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The Dwayne Kerrigan Podcast

The Dwayne Kerrigan Podcast

Dwayne Kerrigan

Welcome to The Dwayne Kerrigan Podcast. Dwayne has navigated the business world for over 35 years, owning close to 30 businesses in 12 distinct industries. Today, entrepreneurship often seems more about glitz, glamour, and a celebrity venture. On this podcast, Dwayne collaborates with overlooked but accomplished entrepreneurs, delving into their journeys of forging exceptional enterprises. Join them as they share their personal journeys, lessons learned, and strategies that keep them moving forward. Let’s celebrate the true essence of entrepreneurship and inspire the next wave of business trailblazers.

167 - 164. Leading with Vision | Brian Scudamore
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  • 167 - 164. Leading with Vision | Brian Scudamore

    In 1994, five years into running his junk removal business, Brian Scudamore called all 11 employees into a morning meeting, apologized for letting them down, and fired every one of them. He went from five trucks to one. What he built next started with a single page describing a future nobody else could see yet.

    In this episode:

    Why Brian's grandparents' San Francisco surplus store was robbed only twice in 20 years while neighbouring shops were hit almost weeklyThe 1994 reset: owning the failure ("it was all on me") and rebuilding around the right peopleThe "painted picture": a one-page, double-sided vision written in present tense, and how the 1998 version's goal of the top 30 metros came down to 28 of 30 with 90 days leftHow a failed 1997 summer franchise model, the only two years the business lost money, led to year-round franchisingThe five-minute sheet-of-paper exercise Brian uses to pull his leadership team out of a dark momentHow one question about a dream trip got former COO Cameron Herold to picture a vision

    Audio Timestamps:

    00:00 - Vision Sets Direction

    00:29 - Podcast Intro Guest Bio

    02:05 - Entrepreneurial Roots

    03:12 - Grandparents Respect Lesson

    06:31 - Wisdom Over Time

    10:12 - Impact Over Status

    13:08 - Firing Everyone Reset

    16:38 - Hiring For Culture Fit

    18:51 - Shared Vision Leadership

    22:36 - Painted Picture Framework

    25:49 - Owning Failure Learning

    27:04 - Clarity Drives Scale

    28:13 - Painted Picture Defined

    29:55 - Vision That Unites Teams

    30:31 - Scaling Vision Across Companies

    32:48 - Making Vision A Ritual

    34:58 - Never Lower The Bar

    37:17 - Courage To Pivot

    40:02 - Willing To Fail Lessons

    45:48 - Possibility As A Mindset

    47:32 - Teaching Vivid Vision

    51:04 - Questions Drive Innovation

    53:26 - Closing And Next Episode

    Guest Bio:

    Serial entrepreneur, Dragons’ Den investor, and author Brian Scudamore has always taken the road less travelled. At just 19 years old, he pioneered the industry of professional junk removal with 1-800-GOT-JUNK?, turning a chore people avoid into an exceptional customer service experience. Then he scaled that success into two more home-service brands, WOW 1 DAY PAINTING and Shack Shine, under theO2E Brands banner.

    Resources mentioned:

    Brian’s Books - WTF: Willing to Fail and BYOB: Build Your Own Business Be Your Own BossVivid Vision book by Cameron HeroldStart With Why book by Simon Sinek

    Connect with Brian Scudamore

    https://www.linkedin.com/in/scudamore/

    https://brianscudamore.com/

    https://www.instagram.com/brianscudamore

    https://www.facebook.com/bscudamore/

    https://www.youtube.com/channel/UCpQVYv5YMEqKZd5u7ANifYA

    Connect with Dwayne Kerrigan

    Facebook

    Instagram

    Linked In

    Website

    Disclaimer: The views, information, or opinions expressed by guests during The Dwayne Kerrigan Podcast are solely those of the individuals involved and do not necessarily represent those of Dwayne Kerrigan and his affiliates. Dwayne Kerrigan or The Dwayne Kerrigan Podcast is not responsible for and does not verify the accuracy of any of the information contained in the podcast series. The primary purpose of this podcast is to educate and inform. Listeners are advised to consult with a qualified professional or specialist before making any decisions based on the content of this podcast.

    Wed, 04 Nov 2026 - 55min
  • 166 - 163. The Power of a Trusted Circle | The Honey Badgers

    Seventeen years ago, four strangers decided to build something almost no one commits to: a mastermind group that outlasts the businesses, marriages, and identities its members walk in with. In Part 2, Dwayne sits back down with three of the four, Curt Cronin, Michael Grandjean, and Sam Hazledine (missing Keiron McCammon)to unpack what actually kept the group alive that long, and what it cost them to get there.

    In this episode:

    Why Curt distinguishes a mentor ("shape me in their likeness"), a coach ("hold a container and ask me questions"), and a consultant ("give me the answer") as three completely different relationships and why conflating them causes frictionSam's case for why "in business, generally speaking, the coaches are not the ones who are successful at business" and what that selection bias means for anyone hiring oneCurt's math on the actual hours he has left with his teenage daughter based on their current visiting cadence, and how that number changed how he shows up for herWhy Sam believes selection, who's in the room, matters more than structure, using the analogy that "date night doesn't work if you're married to the wrong person"The origin story: how Curt, Michael, and Sam actually formed the group after meeting through Tony Robbins' Platinum Partners program, and why Tony himself turned down an invite to joinMichael's take on the single biggest shift that took the group from well-meaning to effective: bringing in real structure and prep

    Episode Timestamps:

    00:00 Mentorship Mindset

    00:35 Podcast Intro

    01:38 Creating Your Reality

    04:21 Beyond Tactics to Mindset

    07:14 Accountability and Growth

    10:03 Aligned Vision Matters

    15:21 Belief and Creation

    21:27 Finding Great Mentors

    25:12 Mentor vs Coach

    28:52 Coaching Limits in Business

    30:51 Curiosity Over Assumptions

    34:12 Resetting Miscommunication

    36:29 Courageous Conversations at Work

    38:51 Building Trust With Windshield Time

    39:58 Starting a Mastermind Group

    41:22 Structure Prep and Standards

    43:36 Finding the Right People

    47:00 Origin Story and Commitment

    51:50 Speaking to the Fifth Person

    52:54 Parting Shots and Farewell

    59:50 Podcast Outro and Disclaimer

    LINKS TO PREVIOUS EPISODES:

    https://www.dwaynekerrigan.com/2-from-navy-seal-to-entrepreneur-the-transformative-journey-with-curt-cronin/

    https://www.dwaynekerrigan.com/24-part-1-curiosity-change-embracing-growth-and-discovery-with-curt-cronin/

    https://www.dwaynekerrigan.com/25-part-2-unlocking-potential-from-beyond-the-comfort-zone-with-curt-cronin/

    https://www.dwaynekerrigan.com/5-beyond-achievement-unlocking-fulfillment-with-dr-sam-hazledine/

    https://www.dwaynekerrigan.com/121-collapse-courage-and-comeback-with-michael-grandjean/

    https://www.dwaynekerrigan.com/122-forgiving-yourself-and-rebuilding-after-failure-with-michael-grandjean/

    Follow The Dwayne Kerrigan Podcast for more conversations like this one, and catch Part 1 of this mastermind episode if you haven't yet.

    Connect with Dwayne Kerrigan

    Facebook

    Instagram

    Linked In

    Website

    Disclaimer: The views, information, or opinions expressed by guests during The Dwayne Kerrigan Podcast are solely those of the individuals involved and do not necessarily represent those of Dwayne Kerrigan and his affiliates. Dwayne Kerrigan or The Dwayne Kerrigan Podcast is not responsible for and does not verify the accuracy of any of the information contained in the podcast series. The primary purpose of this podcast is to educate and inform. Listeners are advised to consult with a qualified professional or specialist before making any decisions based on the content of this podcast.

    Wed, 28 Oct 2026 - 1h 00min
  • 165 - 162. Beyond Advice | The Honey Badgers

    Seventeen years, six men, and one rule: no advice allowed. On this panel, three members of Dwayne Kerrigan's mastermind group, the "Honey Badgers", pull back the curtain on the framework that's carried them through startups, exits, burnout, and grief, and explain why the group that changes them most is the one that refuses to tell them what to do.

    In this episode:

    Curt Cronin breaks down "dynamic subordination," the Navy SEAL handoff principle the group uses to know who leads and who steps back in a crisisSam Hazledine explains why "nature abhors a vacuum" is the real reason humans default to giving advice, and why it usually backfiresMichael Grandjean opens up about losing everything and the one thing that got him through it: learning to forgive himselfDwayne and the group unpack the "event, meaning, emotion, behavior, result" chain and how the stories we attach to events quietly run our livesSam introduces the idea of becoming a "mindful steward" instead of a "benevolent dictator" as a business scalesThe group previews Dwayne's upcoming Founders Council program, built on the same gestalt-style mentorship model

    About the guests: Curt Cronin is a former U.S. Navy SEAL turned entrepreneur and a founding member of the Honey Badgers mastermind group. Michael Grandjean spent 30 years in construction for the Department of Defense and the U.S. government before rebuilding his career after a period of significant personal and financial loss. Sam Hazledine is a physician based in New Zealand and founder of a medical staffing, technology, and research business. All three have been meeting with Dwayne Kerrigan as part of the same mastermind group for 17 years.

    Episode Timestamps:

    00:00 Brotherhood Origins

    01:10 Meet The Honey Badgers

    02:06 Sam Hazledine Introduction

    03:19 Mike Grandjean and Curt Cronin Introductions

    05:04 How the Mastermind Group Formed

    07:07 Why the Group Works

    10:06 Beyond Advice Gestalt Feedback

    16:05 Trust and Safe Space

    20:07 Dynamic Subordination Explained

    23:21 Scaling Leadership Mindful Steward

    28:53 Enough More and Seasons

    31:41 Stuck In The Middle

    32:16 Paying The Price

    33:34 Forgive Yourself

    35:14 Pain Versus Suffering

    38:25 Blind Spots And Truth

    42:26 Power Of Story

    49:38 Intimacy And Proximity

    54:31 Mastermind Framework

    58:31 Proximity Is Power

    01:02:57 Closing And Next Week

    Follow The Dwayne Kerrigan Podcast for Part 2 of this conversation, and find Curt Cronin, Michael Grandjean, and Sam Hazledine's own episodes in the show's back catalog.

    Links to Previous Episodes:

    https://www.dwaynekerrigan.com/2-from-navy-seal-to-entrepreneur-the-transformative-journey-with-curt-cronin/

    https://www.dwaynekerrigan.com/24-part-1-curiosity-change-embracing-growth-and-discovery-with-curt-cronin/

    https://www.dwaynekerrigan.com/25-part-2-unlocking-potential-from-beyond-the-comfort-zone-with-curt-cronin/

    https://www.dwaynekerrigan.com/5-beyond-achievement-unlocking-fulfillment-with-dr-sam-hazledine/

    https://www.dwaynekerrigan.com/121-collapse-courage-and-comeback-with-michael-grandjean/

    https://www.dwaynekerrigan.com/122-forgiving-yourself-and-rebuilding-after-failure-with-michael-grandjean/

    Connect with Dwayne Kerrigan:

    Connect with Dwayne Kerrigan

    Facebook

    Instagram

    Linked In

    Website

    Disclaimer: The views, information, or opinions expressed by guests during The Dwayne Kerrigan Podcast are solely those of the individuals involved and do not necessarily represent those of Dwayne Kerrigan and his affiliates. Dwayne Kerrigan or The Dwayne Kerrigan Podcast is not responsible for and does not verify the accuracy of any of the information contained in the podcast series. The primary purpose of this podcast is to educate and inform. Listeners are advised to consult with a qualified professional or specialist before making any decisions based on the content of this podcast.

    Wed, 21 Oct 2026 - 1h 04min
  • 164 - 161. Scaling FlyGuys with Operational Excellence | FlyGuys CEO Joe Stough

    FlyGuys CEO Joe Stough returns for Part 2 of this conversation on scaling technology companies through operational excellence, culture, and AI.

    Joe breaks down the four-element operational excellence management system he built plus the cultural foundation of the golden rule and iron sharpens iron and explains how the company's AI data infrastructure platform now serves seven industries through one configurable pipeline.

    If you're building a company that needs to scale past its current ceiling, this episode is a playbook.

    In this episode:

    Joe walks through FlyGuys' four-element Operational Excellence Management System (OEMS) — leadership, individual development, incident learning, and continuous improvement — built on a fifth "element zero": culture.He unpacks FlyGuys' five cultural principles: the golden rule, iron sharpens iron, goal zero, raving fans, and one for all and all for one.Joe details the Waitr acquisition that used almost all of the company's post-SPAC cash within two weeks of going public — a transaction later written down by $190 million.He explains how FlyGuys' AI data infrastructure platform now serves seven verticals (construction, solar, asset management, agriculture, public safety, insurance, and telecom) through one configurable pipeline.Joe shares his networking philosophy — prioritizing "vision alignment" over job titles, including the mid-level ExxonMobil manager who opened the door to a multi-year enterprise contract.He gives direct advice for business owners bringing AI into their operations: don't skip the architecture expertise, and pair AI orchestration with real industry knowledge.

    Episode Time Stamps:

    00:00 Iron Sharpens Iron Culture

    00:28 Podcast Intro and Recap

    01:29 Scaling Lessons and AI Risks

    03:21 Pricing and Org Costs Trap

    06:47 Operational Excellence Foundation

    10:15 Mapping the Process Day One

    13:33 Defects and Incident Learning

    15:12 Customer Journey Method

    18:53 Culture Principles Element Zero

    24:55 OEMS Elements Breakdown

    28:20 How It Became Intentional

    30:43 Can OE Reduce Failures

    32:46 Waitr Acquisition Mistake

    37:16 Waitr Deal Fallout

    38:56 Mentor Sam Smolik

    41:17 Networking Beyond Titles

    44:05 Vision Alignment Story

    47:43 Risk and Diversification

    53:22 Platform for Complexity

    57:20 Vertical Workflow Examples

    01:04:56 Agentic AI and Scaling

    01:12:48 Final Scaling Playbook

    01:18:32 Closing and Where to Find

    Resources Mentioned:

    Interpersonal Technology: The Art and Science of Personal and Professional Effectiveness by James A. Gwaltney (Author)

    https://a.co/d/06TD2z2R

    The Power of Goal ZERO: A Practical Leadership Guide for Achieving Superior Performance by Sam Smolik (Author)

    https://a.co/d/06CjUZI2

    The Daily Pursuit of Excellence: The 4 Keys to Achieving Superior Performance by Sam Smolik (Author)

    https://a.co/d/03YXAfrQ

    About Joe Stough: Joe Stough is CEO of FlyGuys, an AI data infrastructure platform serving industries including construction, solar, agriculture, insurance, and public safety. He previously served as President and COO of Waitr, and earlier built Impact, an operational excellence and safety management software adopted by ExxonMobil, Chevron, Total, and Koch Industries. Stough sits on the board of directors of Ducks Unlimited alongside his mentor Sam Smolik, author of Daily Pursuit of Excellence and Goal Zero, whose influence shaped FlyGuys' operational excellence system.

    Connect with Joe Stough:

    https://flyguys.com/

    https://www.linkedin.com/in/joe-stough/

    https://www.linkedin.com/company/flyguys.io/

    Connect with Dwayne Kerrigan

    Facebook

    Instagram

    Linked In

    Website

    Disclaimer: The views, information, or opinions expressed by guests during The Dwayne Kerrigan Podcast are solely those of the individuals involved and do not necessarily represent those of Dwayne Kerrigan and his affiliates. Dwayne Kerrigan or The Dwayne Kerrigan Podcast is not responsible for and does not verify the accuracy of any of the information contained in the podcast series. The primary purpose of this podcast is to educate and inform. Listeners are advised to consult with a qualified professional or specialist before making any decisions based on the content of this podcast.

    Wed, 14 Oct 2026 - 1h 20min
  • 163 - 160. Building an Intentional Culture | FlyGuys CEO Joe Stough

    Joe Stough built a piece of software that ExxonMobil, Shell, and ConocoPhillips ran their worldwide safety operations on and he says none of it would have worked without a psychological framework he almost let disappear along with the mentor who created it. In this episode, he traces the throughline of intentional culture across three very different companies.

    In this episode:

    How Joe's early experience running Dynamic Systems International shaped the fundamentals he built his next company, Syntex, on — starting with hiring a lawyer on day oneThe Interpersonal Technology framework — eight personality styles built on Carl Jung's archetypes — that Joe credits for turning daily blowups with his first CFO into a working partnershipHow Joe's Impact software went from one language in one country to twenty-four languages in a hundred and eighty countries in a single year, landing ConocoPhillips, ExxonMobil, and Shell as worldwide clients within six monthsSelling Syntex to IHS in 2010 in an all-cash deal — and being pulled back to the office six months into "retirement"Why Joe took over teaching the Interpersonal Technology program himself after his mentor, Dr. James Gwaltney, passed away in 2016How FlyGuys runs an "Uberized" marketplace of over 22,000 drone pilots delivering data instead of rides or food

    Time Stamps:

    00:00 Intentional Culture Mindset

    00:40 Podcast Welcome and Guest Intro

    04:58 FlyGuys Business Model Explained

    09:00 From Syntex to Waitr to FlyGuys

    14:40 Early Failure Lessons Learned

    20:09 Finding Mentors and First Investor

    25:22 Interpersonal Technology Origin Story

    31:25 Eight Personality Styles Overview

    35:36 Thinking vs Feeling

    36:17 Choicing and Dreaming Spectrum

    37:12 Organizer vs Presenter Styles

    38:06 Building Teams and Culture

    39:38 Hiring for Strength Balance

    40:50 Mentor Legacy and IP Story

    48:47 Culture as Career Thread

    52:35 Syntex Sale and Return

    54:23 Global Data and Safety Index

    01:00:20 Waitr Origin and Hypergrowth

    01:04:53 Scaling Lessons and Replatforming

    01:06:56 Wrap Up and Next Episode

    About Joe Stough: Joe Stough is CEO of FlyGuys: a drone data collection company operating an Uberized marketplace with more than 22,000 pilots across the U.S. He founded Syntex in 1995, building the Impact software platform into what became a dominant operational excellence system used by companies including ExxonMobil, Shell, and ConocoPhillips, before selling the company in 2010. He later served as President and COO of Waitr, taking the food delivery company public on Nasdaq via SPAC in 2018. Joe now holds the intellectual property rights to the Interpersonal Technology framework and personally teaches it to leadership teams; he has been featured in Forbes, Fortune, and Entrepreneur Magazine, and sits on the board of Ducks Unlimited.

    Connect: Follow The Dwayne Kerrigan Podcast for Part 2 of this conversation, and connect with Joe Stough and FlyGuys to learn more about the Interpersonal Technology program.

    Connect with Joe Stough:

    https://flyguys.com/

    https://www.linkedin.com/in/joe-stough/

    https://www.linkedin.com/company/flyguys.io/

    Resources Mentioned:

    Interpersonal Technology: The Art and Science of Personal and Professional Effectiveness by James A. Gwaltney (Author)

    https://a.co/d/06TD2z2R

    The Power of Goal ZERO: A Practical Leadership Guide for Achieving Superior Performance by Sam Smolik (Author)

    https://a.co/d/06CjUZI2

    The Daily Pursuit of Excellence: The 4 Keys to Achieving Superior Performance by Sam Smolik (Author)

    https://a.co/d/03YXAfrQ

    Connect with Dwayne Kerrigan

    Facebook

    Instagram

    Linked In

    Website

    Disclaimer: The views, information, or opinions expressed by guests during The Dwayne Kerrigan Podcast are solely those of the individuals involved and do not necessarily represent those of Dwayne Kerrigan and his affiliates. Dwayne Kerrigan or The Dwayne Kerrigan Podcast is not responsible for and does not verify the accuracy of any of the information contained in the podcast series. The primary purpose of this podcast is to educate and inform. Listeners are advised to consult with a qualified professional or specialist before making any decisions based on the content of this podcast.

    Wed, 07 Oct 2026 - 1h 08min
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