01:11) The Power of Hard Work Over Privilege (01:39) From Teenage Hustle to Launching His First Website (08:01) Learning Digital Marketing After Agency Failures (08:55) Helping a Client Reach $20M in Revenue at Age 16 (10:17) Attending College Due to Family Expectations (11:55) How Experimentation Reveals Your True Strengths (14:26) Lessons from Surviving Legal Battles at Kissmetrics (19:53) Businesses That Found Success Despite Their Flaws (22:35) Balancing Personal and Corporate Branding for Success (25:24) Shifting from Building to Acquiring Businesses (27:10) Neil’s Strategy for Improving Acquired Businesses (31:15) Why “Renting Your Dreams” Can Lead to Future Success (33:29) How Consistency and Networking Create Opportunities (35:48) Empowering and Trusting Your Team for Results (37:44) Hiring Experts to Reduce Risk and Drive Growth (40:57) Neil Patel's Digital Marketing Services Neil Patel is a New York Times bestselling author, digital marketing expert, and the founder of one of the top 100 most brilliant companies, according to Entrepreneur Magazine. Recognized as a top influencer by The Wall Street Journal and one of Forbes' top marketers, Neil has helped companies like Amazon, Microsoft, and Google grow through marketing. He is also the co-founder of NP Digital, a leading marketing agency. With over 15 years of experience, Neil has been instrumental in helping businesses grow their online presence and revenue. Connect with Neil: Neil’s Website: https://neilpatel.com/ Neil’s LinkedIn: https://www.linkedin.com/in/neilkpatel/ Neil’s YouTube: https://www.youtube.com/neilpatel Resources Mentioned: NP Digital: https://npdigital.com/ Neil’s Book, Hustle: The Power to Charge Your Life with Money, Meaning, and Momentum: https://www.amazon.com/Hustle-Power-Charge-Meaning-Momentum/dp/1623367166 Leap Academy: Ready to make the LEAP in your career? There is a NEW way for professionals to Advance Their Careers & Make 5-6 figures of EXTRA INCOME in Record Time. Check out our free training today at leapacademy.com/training

Mike Fisher’s career has taken him from West Point and flying helicopters in the U.S. Army to leading technology teams at PayPal, serving as CTO of Etsy, and ultimately becoming CEO of MyFitnessPal. In this episode, Mike joins Ilana to unpack the leadership lessons behind that unconventional journey. He shares what the military taught him about giving feedback, building trust, and learning from mistakes, and what he had to unlearn when he transitioned into the tech world. Mike also explains why nearly every major opportunity in his career came through the “hidden market,” why professionals should focus on building skills rather than chasing titles, and what stepping into the CEO seat taught him about imposter syndrome and leading through uncertainty. Plus, Mike shares what ultramarathons have taught him about pushing through dark moments, why great leaders need extraordinary willpower, and why he believes AI could ultimately create entirely new opportunities for entrepreneurs and professionals. Chapters 00:00 Trailer & Introduction 02:58 The Hidden Market: Why Your Best Opportunities Aren’t on Job Boards 04:05 What West Point Taught Mike About Leadership 06:57 Why Great Teams Debrief Their Mistakes 08:12 Learning Leadership the Hard Way as an Army Pilot 10:19 The Helicopter Accident That Changed How Mike Led 14:27 Leaving the Military for a Career in Tech 16:01 The Boss Who Changed the Trajectory of Mike’s Career 19:13 What Mike Had to Unlearn From the Military 20:58 How to Get People to Follow You Without a Title 22:56 Why Great Leaders Tell Great Stories 25:58 The Hidden Job Market & Why Your Network Matters 28:18 Why Weak Ties Can Lead to Your Biggest Opportunities 28:46 How to Make Sure People Remember You 29:04 From Consultant to CTO of Etsy 31:04 The Power of Extreme Focus 35:30 Stop Chasing Titles, Build Skills Instead 37:04 How the Hidden Market Led Mike to MyFitnessPal 38:33 Becoming CEO: What Changes at the Top 41:30 Imposter Syndrome at the CEO Level 44:56 Find the Skill You Can Always Fall Back On 45:27 What Ultramarathons Teach You About Leadership 47:51 “We Do Hard Things”: Transforming Etsy 50:27 Finding Your Reserve Tank in the Darkest Moments 53:09 Why You Should Never Go Through Hard Things Alone 53:28 “You Signed Up for This” 55:06 How to Rise Above the Noise in Your Career 56:08 Why Rejection Should Be Treated Like an Experiment 57:55 Mike’s Take on AI, Jobs & the Future of Work 59:58 Could a One Person Billion Dollar Company Already Exist? About Mike Fisher Mike Fisher is the CEO of MyFitnessPal and a technology executive whose career spans the military, entrepreneurship, consulting, and some of the most recognized technology companies in the world. A West Point graduate, Mike served as a U.S. Army aviation officer and helicopter pilot before transitioning into technology. His career has included leadership roles at PayPal, co-founding AKF Partners, and serving as CTO of Etsy, where he helped lead major technology and organizational transformations. Outside of work, Mike is an ultramarathoner and writes about leadership, technology, and business through his Substack, Fish Food for Thought. 📲 Connect with Ilana: Facebook ▶️ https://www.facebook.com/IlanaGolanLeapAcademy LinkedIn ▶️ https://www.linkedin.com/in/ilanagolan/ Instagram ▶️ https://www.instagram.com/ilanagolanleap Website ▶️ https://www.leapacademy.com/

Tom Cortese helped turn an idea that investors rejected hundreds of times into Peloton—an $8.1 billion public company that completely changed the way millions of people exercise. But his story isn’t just about building Peloton. It’s also about knowing when to walk away from something that has become part of your identity and having the courage to start again.In this episode, Tom joins Ilana to share the real story behind Peloton—from starting the company with just $400,000 and getting rejected by investors to selling the first bikes, building an incredibly loyal community, and eventually taking the company public. Tom also opens up about the difficult decision to leave Peloton, why he realized he was the one who needed to go, and what it took to separate himself from a company that had been intertwined with nearly every part of his life. Now, he’s starting over—this time partnering with Chipotle founder Steve Ells to rethink fast food with Counter Service. Tom shares why leaving Peloton made this next chapter possible and what building something from scratch all over again has taught him about success, failure, identity, and reinvention. Chapters 00:00 From 400+ No’s to an $8.1 Billion Company 01:45 What Philosophy Taught Tom About Building Community 05:50 Why Your Career Doesn't Need to Follow a Straight Line 09:40 The Hidden Market: How Relationships Create Opportunities 12:00 The Opportunity That Turned Tom Into a Product Manager 15:05 Proust: Building a Great Product That Wasn’t a Great Business 18:49 How Tom Handled His First Startup Failure 21:58 The Night John Foley Pitched Him Peloton 25:53 Turning Boutique Fitness Into a Subscription Business 27:21 Starting Peloton With an Idea That Seemed Impossible 29:51 What Exactly Is Peloton? 31:19 Building Hardware, Software, Content & Community at Once 33:39 Start With the Customer Experience 36:20 When SoulCycle Banned the Peloton Founders 37:16 How Peloton Started With Just $400,000 39:40 Raising $5 Million After Investors Said No 43:33 How Tom Kept Going Through Rejection 45:41 Turning the Vision Into Something Investors Could Believe In 47:41 Building Peloton’s First Bike in Taiwan 50:50 Selling the First Bikes Through Kickstarter 52:45 How Peloton’s Community Took on a Life of Its Own 53:15 From 5,000 Bikes to an $8.1 Billion IPO 54:43 The Community That Changed Peloton 58:24 The Hardest Decision: Knowing It Was Time to Leave 1:02:20 “The Odd Man Out Was Me” 1:05:47 Separating His Identity From Peloton 1:08:35 Starting Over With Chipotle Founder Steve Ells 1:11:13 Why Tom Jumped Into the Fast Food Industry 1:13:21 The Problem Counter Service Is Trying to Solve 1:20:08 Why Leaving Peloton Made This Next Chapter Possible 1:23:51 What to Expect From Counter Service 1:27:29 Success, Failure & How Other People Tell Your Story 1:31:20 Dealing With the “Rise and Fall of Peloton” Narrative 1:33:28 What Tom Would Tell His Younger Self 1:35:02 What’s Next for Counter ServiceAbout Tom Cortese ABOUT TOM Tom Cortese is the co-founder of Peloton and CEO of Counter Service. Tom helped build Peloton from its earliest days, developing the product and experience that combined hardware, software, content, and community into a new category of connected fitness. The company grew from an initial $400,000 investment to a public company valued at more than $8 billion at its IPO. After stepping away from Peloton, Tom began exploring what his next chapter could look like. That journey ultimately connected him with Chipotle founder Steve Ells, and today the two are building Counter Service, a technology-driven restaurant concept focused on bringing better food, smarter operations, and a new approach to fast service. LEAP ACADEMY Ready to make the LEAP in your career? There is a NEW WAY for professionals to fast-track their careers and leap to bigger opportunities.Check out Ilana’s free Leap Academy training: leapacademy.com/training 📲 Connect with Ilana: Facebook ▶️ https://www.facebook.com/IlanaGolanLeapAcademy LinkedIn ▶️ https://www.linkedin.com/in/ilanagolan/ Instagram ▶️ https://www.instagram.com/ilanagolanleap Website ▶️ https://www.leapacademy.com/

Sir Richard Harpin put £50,000 of his life savings into a business that nearly collapsed—twice. That company eventually became HomeServe, serving millions of customers globally before being sold for more than £4 billion. In this episode, Richard joins Ilana to share the lessons behind that extraordinary journey, from finding the business model that saved HomeServe with his final £10,000 to learning how to scale internationally, hire leaders better than himself, and stay focused when entrepreneurs are naturally drawn to the next big idea. Richard also shares lessons from his book, How to Make a Billion in Nine Steps, including why copying a proven model can be smarter than inventing something new, why every entrepreneur needs a “not-to-do” list, and the two mistakes he sees holding ambitious founders back. Chapters 00:00 Introduction 01:30 From £50K to a £4 Billion Exit 03:49 Richard’s First Business at Age Five 05:47 What Working at Procter & Gamble Taught Him 07:40 The Problem That Inspired HomeServe 08:37 Losing His Life Savings & Nearly Going Broke 10:12 Why Richard Refused to Give Up 11:19 Finding an Investor When the Business Was Struggling 12:40 The Final £10K That Changed Everything 15:14 Perseverance vs. Knowing When to Quit 16:26 Hiring His Replacement to Scale the Business 17:24 Taking HomeServe International 20:08 Evolution, Not Revolution 23:06 Why Direct Mail Still Works 24:59 Why You Need a “Not-to-Do” List 26:08 How Founders Can Avoid Shiny Object Syndrome 27:46 How Far Is Too Far From Your Core Business? 29:29 Scaling HomeServe Into a Global Business 32:14 Knighthood & Helping the Next Generation of Entrepreneurs 35:10 The Nine Steps Richard Wishes He Knew Earlier 37:42 Why Entrepreneurs Need Both a Coach and a Mentor 39:30 Stop Fixing Your Weaknesses—Build Around Your Strengths 40:52 What Holds High Achievers Back 42:52 Why Founders Need the Courage to Hire Expensive Talent 44:08 When to Bring in an Investor 45:44 You Don’t Need an Original Business Idea 46:26 Why Buying a Business May Be Smarter Than Starting One 47:35 Did Richard Ever Buy the Helicopter? About Sir Richard Harpin Sir Richard Harpin is the co-founder of HomeServe, the international home repairs and improvements business he helped grow from a struggling startup into a global company serving millions of customers. HomeServe was ultimately acquired in a deal valuing the company at more than £4 billion. Today, Richard focuses on helping the next generation of entrepreneurs build and scale successful businesses. He is also the author of How to Make a Billion in Nine Steps, where he shares the lessons he wishes he had known at the beginning of his entrepreneurial journey. 📲 Connect with Ilana: Facebook ▶️ https://www.facebook.com/IlanaGolanLeapAcademy LinkedIn ▶️ https://www.linkedin.com/in/ilanagolan/ Instagram ▶️ https://www.instagram.com/ilanagolanleap Website ▶️ https://www.leapacademy.com/

At 18 years old, Shawn Nelson had a crazy idea: build a beanbag so massive it could fill an entire room. That idea eventually became Lovesac, a publicly traded furniture company and major consumer brand. In this episode, Shawn joins Ilana to share the real journey behind building Lovesac, from taking risks and learning as he went to winning Richard Branson’s The Rebel Billionaire and leading a company at scale. They also dive into what failure teaches us, why success never means you’ve “arrived,” how Shawn gets through the hardest days, and why his philosophy is to maintain top ambition with infinite patience. Chapters 00:00 – Introduction 04:06 – The Idea That Started Lovesac 07:10 – Stop Talking and Start Doing 13:24 – Big Vision, Flexible Execution 17:57 – Risk, Debt & the Fear of Failure 22:36 – Winning Richard Branson’s The Rebel Billionaire 29:11 – Lessons From Richard Branson & Virgin 32:07 – Why You Never Really “Arrive” 40:38 – What Failure Teaches You About Success 43:56 – Taking Lovesac Public & Leading at Scale 50:35 – How Shawn Gets Through the Hard Days 54:16 – The Reality of Entrepreneurship 56:24 – Building Your Career Safety Net & Personal Brand 1:00:59 – Lessons Shawn Wishes He Knew Earlier 1:03:27 – Top Ambition, Infinite Patience 1:05:30 – Redefining What Success Really Means 1:07:58 – Finding Your Personal “Why” 1:09:03 – The Truth Behind the Highlight Reel About Shawn Nelson Shawn Nelson is the founder and CEO of Lovesac, the publicly traded furniture company he started at just 18 years old. He is an entrepreneur, inventor, and winner of Richard Branson’s The Rebel Billionaire. Shawn is also the author of Let Me Save You 25 Years: Mistakes, Miracles, and Lessons from the Lovesac Story, where he shares lessons from more than two decades of building, nearly losing, and ultimately growing Lovesac into the brand it is today. Connect with Shawn Lovesac: Lovesac.com Book & Podcast: Let Me Save You 25 Years Social: @ShawnOfLovesac Leap Academy Ready to make the LEAP in your career? There is a new way for professionals to fast-track their careers and leap into bigger opportunities. Get started with Ilana’s free career training at leapacademy.com/training. 📲 Connect with Ilana: Facebook ▶️ https://www.facebook.com/IlanaGolanLeapAcademy LinkedIn ▶️ https://www.linkedin.com/in/ilanagolan/ Instagram ▶️ https://www.instagram.com/ilanagolanleap Website ▶️ https://www.leapacademy.com/

Manu Sai Bakshi arrived in New York with $2,500, a new wife, and a degree that wasn’t recognized in the U.S. Within weeks, he was applying for a job at Macy’s in Herald Square. That humbling beginning eventually led Manu into the hedge fund world, where he spent nearly a decade learning how the industry identifies and hires elite talent before launching Preeminence Advisors during COVID. In this episode, Manu joins Ilana to break down what separates great portfolio managers from mediocre ones, why reputation matters more than a quick fee, and how taking the harder path can become your greatest competitive advantage. Chapters 00:00 – Introduction 04:38 – What Is a Hedge Fund? Breaking It Down Simply 07:26 – From IBM to Macy’s: Manu’s First Days in New York 11:13 – The Differentiator: Cold Calling When No One Else Would 14:52 – Almost Fired—and Already Planning His Own Firm 18:24 – The Moment That Proved He Could Place Portfolio Managers 22:32 – What Makes a Great Portfolio Manager 25:17 – Why Reputation Is Everything 33:26 – Launching His Own Firm During COVID 37:22 – Building the First Client: Knock Their Socks Off 42:21 – How People Actually Become Portfolio Managers 46:40 – Manu’s Favorite Interview Questions and Red Flags 48:48 – The Biggest Hiring Mistakes Hedge Funds Make 53:47 – Q&A: How Do You Keep Going When You Feel Defeated? About Manu Sai Bakshi Manu Sai Bakshi is the Founder and CEO of Preeminence Advisors, a boutique search firm specializing in placing elite portfolio managers at multibillion-dollar hedge funds. After immigrating from India, Manu built his career from the ground up before spending nearly a decade leading recruiting inside a systematic hedge fund. Today, he works with senior hedge fund leaders as both a recruiter and strategic talent advisor. Leap Academy Ready to make the LEAP in your career? There is a new way for professionals to fast-track their careers and leap into bigger opportunities. Get started with Ilana’s free career training at leapacademy.com/training.

Ilana Golan knows what it feels like to lose everything. After climbing from the Air Force to Intel to VP in a Silicon Valley startup, she thought she had made it. But when a trusted co-founder cut her out of their new business overnight, she was left with nothing. No job, no company, no income, and a shattered ego. That collapse became the turning point, forcing Ilana to ask who she was without the titles and what kind of life she truly wanted to build. In this episode, Ilana breaks down the five shifts you need to reinvent your career and the blueprint she used to bounce back from failure, build one of the fastest-growing startups, and land opportunities with leaders like Richard Branson and GaryVee. Ilana Golan is a serial entrepreneur, keynote speaker, investor, and host of the LEAP Academy podcast. As the founder of LEAP Academy, she teaches professionals how to fast-track opportunities, build portfolio careers, and unlock financial freedom. In this episode, Ilana discusses: (00:00) Introduction (01:11) The Startup Collapse That Changed Everything (04:24) Losing Her Identity and Rebuilding From Scratch (06:22) Launching LEAP Academy and Reaching Startup of the Year (09:10) Reinvention as the Must-Have Skill of Our Era (10:09) The Power of Adaptability: IQ vs. EQ vs. AQ (11:29) The Five Shifts to Fast-Track Your Career (18:30) Commanding Authority: The Three Types of Branding (23:17) Creating a Portfolio Career for Freedom and Wealth Ilana Golan is a serial entrepreneur, board director, global keynote speaker, and investor in over 100 companies. As the founder of Leap Academy, she teaches professionals how to fast-track opportunities, build portfolio careers, and unlock financial freedom. Ilana has been recognized as a Silicon Valley Woman of Influence, a Top 40 Woman to Watch, and a CEO World Award winner. Under her leadership, LEAP Academy was named one of Inc. 500’s Fastest Growing Companies. Connect with Ilana: Ilana’s Website: leapacademy.com Ilana’s LinkedIn: linkedin.com/in/ilanagolan Ilana’s Email: info@leapacademy.com Ready to make the LEAP in your career? There is a NEW WAY for professionals to fast-track their careers and leap to bigger opportunities. Join us for our free challenge August 11- 13th! https://workshops.leapacademy.com/challenge

Christina Tosi didn’t have a clear five-year plan when she graduated from college. She tried different majors, worked odd jobs, and kept searching for the thing that felt like hers. Baking became the answer she could not ignore. With relentless persistence, she went from a hostess stand to New York restaurant kitchens, proving herself one dessert at a time. That same drive eventually turned a tiny laundromat space into Milk Bar, the dessert empire known for bold flavors, nostalgic treats, and joyful care packages shipped across the country. In this episode, Christina joins Ilana to share how experimentation leads to clarity, why failure is essential to mastery, and what it really takes to build a business rooted in creativity, community, and joy. Christina Tosi is the founder and CEO of Milk Bar, the iconic dessert brand known for its bold, nostalgic treats like the Compost Cookie and cereal milk soft serve. She is a two-time James Beard Award winner and New York Times bestselling author. In this episode, Ilana and Christina will discuss: (00:00) Introduction (05:53) How Childhood Baking Sparked a Career (10:04) Testing Different Paths Until One Felt Right (17:56) The Embarrassing Failure That Fueled Her (22:04) Finding Mentors and Moving to New York (28:10) The Simple Networking Move That Opened Doors (31:17) The Cookie That Put Milk Bar on the Map (38:00) Turning Failure Into Fuel for Growth (45:04) Building Milk Bar in a Tiny Laundromat (49:47) Pushing Through Criticism, Burnout, and COVID (1:03:10) The Shift from Pastry Chef to CEO (1:08:11) Why Discomfort Can Become Your Edge (1:16:43) Betting on Yourself Before You Feel Ready Christina Tosi is the founder and CEO of Milk Bar, a nationally beloved dessert brand with locations across the U.S. She is a two-time James Beard Award winner, TED speaker, and New York Times bestselling author of seven cookbooks. Christina also created Bake Club, a free online baking community launched during COVID that continues to bring bakers together around the world. Connect with Christina: Website: christinatosi.com/  Christina’s LinkedIn: linkedin.com/in/christina-tosi   Christina’s Instagram: instagram.com/christinatosi/  Christina’s YouTube: youtube.com/christinatosi  Resources Mentioned:Bake Club: bakeclub.com/  Leap Academy: Ready to make the LEAP in your career? There is a NEW WAY for professionals to fast-track their careers and leap to bigger opportunities.  Check out our free training today at https://bit.ly/leap--free-training 📲 Connect with Ilana: Facebook ▶️ https://www.facebook.com/IlanaGolanLeapAcademy LinkedIn ▶️ https://www.linkedin.com/in/ilanagolan/ Instagram ▶️ https://www.instagram.com/ilanagolanleap Website ▶️ https://www.leapacademy.com/

What does it really take to solve impossible problems? In this episode of Leap Academy with Ilana Golan, Ilana sits down with Astro Teller, CEO of Google X (Alphabet's Moonshot Factory), to uncover the mindset, leadership principles, and innovation frameworks behind some of the world's most groundbreaking technologies—including Waymo, Wing, and Google Brain. Astro shares why the biggest breakthroughs begin with embracing failure, how Google X celebrates shutting down projects that aren't working, and why successful innovators focus on solving the hardest problem first instead of chasing easy wins. From reinventing careers to building billion-dollar ideas, this conversation is packed with practical lessons on taking smarter risks, overcoming fear, and creating a process that leads to extraordinary results. Whether you're an entrepreneur, leader, or simply looking to future-proof your career, this episode will challenge the way you think about success, innovation, and what's possible. 00:00 Introduction 03:30 Meet Astro Teller & the Mission Behind Google X 05:15 How Astro Became CEO of Google's Moonshot Factory 07:30 What Makes a True Moonshot? 10:25 Why Google X Celebrates Failure 15:40 Rethinking Risk: Reward vs. Risk Ratio 19:10 The Reality of Building Breakthrough Innovation 21:45 How Waymo Went from Impossible to Reality 26:45 Wing: Reinventing Delivery with Autonomous Drones 29:20 The "Monkey vs. Pedestal" Framework 34:45 Building a Moonshot Mindset 39:00 The Origins of Google Brain & Today's AI Revolution 43:10 The Future of AI, Recycling & Manufacturing 45:15 Advice for Anyone Reinventing Their Career 47:20 Astro's Personal Journey & Lessons from Failure 52:10 Becoming a Ferocious Learner 54:25 Why Great Innovation Is Built by Teams 56:01 Final Thoughts Dr. Astro Teller is the CEO of Google X, Alphabet's Moonshot Factory, where he leads teams creating breakthrough technologies designed to solve some of humanity's biggest challenges. Since joining Google, Astro has helped launch world-changing innovations including Waymo, Wing, Google Brain, and Tapestry, while developing Google's unique approach to moonshot thinking and breakthrough innovation. Before Google, Astro was a successful entrepreneur, scientist, inventor, Stanford faculty member, and author. Today, he is recognized as one of the world's foremost voices on innovation, leadership, and the future of technology. Connect with Astro Google X (Alphabet's Moonshot Factory)https://x.company Astro Teller – Google X Profilehttps://x.company/astro-teller Astro Teller on LinkedInhttps://www.linkedin.com/in/astroteller LEAP ACADEMY Ready to make the LEAP in your career? There is a NEW WAY for professionals to fast-track their careers and leap to bigger opportunities.Check out our free training today at https://bit.ly/leap--free-training 📲 Connect with Ilana: Facebook ▶️ https://www.facebook.com/IlanaGolanLeapAcademy LinkedIn ▶️ https://www.linkedin.com/in/ilanagolan/ Instagram ▶️ https://www.instagram.com/ilanagolanleap Website ▶️ https://www.leapacademy.com/

At 16, his grandmother fled Kraków after the Nazis killed her father, worked a New York factory floor beside her mother, and applied to every medical school in the state three years running before one finally said yes — then told her second-grade grandson that education is the only thing nobody can ever take away from him.Years later, David Rogier quit his venture capital job with no idea what he wanted to build, and his boss wrote him a check for $500,000 and told him to go think of something; the dark, formless year that followed became MasterClass, whose holding company still carries his grandmother's nickname. Launch day brought so few sales that he went home and cried, and by day four it was obvious he had a real business on his hands. In this conversation, David breaks down how he got Hollywood's biggest names to say yes, why he believes degrees and résumés are quickly becoming worthless, and the three kinds of jobs he thinks will actually survive AI. David Rogier is the founder and CEO of MasterClass, the platform that put instruction from Martin Scorsese, Christina Aguilera, Steph Curry, and dozens of other world-class practitioners into the hands of millions of learners. He built it from a single $500,000 check and has since launched MasterClass Executive, an AI-native alternative to the traditional MBA created in collaboration with OpenAI and the University of Chicago Booth School of Business. IN THIS EPISODE, ILANA AND DAVID WILL DISCUSS: (00:00) Introduction (01:34) The Grandmother Who Survived Kraków and Became a Doctor (05:39) Stuttering, Teasing, and Parents Who Raised the Bar (07:15) Quitting His Job and Getting Handed a $500,000 Check (08:48) The Dark Year: What Happens When You Have No Constraints (12:58) The Three Things That Had to Be True for MasterClass to Work (14:33) The Lost Art of Opening Doors and Influencing People (19:46) Launch Day: No Calls, Almost No Sales, and a Lot of Tears (21:18) What Scorsese, Steph Curry, and Christina Aguilera Do Differently (23:53) Why “Hire Great People and Get Out of Their Way” Is Terrible Advice (27:28) The AI Study That Compressed 18 Months of School Into 18 Hours (34:16) The Skills That Matter Now: Learning Velocity, Execution, People (39:28) The Three Types of Jobs That Survive AI (44:39) Burning the Corporate Ladder: Rebuilding the MBA for $2,500(49:16) What He'd Tell His Younger Self (51:52) Q&A: My Network Feels Crowded — How Do I Get Real Introductions? CONNECT WITH DAVID ROGIER David's Company Website: https://www.masterclass.com David's LinkedIn: https://www.linkedin.com/in/drogier/ RESOURCES MENTIONED MasterClass: https://www.masterclass.com Chris Voss's MasterClass on Negotiation: https://www.masterclass.com/classes/chris-voss-teaches-the-art-of-negotiation LEAP Episode with Chris Voss: https://podcasts.apple.com/us/podcast/leap-academy-with-ilana-golan/id1701718200?i=1000673141824 LEAP Episode with Tom Bilyeu: Tom Bilyeu: https://www.youtube.com/watch?v=rZ4EGDsKudk LEAP ACADEMY Ready to make the LEAP in your career? There is a NEW WAY for professionals to fast-track their careers and leap to bigger opportunities.Check out our free training today at https://bit.ly/leap--free-training 📲 Connect with Ilana: Facebook ▶️ https://www.facebook.com/IlanaGolanLeapAcademy LinkedIn ▶️ https://www.linkedin.com/in/ilanagolan/ Instagram ▶️ https://www.instagram.com/ilanagolanleap Website ▶️ https://www.leapacademy.com/

Revisiting one of our most-downloaded episodes, Tom Bilyeu shares his powerful journey from self-doubt to self-mastery. His early years were shaped by fear of failure, a lack of direction, and doubts from those around him. After struggling to break into the film industry, he joined a startup with the goal of getting rich, but found himself unhappy and in a strained marriage. Taking a leap of faith, Tom walked away from millions to pursue something more meaningful. This gave rise to Quest Nutrition, a billion-dollar company creating nutritious, great-tasting products. Yet, for Tom, wealth was never the endgame. He launched Impact Theory, a media company designed to impact lives positively. In this episode, Tom shares with Ilana the key moments that shaped his career, the philosophies that drive him, and how he defines true success. Tom Bilyeu is a billion-dollar entrepreneur, motivational speaker, co-founder of Quest Nutrition, and founder of Impact Theory. Through his content, he inspires millions by sharing tips on overcoming self-doubt, developing the right mindset, and building resilience for success. In this episode, Ilana and Tom discuss: (01:15) Introduction(01:43) Facing Doubts and Rejection(04:21) How Neuroscience Changed His Mindset(06:28) Why People Struggle to Make Progress(07:59) Learning the Power of Discipline in Film School(12:46) Tom’s Guide to Finding Your Next Step(15:25) Walking Away from $2 Million to Save His Marriage(17:14) Building Quest Nutrition with the Right Team(22:00) Why Tom Launched Quest Nutrition(24:37) The Key to Surviving Entrepreneurship(26:19) Strategies for Thriving in Competitive Markets(30:20) Solving What Others Say Can't Be Done(31:16) Conquering Fear Through Hard Work(36:20) The Journey from Quest to Impact Theory(40:15) Using Entertainment to Inspire Young Minds(45:24) Lessons from Childhood that Built Tom’s Resilience(48:06) Two Beliefs to Unlock Your Potential(49:44) Letting Go of Ego to Grow Connect with Tom: Tom’s Website: https://tombilyeu.comTom’s YouTube: youtube.com/c/TomBilyeuTom’s Twitch: www.twitch.tv/tombilyeu Leap Academy: Ready to make the LEAP in your career? There is a NEW way for professionals to advance their careers and make 5–6 figures of extra income in record time. Check out our free training today at leapacademy.com/training

In one of our most popular episodes, Amy Porterfield had a dream job working with Tony Robbins, one of the world’s top motivational speakers and business strategists. But deep down, she wanted to be her own boss. During a high-level meeting, she realized she was on the wrong side of the table, watching entrepreneurs build wealth instead of becoming one. With no plan, no clients, and no backup, she left corporate life and built a $100 million online business. In this episode, Amy joins Ilana to share how she overcame imposter syndrome, depression, and anxiety to create a balanced life and the mindset shift that took her from employee to multimillion-dollar entrepreneur. Amy Porterfield is an online marketing expert, entrepreneur, and bestselling author. She has helped thousands of people break free from traditional 9-to-5 jobs and create financial freedom through entrepreneurship. In this episode, Ilana and Amy will discuss: (00:00) Introduction  (01:44) Entrepreneurial Lessons from Childhood (03:35) Landing a Dream Job with Tony Robbins (07:46) The Three Biggest Lessons from Working with Tony (11:51) The Moment That Made Her Quit Corporate (14:48) Overcoming Imposter Syndrome and Depression (21:24) Finding Strength in Support Systems (24:24) How to Transition from Employee to Entrepreneur (27:32) Navigating the First Two Years in Business (29:21) Redefining Success to Avoid Burnout (35:20) Handling Hate and Criticism Online (38:19) Shifting Your Money Mindset to Scale Faster (43:35) Creating and Selling Profitable Digital Courses (46:05) Why Mistakes Are the Key to Growth Amy Porterfield is an online marketing expert, entrepreneur, and bestselling author. She runs a $100 million company teaching entrepreneurs how to create, market, and sell profitable digital courses. As the host of the Online Marketing Made Easy podcast and bestselling author of Two Weeks Notice, she has helped thousands of people break free from traditional 9-to-5 jobs and create financial freedom through entrepreneurship. Connect with Amy: Amy’s Website: amyporterfield.com  Amy’s LinkedIn: linkedin.com/in/amyporterfield Resources Mentioned: Amy’s Book, Two Weeks Notice: Find the Courage to Quit Your Job, Make More Money, Work Where You Want, and Change the World: https://www.amazon.com/Two-Weeks-Notice-Courage-Change/dp/1401969879  The Let Them Theory: A Life-Changing Tool That Millions of People Can't Stop Talking About by Mel Robbins: https://www.amazon.com/Let-Them-Theory-Life-Changing-Millions/dp/1401971369  Leap Academy: Ready to make the LEAP in your career? There is a NEW way for professionals to Advance Their Careers & Make 5-6 figures of EXTRA INCOME in Record Time. Check out our free training today at leapacademy.com/training

On our most replayed episode, Gary ‘Vee’ Vaynerchuk talks about how being scrappy wasn’t just a choice for him; it was his only way forward. After years of growing his family’s wine business, he was left with nothing of his own. With no money to rent an office or hire employees, Gary leveraged his grit, relationships, and opportunities to launch VaynerMedia. Overcoming the financial, mental, and emotional hurdles of entrepreneurship, he built his company into a multi-million-dollar media empire. In this episode, Gary joins Ilana to reveal the mindset and strategies you need to overcome obstacles and build your own multi-million-dollar business. Gary Vaynerchuk, famously known as GaryVee, is a serial entrepreneur, chairman of VaynerX, CEO of VaynerMedia and VeeFriends, and a six-time New York Times bestselling author. Recognized as one of the most forward-thinking minds in business, culture, and the internet, Gary helps brands stay ahead by spotting trends early. In this episode, Ilana and Gary will discuss: (00:00) Introduction  (01:40) VaynerMedia's Scrappy Beginnings (06:56) Why Businesses Fail Financially (10:01) Navigating Tough Business Days (17:21) The Risk of Over-Transparency in Leadership (19:44) Dealing with Failure and Public Ridicule (22:10) GaryVee’s Dream of Owning the New York Jets (26:06) The Role of DNA and Accountability in Success (28:35) Finding Joy in Entrepreneurship (31:02) How to Build a Personal Brand as an Employee (32:30) Empowering Employees with Honest Feedback (34:27) Embracing Change and Executing Relentlessly Gary Vaynerchuk, famously known as GaryVee, is a serial entrepreneur, chairman of VaynerX, CEO of VaynerMedia and VeeFriends, and a six-time New York Times bestselling author. He is a prolific angel investor with early investments in companies like Facebook, Twitter, Tumblr, Venmo, Snapchat, Coinbase, and Uber. Recognized as one of the most forward-thinking minds in business, culture, and the internet, Gary helps brands stay ahead by spotting trends early. Connect with Gary: Gary’s Website: ⁠garyvaynerchuk.com⁠  Gary’s LinkedIn: ⁠linkedin.com/in/garyvaynerchuk⁠  Resources Mentioned: Gary’s Book, Day Trading Attention: How to Actually Build Brand and Sales in the New Social Media World: ⁠https://www.amazon.com/Day-Trading-Attention-Actually-Social/dp/0063317591⁠  GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire: ⁠https://podcasts.apple.com/us/podcast/garyvee-from-earning-%242-an-hour-to-running-a/id1701718200?i=1000689595539⁠  Leap Academy: Ready to make the LEAP in your career? There is a NEW way for professionals to Advance Their Careers & Make 5-6 figures of EXTRA INCOME in Record Time. Check out our free training today at⁠ leapacademy.com/training

As a kid struggling with ADHD and financial instability, David watched his family nearly lose their home before taking a door-to-door sales job as a broke college student. He was terrible at it at first, but instead of quitting, he became obsessed with learning sales, systems, and business psychology. That mindset helped him build and sell four companies, scale across 5,000 cities in 34 states, and turn one of the world’s most overlooked industries into a $500 million empire. In this episode, David joins Ilana to share the sales lessons, leadership principles, and mindset shifts that helped him build through rejection, near-bankruptcy moments, and why some of the biggest opportunities today are hiding inside “boring” businesses. David Royce is the chairman of AP Environmental, one of North America's largest residential pest control companies. Starting from door-to-door sales as a college student, he built and sold four companies, reaching over 5,000 cities across 34 states and a $500M valuation at exit. In this episode, Ilana and David will discuss: (00:00) Introduction (04:58) The “Problem Kid” Who Built a $500M Business   (13:22) Sales Skills Every Entrepreneur Needs (17:06) Taking the Leap to Build His Own Business (21:17) Surviving the Early Business Chaos (29:02) Biggest Lessons from Tony Hsieh (33:52) How Scaling Exposes Every Weakness (37:45) The Failure That Forced David to Evolve (41:39) How Bankruptcy Changed His Definition of Success (45:34) “Boring” Businesses That Build Real Wealth (54:37) The Power of Risks in Creating Bigger Lives David Royce is a four-time exit founder and chairman of AP Environmental, one of North America's largest residential pest control companies. Starting from door-to-door sales, he built and sold four companies over the course of his career. His third company sold for a reported $135M, and his fourth, AP Environmental, reached a reported $500M valuation at exit, operating in over 5,000 cities across 34 states.  Connect with David: David’s LinkedIn: linkedin.com/in/david-royce-22539425   Aptive Website: aptivepestcontrol.com/   Resources Mentioned: Delivering Happiness - A Path to Profits, Passion, and Purpose by Tony Hsieh: https://www.amazon.in/dp/145550890X.  Leap Academy: Ready to make the LEAP in your career? There is a NEW WAY for professionals to fast-track their careers and leap to bigger opportunities.  Check out our free training today at https://bit.ly/leap--free-training

Mark Tluszcz had the career most people would chase: a top consulting job, rapid success, and a clear path forward. But eight years in, he made a move very few would dare to make. He left his high-paying job to start his own firm, faced hundreds of rejections while raising capital, and built Mangrove Capital from scratch. That same contrarian mindset led him to back companies others overlooked, becoming an early investor in Skype and later Chairman of Wix. In this episode, Mark joins Ilana to share how he invested early in Skype, spotted Wix before it became a global company, and why he turned down a $400 million acquisition offer. He also breaks down how to build conviction, embrace rejection, and find opportunities where others see risk. Mark Tluszcz is the co-founder and CEO of Mangrove Capital Partners and chairman of Wix, one of the world's leading website-building platforms. He is widely regarded as one of Europe's most influential venture capitalists, known for his early investments in Skype and Wix. In this episode, Ilana and Mark will discuss: (00:00) Introduction (05:36) Growing Up Across Multiple Cultures (09:09) Leaving Corporate Consulting to Build His Own Firm (13:58) Building Mangrove Capital During the Internet Boom (20:54) How to Keep Going After Hundreds of Nos (27:25) How Skype Evolved Beyond Music (36:47) Staying Humble After a Massive Win (43:08) Discovering Wix and Rethinking Venture Capital (50:33) Turning Down a $400M Deal: The Wix Story (57:41) Building Resilience Through Honest Conversations (01:01:14) Spotting the Next Wave of AI Opportunity (01:10:57) The Founder Mindset That Actually Lasts Mark Tluszcz is the co-founder and CEO of Mangrove Capital Partners, a Luxembourg-based venture capital firm he built from the ground up after leaving Arthur Andersen in 2000. He was one of the first investors in Skype, where Mangrove’s $2 million investment reportedly returned $200 million, and he has served as chairman of Wix, where an $8 million investment reportedly yielded $700 million. Connect with Mark: X: x.com/marktluszcz  Mark’s Instagram:  instagram.com/marktluszcz/  Mark’s LinkedIn: linkedin.com/in/mark-tluszcz-a024b51  Mark’s Blog: https://www.daretodreambeyond.com/  Leap Academy: Ready to make the LEAP in your career? There is a NEW WAY for professionals to fast-track their careers and leap to bigger opportunities.  Check out our free training today at https://bit.ly/leap--free-training

John Paul DeJoria grew up with no connections, no money, and no roadmap. He sold encyclopedias door-to-door despite constant rejection, got fired from three consecutive jobs, and lived out of his car while raising his young son. Then, with just $700, he launched John Paul Mitchell Systems and built it into a billion-dollar haircare company. That same relentless spirit later helped him turn Patrón Tequila into one of the most recognized spirit brands in the world. In this episode, John Paul joins Ilana to share what it truly takes to build something from nothing, why rejection is just redirection, and why success unshared is failure. John Paul DeJoria is a self-made billionaire, entrepreneur, and the visionary co-founder behind John Paul Mitchell Systems and Patrón Tequila. Beyond his iconic business achievements, he is a passionate philanthropist dedicated to creating a positive global impact. In this episode, Ilana and John Paul will discuss: (00:00) Introduction (03:40) Growing Up in Foster Care as an Immigrant Kid (11:20) The Navy Lessons That Shaped His Leadership (15:23) Making It Through Sudden Homelessness (23:23) How Getting Fired Led Him to Start Paul Mitchell (28:22) How He Made Billions With Only $700  (40:50) Letting Go of Fear, Failure, and Yesterday’s Mistakes (46:14) Growing Patrón Against the Odds (53:30) What Meeting Gaddafi Taught Him About Kindness (56:57) The New AI Platform That’s Making Entrepreneurship Easier (01:00:15) Why Happiness, Health, and Family Matter Most John Paul DeJoria is a self-made billionaire, philanthropist, and co-founder of John Paul Mitchell Systems, the world’s largest privately owned salon haircare brand. He also co-founded The Patrón Spirits Company, growing it from zero distribution to over 3.5 million cases annually before its landmark sale. His upcoming memoir, Success Unshared Is Failure, details his extraordinary journey and his conviction that giving back is essential. Connect with John Paul: John Paul’s Website: peacelovehappinessfoundation.org John Paul Mitchell Systems: https://www.paulmitchell.com Resources Mentioned: John Paul’s Book, Success Unshared is Failure: https://www.amazon.com/Success-Unshared-Failure-John-DeJoria/dp/B0FSTBMCJ8 Leap Academy: Ready to make the LEAP in your career? There is a NEW WAY for professionals to fast-track their careers and leap to bigger opportunities.  Check out our free training today at https://bit.ly/leap--free-training

Despite his high intelligence, George Barrios nearly flunked out of both high school and college, drifting without discipline or direction. Realizing talent alone wouldn’t build the future he wanted, he cleaned up his act, became obsessive about preparation, and built a reputation for solving hard problems others avoided. That approach helped him rise through HBO and Time Warner before transforming WWE into a global media powerhouse. In this episode, George joins Ilana to share the habits that accelerated his career, the tough leadership decisions behind WWE’s growth, and the mindset shifts that helped him reinvent himself under pressure. George Barrios is the former Co-President and CFO of WWE, where he helped transform the company into a global entertainment business. He is the founder of ISOS Capital, an investment and advisory firm focused on sports, media, and technology. In this episode, Ilana and George will discuss: (00:00) Introduction (08:48) When Talent Turned Into Self-Sabotage (13:12) The Turning Point: Meeting His Wife at UConn (15:49) Fake It Till You Make It: Learning on the Job  (23:17) Creating Opportunities After Rejection (33:31) Driving Digital Growth at The New York Times (39:38) Making Painful Decisions Under Pressure (44:14) Transforming WWE into a Global Media Business (50:35) The Fallout With Vince McMahon and WWE Exit (59:27) Writing His Book and Sharing Hard Lessons (01:05:52) Q&A: How Do I Open Doors in a Crowded Market? George Barrios is a former Fortune 500 executive and the founder of ISOS Capital, an investment firm focused on global opportunities in sports, media, and technology. He previously served as Co-President and CFO of WWE and held leadership roles at The New York Times, HBO, and Praxair, building a track record in strategy, operations, and financial leadership. His new book, Sometimes Wrong but Never in Doubt, shares the lessons behind his unconventional path to success. Connect with George: LinkedIn: linkedin.com/in/georgebarrios/  Resources Mentioned: George’s Book, Sometimes Wrong but Never in Doubt: How a Cuban Kid from Queens Transformed WWE: https://www.amazon.com/Sometimes-Wrong-but-Never-Doubt-ebook/dp/B0G4N4T9XV The World is Flat: The Globalized World in the Twenty-First Century by Thomas Friedman: https://www.amazon.in/dp/0141034890  Tony Khan: Building AEW into a Billion-Dollar Brand and Competing with Wrestling Giants: www.youtube.com/watch?v=Tqqfg-ysj0M  Leap Academy: Ready to make the LEAP in your career? There is a NEW WAY for professionals to fast-track their careers and leap to bigger opportunities.  Check out our free training today at https://bit.ly/leap--free-training

When Eric Ries built his first startup, he believed he had the perfect plan. But when no customers showed up, the business collapsed, exposing a costly truth: being certain does not make you right. That failure forced him to rethink his assumptions and ultimately led him to develop the Lean Startup method, a new way of building companies grounded in testing, learning, and truth. In this episode, Eric chats with Ilana about why most startups fail before they even launch, how to test ideas early to uncover what actually works, and how leaders can build companies that scale without losing their values. Eric Ries is an entrepreneur, author, and startup strategist best known for creating The Lean Startup methodology, a framework that helps founders build businesses through rapid experimentation and continuous iteration.  In this episode, Ilana and Eric will discuss: (00:00) Introduction (02:57) How His Childhood Curiosity Led Him to Computers (08:55) Dropping Out of Yale to Chase a Startup Dream (13:01) The Harsh Reality of the Entrepreneurship Fantasy (14:53) Why Silicon Valley Loves Failed Startups (19:37) Building, Scaling, and Leaving IMVU (23:09) Reinventing Your Identity After Loss (27:10) Tuning Out Bad Advice and Hearing What Matters (30:40) Using Negative Feedback to Fuel Growth (39:11) The Groundbreaking Lean Startup Philosophy (46:13) The Worldwide Resistance to Innovation (51:28) The Controversial Idea Behind Incorruptible (57:18) The Entrepreneurial Near-Death Experience  Eric Ries is an entrepreneur, author, and thought leader best known for creating the Lean Startup methodology, which transformed how startups and large companies build products. He is the founder of Long-Term Stock Exchange and has advised founders, executives, and organizations around the world on innovation, leadership, and long-term growth. Connect with Eric: Eric’s LinkedIn: linkedin.com/in/eries    Eric’s X: x.com/ericries  Resources Mentioned: Eric’s Book, The Lean Startup: https://www.amazon.in/dp/0307887898  Eric’s Book, Incorruptible: https://www.incorruptible.co/  Lean Startup Website: leanstartup.co/   Leap Academy: Ready to make the LEAP in your career? There is a NEW WAY for professionals to fast-track their careers and leap to bigger opportunities.  Check out our free training today at https://bit.ly/leap--free-training

Jason Feifer started his career writing about middle school dances at a tiny local newspaper, frustrated and convinced he was capable of more. Stuck in a role that wasn’t moving him forward, he quit, sat in his dumpy apartment next to a graveyard, and began cold-pitching major publications with no connections. That decision transformed his trajectory, eventually leading him to become Editor-in-Chief of Entrepreneur Magazine and a leading voice on career growth and adaptability. In this episode, Jason chats with Ilana about why doing only what’s expected of you slows your growth, how to identify opportunities, and steps to take control of your career in an unpredictable world. Jason Feifer is the Editor-in-Chief of Entrepreneur Magazine, a podcast host, book author, and keynote speaker who helps people build careers and companies they love by sharing lessons from the world's top entrepreneurs and leaders. In this episode, Ilana and Jason will discuss: (00:00) Introduction  (03:48) Cold Pitches From a Bedroom Next to a Graveyard (06:41) Developing an ‘Opportunity Set B’ Mindset (09:51) Building Skills Strategically Across Jobs (12:58) Renting a Title vs. Owning Your Name (17:02) The Mission Statement That Survives Any Job Loss (24:22) Why Jason Walked Away From His Biggest Hit (31:51) How to Test Multiple Ventures At Once (34:31) How a Lawsuit Accidentally Built Jason’s Success (40:00) The Danger of Labeling Yourself (47:47) Q&A: How Do You Become More Adaptable? Jason Feifer is the Editor-in-Chief of Entrepreneur Magazine, a role he has held for over 10 years. He is the author of Build for Tomorrow, host of the podcast Help Wanted, and a sought-after keynote speaker who has spoken for companies including Pfizer, Alibaba, Clorox, and more. Jason also advises startups, sits on multiple advisory boards, and writes the weekly newsletter One Thing Better. His work centers on adaptability, personal reinvention, and helping individuals and organizations thrive through change. Connect with Jason Jason’s Website: https://www.jasonfeifer.com  Jason’s LinkedIn: linkedin.com/in/jasonfeifer  Jason’s Instagram: https://www.instagram.com/heyfeifer/ Resources Mentioned: Jason's Newsletter, One Thing Better: https://www.jasonfeifer.com⁠  Jason’s Book, Build for Tomorrow: An Action Plan for Embracing Change, Adapting Fast, and Future-Proofing Your Career: https://www.amazon.com/dp/059323538X Leap Academy: Ready to make the LEAP in your career? There is a NEW WAY for professionals to fast-track their careers and leap to bigger opportunities.  Check out our free training today at https://bit.ly/leap--free-training

Tim Draper didn’t become a legendary investor with billions in his account overnight; he started by taking a $6 million loan to launch his first venture fund, knowing failure was a real possibility. That decision didn’t just shape his career; it laid the foundation for backing some of the biggest companies in the world, including Hotmail, Skype, Tesla, and more. In this episode, Tim joins Ilana to break down how to spot world-changing ideas before they make sense, why most people miss their biggest opportunities, and how listening to your gut can be more powerful than logic alone. He shares the lessons behind massive wins like Hotmail, painful misses like Netflix, and the mindset required to navigate uncertainty, fear, and reinvention. Tim Draper is a third-generation venture capitalist, founder of Draper University, and one of Silicon Valley's most legendary investors. He is a lifelong advocate for entrepreneurship, innovation, and the next generation of world-changing founders. In this episode, Ilana and Tim will discuss: (00:00) Introduction  (04:11) Early Lessons on Money, Risk, and Capitalism (08:43) Leaving Home at 13 and Learning to Figure It Out (11:48) Venture Capital Roots and Family Background (14:17) Taking a $6 Million Loan and Betting on Himself (17:14) Spotting Billion-Dollar Companies Before Anyone Else (20:11) The Viral Growth Strategy Behind Hotmail (23:26) How Skype Changed Global Communication Forever (29:18) Navigating the Dot-Com Crash (34:13) Will AI and Crypto Follow the Same Boom Cycle? (35:55) The Power of Listening to Your Gut as an Entrepreneur (46:59) Q&A: How Do I Know What to Invest In?  Tim Draper is a third-generation venture capitalist and founder of Draper University. He backed world-changing companies, including Hotmail, Skype, Tesla, SpaceX, Coinbase, and Robinhood. Known for spotting transformative trends before the mainstream, he's also a passionate advocate for entrepreneurship education, cryptocurrency, and celebrating innovation. His show Meet the Drapers reaches roughly 300 million people globally. Connect with Tim Tim’s Website: https://timothydraper.com/  Tim’s LinkedIn: https://www.linkedin.com/in/timothydraper/  Tim’s Instagram: https://www.instagram.com/timdraper/  Resources Mentioned: Tim’s Book, How to be the Startup Hero - A Guide and Textbook for Entrepreneurs and Aspiring Entrepreneurs: https://www.amazon.com/How-Startup-Hero-Textbook-Entrepreneurs/dp/1973585340/ref=cm_cr_arp_d_product_top?ie=UTF8 Leap Academy: Ready to make the LEAP in your career? There is a NEW WAY for professionals to fast-track their careers and leap to bigger opportunities.  Check out our free training today at https://bit.ly/leap--free-training

When Yancey Strickler moved to New York, he was broke, freelancing for $50, and chasing a writing career. Little did he know, his gift for building on the internet would soon change the world of crowdfunding. A chance encounter with a friend and a half-baked idea about crowd-funded concert tickets led to the founding of Kickstarter, a platform that has raised over $7 billion for creative projects worldwide. In this episode, Yancey joins Ilana to discuss his journey from freelancing on a shoestring budget to building a billion-dollar platform and what it took to survive the hardest moments. He also explains his bold plan to help artists participate in capitalism. Yancey Strickler is the co-founder and former CEO of Kickstarter, the platform that raised over $7 billion for more than 200,000 creative projects. He now runs Metalabel, a studio building tools for creative cooperation. In this episode, Ilana and Yancey will discuss: (00:00) Introduction  (03:11) From Music Households to Manhattan Bylines (06:28) The Side Project That Changed Everything (13:34) The Ladder Vouch System That Launched Kickstarter (18:57) Why Showing Up as an Open Box Wins Every Room (26:31) The Day Two Projects Hit a Million Dollars at Once (33:40) The New Definition of Work in the Age of AI (36:28) Building the Legal Blueprint for the Artist Economy (43:09) Why the Private Internet Is Where the Real World Lives (49:38) Q&A: How to Open Doors to New Connections Yancey Strickler is a writer, serial entrepreneur, and the co-founder of Kickstarter, the global crowdfunding platform that has raised billions for creative projects.  He's the author of This Could Be Our Future and The Dark Forest Anthology of the Internet and the co-host of the New Creative Era podcast. Before Kickstarter, Yancey was a music critic for outlets like Pitchfork and Spin. Today, he leads two bold projects: A Corp, a legislative effort to provide artists with real economic infrastructure, and DFOs, a platform reimagining the private internet.  Connect with Yancey Yancey’s Website: https://www.ystrickler.com Yancey’s LinkedIn: https://www.linkedin.com/in/yancey-strickler-486b4557/  Yancey’s Instagram: https://www.instagram.com/ystrickler/  Yancey’s X: https://x.com/ystrickler  Resources Mentioned: Yancey’s Books, This Could Be Our Future: A Manifesto for a More Generous World: https://www.amazon.com/This-Could-Our-Future-Manifesto/dp/0525560823  The Dark Forest Anthology of the Internet: https://www.amazon.com/Dark-Forest-Anthology-Internet/dp/B0D14NN1DN  On the Creative Life: Conversations Toward a New Creative Era: https://squad.metalabel.com/onthecreativelife?ref=ystrickler.com&variantId=1  Leap Academy: Ready to make the LEAP in your career? There is a NEW WAY for professionals to fast-track their careers and leap to bigger opportunities.  Check out our free training today at https://bit.ly/leap--free-training

Elena Cardone’s life changed the day she watched her best friend die in a house fire. That trauma sent her spiraling into a decade of drugs and alcohol, and as more friends died in the years that followed, she believed she was next. Until one night, a dream forced her to confront the truth: she wasn’t honoring her friend’s life; she was wasting her own. That moment became the turning point that set her on a path to transforming her life and building a $5 billion empire. In this episode, Elena shares how she broke free from destructive patterns and the mindset shifts that transformed her marriage, career, and financial future. Elena Cardone is an entrepreneur, bestselling author, speaker, and real estate investor who has built a $5 billion portfolio alongside her husband, Grant Cardone. She is the co-founder of Cardone Capital, Cardone Foundation, and Cardone Mortgage. In this episode, Ilana and Elena will discuss: (00:00) Introduction  (05:39) The House Fire That Changed Everything (08:52) How Your Mind Works Against You to Self-Sabotage (11:21) Moving to Hollywood and Discovering Its Dark Sides (15:56) How Trauma Almost Cost Her the Right Man (24:15) The 2008 Crisis and a Marriage Breaking Point (27:25) How a Nightly Game Built a Billion-Dollar Mindset (35:41) The Hidden Cost of Believing Money Is Evil (41:40) Why Great People Attack Your Weaknesses (46:38) Elena’s Plan to Build Global Influence (51:29) Q&A: How Do You Get Paid to Speak? Elena Cardone is an entrepreneur, former actress, podcast host, and the bestselling author of Build an Empire. She is a licensed realtor leading a 500-agent organization with eXp Realty, and has built a $5 billion portfolio alongside her husband, Grant Cardone. Elena is also the co-founder of both the Grant Cardone Foundation, which helps underserved youth understand finance and business, and Cardone Mortgage, which makes homeownership more accessible across all 50 states.  Connect with Elena: Elena’s Website: https://elenacardone.com Elena’s LinkedIn: https://www.linkedin.com/in/elenacardone/ Elena’s Instagram: https://www.instagram.com/elenacardone/  Resources Mentioned: Elena’s Book, Build an Empire: How to Have It All: https://www.amazon.com/Build-Empire-How-have-All-ebook/dp/B09RGHGQ4K  Dianetics: The Modern Science of Mental Health by L. Ron Hubbard: https://www.amazon.com/Dianetics-Modern-Science-Mental-Health/dp/B001EPO4Z2 Leap Academy: Ready to make the LEAP in your career? There is a NEW WAY for professionals to fast-track their careers and leap to bigger opportunities.  Check out our free training today at https://bit.ly/leap--free-training

Ra’anan Cohen walked into the tech world with no fancy degree and no startup pedigree; just a phone call from a friend and the promise of free food and a gym membership. From day one, he felt like an outsider, constantly battling imposter syndrome. Yet, he stuck with it, learned the ropes of the startup world, and ultimately founded a billion-dollar company. In this episode, Ra’anan joins Ilana to share his wild 15-year ride: a public company on NASDAQ, a unicorn valued at $1 billion, and a board that tried to fire him at his peak. He reveals everything the startup world doesn't want you to know about the real cost of chasing unicorns. Ra’anan Cohen is a serial entrepreneur, author, and the co-founder of Bringg, a SaaS delivery management platform that achieved unicorn status with a $1 billion valuation. He was also the founder and CEO of MobileMax, which went public on NASDAQ. In this episode, Ilana and Ra’anan will discuss: (00:00) Introduction  (04:30) The Biggest False Beliefs On Entrepreneurship (06:38) The Impact of Imposter Syndrome on Ra'anan's Career (09:16) Quitting a Stable Job to Start a Company (12:09) Raising Capital with No Credentials (15:34) The $10M Mistake That Cost Him Everything (18:55) How a Pizza Night Sparked a Billion-Dollar Idea (24:35) Raising Capital the Second Time: The Stealth Mode Strategy (28:47) Different Types of Modern Investors (32:52) Why Startups Are Marathons, Not Rollercoasters (43:43) When to Make Life-Changing Decisions (and When Not To) (45:39) Redefining Success: The Multi-Bucket Life Philosophy (53:36) Q&A: Handling Rejection Without Losing Your Spark Ra’anan Cohen is a serial entrepreneur, author, and the co-founder of Bringg, a SaaS delivery management platform that achieved unicorn status with a $1 billion valuation. He was the founder and CEO of MobileMax, where he led the company to multimillion-dollar international sales and an IPO. Ra'anan is also the author of Confessions of a Unicorn Founder, a national bestseller in Israel, which is currently being adapted into a TV series. Connect with Ra’anan: Ra’anan’s Website: https://www.raanancohen.com  Ra’anan’s LinkedIn: linkedin.com/in/raananc  Resources Mentioned: Ra’anan’s Book, Confessions of a Unicorn Founder: Obsession, Greed, and the Brutal Truth Behind Chasing the Startup Dream: https://www.raanancohen.com⁠  Leap Academy: Ready to make the LEAP in your career? There is a NEW WAY for professionals to fast-track their careers and leap to bigger opportunities.  Check out our free training today at https://bit.ly/leap--free-training

When Kim Perell was fired, she had to fire all her friends on the same day. The company she thought would make her a millionaire had just gone bankrupt, leaving her with no income or backup plan. Instead of giving up, she took a $10,000 loan from her grandmother to start her first company from her kitchen table. That bet led to a $20 million exit and eventually, a $235 million company. In this episode, Kim joins Ilana to share how to turn setbacks and mistakes into million-dollar breakthroughs and how to overcome the limiting beliefs holding you back. She also reveals the four pillars that helped her achieve success without burning out. Kim Perell is a 9x founder, 3x bestselling author, and investor in 100+ companies. Kim became a multi-millionaire by the time she was 30, and sold her last company for $235 million to Singtel, while simultaneously running multi-million-dollar companies. In this episode, Ilana and Kim will discuss: (00:00) Introduction  (04:08) Growing Up in the Shadow of Her Twin Sister (07:07) Learning Risk and Failure from Entrepreneur Parents (09:46) How Getting Fired Led to a Career Pivot (13:31) Her Grandma’s Life-Changing $10K Loan (16:37) Using The 70% Rule to Make Business Decisions (18:48) The Four Pillars of Business Success (23:50) Selling Her Business for $20 Million (28:02) Building a Money Mindset  (30:59) The Dangers of Failing to Pivot Or Make Mistakes (40:13) Teaching Your Children Resilience (45:01) Q&A: How to Chase Success Despite Fear Kim Perell is a 9-time founder, 3-time bestselling author, top keynote speaker, and investor in over 100 companies. Her book, Mistakes That Made Me a Millionaire, offers a transformative guide to turning setbacks into million-dollar opportunities. An award-winning entrepreneur, Kim has appeared on major platforms and serves as a judge for Entrepreneur Magazine’s Elevator Pitch. She is dedicated to empowering the next generation of business leaders for success. Connect with Kim: Kim’s Website: https://kimperell.com/  Kim’s LinkedIn: https://www.linkedin.com/in/kimperell/  Kim’s Instagram: https://www.instagram.com/kimperell/  Resources Mentioned: Kim’s Book, Mistakes that Made Me a Millionaire: How to Transform Setbacks into Extraordinary Success: https://www.amazon.com/dp/1637747128  Leap Academy: Ready to make the LEAP in your career? There is a NEW WAY for professionals to fast-track their careers and leap to bigger opportunities.  Check out our free training today at https://bit.ly/leap--free-training

Jason Fried didn’t follow the startup rules most founders swear by. He rejected venture capital, refused to chase growth at all costs, and chose to stay small on purpose. What started as a scrappy web design agency turned into Basecamp, a multi-million-dollar business built on profitability, simplicity, and conviction. In this episode, Jason joins Ilana to challenge everything you think you know about scaling a business. He also opens up about how a single leadership decision caused 30% of his company to quit overnight, and how staying principled ultimately made the company stronger. Jason Fried is the co-founder and CEO of 37signals, the company behind Basecamp and HEY. For over 27 years, he has grown Basecamp into a multi-million dollar business without ever taking venture capital or chasing aggressive growth targets. In this episode, Ilana and Jason will discuss: (00:00) Introduction  (03:18) Lessons from Selling Stereo Equipment as a Kid (06:58) Starting 37signals from Scratch (14:13) Pivoting to Software Through Basecamp   (16:41) The Perks of Being a Small Company (27:24) The Policy That Made 30% of the Company Quit  (31:45) Surviving the Backlash and Rebuilding the Team (39:21) Building Thicker Skin as a Leader (42:43) How to Incorporate AI Without Getting Carried Away (45:15) How Basecamp Is Reinventing Itself with Version 5 (48:56) Why Jason Won’t Advise His Younger Self (54:07) Q&A: How to Decide Your Next Career Move Jason Fried is a co-founder and CEO of 37signals, the makers of Basecamp. He is a bestselling author of Rework and It Doesn’t Have to Be Crazy at Work. Known for his contrarian approach to entrepreneurship, Jason emphasizes simplicity, profitability, and long-term thinking. For over 27 years, he has grown Basecamp into a multi-million dollar, fully profitable business without ever taking venture capital or chasing aggressive growth targets. Connect with Jason: LinkedIn: linkedin.com/in/jason-fried  X: https://x.com/jasonfried Resources Mentioned: Jason’s Books:  Rework: https://www.amazon.com/Rework-Jason-Fried/dp/0307463745 It Doesn't Have to Be Crazy at Work: https://www.amazon.com/Doesnt-Have-Be-Crazy-Work/dp/0062874780  37signals’ Website: https://37signals.com  Basecamp’s Website: https://basecamp.com  Leap Academy: Ready to make the LEAP in your career? There is a NEW WAY for professionals to fast-track their careers and leap to bigger opportunities.  Check out our free training today at https://bit.ly/leap--free-training

Don McGuire did not build his career through a straight line. He lost elections as a kid, moved every few years, started over again and again, and had to learn resilience early. After graduating from college, he was still unsure what to do, but a leap into the early cellular industry launched a career that would take him from sales to marketing and ultimately, the CMO seat at Qualcomm. In this episode, Don chats with Ilana about how to stay in control of your career in a world changing at the speed of AI. He shares why resilience matters more than ever, how to spot the right time to leap, and what it takes to stay relevant in a crowded job market. Don McGuire is the Executive Vice President and Chief Marketing Officer of Qualcomm, with over 25 years of experience across service providers, semiconductors, and technology marketing. In 2025, he was named one of Forbes’ World’s Most Influential CMOs. In this episode, Ilana and Don will discuss: (00:00) Introduction (03:14) The Early Experiences That Built Don’s Resilience (10:46) His Love for Marketing and Journey Into Tech (18:00) The Transition From Sales to Marketing (20:18) Why You Must Stay in Control of Your Own Destiny (23:25) Startup Lessons, Consulting, and Selling Yourself (27:43) Knowing When It Was Time to Leap Back Into Corporate (31:45) The Crisis That Forced Qualcomm to Tell Its Story (38:16) The One Trait Gen Z and Gen Alpha Need Most (40:33) How to Stand Out in an AI-Driven Job Market (45:02) Why Portfolio Careers and Side Skills Matter (48:03) What Excites Don Most About Qualcomm’s Future (53:05) Q&A: How to Break the “I Can’t Get a Job” Mindset Don McGuire is the Executive Vice President and Chief Marketing Officer of Qualcomm, where he oversees global marketing as the company expands beyond mobile into automotive, computing, AI, and other growth areas. Before joining Qualcomm, he held senior leadership roles at Intel and other major wireless and technology companies. In 2025, he was named one of Forbes’ World’s Most Influential CMOs. Connect with Don: Don’s LinkedIn: linkedin.com/in/donnymac  Resources Mentioned: Qualcomm: https://www.qualcomm.com/ Leap Academy: Ready to make the LEAP in your career? There is a NEW WAY for professionals to fast-track their careers and leap to bigger opportunities.  Check out our free training today at https://bit.ly/leap--free-training

In the late 1990s, Mike Seckler started a company with little experience, plenty of curiosity, and no idea what was coming. Then the dot-com bubble burst. Almost overnight, capital disappeared. Companies collapsed. And Mike faced one of the hardest decisions of his career: laying off a third of his team to keep the company alive. That moment changed how he builds companies and leads today as CEO of Justworks. In this episode, Mike joins Ilana to share the real lessons behind building and scaling through uncertainty and how founders can avoid the leadership mistakes that derail most companies. Mike Seckler is the President and CEO of Justworks, an HR platform helping over 14,000 small businesses manage payroll, benefits, compliance, and workforce management. In this episode, Ilana and Mike will discuss: (00:00) Introduction  (02:42) From History and Geology Student to Entrepreneur (07:05) The Early Days of Founding Employease (09:08) Navigating the Dot Com Crash as a Founder (14:53) Selling to ADP and Starting a New Venture (17:23) Joining Justworks: From Board Member to COO (24:37) Lessons from Transitioning to Justworks’ CEO (26:00) The Biggest Blindspots for Small Businesses (31:58) How to Beat Founder Loneliness (36:34) Adapting to a Rapidly Evolving Market (42:03) Justworks: Empowering Small Businesses for Growth (44:49) Review and Q&A: BREAD Productivity Framework Mike Seckler is a serial entrepreneur who has built and scaled multiple companies over the past two decades. Before joining Justworks, he co-founded Employease, an HR outsourcing firm that was eventually acquired by ADP, and later co-founded Euclidean Technologies, a company applying machine learning to public market investing. Today, as CEO of Justworks, Mike leads a platform serving thousands of small businesses and helping founders navigate the complexities of building and scaling their teams. Connect with Mike: Mike’s LinkedIn: linkedin.com/in/mikeseckler  Resources Mentioned: Justworks Website: https://www.justworks.com  Leap Academy: Ready to make the LEAP in your career? There is a NEW WAY for professionals to fast-track their careers and leap to bigger opportunities.  Check out our free training today at https://bit.ly/leap--free-training

When Bill Gurley wanted to break into Wall Street, there were no job postings waiting for him. So he flew to New York, knocked on doors, and asked strangers for meetings. That hustle launched a career that would eventually take him to Silicon Valley, where he became one of the most respected venture capitalists in tech. In this episode, Bill joins Ilana to reveal the unconventional lessons that shaped his journey. From chasing curiosity to designing your own career path, he explains how anyone can create opportunities, stand out in a crowded field, and build a career that actually excites them. Bill Gurley is a Silicon Valley venture capitalist and a longtime partner at Benchmark Capital, a Silicon Valley venture capital firm. He has invested in and served on the boards of major companies, including Uber, OpenTable, Zillow, Nextdoor, and Stitch Fix. In this episode, Ilana and Bill will discuss: (00:00) Introduction  (03:14) Where Bill Gurley’s Tech Curiosity Began (05:09) Transitioning from Engineering to Finance (08:25) Breaking Into Wall Street Without a Job Posting (14:24) The Question That Made Him Quit Wall Street (19:59) Making a Pivot to Venture Capital (24:41) The Best Way to Get Into Venture Capital (26:50) How to Know If You’re in the Right Career (30:30) The Role of Experimentation in Career Growth (33:20) How to Stand Out in a Competitive Job Market (37:29) Why Location Can Make or Break Your Career (40:50) Breaking Free From the “Safe Career” Pressure (48:30) The 5–5–5 Rule for Career Experiments Bill Gurley is a venture capitalist, technology investor, and general partner at Benchmark Capital, best known for his early investment in companies like Uber. Before venture capital, he worked as an engineer at Compaq and later as a Wall Street technology analyst. Throughout his career, Bill has been known for identifying transformative companies early and for his widely read blog Above the Cloud. His new book, Running Down a Dream, offers a practical guide to building a fulfilling career Connect with Bill: Bill’s X (Twitter): x.com/bgurley  Bill’s Website: abovethecrowd.com  Resources Mentioned: Bill’s Book, Runnin' Down a Dream: How to Thrive in a Career You Actually Love: https://www.amazon.com/dp/0593799666  One Up On Wall Street: How to Use What You Already Know to Make Money in the Market by Peter Lynch: https://www.amazon.com/dp/0743200403  Range: Why Generalists Triumph in a Specialized World by David Epstein: https://www.amazon.com/dp/0735214484  Greenlights by Matthew McConaughey: https://www.amazon.com/dp/0593139135  Leap Academy: Ready to make the LEAP in your career? There is a NEW WAY for professionals to fast-track their careers and leap to bigger opportunities.  Check out our free training today at https://bit.ly/leap--free-training

Nir Eyal grew up clinically obese, ashamed of his body, and convinced that food controlled him. He tried every diet: low-fat, keto, vegetarian, and intermittent fasting. Each one worked until it didn’t. What finally changed his life wasn’t a meal plan; it was his belief. When he believed a plan would work, it worked. When that belief cracked, the weight returned. And he realized this pattern doesn’t just apply to weight; it shows up in every area of life. In this episode, Nir joins Ilana to reveal the hidden force behind your success or stagnation. He unpacks the science of belief, how it shapes what you see, feel, and do, and the practical framework to break limiting beliefs before they break you. Nir Eyal is a bestselling author, behavioral design expert, and former Stanford lecturer known for his work on habit formation, psychology, and human behavior. As an entrepreneur and angel investor, Nir has backed multi-billion-dollar companies including Canva and Kahoot!. In this episode, Ilana and Nir will discuss: (00:00) Introduction  (03:14) Childhood and Weight Loss Struggles (07:34) Why Affirmations and Vision Boards Don’t Work (09:18) Facts vs Faith vs Beliefs (10:59) His Journey from Founder to Bestselling Author (16:01) The Power of Belief in Success and Failure  (24:49) The ‘Messy Middle’: Knowing When to Persist vs Quit (32:06) Skills Gap vs Belief Gap in Leaders and Teams (34:0) The Four Questions to Rewire a Limiting Belief (46:51) Q&A: Crafting a Memorable Pitch Story Nir Eyal is a bestselling author, behavioral design expert, and former Stanford lecturer. He is the author of Hooked and Indistractable, which have sold over one million copies worldwide and been translated into more than 30 languages. His latest book, Beyond Belief, explores how hidden beliefs shape our limitations and how to replace them to unlock personal and professional growth. An entrepreneur and angel investor, Nir has backed multi-billion-dollar companies including Canva and Kahoot!. Connect with Nir: Nir’s Website: http://nirandfar.com Nir’s Instagram: instagram.com/neyal99 Nir’s LinkedIn: linkedin.com/in/nireyal Resources Mentioned: Nir’s Books: Beyond Belief: The Science-Backed Way to Stop Limiting Yourself and Achieve Breakthrough Results: https://www.amazon.com/dp/0593852036 Indistractable: How to Control Your Attention and Choose Your Life: https://www.amazon.com/dp/194883653X Hooked: How to Build Habit-Forming Products: https://www.amazon.com/dp/1591847788 Nir’s 30-Day Belief Transformation Journal: nirandfar.com/beyond-belief Leap Academy: Ready to make the LEAP in your career? There is a NEW WAY for professionals to fast-track their careers and leap to bigger opportunities.  Check out our free training today at https://bit.ly/leap--free-training

Dr. Amy Shah did everything she was supposed to do. Ivy League education. Elite medical training. Multiple board certifications. On paper, her life looked like a success. But behind the accolades, she was exhausted, disconnected, and running on stress. Then a near-fatal car accident forced her to confront a hard truth. The life she built was slowly breaking her body and mind. In this episode, Amy joins Ilana to share how a personal health crisis became the catalyst for a complete reinvention. She opens up about leaving the traditional medical path without burning the boats, building a science-backed wellness platform, and why women are being failed by modern healthcare. Dr. Amy Shah is a double board-certified physician and nutrition specialist. Through her books and wellness platform, Dr. Amy empowers millions to optimize their health with evidence-based strategies rooted in nutrition, gut health, exercise, and lifestyle medicine. In this episode, Ilana and Dr. Amy will discuss: (00:00) Introduction  (03:30) How a Near-Fatal Accident Became a Wake-Up Call (09:51) From Traditional Medical Path to a Wellness Brand (13:08) Building a Personal Brand Despite Pushback (17:13) The Power of Having a Supportive Network (21:47) How Dr. Amy Built a Powerful Portfolio Career (23:51) Understanding Women's Health: The 30-30-3 Framework (26:41) The Science of Probiotics and Gut Health (30:24) The 4-3-2-1 Movement Framework for Peak Health (37:32) Managing Stress and Cortisol Levels (43:42) Building a Personal Brand and Finding Your Path (47:17) Her Immigrant Roots and Its Impact (51:44) Review and Q&A: Beating Ageism in Your Career Journey Dr. Amy Shah is a double board-certified physician and nutrition specialist. She is the bestselling author of I’m So Effing Hungry and I’m So Effing Tired. Her latest book, Hormone Havoc, offers a science-backed guide to navigating the complexities of perimenopause and menopause. Through her books and wellness platform, Dr. Amy empowers millions to optimize their health with evidence-based strategies rooted in nutrition, gut health, exercise, and lifestyle medicine. Connect with Dr. Amy: Dr. Amy’s Website: https://amymdwellness.com  Dr. Amy’s Instagram: instagram.com/dramyshah  Resources Mentioned: Dr. Amy’s Books,  Hormone Havoc: A Science-Backed Protocol for Perimenopause and Menopause: Sleep Better. Think Better. Feel Better: https://www.amazon.com/dp/0063420856  I'm So Effing Hungry: Why We Crave What We Crave – and What to Do About It: https://www.amazon.com/dp/0063285118  Leap Academy: Ready to make the LEAP in your career? There is a NEW WAY for professionals to fast-track their careers and leap to bigger opportunities.  Check out our free training today at https://bit.ly/leap--free-training

The world tells leaders they must be everything: visionary, innovator, operator, executor. Patrick Lencioni tried, but it nearly crushed him. He wasn’t exhausted from effort; he was exhausted from misalignment. He discovered what most high performers never admit: trying to be everything is the fastest path to burnout. That insight became The Six Types of Working Genius, a simple framework reshaping how teams work by aligning people with the work that gives them energy. In this episode, Patrick joins Ilana to break down the Six Types of Working Genius and show how aligning your strengths can transform your career, your team, and your fulfillment at work. Patrick Lencioni is a bestselling author and organizational health expert, and the founder of The Table Group. Named by Fortune as “one of the new gurus you should know,” Patrick helps leaders build healthy, high-performing organizations grounded in trust and clarity. In this episode, Ilana and Patrick will discuss: (00:00) Introduction  (02:46) Patrick’s Early Life and Career Beginnings (08:31) Joining Oracle and Pitching Ideas (12:36) Turning Down a Job Offer from Steve Jobs (15:40) The Decision to Start the Table Group (20:18) Navigating the Hard Moments in Entrepreneurship (23:30) Short Attention Spans as a Bestselling Author  (28:06) The Birth and Impact of Working Genius  (34:48) Applying Working Genius to Career Choices (41:05) W-I-D-G-E-T: The Six Types of Working Genius (54:57) Healing Childhood Scars and Understanding Self (59:15) Q&A: The Keys to Building a Portfolio Career Patrick Lencioni is a bestselling author and organizational health expert, and the founder of The Table Group. He has written 13 books with over 7 million copies sold worldwide, including The Five Dysfunctions of a Team. He is also the creator of The 6 Types of Working Genius, a framework that helps teams identify the work that energizes them and improves performance. Named by Fortune as “one of the new gurus you should know,” Patrick helps leaders build healthy, high-performing organizations grounded in trust and clarity. Connect with Patrick: Patrick’s LinkedIn: linkedin.com/in/patrick-lencioni-orghealth Patrick’s Instagram: instagram.com/patricklencioniofficial Resources Mentioned: Patrick’s Books:  The Five Temptations of a CEO: https://www.amazon.com/dp/B0062OAEWM The Five Dysfunctions of a Team: https://www.amazon.com/dp/0787960756 The 6 Types of Working Genius: A Better Way to Understand Your Gifts, Your Frustrations, and Your Team: https://www.amazon.com/dp/B09XGPCM36 Working Genius Website: https://www.workinggenius.com Take the Working Genius Assessment: https://www.workinggenius.com/about/assessment  Leap Academy: LeapCon is the #1 Conference for Reinvention, Leadership & Career — a powerful 3‑day experience designed to help you unlock what’s next in your career and life. 📍 San Jose, CA 📅 Feb 26–28, 2025 If you’re ready to step into clarity, confidence, and bold action, this is your moment. 👉 Grab your ticket before doors close at leapacademy.com/leapcon

Before Damian Maldonado was negotiating billion-dollar valuations or building businesses across Puerto Rico, he was a kid living in poverty and sharing bunk beds in a homeless shelter with his brothers. But those early years didn’t break him. They led him to become the co-founder and CEO of American Financing, one of the largest privately held mortgage companies in the U.S. In this episode, Damian joins Ilana to share how growing up in poverty shaped his relationship with risk, money, and resilience, and what it really takes to bootstrap a company through market crashes, massive layoffs, and billion-dollar decisions. Damian Maldonado is a serial entrepreneur, investor, and co-founder and CEO of American Financing, one of the largest privately held mortgage companies in the U.S., which he helped grow from a small startup into a national brand. In this episode, Ilana and Damian will discuss: (00:00) Introduction  (02:57) Growing Up in Poverty and a Homeless Shelter (08:42) Key Lessons from Early Jobs (11:42) Pitching to a CEO at 21 Without Fear of Rejection (14:38) Damian’s Journey into the Mortgage Industry (19:14) Starting America Financing With No Safety Net (22:30) Leading Through Layoffs and Downturns (27:07) Why He Turned Down a Billion-Dollar Offer (30:57) Leadership Lessons from Richard Branson (34:25) Building a Portfolio Career with Adventure (42:53) Q&A: Crafting a Response to ‘Tell Me About Yourself’ Damian Maldonado is the co-founder and CEO of American Financing, one of the largest privately held mortgage companies in the U.S., which he helped grow from a small startup into a national brand. He also co-founded American Home Agents and has expanded his business interests into hospitality and lifestyle ventures in Puerto Rico, including a boutique beachfront hotel, restaurant, and kiteboarding school, creating jobs and adding value to the local community. Connect with Damian: Damian’s Website: https://damianmaldonado.com  Damian’s Instagram: instagram.com/damiankitepr  Resources Mentioned: American Financing Website: americanfinancing.net  Numero Uno Website: numerounopr.com Awaken the Giant Within by Tony Robbins: https://www.amazon.com/Awaken-Giant-Within-Immediate-Emotional/dp/0671791540 Think And Grow Rich by Napoleon Hill: https://www.amazon.com/Think-Grow-Rich-Landmark-Bestseller/dp/1585424331  Rich Dad Poor Dad by Robert Kiyosaki: https://www.amazon.com/Rich-Dad-Poor-Teach-Middle/dp/1612681131/  The 4-Hour Workweek: Escape 9-5, Live Anywhere, and Join the New Rich by Tim Ferriss: https://www.amazon.com/4-Hour-Workweek-Escape-Live-Anywhere/dp/0307465357 Leap Academy: LeapCon is the #1 Conference for Reinvention, Leadership & Career — a powerful 3‑day experience designed to help you unlock what’s next in your career and life. 📍 San Jose, CA 📅 Feb 26–28, 2025 If you’re ready to step into clarity, confidence, and bold action, this is your moment. 👉 Grab your ticket before doors close at leapacademy.com/leapcon

After two decades as a pastor making $50K a year, Eileen Wilder woke up to a terrifying truth: she was meant for more. Her body was breaking down. Her joy was gone. Then she walked into a conference that changed everything. Within 18 months, she went from broke and overwhelmed to generating seven figures as a coach. In this episode, Eileen joins Ilana to share how she pivoted from ministry to million-dollar offers, how immersive events like LeapCon can fast-track your growth, and the powerful exercise that will help you package your expertise and charge your worth. Eileen Wilder is a bestselling author and high-ticket business coach helping individuals package their expertise into profitable high-ticket offers. As a keynote speaker, she has shared stages with leaders like Tony Robbins, Russell Brunson, Ed Mylett, and Bishop T.D. Jakes, empowering others to build wealth, freedom, and impact. In this episode, Ilana and Eileen will discuss: (00:00) Introduction  (04:06) Eileen's Journey from Pastor to Entrepreneur (07:35) Discovering Life Coaching at a Conference (14:01) The Life-Changing Impact of Events (16:17) How a “Janky” Video Took Her from $297 to $250K (18:35) Losing Her Mother and Finding Financial Power (24:00) From $50K Salary to Seven Figures in 18 Months (26:57) Practical Exercise for Commanding Premium Prices (35:22) $1 Million in a Day: The Power of High-Ticket Offers (40:12) Mastering the Art of Public Speaking (42:39) LeapCon 2026: A Transformational Experience (44:53) The Key to Pricing Your Services Eileen Wilder is a bestselling author, business growth consultant, and keynote speaker who helps entrepreneurs and creators turn their expertise into profitable high-ticket offers and virtual events. A former pastor of 20+ years, she transformed her fear of public speaking into a seven-figure speaking career and is now known as “The Queen of Stages.” Eileen has shared stages with leaders like Tony Robbins, Russell Brunson, Ed Mylett, and Bishop T.D. Jakes, empowering others to build wealth, freedom, and impact. Connect with Eileen: Eileen’s Website: https://eileenwilder.com Eileen’s Instagram: instagram.com/eileenwild Resources Mentioned: Eileen’s Book, Financially Free: How To Create Your Own Economy No Matter What's Going On In the World Around You: https://www.financiallyfreebook.com/ff-1 Eileen’s Book, The Pivot Plan: End Emotional Exhaustion, Overcome Depression, Discover Your Strongest Life: https://www.amazon.com/dp/1943127719 The Body Keeps the Score: Brain, Mind, and Body in the Healing of Trauma by Bessel van der Kolk, M.D.: https://www.amazon.com/dp/0143127748 Leap Academy: LeapCon is the #1 Conference for Reinvention, Leadership & Career — a powerful 3‑day experience designed to help you unlock what’s next in your career and life. 📍 San Jose, CA 📅 Feb 26–28, 2025 If you’re ready to step into clarity, confidence, and bold action, this is your moment. 👉 Grab your ticket before doors close at leapacademy.com/leapcon

Stephanie Mehta never chased the CEO title. She chased the story. She built her career in some of the toughest newsrooms in the world, including The Wall Street Journal, Bloomberg, Fortune, and Vanity Fair, where credibility is earned line by line. Those same instincts eventually carried her beyond the newsroom and into leadership, leading her to the CEO seat at Mansueto Ventures, the company behind Fast Company and Inc. In this episode, Stephanie joins Ilana to share her journey from journalism student to leading iconic media brands, the challenges of stepping into executive leadership, and how to prioritize as a leader in an ever-changing industry. Stephanie Mehta is a journalist, business executive, and CEO and chief content officer of Mansueto Ventures, the media company that publishes Fast Company and Inc. magazines. She has held senior editorial roles at Fortune, Bloomberg, and Vanity Fair. In this episode, Ilana and Stephanie will discuss: (00:00) Introduction  (02:52) Stephanie's Early Career in Journalism (05:16) Challenges and Growth at the Wall Street Journal (10:35) Transitioning to Fortune Magazine (17:38) Reflecting on 14 Years at Fortune  (22:42) Taking a Break and Exploring New Opportunities (27:18) Becoming the CEO of Fast Company (35:37) How to Get Stories Published in Major Media (39:11) Rising Above the Noise in Business (42:01) How Stephanie Prioritizes as a CEO (45:26) How Careers are Changing in the Modern Era (49:31) The Impact of Immigrant Upbringing Stephanie Mehta is a journalist, business executive, and CEO and chief content officer of Mansueto Ventures, the media company that publishes Fast Company and Inc. magazines. She previously served as Editor-in-Chief of Fast Company and held senior editorial roles at Fortune, Bloomberg, and Vanity Fair. Stephanie is also the author of the Modern CEO newsletter, where she explores leadership, careers, and the future of work. Connect with Stephanie: Stephanie’s LinkedIn: linkedin.com/in/stephanie-mehta-media-ceo  Resources Mentioned: Modern CEO Newsletter: https://www.fastcompany.com/section/modern-ceo  Leap Academy: LeapCon is the #1 Conference for Reinvention, Leadership & Career — a powerful 3‑day experience designed to help you unlock what’s next in your career and life. 📍 San Jose, CA 📅 Feb 26–28, 2025 If you’re ready to step into clarity, confidence, and bold action, this is your moment. 👉 Grab your ticket before doors close at leapacademy.com/leapcon

At just ten years old, Kim Storin was writing letters to CEOs, asking for donations and clearly outlining why her cause mattered. That instinct to connect people, solve problems, and step forward without permission never left her. Years later, as Chief Marketing Officer at Zoom, that same mindset shapes how she leads one of the most trusted brands in modern work. In this episode, Kim joins Ilana to share Zoom’s evolution from a single, iconic product into a broad portfolio of solutions, and what it takes to reinvent a brand the world already relies on without losing trust. Kim Storin is the Chief Marketing Officer at Zoom and a seasoned marketing leader with experience spanning consulting, enterprise transformation, and global brand leadership. She has held senior leadership roles at companies including Dell, IBM, and Deloitte. In this episode, Ilana and Kim will discuss: (00:00) Introduction  (03:44) Making Bold Requests at Age Ten (06:28) Problem Solving as Her Career Compass (14:53) Receiving the Hardest Feedback of Her Career (17:40) Athletic Pursuits and Influence on Leadership (20:50) Joining Zoom and Leading Its Transformation (23:38) How Zoom Reinvented and Repositioned Itself (27:12) The New Era of Marketing and How to Stay Ahead (30:33) AI as a Teammate, Not a Threat (35:08) Redefining Success Beyond Metrics and Titles (38:30) The Right Way to Build a Portfolio Career Kim Storin is the Chief Marketing Officer at Zoom, where she leads global marketing strategy, brand, and growth as the company evolves into a broader communications platform. Prior to Zoom, Kim held senior leadership roles at companies including Dell, IBM, Deloitte, and multiple high-growth organizations. She is also a lifelong athlete, marathon runner, and is passionate about building the next generation of market leaders. Connect with Kim: Kim’s LinkedIn: linkedin.com/in/kimberlystorin  Resources Mentioned: Zoom: https://www.zoom.com  Leap Academy: LeapCon is the #1 Conference for Reinvention, Leadership & Career — a powerful 3‑day experience designed to help you unlock what’s next in your career and life. 📍 San Jose, CA 📅 Feb 26–28, 2025 If you’re ready to step into clarity, confidence, and bold action, this is your moment. 👉 Grab your ticket before doors close at leapacademy.com/leapcon

Long before ChatGPT became a household name, Zack Kass was walking into boardrooms as Head of Go-To-Market at OpenAI, introducing executives to a technology they barely understood or cared about. Then one simple shift changed everything. Put intelligence into a familiar interface, remove friction, and suddenly the future arrived. In this episode, Zack joins Ilana to unpack what truly drove ChatGPT’s explosive growth, confront the biggest fears leaders have about AI, and explore what the future of work will demand from humans next. Zack Kass is a global AI advisor, keynote speaker, and former Head of Go-To-Market at OpenAI, where he helped bring some of the world’s most transformative AI technologies to market. In this episode, Ilana and Zack will discuss: (00:00) Introduction  (02:59) Zack’s Journey to OpenAI (04:46) Understanding Modern AI and Its Evolution (08:03) The Breakthrough of ChatGPT and Its Impact (17:42) Transitioning from OpenAI to New Beginnings (21:21) Challenging Common Misconceptions About AI (28:32) Adaptability in a Rapidly Changing World (34:54) Lessons from Top Innovators (38:15) The Future of Work and Purpose in the Age of AI Zack Kass is a global AI advisor, futurist, speaker, and former Head of Go-To-Market at OpenAI, where he helped bring some of the world’s most transformative AI technologies to market. He now advises global leaders and organizations on how artificial intelligence will reshape work, leadership, and human potential, turning complex ideas into clear, practical insight for the future. His book, The Next Renaissance, offers an optimistic vision of how AI will shape our future. Connect with Zack: Zack’s Website: zackkass.com  Zack’s LinkedIn: linkedin.com/in/zackkass  Resources Mentioned: Zack’s Book, The Next Renaissance: AI and the Expansion of Human Potential: https://www.amazon.com/dp/1394381085  Leap Academy: LeapCon is the #1 Conference for Reinvention, Leadership & Career — a powerful 3‑day experience designed to help you unlock what’s next in your career and life. 📍 San Jose, CA 📅 Feb 26–28, 2025 If you’re ready to step into clarity, confidence, and bold action, this is your moment.👉 Grab your ticket before doors close at leapacademy.com/leapcon

At just 10 years old, Mick Hunt made a promise that would shape the rest of his life. Growing up in a home marked by abuse, Mick stepped into a role no child should ever have to carry. He became the protector, the emotional anchor, and the one who believed he could change his family’s future. That moment didn’t just force him to grow up fast. It forged a lifelong mission around leadership, accountability, and purpose. In this episode, Mick joins Ilana to share the raw story behind that promise, how it shaped his drive to build businesses and high-performing teams, and why leadership starts with something deeper than your “why.”  Mick Hunt is a leadership coach, entrepreneur, and speaker known for helping ambitious individuals unlock their full potential. He works with leaders who want to grow their influence, scale their thinking, and build companies and teams that people genuinely believe in and follow. In this episode, Ilana and Mick will discuss: (00:00) Introduction  (02:14) How a Traumatic Childhood Built Mick’s Drive (08:48) The Childhood Promise That Defined His Life (10:26) Entrepreneurial Beginnings and Challenges (16:36) His Passion for Building High-Performing Teams (17:14) Why Your ‘Because’ Beats Your ‘Why’ (21:50) The “What If I Fail” Mindset (27:46) Understanding The MICK Factor (30:42) Mick’s Book: How to Be a Good Leader (36:09) The Future of Leadership and Staying Relevant (38:53) The Value of Mentorship (42:28) Daily Practices for Success Mick Hunt is a USA Today bestselling author, international speaker, and leadership expert known for his impact in modern leadership and emotional intelligence. He is the host of the highly rated Mick Unplugged podcast and the author of How to Be a Good Leader When You’ve Never Had One, a modern leadership guide with hands-on insights and actionable frameworks to help you lead with transparency, resilience, and influence. Connect with Mick: Mick’s Website: https://mickhuntofficial.com/  Mick’s LinkedIn: linkedin.com/in/mickhunt  Resources Mentioned: Mick’s Book, How to Be a Good Leader When You've Never had One: The Blueprint for Modern Leadership: http://amazon.com/Good-Leader-When-Youve-Never/dp/1394357958  Mick’s Podcast, Mick Unplugged: https://podcasts.apple.com/us/podcast/mick-unplugged/id1731755953  Leap Academy: LeapCon is the #1 Conference for Reinvention, Leadership & Career — a powerful 3‑day experience designed to help you unlock what’s next in your career and life. 📍 San Jose, CA 📅 Feb 26–28, 2025 If you’re ready to step into clarity, confidence, and bold action, this is your moment. 👉 Grab your ticket before doors close at leapacademy.com/leapcon

As a young mom, primary breadwinner, and full-time professional, Sheila Lirio Marcelo understood the relentless struggle of balancing work and family. The constant search for reliable care left her feeling overwhelmed. Instead of accepting this as the norm, Sheila took matters into her own hands and created Care.com, a platform that has eased the caregiving burden for millions of families worldwide. In this episode, Sheila joins Ilana to discuss her journey of balancing motherhood and a high-powered career, the challenges of building Care.com, and her exciting new venture, Ohai.ai, an AI-powered household assistant. Sheila Lirio Marcelo is the founder of Care.com, an online marketplace for families to find childcare, senior care, pet care, and more. She is also the founder of Ohai, an AI-powered household assistant designed to help reduce the mental load of running a home. In this episode, Ilana and Sheila will discuss: (00:00) Introduction  (02:12) Sheila's Childhood and Family Influence (08:04) Struggling to Balance Motherhood and a Career (11:20) Her Journey Into Entrepreneurship and Care.com (14:57) Why Generalists Are Key in Business (18:12) Care.com’s Success: The Power of Testing Ideas (23:34) Building a Two-Sided Marketplace and Gaining Trust (29:44) The Decision to Go Public With Care.com (31:39) Managing Decision-Making and Stress as a Leader (33:38) Reinventing With Ohai AI for Families (40:01) Her Approach to Mental Clarity and Calm (44:44) Embracing Challenges and Personal Growth Sheila Lirio Marcelo is the founder and former CEO of Care.com, the world’s largest online caregiving marketplace, which went public in 2014 and was acquired for $500 million in 2020. After years of leading Care.com through exponential growth, Sheila transitioned into a new chapter, founding Ohai, an AI-powered household assistant designed to help manage various household activities. She is deeply committed to creating solutions that simplify life, improve well-being, and empower families. Connect with Sheila: Sheila’s LinkedIn: linkedin.com/in/sheilamarcelo  Sheila’s Instagram: instagram.com/sheilaliriomarcelo  Resources Mentioned: Care.com’s Website: https://www.care.com/  Ohai’s Website: https://www.ohai.ai/  Leap Academy: LeapCon is the #1 Conference for Reinvention, Leadership & Career — a powerful 3‑day experience designed to help you unlock what’s next in your career and life. 📍 San Jose, CA 📅 Feb 26–28, 2025 If you’re ready to step into clarity, confidence, and bold action, this is your moment.👉 Grab your ticket before doors close at leapacademy.com/leapcon

Robin Arzón’s leap from lawyer to fitness powerhouse wasn’t just a career shift; it was a radical reinvention. After surviving a traumatic hostage situation, she turned to running as a way to heal, reclaim control, and push past limits. What began as a coping mechanism evolved into a mission: to complete ultra-marathons, build a global fitness brand, and inspire others as a lead instructor at Peloton. Even after being diagnosed with Type 1 diabetes, Robin refused to be defined by anything but her unstoppable drive. In this episode, Robin opens up to Ilana about how she transformed trauma into purpose, made a bold leap into fitness, and became a global force in wellness with Peloton. Robin Arzón is a fitness expert, former lawyer, author, and motivational speaker. She is best known as an instructor at Peloton, where she inspires millions with her high-energy cycling and strength classes. In this episode, Ilana and Robin will discuss: (00:00) Introduction  (01:37) Surviving a Hostage Situation (05:47) Discovering Running as a Healing Tool (08:51) From Casual Runs to Ultra-Marathons (11:29) Transitioning from a Law Career to Fitness (13:19) Landing a Job at Peloton with a Cold Email (15:49) Living and Thriving with Type 1 Diabetes (18:34) Juggling a Career, Motherhood, and Life’s Demands (21:39) Pushing Past Her Limits at the StriveX Challenge (24:54) Building a Global Brand Through Consistency (28:18) Swagger Society and Upcoming Cookbook (31:47) Learning to Trust Life’s Redirections Robin Arzón is a fitness expert, former lawyer, author, and motivational speaker. She is best known for inspiring millions with her high-energy cycling and strength classes as an instructor at Peloton, where she is also the Vice President of Fitness Programming. Robin is also a New York Times bestselling author of Shut Up and Run and Strong Mama, sharing her personal stories and fitness philosophies. She advocates for mental and physical strength, promoting the power of movement and mindset to achieve personal transformation. Connect with Robin: Robin’s Website: https://www.robinarzon.com/  Robin’s Instagram: https://www.instagram.com/robinnyc  Resources Mentioned: Robin’s Books: Shut Up and Run: How to Get Up, Lace Up, and Sweat with Swagger: https://www.amazon.com/dp/0062445685  Eat to Hustle: 75 High-Protein Plant-Based Recipes (A Cookbook): https://www.amazon.com/dp/031659427X Robin’s Journal, Welcome, Hustler: An Empowerment Journal: https://www.amazon.com/dp/1454946342 Leap Academy: LeapCon is the #1 Conference for Reinvention, Leadership & Career — a powerful 3‑day experience designed to help you unlock what’s next in your career and life. 📍 San Jose, CA 📅 Feb 26–28, 2025 If you’re ready to step into clarity, confidence, and bold action, this is your moment. 👉 Grab your ticket before doors close at leapacademy.com/leapcon

Russell Brunson failed more times in his early 20s than most founders do in a lifetime. From broken funnels to failed product launches, he turned every setback into a lesson, refining his craft while navigating near bankruptcy, legal threats, and even moments where he feared jail time. Those hard years became the foundation that ultimately led him to co-found ClickFunnels, one of the fastest-growing bootstrapped tech companies in the world. In this episode, Russell joins Ilana to share how he bounced back from his toughest moments, offering powerful lessons in resilience, leadership, and authentic relationships. Russell Brunson is a serial entrepreneur, bestselling author, and digital marketing expert. He is widely recognized as the co-founder of ClickFunnels, a leading marketing software company that helps businesses worldwide boost conversions and drive sales. In this episode, Ilana and Russell will discuss: (00:00) Introduction  (02:04) The Infomercial That Led Him to Entrepreneurship (05:52) The Influence of Wrestling on His Business Drive (08:18) College Days and the Potato Gun Venture (10:15) The Rollercoaster Journey to His First Million (14:48) Key Lessons from His Toughest Year (21:50) The Birth of ClickFunnels and Its Challenges (34:41) Gaining Lifelong Mentorship from Tony Robbins (37:55) Dream 100 Strategy: The Power of Relationships (43:08) Why Vulnerability Can Lead to Unlikely Success (47:14) Tips for Building a Winning Team (50:17) Turning Your Pain into an Asset Russell Brunson is a serial entrepreneur, bestselling author, and digital marketing expert. He is widely recognized as the co-founder of ClickFunnels, a leading marketing software company that helps businesses worldwide boost conversions and drive sales. Over the past 19 years, he has built a community of over a million entrepreneurs and authored New York Times bestsellers, including DotCom Secrets and Expert Secrets.  Connect with Russell: Russell’s Website: www.russellbrunson.com  Russell’s LinkedIn: linkedin.com/in/russellbrunson Russell’s Instagram: www.instagram.com/russellbrunson  Resources Mentioned: Russell’s YouTube: youtube.com/@russellbrunson The 12 Month Millionaire Droplets: Vincent James's Unmissable Revelations by Vincent James: https://www.amazon.com/dp/B0CXJGPXNN  Dig Your Well Before You're Thirsty: The Only Networking Book You'll Ever Need by Harvey Mackay: https://www.amazon.com/dp/0385485468  Leap Academy: LeapCon is the #1 Conference for Reinvention, Leadership & Career — a powerful 3‑day experience designed to help you unlock what’s next in your career and life. 📍 San Jose, CA 📅 Feb 26–28, 2025 If you’re ready to step into clarity, confidence, and bold action, this is your moment. 👉 Grab your ticket before doors close at leapacademy.com/leapcon

When Kevin Kelly dropped out of college in the 1970s, it was almost unheard of. Instead of following a traditional path, he chose a life driven by curiosity, freedom, and hands-on learning. That decision led him to hitchhike across Asia, document disappearing cultures, and eventually immerse himself in the early internet. Years later, he co-founded Wired, a magazine that soon became the voice of emerging technology and culture. In this episode, Kevin joins Ilana to share how Wired went from fighting for shelf space to redefining what a tech publication could be. He also explains his unique relationship with time, why he tracks the days he has left, and how creators today can thrive with just 1,000 true fans. Kevin Kelly is a writer, photographer, and Senior Maverick at Wired, an award-winning magazine he co-founded in 1993. He is also a former editor and publisher of the Whole Earth Review and the author of multiple bestselling books about the future of technology. In this episode, Ilana and Kevin will discuss: (00:00) Introduction  (02:14) Choosing an Unconventional Path to Success (06:34) The Start of His Adventures in Asia (10:54) Getting into Writing and Publishing (14:17) Creating One of the First Hacker Conferences (20:18) The Grit Behind Wired Magazine’s Success (30:37) The Dot-Com Bust and Why Wired was Split (34:17) The Origin and Power of “1,000 True Fans” (41:18) How a Near-Death Experience Transformed Kevin (47:10) About His Latest Book, Colors of Asia Kevin Kelly is a writer, photographer, and co-founder of the award-winning Wired magazine, and a former editor and publisher of the Whole Earth Review. He is the co-chair of The Long Now Foundation, which champions long-term thinking, and the creator of the Cool Tools website, which has reviewed tools daily for over 20 years. Kevin is also the author of multiple bestselling books on the future of technology, and his latest book, Colors of Asia, captures the culture of all 35 Asian countries through vivid photography. Connect with Kevin: Kevin’s Website: https://kk.org  Kevin’s Twitter: https://x.com/kevin2kelly  Resources Mentioned: Kevin’s Book, Colors of Asia: A Visual Journey: https://www.amazon.com/Colors-Asia-Journey-Kevin-Kelly/dp/B0FGJ18PG5  Leaves of Grass: The Original 1855 Edition by Walt Whitman: https://www.amazon.com/dp/1449505716  Leap Academy: LeapCon is the #1 Conference for Reinvention, Leadership & Career — a powerful 3‑day experience designed to help you unlock what’s next in your career and life. 📍 San Jose, CA 📅 Feb 26–28, 2025 If you’re ready to step into clarity, confidence, and bold action, this is your moment. 👉 Grab your ticket before doors close at leapacademy.com/leapcon

Jordan Ritter didn’t grow up surrounded by tech; he grew up on a farm, tinkering with computers in total isolation. But that early curiosity led him to co-found Napster, the file-sharing service that transformed music distribution. As millions of users flooded the platform, Jordan was instrumental in keeping it alive through sleepless nights and nonstop chaos. The success was massive, the failure was brutal, but the lessons shaped everything he did next. In this episode, Jordan reveals to Ilana the real story behind Napster, the personal sacrifices of innovation, and the mindset required to build something that leaves a legacy. Jordan Ritter is a serial entrepreneur, software architect, and angel investor, recognized for his work at Napster, the file-sharing service that reshaped music distribution and digital technology. Since then, he has launched and advised multiple startups in the tech industry. In this episode, Ilana and Jordan will discuss: (00:00) Introduction  (02:08) Growing Up on a Farm and Discovering Tech (06:40) His Journey into Hacking and Computer Security (12:37) Joining Napster and Disrupting the Music Industry (17:55) Experiencing Napster’s Highs and Crushing Lows (32:20) Why Jordan Decided to Leave Napster (40:16) Reinventing and Building Companies with Value (46:03) The Importance of Culture in Startups (52:19) Navigating Interviews and Culture Alignment (55:18) The Challenges of Starting a Business (1:03:30) Lessons Learned and Giving Back Jordan Ritter is a serial entrepreneur, software architect, angel investor, and co-founder of Napster, where he helped scale the platform to 60 million users. A four-time founder, he has built 20+ large-scale commercial and open-source products across 12 languages, developing systems used by millions. At Cloudmark, Servio, and Augment AI, Jordan built intuitive, scalable, and reliable platforms, and he now advises CoPilotKit on product strategy. Connect with Jordan: Jordan’s  LinkedIn: linkedin.com/in/jordanritter  Leap Academy: LeapCon is the #1 Conference for Reinvention, Leadership & Career — a powerful 3‑day experience designed to help you unlock what’s next in your career and life. 📍 San Jose, CA 📅 Feb 26–28, 2025 If you’re ready to step into clarity, confidence, and bold action, this is your moment. 👉 Grab your ticket before doors close at leapacademy.com/leapcon

Ilana Golan has reinvented herself more times than most people switch job titles. From becoming one of the first women to train F-16 pilots in the Israeli Air Force, to engineering, to product, to Silicon Valley executive, to investor, to founder, she’s rebuilt her identity again and again in industries that weren’t built for people like her. In this episode of the Remarkable People podcast, Guy Kawasaki pulls back the curtain on what it really took for Ilana to leap across careers, break barriers, and build a system that helps thousands do the same. She breaks down the concept of reinvention and what it really takes to leap again and again. Ilana Golan is a former F-16 flight instructor turned Silicon Valley tech executive and investor. As the founder of Leap Academy and host of the LEAP Academy podcast, she teaches professionals how to fast-track opportunities, build portfolio careers, and unlock financial freedom. In this episode, Guy and Ilana will discuss: (00:00) Introduction  (02:20) Breaking Barriers in the Israeli Air Force (06:07) What Reinvention Really Means Today (10:40) The Core Steps to Reinventing Your Career (12:59) Reinventing When Systems are Against You (15:16) Advice for Women on Breaking Glass Ceilings (19:58) The Core Signals That You Need Reinvention (21:52) Case Studies: Reinventing Public Figures (29:37) The Role of Timing in Reinvention (33:41) The Power of Building a Personal Brand Ilana Golan is a serial entrepreneur, board director, global keynote speaker, and investor in over 100 companies. As the founder of Leap Academy and host of the LEAP Academy podcast, she teaches professionals how to fast-track opportunities, build portfolio careers, and unlock financial freedom. Ilana has been recognized as a Silicon Valley Woman of Influence, a Top 40 Woman to Watch, and a CEO World Award winner. Under her leadership, LEAP Academy was named one of Inc. 500’s Fastest Growing Companies. Connect with Ilana:  Ilana’s Website: leapacademy.com  Ilana’s LinkedIn: linkedin.com/in/ilanagolan  Resources Mentioned: Guy’s Podcast, Remarkable People: https://podcasts.apple.com/us/podcast/guy-kawasakis-remarkable-people/id1483081827  LEAP E97 with Guy Kawasaki: https://podcasts.apple.com/us/podcast/guy-kawasaki-the-tech-evangelist-who-built-apple/id1701718200?i=1000703853865  Leap Academy: LeapCon is the #1 Conference for Reinvention, Leadership & Career — a powerful 3‑day experience designed to help you unlock what’s next in your career and life. 📍 San Jose, CA 📅 Feb 26–28, 2025 If you’re ready to step into clarity, confidence, and bold action, this is your moment. 👉 Grab your ticket before doors close at leapacademy.com/leapcon

When Vick Tipnes launched Blackstone Medical Services, it was the worst possible moment: newly divorced, broke, and with two young kids. For years, he operated in survival mode, managing a business that lost money month after month. Instead of giving up, Vick's resilience became the driving force that turned a tiny, run-down $500 office into one of the fastest-growing sleep testing companies in the U.S. In this episode, Vick opens up to Ilana about the sacrifices, powerful mindset shifts, and relentless drive that transformed his company from the brink of collapse to industry leadership. Vick Tipnes is the founder and CEO of Blackstone Medical Services, a leading provider of home sleep testing. Under his leadership, the company has earned recognition five times on the Inc. 5000 list. In this episode, Ilana and Vick will discuss: (00:00) Introduction  (02:03) Growing Up with an Entrepreneurial Father (04:35) Leaving College To Chase Entrepreneurship (06:32) Losing Both Parents and Transitioning to Healthcare (10:45) Exiting the Radiology Business with Almost Nothing (15:34) Being Divorced, Broke, and Starting All Over (19:30) Building Blackstone Medical Services from Scratch (23:27) Achieving Success After Years of Losing Money (31:27) How Vick Manages His Career Without Burning Out (33:07) Investing in Identity and Personal Growth (36:06) Addressing Sleep Issues and Health Solutions (38:18) The Power of Tenacity and Refusing To Quit Vick Tipnes is a self-made entrepreneur, author, and mentor, best known as the founder and CEO of Blackstone Medical Services, a leading provider of home sleep testing. Under his leadership, the company has earned recognition five times on the Inc. 5000 list. Vick is also the founder of Tipnes Capital and Tipnes Health and the author of Did You Sell Your Soul?, where he shares insights on overcoming obstacles, staying focused, and achieving life goals. Connect with Vick: Vick’s Website: vicktipnes.com  Vick’s LinkedIn: linkedin.com/in/vicktipnes  Vick’s Instagram: instagram.com/vicktipnes  Resources Mentioned: Vick’s Book, Did You Sell Your Soul?: It's Never Too Late to Change Your Story: https://www.amazon.com/dp/1662903766  Leap Academy:LeapCon is the #1 Conference for Reinvention, Leadership & Career — a powerful 3‑day experience designed to help you unlock what’s next in your career and life. 📍 San Jose, CA 📅 Feb 26–28, 2025 If you’re ready to step into clarity, confidence, and bold action, this is your moment. 👉 Grab your ticket before doors close at leapacademy.com/leapcon

John Demsey didn’t become a powerhouse in the beauty industry by a mere stroke of luck; he built that influence on retail floors, taking on scrappy roles while learning the business in ways no MBA could ever teach. This helped him scale MAC Cosmetics into a global cultural movement, shape some of the most iconic beauty brands of our time, and ultimately rise to Group President of Estée Lauder Companies. In this episode, John joins Ilana to reveal how to build a career from the ground up, reinvent after setbacks, and lead with the kind of creativity that transforms industries. John D. Demsey is the former Executive Group President of Estée Lauder Companies, where he helped build and scale iconic brands like MAC Cosmetics, Tom Ford Beauty, and more into a multi-billion-dollar global powerhouse. In this episode, Ilana and John will discuss: (00:00) Introduction  (02:38) His Early Exposure to Fashion and Design (06:36) Choosing Stanford Over the Ivy Leagues (09:26) Getting Started in the Beauty Industry (15:35) The Power of Learning Every Role in the Business (24:11) Joining Estee Lauder and Moving to LA (28:42) Building MAC Cosmetics into a Global Powerhouse  (36:02) How John Landed Celebrity Endorsements (42:56) Working with Tom Ford and Revolutionizing Fragrances (52:58) Navigating Controversy and Reinventing Himself (1:01:17) His New Ventures and Future Plans John D. Demsey is the former Executive Group President of Estée Lauder Companies, where he helped build and scale iconic brands like MAC Cosmetics, Tom Ford Beauty, Smashbox, Clinique, and Jo Malone London. Over his 30-year career at Estée Lauder, he played a pivotal role in expanding the company into a multi-billion-dollar business across both established and emerging markets. He is the author of Behind the Blue Door, a visual memoir capturing his bold lifestyle, vibrant career, and personal journey. Connect with John: John’s Instagram: instagram.com/jdemsey  John’s LinkedIn: linkedin.com/in/john-demsey  Resources Mentioned: John’s Book, Behind the Blue Door: A Maximalist Mantra: https://www.amazon.com/dp/0865654344  LEAP E57 with Dan Ariely: https://podcasts.apple.com/us/podcast/surviving-lies-rumors-and-digital-hate-dan-arielys/id1701718200?i=1000678512628  Leap Academy: Ready to make the LEAP in your career? There is a NEW WAY for professionals to fast-track their careers and leap to bigger opportunities.  Check out our free training today at https://bit.ly/leap--free-training

When 19-year-old Anna-Sophie Hartvigsen walked into a bank hoping to secure a loan to buy a property, she was denied on the spot. That “no” pushed her into investing and ultimately led her to co-found Female Invest, a global platform empowering women to take control of their financial futures. In this episode, Anna joins Ilana for a raw, honest conversation about the reality of fundraising as a female founder, from enduring 107 rejections to breaking global crowdfunding records and facing the backlash that followed. She shares what it truly takes to scale a mission-driven company, rise above bias, and empower women financially on a global scale. Anna-Sophie Hartvigsen is an entrepreneur, investor, and co-founder of Female Invest, a financial education platform that has empowered women across more than 100 countries. She’s a leading voice in closing the financial gender gap through education, representation, and access. In this episode, Ilana and Anna will discuss: (00:00) Introduction  (02:51) Her Early Interest in Finance and Investing (05:15) Turning Down McKinsey to Build Female Invest (09:10) Challenges and Misconceptions in Entrepreneurship (11:07) Launching a Facebook Group That Grew Like Wildfire (13:35) Why Money for Women Is Deeply Political (15:29) Bootstrapping to Success After Near Bankruptcy (22:14) Anna’s Y Combinator Experience (25:02) The Reality of Fundraising as a Female Founder (30:35) Raising $24M After 107 Rejections (34:01) Facing Backlash, Anxiety, and Hate (38:08) The Biggest Financial Mistakes Women Make (44:12) Lessons and Advice for Founders Anna-Sophie Hartvigsen is a Danish entrepreneur, investor, and co-founder of Female Invest, a financial education platform that has empowered women across more than 100 countries. A Forbes 30 Under 30 recipient, she helped bootstrap Female Invest from a small Facebook group into one of the most engaged financial communities in the world. Anna is also the bestselling author of Girls Just Wanna Have Funds and a leading voice in closing the financial gender gap through education, representation, and access. Connect with Anna: Anna’s LinkedIn: linkedin.com/in/anna-hartvigsen-46352611a  Anna’s Instagram: instagram.com/anna.hartvigsen  Resources Mentioned: Female Invest: https://www.femaleinvest.com  Anna’s Book, Girls Just Wanna Have Funds: A Feminist's Guide to Investing: https://www.amazon.com/dp/0744077303  Leap Academy: Ready to make the LEAP in your career? There is a NEW WAY for professionals to fast-track their careers and leap to bigger opportunities.  Check out our free training today at https://bit.ly/leap--free-training

Brian Tracy was fired from washing dishes, cars, and floors, and began to believe that “washing things” might be his destiny. But when he learned that the top 20% in any field earn 80% of the money, he committed to becoming one of them. That decision transformed him from a broke high school dropout into a global authority on success, speaking to millions across 84 countries and writing more than 80 bestselling books. In this episode, Brian shares the principles and habits that turned his life around, from the one skill that made him ten times richer to the $1.50 notebook that can make you a millionaire. He breaks down the secret to wealth and how to stay laser-focused on your biggest goals. Brian Tracy is the Chairman and CEO of Brian Tracy International. He is a prolific businessman, renowned speaker, and bestselling author of over 80 books, including his latest, The 32 Unbreakable Laws of Money and Success. In this episode, Ilana and Brian will discuss: (00:00) Introduction (01:37) From Washing Floors to Mastering Sales (06:57) MMM Principle: The Key to Making More Money (10:58) Financial Lessons from Business Giants (15:17) The Golden Triangle of Leadership (18:25) Activating the Superconscious Mind (24:30) The Goal-Setting Exercise That Built Millionaires (33:21) Hiring Your Dream Team with the 3x3x3 Method (42:28) Crushing Financial Fears and “Excusitis” (48:36) The Unbreakable Laws of Money and Success (1:01:22) How to Actually Learn About Money (1:05:21) The Seven Steps to Increase Productivity and Income Brian Tracy is a renowned speaker, bestselling author, and the Chairman and CEO of Brian Tracy International. He trains individuals and organizations to achieve their personal and business goals more effectively. Brian has had successful careers in sales and marketing, investments, real estate development and syndication, importation, distribution, and management consulting. He has authored over 80 books, including bestsellers, Eat That Frog and The Success Secrets of Self-Made Millionaires, and the latest, The 32 Unbreakable Laws of Money and Success. Connect with Brian: Brian’s Website: https://www.briantracy.com/  Brian’s LinkedIn: linkedin.com/company/brian-tracy-international Resources Mentioned: Brian’s Books: The 32 Unbreakable Laws of Money and Success: Transform Your Life and Unlock Your Unlimited Potential: https://www.amazon.com/dp/1523007001  Eat That Frog!: 21 Great Ways to Stop Procrastinating and Get More Done in Less Time: https://www.amazon.com/dp/162656941X  The 21 Success Secrets of Self-Made Millionaires: How to Achieve Financial Independence Faster and Easier than You Ever Thought Possible: https://www.amazon.com/dp/0369307534  Think and Grow Rich by Napoleon Hill: https://www.amazon.com/dp/1585424331  Leap Academy: Ready to make the LEAP in your career? There is a NEW WAY for professionals to fast-track their careers and leap to bigger opportunities. Check out our free training today at https://bit.ly/leap--free-training

When Sharon Price John was a kid, she spent a summer determined to climb a massive tree. After several falls, she reached the top, only to realize she didn’t know how to get down. As darkness fell, she jumped into the pine needles below and learned a lasting lesson: tough goals can be fun. Years later, that same mindset guided her as CEO of Build-A-Bear Workshop, a company that was $49 million in the red. Instead of retreating, she climbed again, leading one of retail’s greatest comebacks. In this episode, Sharon shares how to face fear with curiosity, lead with heart, and use storytelling to spark transformation in business and life. Sharon Price John is the President and CEO of Build-A-Bear Workshop, where she led one of retail’s most inspiring turnarounds. She is also the author of Stories & Heart and Chair of the Toy Association. In this episode, Ilana and Sharon discuss (00:00) Introduction (02:17) The Truth Behind Every “Overnight” Success (03:53) The Tree That Taught Her Courage (07:16) Breaking Into Advertising (13:49) Climbing the Ladder at Mattel (19:41) When Her Startup Collapsed (28:55) Leading a Turnaround When Everything Seems Lost (32:44) The One Rule Every Great Leader Lives By (33:40) Avoiding the Mistakes That Cost You Most (38:12) The Strategy That Saved Build-A-Bear (50:57) Leading With Courage and Clarity Through Crisis(01:04:33) Storytelling as the Heart of Great Leadership Sharon Price John has served as President and CEO of Build-A-Bear Workshop since 2013, leading the brand from a $49 million loss to record profitability. Before Build-A-Bear, she held senior roles at Hasbro, Mattel, and Stride Rite Children’s Group, earning a reputation as a turnaround expert. Sharon is the author of Stories & Heart and serves on the boards of Jack in the Box and First Book. She is also Chair of the Toy Association.  Connect with Sharon: Sharon’s LinkedIn: linkedin.com/in/sharon-price-john-26239820 Sharon’s Website: storiesandheart.com Resources Mentioned: Sharon’s Book, Stories & Heart: Unlock the Power of Personal Stories to Create a Life You Love: https://www.amazon.com/dp/1950863441 First Book: https://firstbook.org Build-A-Bear Workshop: https://www.buildabear.com  Leap Academy: Ready to make the LEAP in your career? There is a NEW WAY for professionals to fast-track their careers and leap to bigger opportunities. Check out our free training today at https://bit.ly/leap--free-training

He could have built a billion-dollar company, but instead, Jimmy Wales built a movement. When the dotcom crash hit and funding vanished, he didn’t sell out or add ads. He doubled down on values, creating Wikipedia, a global temple for the mind that made knowledge free to billions. In this episode, Jimmy joins Ilana to share the story behind that decision, the failures that shaped him, and the community that built the impossible. He breaks down why the best ideas come from doing something interesting, not chasing money. Jimmy Wales is the co-founder of Wikipedia and the founder of the Wikimedia Foundation, the nonprofit that supports Wikipedia and its sister projects. He also co-founded Fandom (formerly Wikia), one of the web’s largest community platforms. In this episode, Ilana and Jimmy discuss: (00:00) Introduction (02:31) How Childhood Curiosity Sparked Wikipedia’s Vision (05:59) Turning Crisis Into Innovation During the Dotcom Crash (08:08) The Creation of Wikipedia (14:19) The Power of Community When Capital Runs Out (20:14) Why Jimmy Refused to Monetize Wikipedia (29:54) Early Fundraising Efforts for Wikipedia (34:21) What Makes Someone Truly Notable on Wikipedia (39:11) AI’s Role in Wikipedia's Future (46:15) Inside The Seven Rules of Trust (57:17) Jimmy’s Ultimate Advice to Just Start Jimmy Wales is the co-founder of Wikipedia, the world’s largest free encyclopedia, and Wikimedia Foundation, the nonprofit that supports it. An advocate for open, collaborative knowledge sharing, he has empowered millions to contribute to a global resource of information. Recognized by TIME as one of the 100 Most Influential People in the World, Jimmy is also the author of The Seven Rules of Trust, where he shares the principles that guided his journey and offers insights on building lasting endeavors. Connect with Jimmy: Jimmy’s Twitter: x.com/jimmy_wales Jimmy’s LinkedIn: linkedin.com/in/jimmy-wales-919a8b Resources Mentioned: Wikipedia: https://www.wikipedia.org/ Jimmy’s book, The Seven Rules of Trust: A Blueprint for Building Things That Last: https://www.amazon.com/dp/0593727460 Your Money or Your Life: 9 Steps to Transforming Your Relationship with Money and Achieving Financial Independence: https://www.amazon.com/dp/0143115766  LEAP E122 with Nathan Blecharczyk: https://podcasts.apple.com/us/podcast/nathan-blecharczyk-the-raw-truth-of-scaling-airbnb/id1701718200?i=1000723574008  Leap Academy Ready to make the LEAP in your career? There is a NEW WAY for professionals to fast-track their careers and leap to bigger opportunities.Check out our free training today at https://bit.ly/leap--free-training

Ben Weiss set out to create the future of footwear. With nothing but conviction and a radical idea to merge AI with design, he reached out to Reebok co-founder Joe Foster, the man who turned a small factory dream into a global empire. What began as a cold message became a collaboration between two builders chasing the next revolution in shoes. In this episode, Ben and Joe join Ilana to unpack what it takes to see opportunity before the world does and how to keep building, no matter the odds or the decade. Joe Foster is the co-founder of Reebok, the small family startup that became one of the world’s most iconic sports brands. Ben Weiss is the founder and CEO of Syntilay, a footwear innovation company building the future of sneakers through AI design and 3D printing. Together, their partnership is transforming the footwear industry. In this episode, Ilana, Ben, and Joe discuss: (00:00) Introduction (03:50) The Birth of Reebok (09:59) Breaking into the U.S. Market Against All Odds (19:04) How Women Skyrocketed Reebok’s Success (20:19) Hollywood and the Rise of Reebok (23:04) Facing Challenges with Optimism (25:27) Syntilay: A New Concept in AI Footwear (28:30) Persistence and White Space Thinking (32:56) Innovating with AI and 3D Printing (36:17) The Future of Footwear and Technology (41:41) Advice for Aspiring Entrepreneurs Joe Foster is the co-founder of Reebok, the small startup he and his brother Jeff built into one of the world’s most iconic sports brands. Through innovation and perfect timing, he helped turn Reebok into a global household name. After stepping away, he authored the bestselling memoir Shoemaker and launched the How to Survive & Thrive series, now in its fourth edition. At 90, he continues to speak worldwide and mentor founders, sharing enduring lessons on creativity, resilience, and reinvention. Ben Weiss is the founder of Syntilay, a Florida-based startup pioneering AI-designed, 3D-printed sneakers. With advisors like Reebok founder Joe Foster and original Shark Tank investor Kevin Harrington, Ben is redefining how shoes are created through technology, speed, and personalization. His mission is to empower creators to design and own their own footwear brands. Connect with Joe and Ben: Joe’s LinkedIn: linkedin.com/in/joe-foster-a38a4b10b  Ben’s LinkedIn: linkedin.com/in/benxweiss/  Resources: Syntilay: https://syntilay.com/  Joe’s Book, Shoemaker: The Untold Story of the British Family Firm that Became a Global Brand: https://www.amazon.com/dp/1471194019  Leap Academy: Ready to make the LEAP in your career? There is a NEW WAY for professionals to fast-track their careers and leap to bigger opportunities. Check out our free training today at https://bit.ly/leap--free-training

Jim McKelvey did the impossible. He beat Amazon. The tech giant launched a product similar to Square’s, undercut their pricing, and leveraged its massive brand. Everyone thought Square was doomed. But a year later, Amazon quit and even mailed Square readers to their customers. That left Jim with a bigger question: “How did we survive when no one else ever has?” The search for that answer inspired his book The Innovation Stack, a blueprint for building a business that cannot be copied. In this episode, Jim joins Ilana to reveal the secret to creating an unbeatable business, why ignorance can be a superpower, and how to survive the impossible as an entrepreneur. Jim McKelvey is the co-founder of Square (now Block), a billionaire entrepreneur, and author of The Innovation Stack. He also founded LaunchCode, a nonprofit providing free tech education and job placement. In this episode, Ilana and Jim will discuss: (00:00) Introduction  (02:04) Growing Up as an ‘Uncool’ Kid in St. Louis (04:01) The Early Hustle That Jumpstarted His Career (07:47) Launching a Business with 15-Year-Old Jack Dorsey (13:50) The Birth of Square: From Glass Blowing to FinTech (20:09) The Art of Selling and Capturing Attention (26:48) How a Single Demo Won Over MasterCard (31:04) Amazon's Failed Attempt to Crush Square (32:17) The Innovation Stack: Building an Unbeatable Business (35:55) Why Most Entrepreneurs Give Up Too Soon (41:32) Why the Best Innovators Are Always “Unqualified” Jim McKelvey is a serial entrepreneur, inventor, and philanthropist best known as the co-founder of Square (now Block), the fintech company that redefined digital payments. He is the author of The Innovation Stack, which explores how companies can survive by creating solutions that can’t be copied. Jim also founded LaunchCode, a nonprofit that provides free tech education and job placement for aspiring coders.  Connect with Jim Jim’s LinkedIn: linkedin.com/in/mckelveyjim Resources Mentioned Jim’s Book, The Innovation Stack: Building an Unbeatable Business One Crazy Idea at a Time: https://www.amazon.com/Innovation-Stack-Building-Unbeatable-Business/dp/0593086732 Leap Academy: Ready to make the LEAP in your career? There is a NEW WAY for professionals to fast-track their careers and leap to bigger opportunities. Check out our free training today at https://bit.ly/leap--free-training

At a 2015 World Cup match in Vancouver, Kara searched nine stores for her daughters’ jerseys and found none. That spark of “joyful irritation” became a movement to build teams, build community, and build an industry. In this episode, Kara joins Ilana to share how that moment ignited Angel City FC, how she, along with her partners, managed to create one of the most valuable women’s soccer teams in the world, and why she embraces rejection as a growth strategy. She breaks down the tension between patience and urgency, the power of finding joy in pursuing one’s passions, and how to choose partners who amplify your mission. Kara Nortman is the co-founder of Angel City FC and managing partner of Monarch Collective, a $250M investment platform driving the growth of women’s sports. A former investor at Upfront Ventures and operator at IAC, Kara brings decades of experience turning bold ideas into lasting movements. In this episode, Ilana and Kara will discuss: (00:00) Introduction (02:03) Realizing the Market Gap in Women’s Sports (04:16) Turning Inspiration into Action (06:44) Finding Joy Through Volunteering and Community (11:54) The Birth of Angel City FC (17:23) Turning Rejection into Fuel (30:48) Breaking into the World of Venture Capital (31:42) Game-Changing Mentorship and Early Career Lessons (33:47) Discovering a Passion for Tech at Battery Ventures (44:19) Building Angel City and Redefining the Playbook (50:04) Launching Monarch and Scaling the Movement Kara Nortman is an investor, founder, and sports operator focused on advancing the women’s sports economy. As a co-founder of the professional women's soccer team, Angel City FC, she pioneered a community-first 10% sponsorship model that drove significant commercial success. Kara co-leads Monarch Collective, investing in women’s sports teams and related businesses across the U.S. and Europe. Previously, she was a managing partner at Upfront Ventures and an executive at IAC, where she helped incubate Tinder through Hatch Labs. Connect with Kara: Kara’s LinkedIn: linkedin.com/in/karanortman Resources Mentioned: Monarch Collective: https://monarchcoll.com Angel City FC: https://angelcity.com   Leap Academy: Ready to make the LEAP in your career? There is a NEW WAY for professionals to fast-track their careers and leap to bigger opportunities. Check out our free training today at https://bit.ly/leap--free-training

Robert Glazer collapsed in his kitchen in front of his son, convinced he was having a heart attack. In reality, it was a massive panic attack triggered by grinding too hard while starting a business, building a house, raising kids, and weathering the 2008 recession. That wake-up call forced him to reevaluate everything: his health, his leadership, and the values that guided his life. In this episode, Robert returns to the show to share how childhood struggles shaped his values, why passion is developed, not discovered, and how to know if you’re climbing the wrong mountain in life. He also reveals the frameworks from his new book to help you align your career, relationships, and purpose with your deepest values. Robert Glazer is a serial entrepreneur, bestselling author, and global keynote speaker. He founded Acceleration Partners, a 300-person marketing agency, and is the author of eight books, including Elevate and his newest release, The Compass Within. In this episode, Ilana and Robert discuss: (00:00) Introduction (02:09) Growing Up as the “Underachiever” Kid (05:20) Discovering a Love for Learning in College (09:00) How Helping One Company Sparked an Agency (10:30) The Health Scare That Sparked a Wake-Up Call (14:18) Leading with Transparency During COVID (16:56) Choosing to Step Aside as CEO (19:29) Writing The Compass Within as a Story (22:00) Understanding Core Values (26:09) The Three Climbs of Success for High Achievers (29:12) Six Questions to Identify Your Core Values Robert Glazer is an entrepreneur, bestselling author, and thought leader on business and personal growth. He founded Acceleration Partners, scaling it into a 300-person agency recognized for its values-driven culture. Robert is the author of eight books, including Elevate and The Compass Within, and the Friday Forward newsletter. Known for his insights on leadership, capacity building, and core values, he speaks on stages around the globe and helps individuals and organizations align success with authenticity. Connect with Robert Robert’s Website: robertglazer.com  Robert’s LinkedIn: linkedin.com/in/glazer   The Compass Within Website: compass-within.com Resources Mentioned LEAP Episode 32 with Robert Glazer: https://podcasts.apple.com/us/podcast/the-art-of-reinvention-how-to-elevate-your-career/id1701718200?i=1000660153819 The Six Core Values Questions: robertglazer.com/six Robert’s Book, The Compass Within: A Little Story About the Values That Guide Us: https://geni.us/values Free Course: robertglazer.com/compass-leap Robert’s Book, Elevate: Push Beyond Your Limits and Unlock Success in Yourself and Others: https://www.amazon.com/Elevate-Beyond-Limits-Success-Yourself/dp/1492691488  The Freak Factor: Discovering Uniqueness by Flaunting Weakness by David Rendall: https://www.amazon.com/Freak-Factor-Discovering-Uniqueness-Flaunting/dp/1599326698  Leap Academy Ready to make the LEAP in your career? There is a NEW WAY for professionals to fast-track their careers and leap to bigger opportunities. Check out our free training today at https://bit.ly/leap--free-training

Most people would assume that raising capital for a celebrity-backed business would be a cakewalk, but Thai Randolph knew that was far from the truth. Securing $100 million in investment for Kevin Hart's Hartbeat Productions required more than just a famous name; it took proving real value, building trust, and navigating rejection. Her success led to one of the largest private-equity rounds ever led by a Black woman in the U.S. In this episode, Thai joins Ilana to share the lessons she’s learned throughout her career, from her time at Sony, Facebook, and Lionsgate. She also opens up about her personal struggles with fertility while building a successful career and the pivotal moments that shaped her leadership style. Thai Randolph is an award-winning entrepreneur and marketer, and the former CEO of Hartbeat, where she led the company’s growth and secured a $100M investment, one of the largest private-equity rounds led by a Black woman in the U.S. In this episode, Ilana and Thai discuss: (00:00) Introduction (01:51) How Thai’s Small-Town Roots Shaped Her Path (04:58) Pivoting from Marketing Missiles to Storytelling (09:36) Breaking into Big Tech: From Sony to Facebook (14:14) Balancing Fertility Struggles and Career Moves (22:11) Joining Lionsgate and Meeting Kevin Hart (26:34) Challenges of Carving Out a New Business (28:20) Raising $100M for Hartbeat Against All Odds (32:40) Transitioning to CEO and Leadership Lessons (37:49) Balancing Work, Life, and Avoiding Burnout (41:57) Redefining Your Identity Beyond the Job Title (49:28) Thai’s Next Big Ventures and Future Plans Thai Randolph is an entrepreneur and marketer, and the former CEO of Hartbeat, where she led the company’s growth and secured a $100M investment, one of the largest private-equity rounds led by a Black woman in the U.S. As President and COO of Laugh Out Loud, she oversees the strategy and operations for Kevin Hart’s comedy network. Thai has driven digital transformation at companies like Facebook and Sony, and provided media strategy for top brands like Verizon, Dell, and more. Connect with Thai:  Thai’s LinkedIn: linkedin.com/in/thairandolph Thai’s Instagram: instagram.com/thairandolph Resources Mentioned: Thai’s Podcast, The Suga: podcasts.apple.com/us/podcast/the-suga/id1502324399  LOL Network: youtube.com/@lolnetwork  Leap Academy: Ready to make the LEAP in your career? There is a NEW WAY for professionals to fast-track their careers and leap to bigger opportunities. Check out our free training today at https://bit.ly/leap--free-training

For eight years, Lisa Bilyeu lived the life others expected: a traditional Greek wife focused on supporting her husband and running the home. But deep down, she knew she was meant for more. With no business background, zero confidence, and no clear roadmap, she decided to rewrite her story. She co-founded Quest Nutrition with her husband and built a billion-dollar business. In this LEAP Replay, Lisa opens up to Ilana about breaking free from cultural expectations, showing up authentically in the face of criticism, and how you can build radical confidence without needing external validation. Lisa Bilyeu is an entrepreneur, bestselling author, and co-founder of Quest Nutrition, a multi-billion-dollar company. Her mission is to use content creation to empower women to break free from limiting beliefs and build extraordinary lives. In this episode, Ilana and Lisa will discuss: (00:00) Introduction  (02:22) Her Upbringing and the Weight of Expectations (06:44) Velvet Handcuffs: The Trap of People Pleasing (10:55) Transitioning from Housewife to Co-Founder (19:13) Handling Your Emotions in Business  (24:25) How Lisa Tackles Online Hate and Criticism (33:12) The Three Keys to Mission-Driven Content Creation (37:25) Lisa’s No-BS Guide to Success  (44:40) Why She Chose Her Mission Over Motherhood  (1:03:06) Building Radical Confidence Through Self-Reliance Lisa Bilyeu is an entrepreneur, author, and co-founder of Quest Nutrition, a multi-billion-dollar company that transformed the health and wellness industry. She is also the founder and host of Women of Impact, co-founder of Impact Theory, and bestselling author of Radical Confidence. Lisa’s mission is to use content creation to empower women to break free from limiting beliefs and embrace their full potential.  Connect with Lisa: Lisa’s Website: https://lisabilyeu.com/ Lisa’s YouTube: www.youtube.com/@LisaBilyeu  Lisa’s Instagram: https://www.instagram.com/lisabilyeu Resources Mentioned: Lisa’s Book, Radical Confidence: 11 Lessons on How to Get the Relationship, Career, and Life You Want: https://www.amazon.com/dp/B09JPHK9C3 Leap Academy: Ready to make the LEAP in your career? There is a NEW WAY for professionals to fast-track their careers and leap to bigger opportunities. Check out our free training today at https://bit.ly/leap--free-training

As a teenager, Sir Richard Branson had already mastered the art of taking bold leaps to pursue opportunities. Dyslexic and struggling in school, he quit at age 15 to launch a youth magazine, a move that eventually led to Virgin Records, Virgin Atlantic, and the Virgin Group empire. In this LEAP Replay, Richard joins Ilana to share how he turned obstacles into opportunities, embraced fearless risk-taking, and uses his influence for international peace initiatives, all while showing that dyslexia can be a superpower. Sir Richard Branson is the founder of Virgin Group, spanning airlines, cruises, hotels, health, entertainment, and space travel. Known for his adventurous spirit and bold pursuits, he has not only transformed industries but also used his influence to champion global humanitarian causes. In this episode, Ilana and Richard will discuss: (00:00) Introduction (02:10) Quitting School at 15 to Run a Magazine (05:26) Launching Virgin Records with a Bold Move (09:20) The Funny Moment That Birthed Virgin Atlantic (11:37) Using His Influence to Negotiate with Saddam Hussein (15:54) The “Reserve Tank” Mindset for Mental Toughness (18:17) Why Dyslexic Thinking Is a Superpower in Business Sir Richard Branson is a serial entrepreneur and founder of the Virgin Group, a global conglomerate of more than 40 companies spanning industries from entertainment to aviation and space travel. Known for his adventurous spirit and bold approach to business, Richard built Virgin into one of the world’s most recognized brands. Beyond entrepreneurship, he is a philanthropist, author of multiple bestsellers, and a passionate advocate for social and environmental causes. Connect with Richard: Richard’s Website: https://www.virgin.com/branson-family/richard-branson  Richard’s LinkedIn: linkedin.com/in/rbranson Resources Mentioned: Richard’s Audiobook: Losing and Finding My Virginity: The Full Story: https://www.amazon.com/Losing-Finding-My-Virginity-Story/dp/B0CW8BS7W7  Leap Academy: Ready to make the LEAP in your career? There is a NEW WAY for professionals to fast-track their careers and leap to bigger opportunities. Check out our free training today at https://bit.ly/leap--free-training

Ilana Golan knows what it feels like to lose everything. After climbing from the Air Force to Intel to VP in a Silicon Valley startup, she thought she had made it. But when a trusted co-founder cut her out of their new business overnight, she was left with nothing. No job, no company, no income, and a shattered ego. That collapse became the turning point, forcing Ilana to ask who she was without the titles and what kind of life she truly wanted to build. In this episode, Ilana breaks down the five shifts you need to reinvent your career and the blueprint she used to bounce back from failure, build one of the fastest-growing startups, and land opportunities with leaders like Richard Branson and GaryVee. Ilana Golan is a serial entrepreneur, keynote speaker, investor, and host of the LEAP Academy podcast. As the founder of LEAP Academy, she teaches professionals how to fast-track opportunities, build portfolio careers, and unlock financial freedom.  In this episode, Ilana discusses: (00:00) Introduction (01:11) The Startup Collapse That Changed Everything (04:24) Losing Her Identity and Rebuilding From Scratch (06:22) Launching LEAP Academy and Reaching Startup of the Year (09:10) Reinvention as the Must-Have Skill of Our Era (10:09) The Power of Adaptability: IQ vs. EQ vs. AQ (11:29) The Five Shifts to Fast-Track Your Career (18:30) Commanding Authority: The Three Types of Branding  (23:17) Creating a Portfolio Career for Freedom and Wealth Ilana Golan is a serial entrepreneur, board director, global keynote speaker, and investor in over 100 companies. As the founder of Leap Academy, she teaches professionals how to fast-track opportunities, build portfolio careers, and unlock financial freedom. Ilana has been recognized as a Silicon Valley Woman of Influence, a Top 40 Woman to Watch, and a CEO World Award winner. Under her leadership, LEAP Academy was named one of Inc. 500’s Fastest Growing Companies. Connect with Ilana:  Ilana’s Website: leapacademy.com  Ilana’s LinkedIn: linkedin.com/in/ilanagolan  Ilana’s Email: ilana@leapacademy.com  Resources Mentioned: LEAP Academy Free Training: leapacademy.com/training  Leap Academy Ready to make the LEAP in your career? There is a NEW WAY for professionals to fast-track their careers and leap to bigger opportunities. Check out our free training today at https://bit.ly/leap--free-training

Despite outward success, Brad Feld struggled with depression, exhaustion, and feelings of emptiness. For years, he hid these challenges while relentlessly pushing forward as an entrepreneur. It wasn’t until his 40s, after seeking therapy and confronting his mental health, that Brad realized success wasn’t just about building companies, but about managing the emotional toll of entrepreneurship. Today, as the co-founder of Techstars and Foundry Group, he leads with a harmonious approach to work and life. In this episode, Brad joins Ilana to share the lessons he learned from early failures, why every successful founder faces ‘near-death moments’, and the mental health practices that helped him find joy again. Brad Feld is a venture capitalist, entrepreneur, and co-founder of Techstars, one of the world’s leading startup accelerators. He is also the co-founder of two venture capital firms, Foundry Group and Mobius Venture Capital. In this episode, Ilana and Brad discuss: (00:00) Introduction (01:07) Growing Up in Dallas and Discovering Computers (07:29) MIT Years and Early Startup Failures (14:17) Why Every Startup Faces a Near-Death Experience (16:54) Battling Fear, Shame, and Depression in His Twenties (26:52) Breaking Down at 47 Despite “Having It All” (29:05) Brad’s Practical Steps for Rediscovering Joy (41:54) The Random Day Experiment and Birth of Techstars (52:47) Writing Venture Deals, Startup Communities, and Give First (59:26) Coming Out of “Hibernation” to Write His Last Non-Fiction (1:13:39) Work-Life Balance vs. Work-Life Harmony Brad Feld is a venture capitalist, entrepreneur, and co-founder of Techstars, one of the world’s leading startup accelerators. He is also the co-founder of two venture capital firms, Foundry Group and Mobius Venture Capital. Brad is the author of nine books, including Venture Deals, Startup Communities, and Give First. Through his books, investments, and philosophy of “give first,” Brad has become a mentor to thousands of entrepreneurs navigating the brutal highs and lows of building a business. Connect with Brad:  Brad’s Website: feld.com Brad’s LinkedIn: linkedin.com/in/bfeld  Resources Mentioned Brad’s Book, Give First: The Power of Mentorship: https://www.amazon.com/dp/1646871324  Brad’s Book, Startup Communities: Building an Entrepreneurial Ecosystem in Your City: https://www.amazon.com/dp/1118441540  Venture Deals: Be Smarter Than Your Lawyer and Venture Capitalist by Brad Feld and Jason Mendelson: https://www.amazon.com/dp/1118443616  Reboot: Leadership and the Art of Growing Up by Jerry Colonna: https://www.amazon.com/dp/0062749536 Leap Academy Ready to make the LEAP in your career? There is a NEW WAY for professionals to fast-track their careers and leap to bigger opportunities.Check out our free training today at https://bit.ly/leap--free-training

Brendan Kane didn’t break into Hollywood through connections. He started out making coffee on film sets. Spotting the untapped power of MySpace and YouTube, he launched one of the first influencer campaigns, catching the attention of studio executives and A-list actors like Jason Statham. That bold move launched his journey from Hollywood to advising global icons such as Taylor Swift and Rihanna on social media strategy. In this episode, Brendan joins Ilana to reveal how he built one million followers in just 30 days, the formula for going viral, and the psychology behind grabbing and holding attention. Brendan Kane is a digital marketing expert who has helped top celebrities, Fortune 500 companies, and entrepreneurs dominate social media and generate millions in revenue. He specializes in data-driven strategies that drive massive social media engagement. In this episode, Ilana and Brendan will discuss: (00:00) Introduction  (02:07) His Childhood Love for Movies and Storytelling (03:17) Breaking into Hollywood Without Connections (08:16) The Bold Move That Led to Working With A-List Actors (10:37) Diving into Tech and Working with Taylor Swift, Rihanna, etc (17:51) Lessons from Managing $100M in YouTube Ad Spend (22:06) Uncovering the Secrets to Social Media Success (27:40) How Brendan Hit a Million Followers in 30 Days (34:51) Strategies for Marketing Bestselling Books (39:10) How to Adapt to Ever-Changing Platforms (44:01) Low-Cost Strategies to Stand Out on Social Media (45:35) Navigating the Challenges of Entrepreneurship Brendan Kane is a digital marketing expert who has helped top celebrities, Fortune 500 companies, and entrepreneurs dominate social media and generate millions in revenue. Known for building a following of over 1 million in just 30 days, Brendan specializes in data-driven strategies that drive massive social media engagement. He is the bestselling author of One Million Followers, Hook Point, and The Guide to Going Viral, where he reveals proven methods for scaling influence in today’s noisy digital world. Connect with Brendan: Brendan’s Website: brendanjkane.com  Brendan’s Instagram: instagram.com/brendankane  Resources Mentioned: Get Brendan’s Book, The Guide to Going Viral, for FREE: hookpoint.com/leap  Download Brendan’s Book, Hook Point for Free: hookpoint.com  Brendan’s Book, One Million Followers: How I Built a Massive Social Following in 30 Days: https://www.amazon.com/One-Million-Followers-Updated-Following/dp/195066547X  The 4-Hour Workweek: Escape 9-5, Live Anywhere, and Join the New Rich by Timothy Ferriss: https://www.amazon.com/4-Hour-Workweek-Escape-Live-Anywhere/dp/0307465357  Leap Academy: Ready to make the LEAP in your career? There is a NEW WAY for professionals to fast-track their careers and leap to bigger opportunities. Check out our free training today at https://bit.ly/leap--free-training

George Kurian’s journey from a modest upbringing in Kerala, India, to becoming CEO of NetApp is an extraordinary story. George worked cafeteria shifts and construction jobs to pay his way through Princeton before climbing the ranks at Oracle, McKinsey, and Cisco. In this episode, George opens up about the weight of being a “rookie CEO” responsible for 12,000 people, the discipline of saying no to 97% of ideas, and the humility it takes to lead through uncertainty. He and Ilana explore resilience, focus, and the future of AI, while revealing how diverse experiences and family values shaped his leadership philosophy. George Kurian is CEO of NetApp, a Fortune 500 data infrastructure and cloud services company. Under his leadership, NetApp has strengthened its cloud-first and data services strategy, growing into a $20 billion company. In this episode, Ilana and George will discuss: (00:00) Introduction (02:20) Family Role Models and Upbringing (06:00) Landing a Princeton Scholarship and Learning to Survive (09:20) Lessons from Oracle and McKinsey (13:50) Why George Left Cisco to Join NetApp (16:45) How Cafeteria Work Inspired NetApp’s Engineering Process (19:40) The ‘30-30-30’ Rule for Driving Organizational Change (22:40) George’s Journey to Becoming CEO Overnight (26:30) First-Time CEO Challenges and Leadership Struggles (30:40) Why a CEO Should Say “No” to 97% of Ideas (33:10) Betting on Cloud Partnerships Instead of Competing (37:15) The Power of Choosing Your Path and Tackling Hard Problems George Kurian is CEO of NetApp, a Fortune 500 data infrastructure and cloud services company. Before joining NetApp in 2011, he had built a diverse tech career that included leadership roles at Oracle, McKinsey, Cisco, and Akamai. Under his leadership, NetApp has strengthened its cloud-first and data services strategy, growing into a $20 billion company. Connect with George: George’s LinkedIn: linkedin.com/in/georgekuriannetapp Leap Academy: Ready to make the LEAP in your career? There is a NEW WAY for professionals to fast-track their careers and leap to bigger opportunities. Check out our free training today at https://bit.ly/leap--free-training

Klaus Kleinfeld’s journey from a difficult childhood in Germany to leading two Fortune 500 companies, Siemens and Alcoa, was anything but easy. He experienced  the true cost of leadership: the loneliness of making impossible decisions and the grit to push forward when every alternative seems bleak. In this episode, Klaus joins Ilana to share how resilience and freedom shaped his leadership philosophy. They dive into his shift from time management to energy management, exploring lessons from sports, breathing techniques, and mindset practices that helped him lead various multi-billion dollar businesses without burnout.  Dr. Klaus Kleinfeld is a German entrepreneur, investor, and former CEO of Siemens AG, Alcoa Inc., and ARconic. He is also the founder and CEO of the investment firm K2Elevation and was named director of Saudi Arabia's Neom initiative, later becoming an advisor to the Crown Prince. In this episode, Ilana and Klaus will discuss: (00:00) Introduction (02:01) Early Life and Family Tragedy (07:31) East vs. West Germany and Freedom (12:01) His Love for Problem-Solving (18:01) Creating a Strong Feedback Culture (23:31) Becoming the CEO of Siemens (30:01) The Loneliness of Leadership (35:31) Letting People Go with Respect (40:01) Facing Fear and Regret (45:31) Energy Over Time Management (50:01) Building a Passionate and High-Performance Team Dr. Klaus Kleinfeld is a German entrepreneur, investor, and former CEO of Siemens AG, Alcoa Inc., and ARconic. He is also the founder and CEO of the investment firm K2Elevation and was named director of Saudi Arabia's Neom initiative, later becoming an advisor to the Crown Prince. As the author of Leading to Thrive, Klaus offers a framework for blending personal well-being with strategic leadership.  Connect with Klaus: Klaus’s LinkedIn: linkedin.com/in/klauskleinfeld Resources Mentioned: Klaus’s Book, Leading to Thrive: Mastering Strategies for Sustainable Success in Business and Life: https://www.amazon.com/Leading-Thrive-Mastering-Strategies-Sustainable/dp/1544546718 The Power of Regret: How Looking Backward Moves Us Forward by Daniel Pink: https://www.amazon.com/Power-Regret-Looking-Backward-Forward/dp/0735210659 Open: An Autobiography by Andre Agassi: https://www.amazon.com/Open-Autobiography-Andre-Agassi/dp/0307388409 Leap Academy: Ready to make the LEAP in your career? There is a NEW WAY for professionals to fast-track their careers and leap to bigger opportunities. Check out our free training today at https://bit.ly/leap--free-training

Nathan Blecharczyk, co-founder of Airbnb, built his first software business as a teenager, earning nearly a million dollars before shutting it down to attend Harvard. Years later, Nathan and his roommates turned an air mattress idea into Airbnb, facing investor rejection, financial hardship, and moments when quitting seemed inevitable. From creating satirical cereal boxes to joining Y Combinator after a near-failed interview, Nathan’s story is one of perseverance and resilience. He shares how Airbnb overcame early struggles, scaled globally, and survived COVID-19 to go public successfully. Nathan Blecharczyk is the co-founder and Chief Strategy Officer of Airbnb, where he helped grow the platform from a spare air mattress idea to a $75 billion global travel company. According to Forbes, he is one of the richest people in the world, with a net worth of $9 billion. In this episode, Ilana and Nathan will discuss: (00:00) Introduction (01:36) Building a Software Business as a Teen (05:28) Harvard, First Job, and the Decision to Move West (11:58) The Birth of AirBed & Breakfast (15:07) Landing Their  First Guests and Gaining Early Validation (18:03) Investor Rejection and the Obama O’s Cereal Stunt (30:45) Applying to Y Combinator and Getting In (36:29) Finding Evangelists and Meeting Hosts in New York (42:34) From $200 a Week to $4,200: Airbnb’s First Growth Curve (44:59) Global Expansion, Competitors, and Building Teams Abroad (52:22) The 2020 Crisis: COVID, Collapse, and Reinvention (59:21) The Future of Travel  Nathan Blecharczyk is the co-founder and Chief Strategy Officer of Airbnb, where he helped grow the platform from a spare air mattress idea to a $75 billion global travel company. A Harvard graduate and self-taught programmer, Nathan has been instrumental in Airbnb’s international expansion and strategy, navigating challenges from investor rejection to the COVID-19 crisis. According to Forbes, he is one of the richest people in the world, with a net worth of $9 billion. Connect with Nathan: Nathan’s LinkedIn: ⁠https://www.linkedin.com/in/blecharczyk⁠ Airbnb’s Website: ⁠https://www.airbnb.com⁠ Resources Mentioned: Y Combinator: ⁠https://www.ycombinator.com⁠Only the Paranoid Survive by Andy Grove: ⁠https://www.amazon.com/Only-Paranoid-Survive-Exploit-Challenge/dp/0385483821⁠ Leap Academy: Ready to make the LEAP in your career? There is a NEW WAY for professionals to fast-track their careers and leap to bigger opportunities. Check out our free training today at https://bit.ly/leap--free-training

After 12 years of working in corporate advertising, Case Kenny launched a podcast, New Mindset, Who Dis? as a personal experiment. In its first month, the show drew 57,000 downloads, yet Case kept it hidden, afraid it didn’t fit his professional image. Over time, he embraced his vulnerability, created bestselling guided journals, and built a brand helping millions live more optimistic and mindful lives. In this episode, Case joins Ilana to share how a side project turned into a multi-million-dollar portfolio career, why regret is his decision-making compass, and how choosing the right words can change the way you live. Case Kenny is an author, entrepreneur, and host of the globally recognized podcast, New Mindset, Who Dis?. Known for his work in mindfulness and personal growth, he has built a multi-million-dollar brand through writing, guided journals, and speaking engagements. In this episode, Ilana and Case will discuss: (00:00) Introduction (01:42) From Language Studies to Corporate Advertising (05:07) Starting the Podcast Without Clarity (07:43) Overcoming the Fear of Vulnerability (09:04) Stepping Fully into a New Identity (14:14) When Passion Becomes a Business (16:53) COVID, Journals, and a Turning Point in Sales (18:10) Why Journaling Works and How to Start (25:01) Building a Connected Portfolio Career (27:40) Business Challenges and Six-Figure Losses (33:09) Battling Expectations, Regret, and Trust as a Default (42:10) Defining Mindfulness and Advice to Case’s Younger Self Case Kenny is an author, entrepreneur, and host of the globally recognized podcast, New Mindset, Who Dis?, a podcast with tens of millions of downloads. Known for his work in mindfulness and personal growth, he has built a multi-million-dollar brand through writing, guided journals, and speaking engagements. His work has been featured on The Today Show, Good Morning America, Forbes, and NBC. Connect with Case: Case’s Website: casekenny.com Case’s LinkedIn: linkedin.com/in/casekenny/ Case’s Instagram: instagram.com/case.kenny Case’s YouTube: youtube.com/c/CaseKenny Resources Mentioned: Case’s Podcast, New Mindset, Who Dis?:  pod.link/1383599078 The Opposite of Settling by Case Kenny: https://www.amazon.com/Opposite-Settling-Everything-Without-Losing/dp/1401995918 The Soul’s Code by James Hillman: https://www.amazon.com/Souls-Code-James-Hillman/dp/0517271036 That’s Bold of You by Case Kenny: https://www.amazon.com/Thats-Bold-You-Thrive-Vibrant/dp/B0BRDFLJNZ Leap Academy: Ready to make the LEAP in your career? There is a NEW WAY for professionals to fast-track their careers and leap to bigger opportunities. Check out our free training today at https://bit.ly/leap--free-training

What do you do when the dream you've chased no longer fits? For Julia Hartz, it meant walking away from a promising career in Hollywood to dive into the unknown world of startups. As an intern on the set of Friends, she learned the value of kindness, clarity, and high standards. But the real test came in tech, where she bootstrapped through a downturn, faced 27 VC rejections, and ultimately co-founded Eventbrite, one of the world’s leading event ticketing platforms. In this episode, Julia joins Ilana to discuss her leap from TV to tech, how she led Eventbrite through a crisis, and how she continues to reinvent herself and her business.  Julia Hartz is the co-founder and CEO of Eventbrite, a global ticketing and event technology platform that empowers creators to bring people together through live experiences. In 2018, she took the company public on the New York Stock Exchange, making her one of the few female founders to lead a tech IPO. In this episode, Ilana and Julia will discuss: (00:00) Introduction (01:02) Julia’s Leap from Performance to Broadcasting (04:28) Her Internship on the Set of Friends (07:15) Discovering Her Path in TV Development at MTV (10:59) The Original Jackass Pilot and Startup-Like Creativity (14:55) Transitioning from MTV to FX and Facing Uncertainty (18:47) Leaving Hollywood to Build a Startup (26:43) The Product Strategy That Transformed Their Business (32:29) Getting 27 Rejections from VCs and Refusing to Quit (35:50) How the Financial Crisis Created Their Breakthrough (40:03) Reinventing Herself to Become CEO (46:05) How COVID Nearly Took Down Eventbrite (51:09) The One Rule She Always Comes Back To Julia Hartz is the co-founder and CEO of Eventbrite, a global ticketing and event technology platform that empowers creators to bring people together through live experiences. In 2018, she took the company public on the New York Stock Exchange, making her one of the few female founders to lead a tech IPO. Today, Eventbrite has powered millions of events and facilitated billions in ticket sales in 180 countries. Connect with Julia: Julia’s Website: eventbrite.com Julia’s LinkedIn: linkedin.com/in/juliahartz Julia’s Instagram: instagram.com/juliahartz Leap Academy: Ready to make the LEAP in your career? There is a NEW way for professionals to Advance Their Careers & Make 5-6 figures of EXTRA INCOME in Record Time. Check out our free training today at leapacademy.com/training

After getting laid off from his corporate job, Dan Shapiro launched his first startup, Photobucket Inc. (formerly Ontela), but faced nine months of rejection from investors and no funding. Despite these setbacks, his persistence led to a successful partnership, which later turned sour due to a managerial dispute. He took these lessons and went on to build multiple successful startups, including Glowforge, a $100M company revolutionizing 3D laser printing. In this episode, Dan joins Ilana to share the secrets to startup success, how to navigate entrepreneurial challenges, and what it takes to build a company that not only thrives but also transforms industries. Dan Shapiro is a serial entrepreneur, innovator, and CEO of Glowforge, a company that pioneered desktop laser technology, enabling creators to produce millions of custom products. He previously created Robot Turtles, the most successful board game in Kickstarter history, and founded Photobucket Inc. In this episode, Ilana and Dan will discuss: (00:00) Introduction  (01:56) Early Upbringing and Entrepreneurial Drive (04:47) Corporate Experience at Microsoft (08:14) The "Poop Umbrella" Leadership Principle (11:42) The Darkest Nine Months of Dan's Career (16:39) Securing Funding Against All Odds (20:35) The Brutal Truth About Entrepreneurship (24:32) The PhotoBucket Merger: What Went Wrong? (27:56) From 67 Rejections to a Google Acquisition (31:38) CEO Strategy: Delegate vs. Lead (36:24) The Bold Strategy Behind Robot Turtles' Success (45:16) Building Glowforge: From Idea to $100M Business (51:47) Leadership Challenges and Ethical Dilemmas Dan Shapiro is a serial entrepreneur, innovator, and CEO of Glowforge, a company that pioneered desktop laser technology, enabling creators to produce millions of custom products. He previously created Robot Turtles, the most successful board game in Kickstarter history, and founded Photobucket Inc. Dan also served as CEO of Google Comparison Inc. after Google acquired his startup, Sparkbuy. He is the author of Hot Seat and a prolific innovator with over 60 patents to his name.  Connect with Dan: Dan’s Website: danshapiro.com  Dan’s LinkedIn: linkedin.com/in/danshapiro  Resources Mentioned: Dan’s Book, Hot Seat: The Startup CEO Guidebook: https://www.amazon.com/Hot-Seat-Startup-CEO-Guidebook/dp/1449360734  Glowforge: https://glowforge.com  From $500 Startup to Open Source Pioneer: How Tim O’Reilly Built a Media and Tech Legacy | E109: bit.ly/tim-oreilly-leap-academy  Bad Blood: Secrets and Lies in a Silicon Valley Startup by John Carreyrou: https://www.amazon.com/Bad-Blood-Secrets-Silicon-Startup/dp/152473165X  Leap Academy: Ready to make the LEAP in your career? There is a NEW way for professionals to Advance Their Careers & Make 5-6 figures of EXTRA INCOME in Record Time. Check out our free training today at leapacademy.com/training

Dr. Josh Axe’s passion for health and wellness began when his mother’s breast cancer diagnosis led to chronic health issues after chemotherapy. Inspired by this, Josh pursued natural medicine, which helped her make a remarkable recovery when cancer returned. Years later, Josh faced a spinal infection that left him unable to walk. Doctors predicted permanent disability, but using the same healing mindset and natural methods that saved his mom, he defied the odds. In this episode, Josh joins Ilana to discuss the transformative power of belief, the keys to true health and success, and the secrets behind building a powerful personal brand. Dr. Josh Axe is a physician, entrepreneur, and leadership expert passionate about helping individuals use food and natural remedies to achieve optimal health and wellness. He is the founder of DrAxe.com and The Health Institute and the co-founder of Ancient Nutrition. In this episode, Ilana and Josh will discuss: (00:00) Introduction  (02:06) The Cancer Battle That Sparked His Health Mission (05:29) The Role of Belief in Healing, Growth, and Success (14:34) Building DrAxe.com into a Digital Health Powerhouse (20:55) The Scary Moment He Almost Lost Everything (24:05) Overcoming the Fear of Charging What You’re Worth (26:06) Josh’s Strategies for Building a Scalable Brand (31:12) Simple Habits for Total Health Transformation (34:37) From Bedridden to Healed: The Power of Belief (42:38) Why Character Beats Accomplishments Dr. Josh Axe is a physician, entrepreneur, and leadership expert passionate about helping individuals use food and natural remedies to achieve optimal health and wellness. He is the founder of DrAxe.com and The Health Institute and the co-founder of Ancient Nutrition. His businesses have ranked among the Inc. 500’s fastest-growing companies. Josh is the host of The Dr. Josh Axe Show and the bestselling author of Eat Dirt, The Keto Diet, and Think This, Not That. Connect with Josh: Josh’s Website: draxe.com  Josh’s LinkedIn: linkedin.com/in/joshaxe  Resources Mentioned: Josh’s Book, Think This, Not That: 12 Mindshifts to Breakthrough Limiting Beliefs and Become Who You Were Born to Be: https://www.amazon.com/Think-This-Not-That-Breakthrough/dp/1400337844  Josh’s Podcast, The Dr. Josh Axe Show: https://podcasts.apple.com/us/podcast/the-dr-josh-axe-show/id1700689487  The Health Institute: thehealthinstitute.com  Good to Great: Why Some Companies Make the Leap...And Others Don't by Jim Collins: https://www.amazon.com/Good-Great-Some-Companies-Others/dp/0066620996  Leap Academy: Ready to make the LEAP in your career? There is a NEW way for professionals to Advance Their Careers & Make 5-6 figures of EXTRA INCOME in Record Time. Check out our free training today at leapacademy.com/training

Sahil Bloom was living the "dream" life, climbing the corporate ladder, earning well, and hitting all the career milestones. Yet, he felt unfulfilled. During a conversation with an old friend, he mentioned how he only saw his parents once a year. His friend's blunt remark, "You're going to see your parents 15 more times before they die," hit him hard, forcing him to reevaluate his priorities and reassess his idea of success. In this episode, Sahil joins Ilana to share how to overcome the fear of career transitions, build a life that aligns with your values, and find fulfillment beyond a paycheck. Sahil Bloom is an entrepreneur, investor, and writer focused on redefining wealth beyond money. Through his newsletter, The Curiosity Chronicle, Sahil offers actionable ideas for building a high-performing, healthy, and wealthy life. In this episode, Ilana and Sahil will discuss: (00:00) Introduction  (01:46) The Cost of Chasing Traditional Success (04:33) Family Background and the Pressure to Succeed (08:41) What Baseball Taught Him About Life and Business (13:17) Unfulfillment Despite Corporate Success (18:50) Overcoming the Fear of Career Transition (23:35) Why Personal Growth and Change Can Feel Lonely (26:51) Turning Criticism into Fuel for Growth (29:34) Embracing Life’s Different Seasons (31:55) Writing The Five Types of Wealth (36:55) The Real Challenges in Entrepreneurship (41:24) How to Break Free When You’re Feeling Stuck Sahil Bloom is an entrepreneur, investor, and writer focused on redefining wealth beyond money. He is the author of the New York Times bestselling book The 5 Types of Wealth and the founder of SRB Ventures, an early-stage investment firm. Through his newsletter, The Curiosity Chronicle, Sahil offers actionable ideas for building a high-performing, healthy, and wealthy life. Connect with Sahil: Website: https://www.sahilbloom.com/#Hero  LinkedIn: linkedin.com/in/sahilbloom  Resources Mentioned: Sahil’s Book, The 5 Types of Wealth: A Transformative Guide to Design Your Dream Life: https://www.amazon.com/Types-Wealth-Transformative-Guide-Design/dp/059372318X  Leap Academy: Ready to make the LEAP in your career? There is a NEW way for professionals to Advance Their Careers & Make 5-6 figures of EXTRA INCOME in Record Time. Check out our free training today at leapacademy.com/training

When Christiana Figueres was a young mother, she longed to share her love of nature with her daughters, a love sparked by watching golden toads shimmer like coins under the moonlight in a Costa Rican forest. Hoping to show them this rare beauty, she returned to the same park, only to learn that the species had gone extinct due to rising temperatures. That moment ignited her mission to leave a better planet for her children. In this episode, Christiana joins Ilana to share her journey to becoming a United Nations Climate Change Executive Secretary and leading global climate efforts, including the historic 2015 Paris Agreement. Christiana Figueres is a Costa Rican diplomat and former Executive Secretary of the United Nations Framework Convention on Climate Change (UNFCCC). She is best known for her role in securing the Paris Agreement, a landmark international climate treaty.  In this episode, Ilana and Christiana will discuss: (00:00) Introduction  (01:53) Growing Up as Costa Rica’s President’s Daughter (06:24) The Life-Changing Experience in Rural Costa Rica (15:28) The Journey to Climate Change Advocacy (24:40) Key Lessons from the COP15 Climate Failure (30:45) Becoming UNFCCC Executive Secretary (35:50) Leading the Paris Agreement Negotiations (41:06) Building Trust in Global Climate Negotiations (47:39) Taking the Climate Mission Beyond the UN (51:03) Advice for Aspiring Change-Makers (54:05) Upcoming Projects and Digital Initiatives Christiana Figueres is a Costa Rican diplomat and former Executive Secretary of the United Nations Framework Convention on Climate Change (UNFCCC). She is best known for her role in securing the Paris Agreement, a landmark international climate treaty. With decades of experience in climate diplomacy, Christiana is a passionate global advocate for climate action and sustainable development. She is also the co-founder of Global Optimism, co-host of the Outrage + Optimism podcast, and co-author of The Future We Choose. Connect with Christiana: Christiana’s Website: christianafigueres.com  Christiana’s LinkedIn: linkedin.com/in/christianafigueres  Resources Mentioned: Christiana’s Book, The Future We Choose: Surviving the Climate Crisis: https://www.amazon.com/Future-We-Choose-Surviving-Climate/dp/0525658351  Christiana’s Podcast, Outrage + Optimism: outrageandoptimism.org Global Optimism: globaloptimism.com  Leap Academy: Ready to make the LEAP in your career? There is a NEW way for professionals to Advance Their Careers & Make 5-6 figures of EXTRA INCOME in Record Time. Check out our free training today at leapacademy.com/training

Being scrappy wasn’t just a choice for Gary ‘Vee’ Vaynerchuk; it was his only way forward. After years of growing his family’s wine business, he was left with nothing of his own. With no money to rent an office or hire employees, Gary leveraged his grit, relationships, and opportunities to launch VaynerMedia. Overcoming the financial, mental, and emotional hurdles of entrepreneurship, he built his company into a multi-million-dollar media empire. In this episode, Gary joins Ilana to reveal the mindset and strategies you need to overcome obstacles and build your own multi-million-dollar business. Gary Vaynerchuk, famously known as GaryVee, is a serial entrepreneur, chairman of VaynerX, CEO of VaynerMedia and VeeFriends, and a six-time New York Times bestselling author. Recognized as one of the most forward-thinking minds in business, culture, and the internet, Gary helps brands stay ahead by spotting trends early. In this episode, Ilana and Gary will discuss: (00:00) Introduction  (01:40) VaynerMedia's Scrappy Beginnings (06:56) Why Businesses Fail Financially (10:01) Navigating Tough Business Days (17:21) The Risk of Over-Transparency in Leadership (19:44) Dealing with Failure and Public Ridicule (22:10) GaryVee’s Dream of Owning the New York Jets (26:06) The Role of DNA and Accountability in Success (28:35) Finding Joy in Entrepreneurship (31:02) How to Build a Personal Brand as an Employee (32:30) Empowering Employees with Honest Feedback (34:27) Embracing Change and Executing Relentlessly Gary Vaynerchuk, famously known as GaryVee, is a serial entrepreneur, chairman of VaynerX, CEO of VaynerMedia and VeeFriends, and a six-time New York Times bestselling author. He is a prolific angel investor with early investments in companies like Facebook, Twitter, Tumblr, Venmo, Snapchat, Coinbase, and Uber. Recognized as one of the most forward-thinking minds in business, culture, and the internet, Gary helps brands stay ahead by spotting trends early. Connect with Gary: Gary’s Website: garyvaynerchuk.com  Gary’s LinkedIn: linkedin.com/in/garyvaynerchuk  Resources Mentioned: Gary’s Book, Day Trading Attention: How to Actually Build Brand and Sales in the New Social Media World: https://www.amazon.com/Day-Trading-Attention-Actually-Social/dp/0063317591  GaryVee: From Earning $2 an Hour to Running a $350M Digital Empire: https://podcasts.apple.com/us/podcast/garyvee-from-earning-%242-an-hour-to-running-a/id1701718200?i=1000689595539  Leap Academy: Ready to make the LEAP in your career? There is a NEW way for professionals to Advance Their Careers & Make 5-6 figures of EXTRA INCOME in Record Time. Check out our free training today at leapacademy.com/training

Matt Abrahams's passion for communication was shaped by his parents during his childhood. In the corporate world, he noticed that great ideas often went unheard because people were too anxious to speak up, particularly in high-pressure situations. Realizing that fear, not a lack of ideas, was the barrier to success, Matt made it his mission to help individuals overcome anxiety and communicate with confidence. In this episode, Matt joins Ilana to share his top techniques for managing public speaking anxiety and how you can transition from rambling to speaking with clarity, confidence, and impact. Matt Abrahams is a bestselling author, communication coach, and lecturer at the Stanford Graduate School of Business. He has helped individuals deliver impactful presentations, from IPO roadshows to Nobel Prize speeches, TED Talks, and World Economic Forum sessions. In this episode, Ilana and Matt will discuss: (00:00) Introduction  (01:50) His Path to Becoming a Communication Expert (05:50) Corporate Lessons and the Transition to Teaching (09:36) Mastering Communication as a Teacher (12:54) Understanding and Managing Anxiety (18:19) Matt’s Top Anxiety Management Techniques (23:15) The Keys to His Career Growth and Success (25:11) Turning Mistakes into Business Opportunities (28:49) Navigating Social Media and Feedback (33:29) How to Stop Rambling and Speak with Confidence (36:30) How to Understand and Connect with Your Audience Matt Abrahams is a bestselling author, communication coach, and lecturer at the Stanford Graduate School of Business. He is the author of Speaking Up Without Freaking Out and Think Faster, Talk Smarter, and host of the award-winning Think Fast, Talk Smart podcast. Matt has helped individuals deliver impactful presentations, from IPO roadshows to Nobel Prize speeches, TED Talks, and World Economic Forum sessions. Connect with Matt: Website: fastersmarter.io  LinkedIn: linkedin.com/in/maabrahams  Resources Mentioned: Matt’s Book, Think Faster, Talk Smarter: How to Speak Successfully When You're Put on the Spot: https://www.amazon.com/Think-Faster-Talk-Smarter-Successfully/dp/1668010305  Matt’s Book, Speaking Up without Freaking Out: 50 Techniques for Confident and Compelling Presenting: https://www.amazon.com/Speaking-without-Freaking-Out-Techniques/dp/1465290478  Matt’s Podcast, Think Fast Talk Smart: https://podcasts.apple.com/us/podcast/think-fast-talk-smart-communication-techniques/id1494989268  Leap Academy: Ready to make the LEAP in your career? There is a NEW way for professionals to Advance Their Careers & Make 5-6 figures of EXTRA INCOME in Record Time. Check out our free training today at leapacademy.com/training

As a teenager performing on New York’s streets and parks, Adam Met never imagined selling out arenas nationwide. Alongside his brothers Jack and Ryan, he formed the band AJR, playing for hours each summer while learning to capture the attention of indifferent passersby. A single tweet to Sia changed everything, launching their breakthrough. Balancing music with demanding academic work and nonprofit leadership, Adam mastered the art of building an engaged fan base that is driven to action. In this episode, Adam joins Ilana to share insights from his new book, Amplify, which blends his experiences in music and climate advocacy to inspire community building across various fields. Adam Met is a musician, climate advocate, educator, and member of the multiplatinum band AJR. He is the Executive Director of Planet Reimagined, a nonprofit leveraging media and strategic advocacy to mobilize climate action. In this episode, Ilana and Adam will discuss: (00:00) Introduction  (01:51) Early Musical Influences and Street Performances (04:04) Coping with Rejection as a Child Performer (05:52) Attracting an Audience While Embracing Nerves (09:30) How One Tweet to Sia Changed AJR’s Career (13:01) Why “I’m Ready” Became a Smash Hit (16:58) Overcoming the Fear of Being a One-Hit Wonder (21:29) The Innovative Strategies Behind AJR’s Success (26:56) Two Key Tactics to Build an Engaged Fan Base (28:48) The Birth of Adam’s Debut Book, Amplify (31:28) How Adam Merges Music and Climate Advocacy (34:21) Adapting Quickly: The Drive-In Concert Pivot (39:21) Funding Climate Action Through Bipartisan Support Adam Met is a musician, climate advocate, educator, and member of the multiplatinum band AJR. He is the Executive Director of Planet Reimagined, a nonprofit using media and strategic advocacy to mobilize climate action. Adam works closely with Congress and the White House to promote renewable energy and serves as a sustainability advocate for the United Nations Development Programme. In recognition of his efforts, Adam received the 2024 TIME Earth Award and was named a New York Times Changemaker. Connect with Adam: Adam’s Website: adammet.net  Adam’s LinkedIn: linkedin.com/in/adam-met-38274379  Resources Mentioned: Adam’s Book, Amplify: How to Use the Power of Connection to Engage, Take Action, and Build a Better World: https://www.amazon.com/Amplify-Connection-Engage-Action-Better/dp/0593735900  Planet Reimagined: planetreimagined.com  Leap Academy: Ready to make the LEAP in your career? There is a NEW way for professionals to Advance Their Careers & Make 5-6 figures of EXTRA INCOME in Record Time. Check out our free training today at leapacademy.com/training

Kass and Mike Lazerow’s entrepreneurial journey began with a leap of faith and a lot of grit. They started Golf.com with funding from friends and family, only to be acquired by a company that later went bankrupt. Forced to raise capital and revive their business against all odds, they quickly learned that entrepreneurship means facing setbacks every day and building the resilience to keep going when it feels impossible. In this episode, Kass and Mike join Ilana to dive into their new book, Shoveling $h!t, sharing the struggles behind their wins, the fears they confronted, and how they built successful businesses while balancing parenthood, marriage, and health challenges. Kass and Mike Lazerow are serial entrepreneurs, investors, and co-founders of Golf.com and Buddy Media. After selling Golf.com to Time Warner, they co-founded Buddy Media, a leading social media marketing platform that was acquired by Salesforce for $745 million. In this episode, Ilana, Kass, and Mike will discuss: (00:00) Introduction  (00:35) Meeting and Collaborating with GaryVee (03:20) Childhood Challenges and Family Struggles (09:43) Early Ventures and the Birth of Golf.com (13:40) Kass and Mike’s Relationship Journey (18:20) Facing Near Bankruptcy After Acquisition Offers (23:02) Leading with Transparency in Crisis (26:08) Fundraising Success and Tiger Woods's Influence (28:44) Navigating Parenthood While Building a Business (35:33) Prioritizing Health Amid Career Demands (39:38) Breaking Gender Bias in Entrepreneurship (43:57) Building a Thick Skin as an Entrepreneur (47:31) Overcoming Fear and Taking Action Kass and Mike Lazerow are serial entrepreneurs, investors, and co-founders of Golf.com and Buddy Media. After selling Golf.com to Time Warner, they co-founded Buddy Media, a leading social media marketing platform that was acquired by Salesforce for $745 million. Together, Mike and Kass have supported nearly 100 early-stage startup founders and have received multiple awards recognizing their leadership and impact in entrepreneurship and philanthropy. Connect with Kass and Mike: Kass and Mike’s Website: www.kassandmike.com  Kass and Mike’s Email: info@kassandmike.com    Resources Mentioned: Kass and Mike Book, Shoveling $H!t: A Love Story about the Entrepreneur's Messy Path to Success: https://www.amazon.in/Shoveling-Story-about-Entrepreneurs-Success/dp/B0DY21NS7W  Leap Academy: Ready to make the LEAP in your career? There is a NEW way for professionals to Advance Their Careers & Make 5-6 figures of EXTRA INCOME in Record Time. Check out our free training today at leapacademy.com/training

Bonnie Hammer’s passion for photography and storytelling led her to an internship on a TV production set, but instead of a glamorous role, her first job involved cleaning up dog poop. Despite these humble beginnings, Bonnie’s curiosity, strong work ethic, and willingness to tackle any task helped her rise through the ranks at NBC Universal, eventually becoming vice chairman and a powerhouse in the cable industry In this episode, Bonnie shares how her ability to learn, embrace opportunities, and adapt to change shaped her success, and how tough mentors and tough love played crucial roles in her career growth. Bonnie Hammer is an author, businesswoman, and media executive. She served as vice chair of NBCUniversal, where she spent decades transforming the television industry. Under her leadership, the company’s cable group and studios achieved record profits, garnered 167 Emmy nominations, and launched hundreds of hit series, including Suits.  In this episode, Ilana and Bonnie will discuss: (00:00) Introduction  (01:58) From Photography Passion to TV Career Launch (10:11) Embracing Career Growth Opportunities (16:46) The Impact of Mentorship on Her Career (22:06) Tough Love as a Driver for Success (29:44) Bonnie’s Key to Overcoming Imposter Syndrome (31:52) How to Thrive During Organizational Changes (34:29) Transforming Career Setbacks into Opportunities (40:16) How to Communicate Your Professional Value (43:16) The Power of Hunger and Resilience (46:34) Turning Small Opportunities into Big Breaks (51:05) Redefining Success on Your Own Terms Bonnie Hammer is an author, businesswoman, and media executive. She served as vice chair of NBCUniversal, where she spent decades transforming the television industry. Under her leadership, the company’s cable group and studios achieved record profits, garnered 167 Emmy nominations, and launched hundreds of hit series, including Suits. Bonnie was named “the Queen of Cable” by The New York Times and hailed as “the most powerful woman in entertainment” by The Hollywood Reporter. Resources Mentioned: Bonnie’s Book, 15 Lies Women Are Told at Work: …And the Truth We Need to Succeed: https://www.amazon.com/Lies-Women-Are-Told-Work/dp/1668027615  Leap Academy: Ready to make the LEAP in your career? There is a NEW way for professionals to Advance Their Careers & Make 5-6 figures of EXTRA INCOME in Record Time. Check out our free training today at leapacademy.com/training

In 2016, former Fox News host Gretchen Carlson made a bold move that transformed the conversation around workplace harassment. After enduring years of mistreatment, she filed a lawsuit against Fox News Chairman Roger Ailes for sexual harassment. Despite the immense personal and professional risks, this courageous act helped spark the #MeToo movement, giving a voice to countless women who had suffered in silence. Now, through her nonprofit, Gretchen is working to dismantle the silencing mechanisms that allow harassment to thrive in the workplace. In this episode, Gretchen joins Ilana to share how her painful experiences fueled her mission to create safer, more inclusive environments for all. Gretchen Carlson is a journalist, author, and women’s rights advocate. As the co-founder of Lift Our Voices, a nonprofit combating forced arbitration and toxic workplace environments, her advocacy has led to significant legislative changes. In this episode, Ilana and Gretchen will discuss: (00:00) Introduction  (02:15) The Decision to File a Sexual Harassment Lawsuit (04:42) Why Most Victims Struggle to Speak Out (11:40) The Role of a Support System in Tough Times (15:19) Learning to Advocate for Herself as a Child (17:57) From Violin Prodigy to Miss America (23:37) Building a Thick Skin as Miss America (26:47) Facing Sexual Assault Early in Her Career (30:00) How to Foster Safe and Inclusive Workplaces (37:11) Balancing Ambition, Family, and Career in TV (42:19) Creating Change Through Reforms and Advocacy (48:24) Overcoming Rejection in Nonprofits Gretchen Carlson is a journalist, author, and women’s rights advocate. As the co-founder of Lift Our Voices, a nonprofit combating forced arbitration and toxic workplace environments, her advocacy has led to significant legislative changes, including the Ending Forced Arbitration of Sexual Assault and Sexual Harassment Act. The bestselling author of Getting Real and Be Fierce, Gretchen was named one of Time magazine’s 100 Most Influential People in 2017. Connect with Gretchen: Gretchen’s Website: gretchencarlson.com  Gretchen’s LinkedIn: linkedin.com/in/gretchen-carlson  Resources Mentioned: Gretchen’s Book, Getting Real:  https://www.amazon.com/Getting-Real-Gretchen-Carlson/dp/0143109243  Gretchen’s Book, Be Fierce: Stop Harassment and Take Your Power Back: https://www.amazon.com/Be-Fierce-Stop-Harassment-Power/dp/1478992174  Lift Our Voices: liftourvoices.org  Leap Academy: Ready to make the LEAP in your career? There is a NEW way for professionals to Advance Their Careers & Make 5-6 figures of EXTRA INCOME in Record Time. Check out our free training today at leapacademy.com/training

Tim O'Reilly’s entrepreneurial journey began with odd jobs like being a janitor, cemetery caretaker, and dishwasher. With just $500, he founded O'Reilly Media, initially focusing on publishing tech manuals. After a major setback during the dot-com bust, which saw revenue drop by $20 million, Tim continued building his business and creating a huge impact in the tech world. His work with Web 2.0 and open-source technologies like Linux and Perl helped position O'Reilly Media as a key player in the internet’s evolution. In this episode, Tim shares how he built O'Reilly Media from the ground up, navigated industry shifts, and why focusing on value is essential for long-term business success. Tim O'Reilly is an entrepreneur, author, and the founder of O'Reilly Media, a leading tech publishing company known for its groundbreaking books, conferences, and online learning platforms. In this episode, Ilana and Tim will discuss: (00:00) Introduction  (02:29) Growing Up with Poor Vision and a Love for Books (03:53) Building O'Reilly Media with Just $500 (07:07) Leadership Lessons from the Dot-Com Crash (11:32) How Web 2.0 and Open Source Transformed the Web (19:27) The Problem with Silicon Valley’s Business Model (26:15) Scaling a Business with Limited Resources (31:11) AI and the Future of Programming (35:11) Tim’s Key Lessons in Entrepreneurship (37:47) Why Every Business Should Prioritize Value Tim O'Reilly is an entrepreneur, author, and the founder of O'Reilly Media, a leading tech publishing company known for its groundbreaking books, conferences, and online learning platforms. A key figure in the evolution of the internet, Tim played a major role in popularizing tech concepts such as open-source software and Web 2.0. He has been a strong advocate for ethical technology and continues to explore the future of AI, programming, and innovation. Connect with Tim: Tim’s Website: oreilly.com  Tim’s LinkedIn: linkedin.com/in/timo3  Resources Mentioned: The Whole Internet User's Guide & Catalog by Ed Krol: https://www.amazon.com/Whole-Internet-Users-Guide-Catalog/dp/1565920635  Sailing Alone Around the World by Joshua Slocum: https://www.amazon.com/Sailing-Alone-Around-Joshua-Slocum/dp/0486203263  Dune Mass Market by Frank Herbert: https://www.amazon.com/Dune-Frank-Herbert/dp/0441172717  The Golden Warrior, the Story of Harold and William, a Novel of the Norman Conquest by Hope Muntz: https://www.amazon.com/Golden-Warrior-Harold-William-Conquest/dp/B001DA6IKC  Leap Academy: Ready to make the LEAP in your career? There is a NEW way for professionals to Advance Their Careers & Make 5-6 figures of EXTRA INCOME in Record Time. Check out our free training today at leapacademy.com/training

As a curious eight-year-old, Adva Amir was mesmerized by the cockpit during a family trip, sparking a lifelong dream of becoming a pilot. After failing to become a military pilot in Israel, Adva felt broken. Shifting her mindset and picking up the pieces, she moved to the U.S. to pursue civilian flight training. Despite language barriers, naysayers, and grueling hours, she broke into this male-dominated field and became one of the few female airline captains in the world. In this episode, Adva joins Ilana to share insights on chasing your dream, even when the odds are stacked against you. Adva Amir is a commercial airline pilot, TEDx speaker, and LinkedIn Top Voice. Recognized by the National Business Aviation Association as one of the top 40 most influential people in aviation, Adva actively advocates for diversity and inclusion while mentoring aspiring pilots. In this episode, Ilana and Adva will discuss: (00:00) Introduction  (01:54) Her Childhood Fascination with Flying (03:16) Failing to Become a Military Pilot (05:51) Leading a Military Unit at 19 Years Old (07:15) Moving to the U.S. for Flight Training (12:06) The Challenging Path to Becoming a Pilot (17:15) Landing First Airline Job Amid COVID-19 (20:11) Breaking Barriers and Expectations in Aviation (23:06) Adva’s Viral LinkedIn Post Inspiring Millions (26:50) Adjusting to Long-Haul Flights with Hawaiian Airlines (30:34) Discovering a Passion for Surfing (36:54) Competing in the Maccabiah Games (39:01) Pursuing Dreams Despite Naysayers Adva Amir is a commercial airline pilot, TEDx speaker, and LinkedIn Top Voice. While at SkyWest Airlines, she became one of the few female airline captains, breaking barriers and inspiring others. Currently at Hawaiian Airlines, she flies long-haul routes as a First Officer. Recognized by the National Business Aviation Association as one of the top 40 most influential people in aviation, Adva actively advocates for diversity and inclusion while mentoring aspiring pilots. Connect with Adva: Adva’s Website: advamir.com  Adva’s LinkedIn: linkedin.com/in/adva-amir-3bb2a6136  Leap Academy: Ready to make the LEAP in your career? There is a NEW way for professionals to Advance Their Careers & Make 5-6 figures of EXTRA INCOME in Record Time. Check out our free training today at leapacademy.com/training

Brian Keane’s journey is a powerful example of embracing change and conquering fear. Originally a primary school teacher in London, Brian realized teaching wasn’t his true calling and made a bold leap into fitness, despite doubts from family and peers. With his mom’s support, he overcame numerous challenges to become a three-time bestselling author, certified strength and conditioning coach, and ultra-marathon runner. In this episode, Brian joins Ilana to share how he tackled fear, turned his career around, and undertook the most daring endurance challenges, including running through the Sahara Desert and the Arctic. Brian Keane is a bestselling author, online fitness coach, and nutritionist. He is the founder of Brian Keane Fitness, where he helps clients transform their bodies and mindset for the long term, and the host of The Brian Keane Podcast, one of Ireland and the UK’s top health podcasts. In this episode, Ilana and Brian will discuss: (00:00) Introduction  (02:02) From Teaching to Full-Time Fitness (09:17) Crushing the Fear of Failure in Career Transitions (12:31) Navigating Burnout While Building a Fitness Career (18:22) Balancing Passion with Business Skills (23:40) The Power of Mindset in Achieving Success (30:57) The Framework for Building Sustainable Habits (35:39) How to Overcome Comparison and Stay Focused (43:12) Tackling Ultra Marathons and Extreme Challenges (52:00) Learning from Setbacks and Building Resilience (1:00:00) Embracing Change and Taking Action Brian Keane is a bestselling author, online fitness coach, and nutritionist. He is the founder of Brian Keane Fitness, where he helps clients transform their bodies and mindset for the long term, and the host of The Brian Keane Podcast, one of Ireland and the UK’s top health podcasts. As an ultra-endurance athlete, Brian has completed several challenging races, including six back-to-back marathons through the Sahara Desert, a 230 km race through the Arctic Circle, and has also led an expedition to the summit of Mount Kilimanjaro. Connect with Brian: Brian’s Website: briankeanefitness.com  Brian’s Instagram: instagram.com/brian_keane_fitness  Resources Mentioned: Brian’s Book, The Fitness Mindset: Eat for Energy, Train for Tension, Manage Your Mindset, Reap the Results: https://www.amazon.com/Fitness-Mindset-tension-mindset-results/dp/1781332525  Brian’s Book, Rewriting Your Story: Seven Habits to Help You Reclaim Your Power, Let Go of Fear, and Change the Narratives That Hold You Back: https://www.amazon.co.uk/REWRITING-YOUR-STORY-RECLAIM-NARRATIVES/dp/B0DWB1ZSL3  Brian’s Book, Rewire Your Mindset: Own Your Thinking, Control Your Actions, Change Your Life: https://www.amazon.com/Rewire-Your-Mindset-Thinking-Control/dp/1781334234  The Power of Habit: Why We Do What We Do in Life and Business Paperback by Charles Duhigg: https://www.amazon.com/Power-Habit-What-Life-Business/dp/081298160X Atomic Habits: An Easy & Proven Way to Build Good Habits & Break Bad Ones by James Clear: https://www.amazon.com/Atomic-Habits-Proven-Build-Break/dp/0735211299  Leap Academy: Ready to make the LEAP in your career? There is a NEW way for professionals to Advance Their Careers & Make 5-6 figures of EXTRA INCOME in Record Time. Check out our free training today at leapacademy.com/training

Tony Khan was captivated by sports and wrestling from a young age. After immersing himself in sports analytics, he joined his father’s ventures, using his expertise to build a data-driven team at the Jacksonville Jaguars. Witnessing Fulham’s struggles, Tony saw an opportunity to apply his skills to improve the team and took it. His passion for wrestling ultimately led him to launch All Elite Wrestling (AEW). Despite initial skepticism, Tony’s vision and perseverance allowed AEW to thrive, becoming a major disruptor in the wrestling world. In this episode, Tony joins Ilana to share the power of taking bold actions and seizing opportunities. Tony Khan is the founder, president, and CEO of All Elite Wrestling (AEW), a leading professional wrestling promotion. He also holds executive roles with the Jacksonville Jaguars in the NFL and Fulham F.C. in the English Premier League. In this episode, Ilana and Tony will discuss: (00:00) Introduction  (01:56) His Early Passion for Sports and Wrestling (04:52) Shifting from Engineering to Finance (08:35) Building a Data-Driven Sports Team at the Jaguars (14:24) Overcoming Setbacks at Fulham FC (18:41) The Birth of All Elite Wrestling (AEW) (22:22) Earning Trust and Disrupting the Wrestling World (28:55) Navigating AEW Through the Pandemic (35:53) Acquiring Ring of Honor to Preserve Its Legacy (38:21) Honoring Wrestling Legends and Their Impact (41:10) Thriving in a Highly Competitive Industry (43:03) The Key to Breaking into Media and Entertainment (46:36) Making the Most of Opportunities in Life Tony Khan is the founder, president, and CEO of All Elite Wrestling (AEW), a leading professional wrestling promotion. He also holds executive roles with the Jacksonville Jaguars in the NFL and Fulham F.C. in the English Premier League. With a background in finance and sports analytics, Tony has revolutionized the business of sports entertainment, positioning AEW as a major competitor to WWE. He was awarded "Promoter of the Year" and "Best Booker" by the Wrestling Observer Newsletter for three consecutive years. Connect with Tony: Tony’s Instagram: instagram.com/tonyrkhan  Leap Academy: Ready to make the LEAP in your career? There is a NEW way for professionals to Advance Their Careers & Make 5-6 figures of EXTRA INCOME in Record Time. Check out our free training today at leapacademy.com/training

Tim Storey grew up facing financial struggles, family instability, and a devastating loss at a young age. When his father tragically passed away in a car accident, it could have broken him. Instead, Tim leaned on his family for support and drew strength from his faith and community. This resilience led him to become a life coach, eventually earning the title of "comeback coach" for stars like Robert Downey Jr., Charlie Sheen, and Grant Cardone. In this episode, Tim joins Ilana to share the pivotal moments that shaped his life, the power of maintaining a "miracle mentality," and the role of resilience, discipline, and consistency in achieving success. Tim Storey is a life coach, motivational speaker, and bestselling author, known as the "Original Comeback Coach." With over three decades of experience, he has helped individuals, including high-profile clients, turn setbacks into comebacks.  In this episode, Ilana and Tim will discuss: (00:00) Introduction  (02:00) Growing Up in a Challenging Childhood (03:56) Coping with Tragedy and Finding Strength (07:54) How Mentors and Teachers Shaped His Life (13:34) Building His Own Path to Success (18:46) The Mindset to Overcome Life’s Challenges (20:39) Understanding the Miracle Mentality (22:29) Thriving in the Age of Digital Overload (25:48) Pushing Through Pain to Achieve Success (31:29) How to Create Opportunities and Get Results (34:07) The Power of Living in the Moment Tim Storey is a life coach, motivational speaker, and bestselling author, known as the "Original Comeback Coach." With over three decades of experience, he has helped individuals, including high-profile clients, turn setbacks into comebacks. Tim is the author of several bestselling books, including The Miracle Mentality, and has spoken in 78 countries, reaching millions through his books, keynotes, and media appearances. Connect with Tim: Tim’s Website: timstorey.com  Tim’s Instagram: instagram.com/timstoreyofficial  Resources Mentioned: Tim’s Book, The Miracle Mentality: Tap into the Source of Magical Transformation in Your Life: https://www.amazon.com/Miracle-Mentality-Source-Magical-Transformation/dp/0785236724  The Agony and the Ecstasy: A Biographical Novel of Michelangelo by Irvin Stone: https://www.amazon.com/Agony-Ecstasy-Biographical-Novel-Michelangelo/dp/0451171357 Leap Academy: Ready to make the LEAP in your career? There is a NEW way for professionals to Advance Their Careers & Make 5-6 figures of EXTRA INCOME in Record Time. Check out our free training today at leapacademy.com/training

Bernard Hampton’s journey from modest beginnings to Managing Director and The Head of The Academy at Bank of America is a testament to hard work, learning, and leadership. Raised in a middle-class family with a strong work ethic, Bernard’s early experiences shaped his leadership approach. From his start as a sales associate at RadioShack to leading over a thousand employees globally at Bank of America, he has always believed in the power of people and emotional intelligence. In this episode, Bernard shares strategies for transitioning into leadership, navigating crises, and the power of continuous learning in career growth. Bernard Hampton is a Managing Director and The Head of The Academy at Bank of America, where he leads global employee training and development initiatives for over 200,000 employees. In this episode, Ilana and Bernard will discuss: (00:00) Introduction  (01:39) Early Experiences That Shaped His Leadership (07:17) Joining Bank of America (09:02) Leading Through Crisis and Uncertainty (12:42) Four Keys to Stronger Team Dynamics (19:31) The Power of Origin Stories in Leadership (24:15) Leading Talent Development at Bank of America (30:07) The Value of Career Mentors and Sponsors (33:40) Building a Culture of Learning and Growth (38:10) Empowering Your Community as a Leader (39:45) Four Steps to Unlock Your Leadership Potential (45:30) Balancing Leadership with Personal Life Bernard Hampton is a Managing Director and The Head of The Academy at Bank of America, where he leads global employee training and development initiatives for over 200,000 employees. He is also a member of Leadership Florida's Executive Class 12 and serves on the Board of Directors for the Urban League of Palm Beach County, contributing to efforts that promote economic growth and community development. Connect with Bernard: Bernard’s LinkedIn: linkedin.com/in/bernardfhampton  Resources Mentioned: Bank of America: bankofamerica.com  The Academy: https://careers.bankofamerica.com/en-us/career-development/the-academy  Do Hard Things: Why We Get Resilience Wrong and the Surprising Science of Real Toughness by Steve Magness: https://www.amazon.com/Hard-Things-Resilience-Surprising-Toughness/dp/006309861X  Leap Academy: Ready to make the LEAP in your career? There is a NEW way for professionals to Advance Their Careers & Make 5-6 figures of EXTRA INCOME in Record Time. Check out our free training today at leapacademy.com/training

Mo Gawdat was thriving in his career as Chief Business Officer at Google X, enjoying wealth, success, and a loving family. However, his life took a dramatic turn after the tragic loss of his son, Ali. This loss made Mo realize that happiness isn’t defined by external factors but by how we perceive and navigate life’s challenges. Letting go of everything that once defined success, including his career, Mo reinvented himself as an advocate for happiness, dedicating his life to helping others live with less stress and more joy. In this episode, Mo joins Ilana to share how he transformed his life after tragedy and reveals his formula for finding happiness, managing stress, and creating lasting fulfillment. Mo Gawdat is an Egyptian entrepreneur, four-time bestselling author, and former Chief Business Officer at Google X. He founded the mission #OneBillionHappy, dedicated to helping others lead happier lives. In this episode, Ilana and Mo will discuss: (00:00) Introduction  (02:07) Growing up in Egypt with a Passion for Tech (05:38) Coding and Landing a Job at IBM (11:02) Building Trust and Success in Sales (16:14) Struggling with Happiness Despite Success (21:35) Discovering the Algorithm of Happiness (27:02) The Devastating Loss of His Son (33:01) Turning Grief Into a Global Mission of Happiness (40:00) Leaving Google in Pursuit of True Fulfillment (46:47) Understanding and Managing Stress (01:00:24) Why Life is Like a Video Game Mo Gawdat is an Egyptian entrepreneur, four-time bestselling author, and former Chief Business Officer at Google X. With a background in engineering and over 30 years in the tech industry, he has held leadership roles at IBM, NCR, Microsoft, and Google, where he helped launch operations in over 50 countries. Mo developed a formula for happiness, which he shares in his book Solve for Happy, and founded the mission #OneBillionHappy, dedicated to helping others lead happier lives. Connect with Mo: Mo’s Website: mogawdat.com  Mo’s LinkedIn: linkedin.com/in/mogawdat  Mo’s Substack: substack.com/@mogawdat  Resources Mentioned: Mo’s Book, Solve for Happy: Engineer Your Path to Joy: https://www.amazon.com/Solve-Happy-Engineer-Your-Path/dp/1501157558  Mo’s Book, Unstressable: A Practical Guide to Stress-Free Living: https://www.amazon.com/Unstressable-Practical-Guide-Stress-Free-Living/dp/1035022729 Mo’s Book, That Little Voice In Your Head: Adjust the Code That Runs Your Brain: https://www.amazon.com/That-Little-Voice-Your-Head/dp/152906614X  Mo’s Book, Scary Smart: The Future of Artificial Intelligence and How You Can Save Our World: https://www.amazon.com/Scary-Smart-Future-Artificial-Intelligence/dp/1529077621 Leap Academy: Ready to make the LEAP in your career? There is a NEW way for professionals to Advance Their Careers & Make 5-6 figures of EXTRA INCOME in Record Time. Check out our free training today at leapacademy.com/training

James Currier was born an entrepreneur. Before turning 18, he had launched 18 businesses. After years in corporate jobs, he fully embraced his entrepreneurial calling. He co-founded Tickle, one of the internet’s first successful user-generated platforms, which grew to 150 million users before being acquired by Monster.com for $110 million. Now, as a founding partner at NFX, he invests in high-growth startups leveraging network effects. In this episode, James joins Ilana to discuss the power of network effects in scaling businesses, the key traits of great founders, and how to spot technology windows for timely investments. James Currier is a five-time founder, angel investor in DoorDash, Lyft, and Patreon, and a founding partner at NFX, an early-stage venture capital firm. He is an expert in building high-growth companies that leverage network effects.  In this episode, Ilana and James will discuss: (00:00) Introduction  (00:27) Embracing Entrepreneurship from a Young Age (04:35) From Corporate Jobs to Building His First Startup (08:45) Navigating Rejections and the Dot-Com Crash (12:24) Understanding Viral vs. Network Effects (19:12) The Reality of Running Multiple Startups  (21:26) Why Attempting to Fix Healthcare Was a Mistake (27:10) Building NFX into a Leading Venture Firm (31:58) Balancing Optimism and Risk in Investing (35:16) The Key Traits that Make a Great Founder (37:45) What It Takes to Be a Successful Entrepreneur (40:33) The Role of Technology Windows in Startup Success James Currier is a five-time founder, angel investor in DoorDash, Lyft, and Patreon, and a founding partner at NFX, an early-stage venture capital firm. He co-founded Tickle, one of the internet’s first successful user-generated companies, which was acquired by Monster.com. James also co-founded Wonderhill (merged with Kabam), IronPearl (acquired by PayPal), and Jiff (merged with Castlight). He is an expert in building high-growth companies that leverage network effects.  Connect with James: James’s Website: nfx.com James’s LinkedIn: linkedin.com/in/jamescurrier  Resources Mentioned: NFX Article, Viral Effects Are Not Network Effects: https://www.nfx.com/post/viral-effects-vs-network-effects  NFX Article, Technology Windows: The Unseen Force Driving Your Startup: https://www.nfx.com/post/technology-windows NFX Article, How “Venture Capital 3.0” Impacts Founders in the AI Age: https://www.nfx.com/post/venture-capital-3  Leap Academy: Ready to make the LEAP in your career? There is a NEW way for professionals to Advance Their Careers & Make 5-6 figures of EXTRA INCOME in Record Time. Check out our free training today at leapacademy.com/training

After studying law, Daniel Pink transitioned into politics, serving as the chief speechwriter for Vice President Al Gore. However, he soon felt unfulfilled and realized his true calling wasn’t in a structured career with defined rules, but in writing. Despite the uncertainty, he made the leap, leaving politics behind to pursue writing full-time. This decision led to multiple bestselling books, including his latest, The Power of Regret. In this episode, Daniel joins Ilana to discuss how embracing regret, rather than avoiding it, leads to profound growth and how we can turn our past decisions into catalysts for a better future. Daniel Pink is a bestselling author and speaker known for his work on business, work, and human behavior. His books have been translated into 46 languages and have sold millions of copies worldwide. In this episode, Ilana and Daniel will discuss: (00:00) Introduction  (01:51) Growing Up with a Love for Books (06:13) Transitioning from Law School to Politics (09:49) Becoming a Speechwriter for Vice President Al Gore (12:24) Why He Chose a Career in Writing Over Politics (16:07) From Struggling Writer to Bestselling Author (18:06) Uncovering the Key to Human Motivation (21:55) The Science of Timing and the Midpoint Slump (26:43) Embracing Regret as a Catalyst for Growth (30:21) The Four Types of Regret and Their Impact (34:59) Turning Regret Into Action and Growth (40:08) Daniel’s Motivation for Writing Books (42:04) The Power of Ignoring What Others Think Daniel Pink is a bestselling author and speaker known for his work on business, work, and human behavior. Before becoming a full-time author, he held several positions in politics and government, including serving as the chief speechwriter for Vice President Al Gore. Daniel has since written seven New York Times bestsellers, including Drive, When, and his latest, The Power of Regret. His books have been translated into 46 languages and have sold millions of copies worldwide. Connect with Daniel: Daniel’s Website: danpink.com  Daniel’s LinkedIn: linkedin.com/in/danielpink  Resources Mentioned: Daniel’s Book, The Power of Regret: How Looking Backward Moves Us Forward: https://www.amazon.com/Power-Regret-Looking-Backward-Forward/dp/B098VRLZ2H  Daniel’s Book, A Whole New Mind: Why Right-Brainers Will Rule the Future: https://www.amazon.com/Whole-New-Mind-Right-Brainers-Future/dp/1594481717 Daniel’s Book, When: The Scientific Secrets of Perfect Timing: https://www.amazon.com/When-Scientific-Secrets-Perfect-Timing/dp/B076MBR89W Daniel’s Book, Drive: The Surprising Truth About What Motivates Us: https://www.amazon.com/Drive-Surprising-Truth-About-Motivates/dp/B0032COUMC Leap Academy: Ready to make the LEAP in your career? There is a NEW way for professionals to Advance Their Careers & Make 5-6 figures of EXTRA INCOME in Record Time. Check out our free training today at leapacademy.com/training

Dr. John Demartini’s childhood was marked by major obstacles, from a severe speech impediment and dyslexia to a rough start in school. Told that he would never read, write, or communicate, he defied the odds. At age 13, he left home and embarked on a journey that would take him from street life to a global career as a human behavior specialist and entrepreneur. In this episode, John joins Ilana to share how he turned adversity into fuel for success, the mindset that led him to create the Demartini Institute, and how he overcame his learning disabilities to become one of the world’s most influential speakers. Dr. John Demartini is a human behavior expert, researcher, author, and founder of the Demartini Institute. He has studied over 30,000 books, written more than 40, and shared his knowledge in 161 countries. In this episode, Ilana and John will discuss: (00:00) Introduction  (01:48) Early Life Struggles and Dyslexia (04:47) Surviving on the Streets as a Teenager (08:26) Finding Purpose After a Near-Death Experience (12:10) Overcoming Learning Challenges (18:28) Discovering His Passion for Teaching (31:34) Leveraging Personal Values for Success (34:01) Turning Fear into a Business Ally (38:00) Adapting to Market Shifts (41:30) The Key to Charging What You’re Worth (49:56) Living Life by Design, Not Duty Dr. John Demartini is a human behavior expert, researcher, author, and founder of the Demartini Institute. With over 40 years of research, he has developed methodologies to help individuals unlock their potential by understanding their values. Despite being diagnosed with dyslexia at an early age, John overcame this challenge, turning it into a driving force. He has studied over 30,000 books, written more than 40, and shared his knowledge in 161 countries. Connect with John: John’s Website: https://drdemartini.com  John’s LinkedIn: linkedin.com/in/drjohndemartini   Resources Mentioned: The Time Trap: The Classic Book on Time Management by Alec Mackenzie: https://www.amazon.com/Time-Trap-Classic-Book-Management/dp/0814413382  Leap Academy: Ready to make the LEAP in your career? There is a NEW way for professionals to Advance Their Careers & Make 5-6 figures of EXTRA INCOME in Record Time. Check out our free training today at leapacademy.com/training

As a shy kid, Alex Carter struggled to speak up for herself. Her parents’ divorce sparked her interest in advocacy and mediation, which led her to pursue a law degree. Despite facing self-doubt early in her career, Alex bet on herself and built a career as a Columbia Law professor and renowned negotiation expert. Now, she helps others find their voice, advocate for themselves, and unlock career success. In this episode, Alex joins Ilana to share actionable strategies for negotiating with confidence, landing promotions, charging your worth, and scaling a business. Alex Carter is a negotiation expert, Columbia Law professor, and bestselling author. She specializes in helping professionals and entrepreneurs build the confidence to negotiate effectively in high-stakes situations. In this episode, Ilana and Alex will discuss: (00:00) Introduction  (01:49) Finding Her Voice and Building Confidence (06:56) Pursuing a Career in Law and Mediation (10:52) Betting on Yourself Despite Self-Doubt (14:25) The Power of Negotiating for Yourself (19:48) How to Secure Your First Big Client (24:39) Negotiating Your Way to Career Success (30:41) Key Steps in Preparing for a Negotiation (39:36) Face-to-Face vs. Email Negotiations (41:44) Negotiating Across Cultures (43:06) Practical Solutions to Business Challenges (45:52) How to Scale by Leveraging Your Time Alex Carter is a negotiation expert, Columbia Law professor, and bestselling author. She specializes in helping professionals and entrepreneurs build the confidence to negotiate effectively in high-stakes situations. With a background in law and mediation, Alex teaches practical strategies for securing promotions, landing clients, and navigating complex negotiations. Her work empowers individuals to advocate for themselves and achieve career success. Connect with Alex: Alex’s Website: alexcarterasks.com  Alex’s LinkedIn: linkedin.com/in/alexandrabcarter  Resources Mentioned: Alex’s Book, Ask for More: 10 Questions to Negotiate Anything: https://www.amazon.com/Ask-More-Questions-Negotiate-Anything/dp/1982130482  Leap Academy: Ready to make the LEAP in your career? There is a NEW way for professionals to Advance Their Careers & Make 5-6 figures of EXTRA INCOME in Record Time. Check out our free training today at leapacademy.com/training

Chemi Peres’s journey to success was shaped by both professional challenges and personal loss. After losing his job, he felt humiliated and vowed never to face such a setback again. He pivoted to venture capitalism, co-founding Pitango Venture Capital, Israel’s largest venture fund. Despite his success, Chemi experienced the profound losses of both his father and son. These tragedies fueled his drive to honor their legacies through innovation. In this episode, Chemi joins Ilana to share how he navigated grief and adversity, transforming these experiences into a force for lasting impact. Chemi Peres is the co-founder and managing partner of Pitango Venture Capital, Israel’s largest venture fund, which has invested in over 250 startups. He is also the Chairman of the Peres Center for Peace and Innovation, a non-profit dedicated to advancing peace and technology in the Middle East. In this episode, Ilana and Chemi will discuss: (00:00) Introduction  (02:00) Growing Up in a Political Legacy (05:21) The Challenges in Becoming a Combat Pilot (07:59) Lessons from the Israeli Defense Forces (11:59) Transitioning to Aerospace and Career Setback (20:13) Entering the Venture Capital World (27:01) Building Israel's Venture Ecosystem (31:14) Navigating Challenges in Venture Capital (34:52) Turning Personal Loss into a Legacy of Innovation (41:27) Healing by Honoring a Loved One’s Dreams (49:34) How the Peres Center is Shaping Israel’s Future Chemi Peres is the co-founder and managing partner of Pitango Venture Capital, Israel’s largest venture fund, which has invested in over 250 startups. As the son of former Israeli Prime Minister Shimon Peres, Chemi continues his father's legacy by promoting innovation and entrepreneurship. He is also the Chairman of the Peres Center for Peace and Innovation, a non-profit dedicated to advancing peace and technology in the Middle East. Connect with Chemi: Chemi’s LinkedIn: linkedin.com/in/chemiperes  Resources Mentioned: Pitango’s Website: pitango.com  Yuka Monsters’ Website: yukamonsters.com  Leap Academy: Ready to make the LEAP in your career? There is a NEW way for professionals to Advance Their Careers & Make 5-6 figures of EXTRA INCOME in Record Time. Check out our free training today at leapacademy.com/training

Guy Kawasaki’s journey from a lower-middle-class neighborhood in Hawaii to becoming a Silicon Valley icon is clear proof of grit and transformation. After working in the jewelry business, he pivoted to tech and joined Apple as Chief Evangelist. There, he played a key role in launching the Macintosh, shaping Apple’s brand, and transforming how technology is marketed. Today, Guy is a venture capitalist, startup advisor, and Chief Evangelist at Canva. In this episode, Guy shares his battle with hearing loss, why passion is overrated, his top sales strategies, and advice for scaling a business as an entrepreneur. Guy Kawasaki is a marketing specialist, bestselling author, venture capitalist, and speaker. As the former Chief Evangelist for Apple, he played a pivotal role in launching the Macintosh and now serves as Chief Evangelist at Canva. In this episode, Ilana and Guy will discuss: (00:00) Introduction  (02:11) From Humble Beginnings to Studying at Stanford (06:24) Why Sales Is the Key to Business Success (11:01) Knowing When to Pivot vs. Stick with Your Career (17:26) Transitioning from Jewelry Business to Tech (21:48) Key Lessons from Working with Steve Jobs (24:38) How to Evangelize Great Ideas (26:31) The Promotion That Led Guy to Quit Apple (31:58) The Myth of “Finding Your Passion” (38:26) Building Resilience After Hearing Loss (43:15) Strategies to Scale Your Career and Business (49:33) How to Truly Understand Customers’ Needs Guy Kawasaki is a marketing specialist, bestselling author, venture capitalist, and speaker. As the former Chief Evangelist for Apple, he played a pivotal role in launching the Macintosh and now serves as Chief Evangelist at Canva. Despite experiencing hearing loss and receiving a cochlear implant, Guy’s passion for sharing ideas remains unwavering. He hosts the Remarkable People podcast and delivers over fifty keynote speeches annually for clients like Apple, Nike, Google, and Microsoft. Connect with Guy: Guy’s Website: guykawasaki.com  Guy’s LinkedIn: linkedin.com/in/guykawasaki Resources Mentioned: Guy’s Podcast, Remarkable People: bit.ly/RemarkablePeoplePod  Guy’s Book, Think Remarkable: 9 Paths to Transform Your Life and Make a Difference: https://www.amazon.com/Think-Remarkable-Paths-Transform-Difference/dp/139424522X  Leap Academy: Ready to make the LEAP in your career? There is a NEW way for professionals to Advance Their Careers & Make 5-6 figures of EXTRA INCOME in Record Time. Check out our free training today at leapacademy.com/training

Growing up, Shai Reshef wasn’t the most enthusiastic student, but after earning a master’s degree in Chinese politics, he discovered the transformative power of education. Inspired by a UNESCO report predicting the future lack of access to higher education, Shai decided to act. He sold two businesses, leveraged open-source technology, and partnered with volunteer professors to create University of the People, the world’s first tuition-free, accredited online university. In this episode, Shai joins Ilana to share how the university is empowering over 150,000 students from marginalized communities and offers valuable advice for those seeking to make a meaningful impact. Shai Reshef is the founder and president of University of the People, a nonprofit, tuition-free, accredited online university dedicated to providing accessible higher education to underserved populations across 206 countries. In this episode, Ilana and Shai will discuss: (00:00) Introduction  (01:52) The Power of Education in Nation-Building (04:41) Founding the First Online University in Europe (09:08) Creating a Global, Tuition-Free University (16:05) Overcoming Accreditation Challenges (19:34) The Global Impact of the University of the People (26:41) Building a Sustainable Model for Free Education (30:59) How University of the People Screens Students (34:18) Keys to Launching a Meaningful Project (38:18) Balancing Leadership Stress with Team Dynamics (40:33) Success Stories from University of the People (43:41) The Power of Philanthropy and Nonprofits Shai Reshef is the founder and president of University of the People, a nonprofit, tuition-free, accredited online university dedicated to providing accessible higher education to underserved populations across 206 countries. Previously, he led Kidum Group, Israel’s largest for-profit educational services company, and chaired KIT eLearning, the first online university in Europe. Recognized for his impact on education, Shai also serves as an adviser to the UN’s Global Alliance for ICT and Development. Connect with Shai: Shai’s LinkedIn: linkedin.com/in/shaireshef  Resources Mentioned: University of the People’s Website: www.uopeople.edu Leap Academy: Ready to make the LEAP in your career? There is a NEW way for professionals to Advance Their Careers & Make 5-6 figures of EXTRA INCOME in Record Time. Check out our free training today at leapacademy.com/training

Growing up with dyslexia and ADHD, Rosanna Pansino struggled to find her career path. After being fired from every job, she found her calling on YouTube, combining her love for baking with nerdy pop culture. Despite financial struggles, she invested her life savings into building her channel, Nerdy Nummies, which quickly became a sensation. With over 14 million subscribers, bestselling cookbooks, and her own product line, Rosanna turned content creation into a thriving business. In this episode, Rosanna joins Ilana to share how she sustains a long-lasting digital career, navigates platform algorithms, and diversifies her entrepreneurial ventures. Rosanna Pansino is a YouTuber, actress, author, entrepreneur, and baker, best known for her channel Nerdy Nummies, where she creates visually stunning baked goods inspired by pop culture. In this episode, Ilana and Rosanna will discuss: (00:00) Introduction  (02:24) Growing up with Dyslexia and ADHD (05:07) Discovering a Passion for Baking (06:51) Lessons from Random Jobs and Failure (10:13) Transitioning from Acting Career to Nerdy Nummies (14:09) Investing Her Savings in YouTube Growth (17:04) How Getting Fired Sparked YouTube Success (25:44) Grief and Mentorship from Susan Wojcicki (31:40) Expanding Beyond YouTube (34:03) Sustaining a Long-Term Digital Career (36:52) Adapting Content to Platform Algorithms (41:24) Balancing Family and Business Partnerships (47:03) How Your Inner Circle Drives Success Rosanna Pansino is a YouTuber, actress, author, entrepreneur, and baker, best known for her channel Nerdy Nummies, where she creates visually stunning baked goods inspired by pop culture. With over 14 million subscribers, she has become one of the most influential figures in the baking and YouTube communities. Rosanna is the author of two cookbooks, The Nerdy Nummies Cookbook and Baking All Year Round, and hosted the HBO Max series Baketopia. Connect with Rosanna: Rosanna’s Website: rosannapansino.com  Rosanna’s YouTube: youtube.com/@RosannaPansino  Resources Mentioned: Star Trek: Phoenix - Cloak & Dagger Part I: https://www.imdb.com/title/tt1704271/  Leap Academy: Ready to make the LEAP in your career? There is a NEW way for professionals to Advance Their Careers & Make 5-6 figures of EXTRA INCOME in Record Time. Check out our free training today at leapacademy.com/training

John Hennessey’s passion for cars began as a child, sitting on his father’s lap as he drove and feeling the thrill of shifting gears. What started as a love for fast cars grew into a pursuit of speed and performance. Despite limited finances, John’s entrepreneurial drive led him to start a car modification business with no formal training. Through trial and error, he founded Hennessey Performance Engineering, known for the Venom F5, the world’s fastest car. In this episode, John shares how passion fueled his success, how he navigates criticism and competition, the role of branding in building a powerful business, and his mission to mentor future engineers through Tuner School. John Hennessy is the founder and CEO of Hennessey Special Vehicles and Hennessey Performance Engineering, known for high-performance, custom-built vehicles. Under his leadership, Hennessey Performance has become a recognized leader in automotive innovation, specializing in speed, power, and precision. In this episode, Ilana and John will discuss: (00:00) Introduction  (01:30) Falling in Love With Cars as a Kid (04:51) Lessons from Early Jobs and Entrepreneurship (09:38) Racing Adventures and Early Successes (17:37) Turning His Passion for Cars into a Business (20:09) Leveraging Media Relationships to Build a Brand (29:15) How YouTube Helped Scale His Business (32:58) Overcoming Challenges to Build the Venom F5 (38:09) Financial Management and Business Growth (40:46) Embracing Haters as a Sign of Relevance (42:44) Building a Brand on Authenticity and Value (45:13) Training the Next Generation with Tuner School (49:00) Lessons From 35 Years of Entrepreneurship John Hennessy is the founder and CEO of Hennessey Special Vehicles and Hennessey Performance Engineering, known for high-performance, custom-built vehicles. An engineer with a passion for speed, John created the Hennessey Venom F5, a hypercar designed to exceed 300 mph. He also founded Tuner School to train future vehicle engineers and tuners. Under his leadership, Hennessey Performance has become a recognized leader in automotive innovation, specializing in speed, power, and precision. Connect with John: John’s LinkedIn: linkedin.com/in/john-hennessey-9645a0b John’s Instagram: instagram.com/john_hennessey_texas Resources Mentioned: Hennessey Performance: hennesseyperformance.com  Tuner School: https://tunerschool.com  Leap Academy: Ready to make the LEAP in your career? There is a NEW way for professionals to Advance Their Careers & Make 5-6 figures of EXTRA INCOME in Record Time. Check out our free training today at leapacademy.com/training

After quitting her job at Google, Elizabeth Yin took a bold leap into entrepreneurship by founding LaunchBit, an adtech company. Despite facing challenges with fundraising and customer acquisition, LaunchBit was acquired. Drawing on these experiences, Elizabeth joined 500 Startups, where she invested in early-stage companies. As co-founder of Hustle Fund, she now backs startups focused on speed and execution. In this episode, Elizabeth joins Ilana to share the challenges of starting a business, how she evaluates founders to invest in, and the realities of fundraising in the competitive world of venture capital. Elizabeth Yin is a co-founder and General Partner at Hustle Fund, a seed-stage venture capital firm that invests in early-stage startups. She has reviewed over 20,000 startup pitches and assisted numerous portfolio founders in raising hundreds of millions of dollars. In this episode, Ilana and Elizabeth will discuss: (00:00) Introduction  (01:39) Falling in Love with Startups in High School (05:32) Adapting to Global Work Cultures (07:25) Leaving Google to Launch Her Startup (13:08) The Challenges of Starting a Business (16:28) How Mentors Shaped Her Startup Journey (18:15) How to Approach Mergers and Acquisitions (21:03) Key Lessons From Investing in 200+ Startups (29:41) Fundraising Realities and Strategies (33:36) The Mission Behind Hustle Fund (35:23) Navigating Stereotypes and Rejection (41:13) How to Decide Whether to Raise Capital (45:16) Handling Identity Shifts as an Entrepreneur (51:14) Building a Network Through Angel Investing Elizabeth Yin is a co-founder and General Partner at Hustle Fund, a seed-stage venture capital firm that invests in early-stage startups. She founded LaunchBit, an adtech company acquired in 2014, and was a partner at 500 Startups, where she invested in seed-stage companies. Elizabeth has reviewed over 20,000 startup pitches and assisted numerous portfolio founders in raising hundreds of millions of dollars. Connect with Elizabeth: Elizabeth’s Website: elizabethyin.com  Elizabeth’s LinkedIn: linkedin.com/in/elizabethyin/  Resources Mentioned: Hustle Fund’s Website: hustlefund.vc/  Leap Academy: Ready to make the LEAP in your career? There is a NEW way for professionals to Advance Their Careers & Make 5-6 figures of EXTRA INCOME in Record Time. Check out our free training today at leapacademy.com/training

After her first startup collapsed, Ilana Golan lost her job, salary, and investment. Feeling like a failure, she spiraled into doubt and uncertainty. But instead of giving up, she made a promise not to be the person who does nothing. That decision led her to reinvent herself and found Leap Academy, a community helping others make bold career shifts. In this 2025 LeapCon, Ilana shares her emotional journey from feeling stuck in her career to becoming an impactful leader. She provides actionable insights for navigating hidden markets, building a personal brand, and growing continuously in your career. Ilana Golan is an entrepreneur, board director, and investor in over 100 companies. As the founder of Leap Academy, she helps professionals navigate career transitions, leadership, and personal branding. In this episode, Ilana will discuss: (00:00) Introduction (02:27) The Power of Dreaming Big (05:06) Breaking Free From Career Stagnation (09:21) Turning Tragedy into Fuel (11:49) The Collapse of Her First Startup (16:06) How to Reinvent Yourself Again and Again (18:12) The Cycle of Ego, Fear, and Growth (21:35) Handling Critics and Naysayers (22:49) Building True Confidence in Business (25:34) How to Open Doors in Hidden Markets (26:36) The Three Levels of Personal Branding (30:11) Learning From Others to Accelerate Growth (31:41) Inspiring Success Stories From Leap Academy Ilana Golan is an entrepreneur, board director, and investor in over 100 companies. As the founder of Leap Academy, she helps professionals navigate career transitions, leadership, and personal branding. She has been recognized as a Silicon Valley Woman of Influence, a Top 40 Woman to Watch, and a CEO World Award winner. Ilana is also a sought-after keynote speaker and has been featured on Yahoo Finance, Fox, NBC, and more. Connect with Ilana: Ilana’s Website: ilanagolan.com  Ilana’s LinkedIn: linkedin.com/in/ilanagolan  Resources Mentioned: Leap Academy Website: leapacademy.com  Leap Academy: Ready to make the LEAP in your career? There is a NEW way for professionals to Advance Their Careers & Make 5-6 figures of EXTRA INCOME in Record Time. Check out our free training today at leapacademy.com/training

Bastiano Ferrari’s journey is one of resilience and perseverance against all odds. At just 11 years old, he faced financial hardship when his father lost everything. Despite his family’s disapproval, he pursued his passion for acting, even when it meant sleeping on beanbags and struggling to eat. But with his mother to care for, Bastiano had to pause acting to launch a tech company that ultimately gave him the financial freedom to return to Hollywood, where he earned an Emmy nomination. In this episode, Bastiano joins Ilana to share how resilience and bold decisions shaped his success in both Hollywood and tech, bridging two seemingly different worlds. Bastiano Ferrari is an Emmy-nominated producer, actor, and entrepreneur. Despite setbacks, Bastiano leveraged his experiences to create a unique portfolio career that spans film, tech, and entrepreneurship. In this episode, Ilana and Bastiano will discuss: (00:00) Introduction  (01:20) From Wealth to Hardship as a Child (05:11) Pursuing Acting Despite Family Opposition (06:36) Launching and Selling His Startup (07:38) Balancing a Career in Tech and Film (10:37) Overcoming Challenges Through Resilience (15:28) The Key to Thriving in Adversity (17:43) How to Build Valuable Connections (21:14) Thriving in Multiple Careers Without Burning Out (23:39) Hollywood vs. Tech: The Illusion of Success (28:20) The Power of Big, Scary Dreams (31:29) Why He Has No Regrets About Failure (33:30) New Film Project and AI Innovations Bastiano Ferrari is an Emmy-nominated producer, actor, and entrepreneur. After facing significant financial hardship, he took a break from acting and co-founded a tech startup that was acquired in 2013. Returning to Hollywood, he worked with major stars like Will Smith, earning Emmy nominations along the way. Despite setbacks, Bastiano leveraged his experiences to create a unique portfolio career that spans film, tech, and entrepreneurship. Connect with Bastiano: Bastiano’s Instagram: instagram.com/bastianoferrari  Resources Mentioned: Bad Boys for Life: imdb.com/title/tt1502397  Leap Academy: Ready to make the LEAP in your career? There is a NEW way for professionals to Advance Their Careers & Make 5-6 figures of EXTRA INCOME in Record Time. Check out our free training today at leapacademy.com/training

David Simas grew up in a Portuguese immigrant family in Massachusetts. His mother, who lost two fingers in a factory accident, instilled in him the power of resilience and the importance of community. These lessons shaped his career, from practicing law to advising President Obama on key national issues and eventually leading the Obama Foundation, where he worked with global leaders to promote democracy and address critical global challenges. In this episode, David joins Ilana to share valuable insights on navigating political crises, leading with empathy, and maintaining personal balance during high-stress moments in public service.  David Simas is a lawyer, political strategist, and former CEO and president of the Obama Foundation. He served as White House Director of Political Strategy and Outreach during the Obama administration and has held key roles in state and federal government. In this episode, Ilana and David will discuss: (00:00) Introduction  (01:53) Growing Up in a Portuguese Immigrant Family (05:10) Family Struggles and Community Support (09:03) How Legal Training Shaped His Perspective (16:57) Transitioning from Law to Politics (19:44) The Call That Led Him to the White House (23:19) Why Obama’s Team Chose David (27:30) Giving the People a Voice in the Oval Office (32:11) How Great Leaders Handle Crisis (36:38) Balancing Humility and Authority in Leadership (40:28) Navigating Political Pressure and Public Scrutiny (51:12) The Power of Personal Responsibility David Simas is a lawyer, political strategist, and former CEO and president of the Obama Foundation. He served as White House Director of Political Strategy and Outreach during the Obama administration and has held key roles in state and federal government, advising on political engagement and policy strategy. He is currently the Managing Director of Research and Impact at Emerson Collective, where he focuses on democracy, immigration, education, and climate initiatives. Connect with David: David’s LinkedIn: linkedin.com/in/david-simas/  Leap Academy: Ready to make the LEAP in your career? There is a NEW way for professionals to Advance Their Careers & Make 5-6 figures of EXTRA INCOME in Record Time. Check out our free training today at leapacademy.com/training

Amy Porterfield had a dream job working with Tony Robbins, one of the world’s top motivational speakers and business strategists. But deep down, she wanted to be her own boss. During a high-level meeting, she realized she was on the wrong side of the table, watching entrepreneurs build wealth instead of becoming one. With no plan, no clients, and no backup, she left corporate life and built a $100 million online business. In this episode, Amy joins Ilana to share how she overcame imposter syndrome, depression, and anxiety to create a balanced life and the mindset shift that took her from employee to multimillion-dollar entrepreneur. Amy Porterfield is an online marketing expert, entrepreneur, and bestselling author. She has helped thousands of people break free from traditional 9-to-5 jobs and create financial freedom through entrepreneurship. In this episode, Ilana and Amy will discuss: (00:00) Introduction  (01:44) Entrepreneurial Lessons from Childhood (03:35) Landing a Dream Job with Tony Robbins (07:46) The Three Biggest Lessons from Working with Tony (11:51) The Moment That Made Her Quit Corporate (14:48) Overcoming Imposter Syndrome and Depression (21:24) Finding Strength in Support Systems (24:24) How to Transition from Employee to Entrepreneur (27:32) Navigating the First Two Years in Business (29:21) Redefining Success to Avoid Burnout (35:20) Handling Hate and Criticism Online (38:19) Shifting Your Money Mindset to Scale Faster (43:35) Creating and Selling Profitable Digital Courses (46:05) Why Mistakes Are the Key to Growth Amy Porterfield is an online marketing expert, entrepreneur, and bestselling author. She runs a $100 million company teaching entrepreneurs how to create, market, and sell profitable digital courses. As the host of the Online Marketing Made Easy podcast and bestselling author of Two Weeks Notice, she has helped thousands of people break free from traditional 9-to-5 jobs and create financial freedom through entrepreneurship. Connect with Amy: Amy’s Website: amyporterfield.com  Amy’s LinkedIn: linkedin.com/in/amyporterfield Resources Mentioned: Amy’s Book, Two Weeks Notice: Find the Courage to Quit Your Job, Make More Money, Work Where You Want, and Change the World: https://www.amazon.com/Two-Weeks-Notice-Courage-Change/dp/1401969879  The Let Them Theory: A Life-Changing Tool That Millions of People Can't Stop Talking About by Mel Robbins: https://www.amazon.com/Let-Them-Theory-Life-Changing-Millions/dp/1401971369  Leap Academy: Ready to make the LEAP in your career? There is a NEW way for professionals to Advance Their Careers & Make 5-6 figures of EXTRA INCOME in Record Time. Check out our free training today at leapacademy.com/training

Norma Kamali built a business with her then-husband, but he controlled the money and decisions and even rehired the woman she had fired. Realizing the partnership was toxic, she walked away with just $98. No company. No safety net. No guarantees. Most people would have crumbled, but Norma reinvented herself. Within months, her bold designs took off, attracting lifelong, high-profile clients. Five decades later, she is still shaping the industry. In this episode, she joins Ilana to share how she overcame early setbacks, left a toxic partnership, and built lasting success. Norma Kamali is a fashion designer and entrepreneur known for her bold, timeless designs. Her designs have been worn by stars across generations. Always innovating, she recently explored AI, training a model to create designs in her signature style. In this episode, Ilana and Norma will discuss: (00:00) Introduction  (01:49) Finding Her Path as a Child (04:09) How Her Mother Shaped Her Ambition (10:33) Discovering a Passion for Drawing (14:41) Pursuing Fashion Illustration (16:42) Walking Out of a Humiliating Job Interview (18:32) How an Airline Job Led Her into Fashion (23:22) Starting a Fashion Business Accidentally (30:48) Marriage, Business, and a Toxic Partnership (36:42) Leaving Her Company with Just $98 (41:50) Rebuilding as Omo Norma Kamali (46:06) Styling Celebrities Across Generations (49:52) Mastering Sales and Its Challenges (54:42) Norma’s Secret to Navigating Fear in Business (56:32) Embracing AI and Future Plans (01:00:28) The Mindset That Turns Failure into Fuel Norma Kamali is a fashion designer and entrepreneur known for her bold, timeless designs. Over the past five decades, she has helped shape fashion, from popularizing shoulder pads in the 1980s to creating iconic pieces like the sleeping bag coat, high-heeled sneakers, and Farrah Fawcett’s red swimsuit. Her designs have been worn by stars across generations. Always innovating, she recently explored AI, training a model to create designs in her signature style. Connect with Norma: Norma’s Website: normakamali.com  Norma’s LinkedIn: linkedin.com/company/norma-kamali-inc./  Norma’s Instagram: instagram.com/normakamali  Leap Academy: Ready to make the LEAP in your career? There is a NEW way for professionals to Advance Their Careers & Make 5-6 figures of EXTRA INCOME in Record Time. Check out our free training today at leapacademy.com/training

Ilana Golan knows what it means to start over. After losing her job, startup, and investment all at once, she faced uncertainty head-on. Instead of settling for what she was merely good at, she uncovered her ‘zone of genius’ and focused on what she truly excelled at. Through this journey, she rebuilt her career and created a system to help others do the same. In this episode, Ilana shares how to identify your strengths, stand out, and take control of your reputation. Ilana Golan is an entrepreneur, board director, and investor in over 100 companies. As the founder of Leap Academy, she helps professionals navigate career transitions, leadership, and personal branding. In this episode, Ilana will discuss: (00:00) Introduction  (00:34) Identifying Your Unique Value (01:15) The Four Categories of Skills (03:27) How to Discover Your Strengths (04:38) Leveraging Feedback to Find Your Genius (05:44) Creating a 'Brag Bank' to Build Authority (06:34) How Challenges Reveal Your True Strengths (07:10) Using Your Strengths to Build Your Brand Ilana Golan is an entrepreneur, board director, and investor in over 100 companies. As the founder of Leap Academy, she helps professionals navigate career transitions, leadership, and personal branding. She has been recognized as a Silicon Valley Woman of Influence, a Top 40 Woman to Watch, and a CEO World Award winner. Ilana is also a sought-after keynote speaker and has been featured on Yahoo Finance, Fox, NBC, and more. Connect with Ilana: Ilana’s Website: ilanagolan.com  Ilana’s LinkedIn: linkedin.com/in/ilanagolan  Resources Mentioned: Free Training: https://training.leapacademy.com/pass  Leap Academy: Ready to make the LEAP in your career? There is a NEW way for professionals to Advance Their Careers & Make 5-6 figures of EXTRA INCOME in Record Time. Check out our free training today at leapacademy.com/training

At just 36 years old, Rajiv Shah got a call from Hillary Clinton. Days later, he was running USAID. Less than a week into the job, a massive earthquake leveled Haiti. He had no time to prepare. He had to act. That was one of many high-stakes bets in his career. From launching a $5 billion vaccine program with the Gates Foundation to fighting Ebola and leading global humanitarian efforts, he has tackled some of the world’s biggest challenges and won. In this episode, Rajiv joins Ilana to share how he makes big bets, leads through crisis, and asks the right questions to solve impossible challenges. Dr. Rajiv Shah is a physician, economist, global development leader, author, and President of the Rockefeller Foundation. Known for achieving the impossible to drive global change, he led U.S. responses to crises like the Haiti earthquake and Ebola outbreak as USAID Administrator.. In this episode, Ilana and Rajiv will discuss: (00:00) Introduction  (01:55) From Immigrant Kid to Global Leader (04:02) A Life-Changing Service Trip to India (07:00) Leaving Medical School for Politics (11:22) Joining the Gates Foundation (13:10) A 'Big Bet' That Saved 20 Million Lives (15:00) How Strategic Questions Unlock Big Solutions (19:31) Leading USAID Through Haiti’s Earthquake (26:38) Earning Obama and Biden’s Trust in a Crisis (30:22) Fighting the Ebola Outbreak with Military Support (33:22) Tackling Energy Poverty at the Rockefeller Foundation (38:54) Why Real Change Requires Big Risks (44:38) How Great Leaders Balance Change and Stability (47:08) The Power of Connection and Shared Values Dr. Rajiv Shah is a physician, economist, global development leader, author, and President of the Rockefeller Foundation. Known for achieving the impossible to drive global change, he led U.S. responses to crises like the Haiti earthquake and Ebola outbreak as USAID Administrator. Previously, at the Gates Foundation, he helped expand childhood vaccinations and led health and agriculture initiatives. His book, Big Bets, explores bold solutions to the world’s toughest challenges. Connect with Rajiv: Rajiv’s Website: rockefellerfoundation.org/  Rajiv’s LinkedIn: linkedin.com/in/drrajivjshah/  Resources Mentioned: Rajiv’s Book, Big Bets: How Large-Scale Change Really Happens: https://www.amazon.com/Big-Bets-Large-Scale-Change-Happens/dp/1668004380  Leap Academy: Ready to make the LEAP in your career? There is a NEW way for professionals to Advance Their Careers & Make 5-6 figures of EXTRA INCOME in Record Time. Check out our free training today at leapacademy.com/training

Ilana Golan watched others rise while she felt stuck in her career. Her identity was built around job titles and companies until she lost it all. Realizing she had spent years growing businesses but not herself, she invested tens of thousands to master public speaking and build her brand. That decision led to high-paying keynotes, advisory roles, board seats, and even the sale of her tech startup. In this episode, Ilana shares how she went from feeling stuck to unlocking massive opportunities through public speaking and personal branding. Ilana Golan is an entrepreneur, board director, and investor in over 100 companies. As the founder of Leap Academy, she helps professionals navigate career transitions, leadership, and personal branding. In this episode, Ilana will discuss: (00:00) Introduction  (00:14) Her Career Wake-Up Call (00:54) The Power of Public Speaking (01:52) Why Investing in Your Brand Pays Off (02:50) Transforming Your Career with Personal Branding Ilana Golan is an entrepreneur, board director, and investor in over 100 companies. As the founder of Leap Academy, she helps professionals navigate career transitions, leadership, and personal branding. She has been recognized as a Silicon Valley Woman of Influence, a Top 40 Woman to Watch, and a CEO World Award winner. Ilana is also a sought-after keynote speaker and has been featured on Yahoo Finance, Fox, NBC, and more. Connect with Ilana: Ilana’s Website: ilanagolan.com  Ilana’s LinkedIn: linkedin.com/in/ilanagolan  Resources Mentioned: Free Training: https://training.leapacademy.com/pass  Leap Academy: Ready to make the LEAP in your career? There is a NEW way for professionals to Advance Their Careers & Make 5-6 figures of EXTRA INCOME in Record Time. Check out our free training today at leapacademy.com/training