Hustle Humbly Podcast

Alissa Jenkins & Katy Caldwell
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  • Entrepreneurship
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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.

  1. 6 days ago ·  Video

    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

  2. 24 Aug ·  Video

    368: How to Qualify Real Estate Clients Before You Waste Your Time

    Have you ever gotten a message from a total stranger asking you to show them a house tomorrow? Or, worse, NOW? This episode covers a little bit of everything: client intake, boundaries, and buyer and seller consultations, because honestly this topic touches almost every system we've built our businesses on. Lately we've both had new clients come to us in a completely different state than we're used to. Ready to go, no pre-approval, no idea what the process actually looks like, and a whole lot of whiplash for us. We walk through exactly how we intake a brand new buyer starting with that very first phone call, why pre-approval has to happen before we ever get in the car, and how the buyer representation agreement fits into that conversation. We share the story of a buyer we've worked with off and on since 2018 (yes, eight years), a listing referral that nearly fell apart over price, and a listing appointment where being honest about a renovation almost cost the job... until it didn't. If you've been letting your own rules slide because you're busy, or slow, or scared of losing a referral, this one is your permission slip to take control back from the very first conversation. Here's what we cover in this episode: Why client intake, boundaries, and buyer and seller consultations all overlap What to do when a brand new buyer wants to see a house before you've even met How to explain the buyer representation agreement without scaring people off Why pre-approval needs to happen before the buyer consultation, not after The "may I have a preferred lender call you" question that actually gets buyers moving A story about learning the hard way to meet at a seller's house before showing them other homes Why a referral doesn't automatically mean you have a real client A listing interview where honesty about an overpriced renovation almost cost the appointment Why fair housing means running your process the exact same way every single time What to do when a seller's neighbors are talking, and it starts affecting your reputation Key Quotes & Takeaways: "I don't like to list houses. I like to sell them." -Alissa "I want you to find somebody that you like, that you trust." -Alissa "Just because they sent you a human doesn't mean they sent you a client." -Katy "It's really up to you what you can endure." -Katy "You have to do it the same every time, whether you're busy or you're slow." -Alissa   Products, People & Previous Episodes Mentioned: Episode 113: Be the Boss (hustlehumblypodcast.com/113) Episode 210: Buyer Consultation (hustlehumblypodcast.com/210) Episode 143: Working with Sellers: Pre-Listing Prep (hustlehumblypodcast.com/143) Episode 79: Buyers, Buyers, Buyers (hustlehumblypodcast.com/79) Episode 365: Check Yourself Before You Wreck Your Business (hustlehumblypodcast.com/365) Build Your Own Business (BYOB), live starting September 8th (hustlehumblypodcast.com/byob-waitlist) Hustle Humbly Community (hustlehumblypodcast.com/membership)   This episode's toast is from Allison, honoring her mom, April Jeera, a Realtor in the Austin and San Antonio areas and president-elect of the Women's Council of Realtors Austin. 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

  3. 17 Aug ·  Video

    367: How to Mine Your Real Estate Database

    Happy birthday to us! 🥳Hustle Humbly is turning seven this week, and in seven years we still haven't found a better way to build a real estate business than the good ole fashioned database. So we're celebrating the only way we know how: talking database again! If you're new here, this is your sign to go listen to Episode 9, the original database episode, and grab our free database template at hustlehumblypodcast.com/starthere. But if you already have a database, this episode is for you, because today we're not building one, we're mining it. We walk through the questions you need to ask yourself about your own database (when's the last time you actually opened it and read through it?), the two check-in messages every agent should be sending, and how to go name by name to figure out who's a buyer, who's a seller, and who's sitting on a referral you haven't asked for yet. We even share our own numbers. One of us found that 6.5% of our database has sent more than one referral, the other found 4.7%.  Here's what we cover in this episode: Why you can never truly be "done" with your database The "who do you know" list and how it helps you refresh who belongs on there Why someone who makes you dread seeing their name shouldn't be on your list The two check-in messages to send. A real story about an email that went out to 390 contacts and got 20 responses, no call to action needed Why "everybody already knows a Realtor" is a story you're telling yourself Adding a referral column to track who sends you repeat business How to use closed dates to figure out who's warming up to move again Moving people up the "thermometer" from cold to warm to hot How to track and thank your referral sources so they keep sending more The exercise we did before recording: going through our own databases and finding our repeat referrer percentage Action steps to open your database this week and start sorting Why database is still the best business insurance you have against "the machine" A sneak peek at Build Your Own Business, our live database class starting September 8th Key Quotes & Takeaways: "You can never be done with your database." "If there is someone in your database that makes you go, oh, I don't want to get to this name, they shouldn't be there." "When your business is struggling, database is the answer." "You have to be better than the machine." Products, People & Previous Episodes Mentioned: Episode 9: How to Use Our Database (hustlehumblypodcast.com/9) FREE Database Template (hustlehumblypodcast.com/starthere) Build Your Own Business (BYOB), live starting September 8th Atomic Habits by James Clear 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

  4. 10 Aug ·  Video

    366: What Agents Are Really Saying Online

    Ever wonder what real estate agents are talking about when nobody's watching? We went straight to the source: Reddit. We dug through the subreddits: r/realtor and r/realestateagent, reading through 2025 and 2026 posts to see what agents are actually saying when they think no one from their brokerage is looking. And y'all, it was a lot. One out of every three posts was a vendor or marketer trying to sell agents a shiny solution to a problem they just admitted to having in public. The most engaged posts were not the wins or the strategy questions. They were confusion, hurt feelings, and agents who felt completely lost. So we broke it all down by topic: vendor fatigue, new agents who are drowning, a commission split that made everyone (including us) mad, what happens when your best friend uses another agent, the listening mistake that cost one agent a listing, social media chaos, CRM overload, the professionalism gap, and the agents juggling real estate with a second job. If you have ever felt like you were the only one struggling with any of this, we promise you are not. Here's what we cover in this episode: Why one in three posts on real estate Reddit is really just a vendor pitch in disguise What it means that the most engaged posts are about confusion, not wins Why new agents commenting on Reddit made us so sad, and what's really going on What "character creation syndrome" is and why the perfect headshot and business cards don't build a business Episodes to check out if you or someone you know is a drowning new agent The commission split story that had everyone up in arms and what she should have known before saying yes What happened when a good friend went under contract with a Zillow agent without saying a word The listing an agent lost because she forgot a detail the seller told her three weeks earlier Why posting "just sold" content is officially spam, and what to post instead Why agents are sitting on thousands of contacts they never actually use The professionalism gap showing up in nearly every single thread we read What dual career and part-time agents are up against, and the encouragement they need to hear Key Quotes & Takeaways:   "The most engaged posts weren't about strategy or wins. They were about confusion, hurt feelings, and feeling lost." "We've got to stop trying to automate the relationship building part of our job. It's reps." "Building the image of a successful agent doesn't actually create success. Doing the things successful agents do should be your only focus." "Fifty percent of the time the other agents are way harder than my clients." Products, People & Previous Episodes Mentioned: Episode 361: Agent Vendor Relations (hustlehumblypodcast.com/361) Episode 356: Mistakes New Agents Make (hustlehumblypodcast.com/356) Episode 336: Growing Realtor Confidence (hustlehumblypodcast.com/336) Episode 103: New Agent 101 (hustlehumblypodcast.com/103) Episode 26: Everything We Wished We Knew Before We Started (hustlehumblypodcast.com/26) Episode 334: What to Say When Friends or Family Use Another Agent (hustlehumblypodcast.com/334) Episode 39: How to Deal with Rejection (hustlehumblypodcast.com/39) Episode 116: Communication (hustlehumblypodcast.com/116) Episode 326: Managing Sellers with Confidence (hustlehumblypodcast.com/326) Episode 343: The Social Media Mindset Shift (hustlehumblypodcast.com/343) Episodes 301, 308 & 274: Social Media Episodes (hustlehumblypodcast.com/301, /308, /274) Episode 335: Before You Join the Real Estate Jam (hustlehumblypodcast.com/335) Episode 23: The Three P's of Professionalism (hustlehumblypodcast.com/23) Episode 360: Feel Good Stories From the Field (hustlehumblypodcast.com/360) Episode 355: Treat Your Business Like a Business (hustlehumblypodcast.com/355) Episode 198: Real Estate Side Hustles (hustlehumblypodcast.com/198) Plaud recorder (mentioned as a tool agents are using to capture appointment details) 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

  5. 3 Aug ·  Video

    365: Check Yourself Before You Wreck Your Business

    Do you ever feel like you're working hard in your real estate business, but nothing is actually happening? You might be busy without being productive, and that is exactly what we are digging into today. When you work for yourself, nobody is forcing you to audit your business. You just stay in it instead of working on it. So we decided to hold up a mirror and do a full accountability check in, together, out loud, on the mic. We walk through the same audit questions we ask ourselves: did I actually do the thing, did I do it once or consistently, did I have a follow up plan, am I measuring results too soon, and did I tell people what I do and how I help. We use a real case study (73 hand written letters to one neighborhood) to show exactly how this plays out, then we take you through marketing, database, consistency, ROI, and real life scenario audits including the gym, your sphere, and past clients who used another agent. Here's what we cover in this episode: Why "hiding behind busy work" isn't the same as growing your business The real reason your business "clock" hasn't started (and why it now takes closer to four years, not three, to really get momentum) The five big questions to ask before you decide something "worked" or "didn't work" A live case study auditing Alissa's 73 hand written letters to one neighborhood Why doing something once is never enough to judge results How to build a real follow up plan instead of just hoping something works Auditing your general marketing activities and tracking your actual ROI Why comparing yourself to the other agents in your market is a trap How to know if you're giving something enough time before you quit The database and relationship questions every agent should be asking Why adding new people to your database in the last 30 days matters The consistency check: are you working every week, or only when it's slow? Real life scenario audits: lost past clients, mailers that didn't work, and sphere referrals Why the gym, school, or church community isn't producing referrals (and what actually will) What to ask yourself when marketing spend didn't produce results The "then what" question that changes everything about your follow up Why relationships, not transactions, are the real long game in real estate Key Quotes & Takeaways: "If you've been in the business for five years and you've never treated it like a business or had systems in place and tracked what you're doing, I hate to tell you, but your clock hasn't started." - Alissa "You're not working on it, you're working in it." - Katy "Preparation is the highest form of procrastination." - Alissa "It's like you keep saying, then what?" - Alissa "We should enjoy our marketing. It should feel natural to you. It should be your vibe. And that is how you connect with people." - Katy Products, People & Previous Episodes Mentioned: Hustle Humbly Community (hustlehumblypodcast.com/membership) Episode 17: What to Do When You Are New OR Slow Episode 19: all about consistency Leave us a review at RateThisPodcast.com/HustleHumbly Get your FREE Database Template Email Templates 101 All Resources Submit your topic ideas and toasts to Team@HustleHumblyPodcast.com.

  6. 27 Jul ·  Video

    364: How to Handle Losing a Client

    You win some, you lose some. So why does losing one always feel like it means so much more? This week we get into what happens after the deal falls through, the client picks another agent, or a friend quietly lists their house with someone else. We talk about the "one day rule" a friend taught us for grieving a lost deal, and why real estate karma means the good and the bad even out over time if you let it. We share the moment a nervous friend told us she wasn't hiring us, and why we've learned to respond with grace instead of guilt-tripping. We get into the client who broke the news she was moving out of state over text, the ones who ghost instead of confronting you, and why the people who face you directly deserve to never regret it. We also cover the awkward reality of splitting business between two agents in one household, the ChatGPT trick for cooling down an angry email before you hit send, and a listener's story about a "shopper" who keeps circling back without ever committing. Then we tell the story of a seven figure deal that turned into a $70,000 condo, then into no deal at all, and how walking away with honesty turned into a stream of referrals instead. And we close with the story of an eight year strained friendship that got repaired with one honest text message. Here's what we cover in this episode: Why we believe in real estate karma and how it evens out over time The "one day rule" for grieving a lost deal and moving on What to say when someone nervously tells you they're not hiring you Why business gets messier when it's built on relationships, not just transactions The client who confessed she was relocating out of state over text Being the icebreaker when a client lists with someone else and never tells you How to handle it when a buyer's spouse already has "his" agent Splitting a household's business between two different agents Using ChatGPT to turn an angry email into a professional one A listener's letter about a shopper who never quite commits Sticking to your boundaries even when it might cost you the deal The seven figure deal that shrank to a $70,000 condo, then to nothing How honesty about a bad purchase turned into new referrals Repairing an eight year strained friendship with one text Our rapid fire list of real estate karma quotes to remember Key Quotes & Takeaways: "Be the agent who says no worries, I'm happy for you, and actually means it." "Every time you choose grace over resentment, you're playing the long game." "Don't burn a bridge because you're hurt. You may need to cross it again later." "Real estate is hard enough without carrying a backpack full of grudges." "If you take every business decision personally, this business will eat you alive. Your value is not determined by whether someone hires you." "We're building a reputation, not collecting scorecards." Products, People & Previous Episodes Mentioned: Episode 346: Desperate Agent Behavior (hustlehumblypodcast.com/346) Hustle Humbly Community (hustlehumblypodcast.com/membership) 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

  7. 20 Jul ·  Video

    363: What to Do When the Appraisal Comes In Low

    Three low appraisals. Ten days. One Realtor who used to be an appraiser herself, with a dad and sister still in the field. If you've been hearing agents in your market say appraisals are coming in low right now, you're not imagining it. In this episode, Alissa walks us through three real, current transactions where the appraisal came in under contract price, and what she actually did about each one. From a $20,000 gap that took two hours of dispute writing to a $55,000 shortfall that made her question her entire career, this is a real look at what it takes to fight for your seller, or protect your buyer, when the number comes back low. We get into why appraisers are often behind the market, what actually goes into a strong appraisal dispute letter, why you should never let ChatGPT write the whole thing for you, and how to keep your sellers grounded without ever making promises you can't keep. Here's what we cover in this episode: Why appraisals are coming in low right now, and why appraisers are always a little behind the market Case Study #1: the $20,000 low appraisal that got resolved for a $13,000 gap Exactly how to start an appraisal dispute (and why you review before you call your seller) What actually goes in a dispute letter: facts only, no feeling words Why you can't rely on ChatGPT to write your dispute for you Buyer and seller options when an appraisal comes in low, and who really has to sign off Case Study #2: the small $3,000 gap where the seller chose not to dispute at all Case Study #3: the $55,000 appraisal gap that took two of the longest dispute letters of the week How to set your sellers' expectations at the listing appointment so a low number doesn't blindside them Why you're just the messenger with data, and how to keep that from feeling personal Key Quotes & Takeaways: "It needs to be written as factual. Only the facts." – Alissa "You have to know these houses. If the appraiser makes a mistake, the computer doesn't know it's a mistake." – Alissa "You're just a messenger with data." – Katy "It's not that I'm not confident. It's that I know a second appraisal could come in lower too." – Alissa Products, People & Previous Episodes Mentioned: ChatGPT / AI tools (referenced as a starting point for reviewing an appraisal, not a replacement for agent fact-checking) Got a toast for someone who's helped you in your business? This episode's toast is from Samantha Gonzalez, honoring her mentor Teena Marie Mateo. Send yours to team@hustlehumblypodcast.com and we might read it on the show! 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

  8. 13 Jul ·  Video

    362: Why Buyers Are Struggling Right Now

    You want to buy a house. But you can't. Or it's just really, really hard. We've both got buyers right now who are struggling, and it's not because they're not trying. It's because the math has changed. Back in the 60s, 70s, and 80s, houses were $20,000 to $40,000 and you needed 20% down. Now that down payment number is basically what a whole house used to cost, and the median price in our market has nearly tripled since one of us started selling real estate in 2005. So in this episode we're getting into what it actually looks like to help a buyer who is priced out, unsure, or just starting to gather their numbers. From lender grant programs you may not know exist, to the buyer consultation questions that save everyone time, to the client who thought they had a million dollars covered and didn't, we're sharing the real stories behind helping buyers navigate an affordability crunch without losing hope (or your sanity). Here's what we cover in this episode: - Why the math is so different now than it was even ten years ago - Why you need more than one go-to lender, and how to find out what specialized or grant programs are available in your market - The Regions Bank 100% doctor loan and why niche lender programs matter - A real buyer consultation story and why starting with the numbers first changes everything - How to handle a referral when the buyer's expectations and budget don't match reality - What a credit re-score is and why it matters for buyers who aren't quite ready - The overconfident buyer story that still makes us wince - Why "congrats on your pre-approval" doesn't mean go start showing houses - Why you always need to see a house with your own eyes before writing an offer - How to manage parents who show up excited (and a little too opinionated) during a buyer's search - Why some inspection issues are dealbreakers and others just need a little imagination Key Quotes & Takeaways: - "It's not that I'm too good for the price point. It's that I know the mental toll." - "There's no secret. There's no secret foreclosure. There's no secret fixer upper." - "I just want my buyers to have the information and the education to make a good, sound decision. I don't want the decision made off of emotions or fear." - "Owning the house fixed my credit. Every month I paid that mortgage, my credit just went up, up, up, up." - "You have to start somewhere. It's an investment." (Speaker unconfirmed on all quotes above, this transcript's labels all read "Unknown" instead of Alissa/Katy.) Products, People & Previous Episodes Mentioned: - Episode 361: Agent Vendor Relationships (hustlehumblypodcast.com/361) - 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

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Hosts & Guests

About

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.

Information

  • Creator
    Alissa Jenkins & Katy Caldwell
  • Years Active
    2019 - 2026
  • Episodes
    380
  • Rating
    Clean
  • Show Website
    Hustle Humbly Podcast

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