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Hustle Humbly Podcast

Hustle Humbly Podcast

Alissa Jenkins & Katy Caldwell

Join us for Hustle Humbly where we hope you will build the confidence to find your voice and your way to a successful real estate business and beyond. Listen in as Alissa & Katy, two top producing Realtors, talk about fostering community over competition while navigating the often times cutthroat real estate industry. With over 1000 homes sold between them and 13 and 19 years each in the business, they have seen it first hand. Deep dive into conversations and interviews about mindset and best practices with real life stories mixed in. The goal of Hustle Humbly is to reach out and encourage Realtors and business people alike to stop comparing themselves and start embracing their own strengths.

419 - 373: The Types of Burnout Every Realtor Feels
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  • 419 - 373: The Types of Burnout Every Realtor Feels

    This week we're doing a little podcast therapy of our own, because burnout comes for all of us. We started this episode because we needed it, and if we're honest, we figured a lot of you needed it too. So instead of just handing you a list of quick fixes, we decided to do the harder thing first: name it. Burnout, it seems, can come at us for a lot of reasons.

    We're breaking burnout down two ways. First by where you are in your career: seasoned agent, new agent, or part timer. Then by the universal types that don't care about your years in the business at all: market related, personality based and situational. We even confess our own personal "burnout cocktails" so you know you're not alone.

    This one is part pep talk, part permission slip. You don't have to quit. You just have to learn to rest.

    Here's what we cover in this episode:

    Why we're starting with "name it to tame it" instead of jumping straight to tips

    Seasoned agent burnout: seeing the process and consumer get more difficult

    New agent burnout: rejection, comparison, and the overwhelm of trying to learn everything at once

    Part time agent burnout: the honest conversation about whether your goals actually match the effort you're able to give

    Market related burnout: rising interest rates, affordability struggles, and a real client story about a buyer's max budget dropping almost overnight

    Feast or famine burnout: the cycle of busy to crickets to panic, and why real estate paychecks are always "future" money

    Comparison driven burnout and why social media numbers are just a vanity metric

    Systems failure burnout: chasing shiny new tools instead of building repeatable systems

    Financial stress burnout, and why we think it's the most dangerous type of all

    Practical ways to rest without quitting

    Key Quotes & Takeaways:

    "You have to name it to tame it." -Dr. Daniel Siegel

    "Learn to rest, not to quit." -John Greenleaf Whittier

    "Don't kill yourself for a job that would replace you in a week." -Alissa

    "The goalposts do continually move. No matter how well you do, you're constantly climbing the mountain, and you're never at the top." -Katy

    "Grant me the serenity to accept the things I cannot change." -serenity prayer

    Products, People & Previous Episodes Mentioned:

    Episode 3: Mindset Meltdown (hustlehumblypodcast.com/3)

    Agent Systems 101 (agentsystems101.com)

    Hustle Humbly Community (hustlehumblypodcast.com/membership)

    Want to toast someone on the show? Send us a voice or video message with your name, who you're toasting, and why! Email it to team@hustlehumblypodcast.com.

    Leave us a review at http://ratethispodcast.com/hustlehumbly

    Get your FREE Database Template: http://hustlehumblypodcast.com/starthere

    Email Templates 101: http://emailtemplates101.com

    Agent Systems 101: http://agentsystems101.com

    All Resources: http://hustlehumblypodcast.com

    Submit your topic ideas and toasts to Team@HustleHumblyPodcast.com

    Music:

    Straight A's by Connor Price → https://connorprice.shop/

    The Good Life by Summer Kennedy → https://soundcloud.com/summerkennedy/the-good-life

    Be The One by Matrika → https://uppbeat.io/t/matrika/be-the-one

    Mon, 28 Sep 2026 - 48min
  • 418 - 372: How to Give Your Clients a 5-Star Experience

    What does Trader Joe's know that most Realtors don't?

    We went down a rabbit hole this week pulling data from the American Customer Satisfaction Index and the results surprised us. We also sourced stories from Trader Joe's, Chick-fil-A, and Disney. So we started asking, what do these brands actually do that makes people love them so much, and how does that apply to our real estate businesses?

    Turns out it's not fancy. It's not expensive. It's mastering the basics and doing them the same way every single time. As AI takes over more of the automated, robotic parts of this business, being the most human Realtor in the room is about to become your biggest competitive advantage. We're talking about the difference between delivering what you promised and giving someone an actual experience, and why so many agents skip straight to the closing gift instead of doing the boring, consistent work in the middle of the transaction.

    We share real stories, including a seller who wanted to pull her overpriced listing after two weeks with no showings, a buyer family with two kids under five who needed way more than an MLS printout, and a Hustle Humbly Community member whose vendor list mailer turned a football magnet into something people actually looked forward to getting.

    Here's what we cover in this episode:

    What the American Customer Satisfaction Index says about our favorite businesses

    Why the two questions Trader Joe's cashiers always ask are designed to get you talking

    Why being the most human Realtor is about to matter more than ever as AI use increases

    Why simpler, less produced content (a phone video walking through a house) beats a glossy production every time

    A real story about sending a video instead of a text when a seller wanted to pull her listing

    Why handwritten notes with a sheet of stickers slipped inside get remembered

    The "nervous gift" basket built for a buyer family touring ten houses with two little kids

    Why listening for small clues, like an offhand comment about a favorite baseball team, matters more than a big gesture

    What goes in a pre-listing gift basket to help sellers actually prep for showings

    Why looking at 27 houses is a customer service failure, not a badge of honor

    The attract, convert, deliver framework and why most agents skip straight to marketing without delivering

    A Hustle Humbly Community member's genius vendor list mailer campaign

    Which industries scored the worst on the customer satisfaction index (hint: you already know)

    Key Quotes & Takeaways:

    "The best thing we can do for customer service is our job." Katy

    "It's free to be transparent, responsive, to listen, to have urgency." Katy

    "The customer experience isn't about you. It's about that person." Alissa

    "You can't do the fancy, fun, frilly stuff if your clients haven't heard from you in three days." Alissa

    "Your face and your voice being part of that transaction is the thing that's you, that no one can take away from you. That's what sets you apart." Katy

    Products, People & Previous Episodes Mentioned:

    American Customer Satisfaction Index (ACSI)

    Episode 370: Whatever Your Business Is, The Fundamentals Are The Same (hustlehumblypodcast.com/370)

    Hustle Humbly Community (hustlehumblypodcast.com/membership)

    Want to toast someone on the show? Send us a voice or video message with your name, who you're toasting, and why! Email it to team@hustlehumblypodcast.com.

    Leave us a review at http://ratethispodcast.com/hustlehumbly

    Get your FREE Database Template: http://hustlehumblypodcast.com/starthere

    Email Templates 101: http://emailtemplates101.com

    All Resources: http://hustlehumblypodcast.com

    Submit your topic ideas and toasts to Team@HustleHumblyPodcast.com

    Music:

    Straight A's by Connor Price

    The Good Life by Summer Kennedy

    Be The One by Matrika

    Mon, 21 Sep 2026 - 52min
  • 417 - 371: Property Safety: When Your Listing Gets Robbed

    It's Realtor Safety Month, and this year we're taking a different angle: property safety.

    We've covered personal safety plenty of times before (episodes 317, 216, 161, 112, and 6 & 7 with Carl Carter), but this time Alissa is sharing a story straight from the trenches: the time one of her vacant listings got robbed, mid-listing, appliances and all.

    Repeat clients moved out of state and handed off a vacant house with an alarm code buried in a five-month-old text message. The camera system looked impressive, eight angles of surveillance, but it hadn't actually recorded anything in two and a half years. Somewhere between painters, cleaners, and showings, the alarm never got set again, and it was never on Alissa's radar to ask.

    Then came the Saturday phone call every agent dreads: a showing agent reporting a kicked-in back door, a stolen oven, a missing washer and dryer, and a fridge the thieves gave up on halfway out the front door. Police, fingerprints, dead-end cameras, and a seller relationship that went from grateful to accusatory in the span of a few days.

    This one is a real, honest look at what happens when property safety falls through the cracks, what Alissa changed in her process because of it, and why y'all need a plan for your vacant listings before something goes wrong, not after.

    Here's what we cover in this episode:

    Why Realtor Safety Month usually focuses on personal safety, and why property safety deserves its own spotlight

    What actually got stolen (and what the thieves gave up on)

    How Alissa handled calling police, meeting them at the property, and coordinating repairs for out-of-state sellers

    How her broker helped negotiate a fair resolution tied to closing

    Why you are not your seller's property manager, and how to set that expectation early

    The new questions Alissa now asks every seller about alarms, cameras, and monitoring

    Why virtually staging vacant listings can be a safety move, not just a marketing one

    A past story about a garage door left open, and why "who showed it last" matters more than you think

    Key Quotes & Takeaways:

    "You're not a property manager. When they hired you to sell the home, they didn't hire you to be the lawn company or the security company." Katy

    "I trust no one and nothing." Katy

    "It's just proof that even when you have good systems, things can go wrong. It's really about handling it professionally and learning from it." Alissa

    "I virtually stage all my vacant properties for safety. I don't want them to appear vacant." Alissa

    "It's Realtor Safety Month. Be careful. Take your safety and the property safety seriously." Alissa

    Products, People & Previous Episodes Mentioned:

    Episode 317: Realtor Safety Month: Scams, Showings, and Survival (hustlehumblypodcast.com/317)

    Episode 216: Important Safety Stories & Tips for Realtors (hustlehumblypodcast.com/216)

    Episode 161: Realtor Safety Tips from a LEO (hustlehumblypodcast.com/161)

    Episode 112: Safety First (hustlehumblypodcast.com/112)

    Episodes 6 & 7: Realtor Safety with Carl Carter (Beverly Carter Foundation)

    Hustle Humbly Email Templates (new security checklist)

    Want to toast someone on the show? Send us a voice or video message with your name, who you're toasting, and why! Email it to team@hustlehumblypodcast.com

    Leave us a review at http://ratethispodcast.com/hustlehumbly

    Get your FREE Database Template: http://hustlehumblypodcast.com/starthere

    Email Templates 101: http://emailtemplates101.com

    Agent Systems 101: http://agentsystems101.com

    All Resources: http://hustlehumblypodcast.com

    Submit your topic ideas and toasts to Team@HustleHumblyPodcast.com

    Music:

    Straight A's by Connor Price

    The Good Life by Summer Kennedy

    Be The One by Matrika

    Mon, 14 Sep 2026 - 58min
  • 416 - 370: Whatever Your Business Is, The Fundamentals Are The Same

    Happy Labor Day! In honor of all the laboring people out there, we're doing something a little different this week.

    We are always surprised to hear of listeners not in real estate at all, and we love hearing how this podcast has still helped your business. So today we're speaking straight to the masses. We made ourselves a rule: no saying "real estate," "realtor," "buyer," or "seller" for the whole episode (we mostly stuck to it). Because the truth is, whatever your business is, the fundamentals are the same: attract people, convert them, take really good care of them, stay in touch, know your numbers, and build systems so you don't have to start over every single Monday.

    We're walking through nine categories that apply to literally any business, from a hairdresser to a landscaper to a lawyer to an Etsy shop owner. We share real stories (including a dentist who ghosted Katy without so much as a goodbye, and a yard service that over-communicated its way into her heart during a rain delay), and we break down exactly what separates a business that thrives from one that closes after two months.

    If this one resonates, send it to a friend who isn't in real estate. We promise it still applies.

    Here's what we cover in this episode:

    Know how your business actually works: the attract, convert, deliver framework and why most people get stuck avoiding the "convert" (aka sell) part

    Set expectations before they become problems: business hours, response times, cancellation policies, and why an auto-email-responder can save your sanity

    Make decisions once and repeat them: email templates, pricing, and writing your own standard operating procedures

    Communicate clearly: admitting mistakes, having hard conversations, and why "the customer is always right" isn't actually true

    Know your numbers: cost to acquire a customer, profit after expenses, and why being busy isn't the same as being profitable

    Treat past customers as an asset: staying top of mind, asking for reviews and referrals, and why repeat business beats chasing new leads every time

    Make your marketing easy to understand: sounding like a human instead of an industry brochure

    Protect your time: shutdown routines, office hours, and why your business shouldn't require 24/7 access to you

    Professionalism is a competitive advantage: showing up, following through, and answering your messages

    Key Quotes & Takeaways:

    "You cannot ask for more business if you are not handling the business that you have right now." Alissa

    "Being good at your craft and being good at running your business are two different skills." Katy

    "It's tricky being an entrepreneur because all sides of the brain are needed." Alissa

    "It is so easy to confuse being busy with being profitable." Katy

    "You don't have to be the best at what you do. You just have to do what you say you're going to do." Alissa

    Products, People & Previous Episodes Mentioned:

    Emily Ley / The Simplified Planners (referenced for her "make the decision once" philosophy)

    Episode 17: What to Do When You Are New OR Slow

    Want to toast someone on the show? Send us a voice or video message with your name, who you're toasting, and why! Email it to team@hustlehumblypodcast.com.

    Leave us a review at http://ratethispodcast.com/hustlehumbly

    Get your FREE Database Template: http://hustlehumblypodcast.com/starthere

    Email Templates 101: http://emailtemplates101.com

    Agent Systems 101: http://agentsystems101.com

    All Resources: http://hustlehumblypodcast.com

    Submit your topic ideas and toasts to Team@HustleHumblyPodcast.com

    Music:

    Straight A's by Connor Price → https://connorprice.shop/

    The Good Life by Summer Kennedy → https://soundcloud.com/summerkennedy/the-good-life

    Be The One by Matrika → https://uppbeat.io/t/matrika/be-the-one

    Mon, 07 Sep 2026 - 1h 11min
  • 415 - 369: Where Communication Breaks Down

    Have you ever sent an email, assumed it was read, and then found out three days later it wasn't?

    This week we're digging into where communication breaks down in a real estate transaction, and it's happening more than ever right now. Everyone has a hundred tabs open in their brain, clients are getting information from a dozen different places, and somehow we're still expected to be the ones who keep it all straight.

    We start with the basics: verifying who your actual client is (still learning that lesson years in), and why "I sent the email" is not the same as "they read the email." Alissa shares her blind copy and snooze trick for following up on important messages, plus how she handles group texts and email chains when there's a spouse, a divorce, or a court-ordered communication app involved.

    Then we get into a story from Alissa's very first listing appointment as a brand new agent, and the lesson in taking the high road instead of over-explaining or defending yourself when a client questions you.

    We also talk about voice notes, why tone gets lost the second you're not talking to someone in person, and the very real, very current problem of clients running everything through ChatGPT before they even talk to us. Katy tells the story of a seller's AI-drafted repair response that read as cold and rude, the two hours she spent recategorizing repair costs on a Saturday morning to try to save the deal, and how the whole thing resolved itself while she was feverishly working. It's a good reminder that in this market, we have to be more prepared than ever, because our clients are showing up to conversations having already asked the machine first.

    Here's what we cover in this episode:

    Why "I sent it" doesn't mean "they read it," and the blind copy and snooze trick for following up

    Verifying who your actual client is before you assume everyone already knows

    Keeping everyone in the loop with group texts and email chains

    A story from Alissa's very first listing appointment

    Why voice notes are becoming a go-to for tone when a text or email just won't cut it

    How a couple's phone consultation revealed they weren't even on the same page about buying

    A seller's AI-drafted repair response that read as cold and rude, and what it took to smooth it over

    Why you have to assume every text, email, and voice note gets forwarded to someone else

    Why clients are checking with ChatGPT before they check with you, and what that means for how prepared you need to be

    The importance of being the calm, confident, professional voice in every transaction, especially now

    Key Quotes & Takeaways:

    "You have to assume everything you text and email and say is forwarded." Alissa

    "The tone from the machine was not going to work in a real life scenario." Katy

    "We now more than ever need to be the boss." Alissa

    "Your client needs to know what you know to make the best decision." Katy

    "It's a fine line between too much and too little." Katy

    Products, People & Previous Episodes Mentioned:

    Episode 358: Who Actually Has to Sign? How to Protect Your Business (hustlehumblypodcast.com/358)

    Never Split the Difference by Chris Voss

    Trello (for tracking your pipeline)

    Want to toast someone on the show? Send us a voice or video message with your name, who you're toasting, and why! Email it to team@hustlehumblypodcast.com.

    Leave us a review at http://ratethispodcast.com/hustlehumbly

    Get your FREE Database Template: http://hustlehumblypodcast.com/starthere

    Email Templates 101: http://emailtemplates101.com

    Agent Systems 101: http://agentsystems101.com

    All Resources: http://hustlehumblypodcast.com

    Submit your topic ideas and toasts to Team@HustleHumblyPodcast.com

    Mon, 31 Aug 2026 - 48min
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