The Smart Real Estate Coach Podcast|Real Estate Investing

Chris Prefontaine
undefined
Dec 3, 2025 • 43min

Episode 536: AI Search Visibility & the Future of Real Estate Lead Gen with Trevor Mauch

In this masterclass episode of the Smart Real Estate Coach Podcast, I sit down with Trevor Mauch, founder and CEO of Carrot, a five-time Inc. 5000 company that's helped thousands of real estate investors and agents generate highly motivated seller leads online. Trevor's not just a "software guy" either—he's a buy-and-hold commercial investor himself, doing owner-carry deals and turning dead space into productive luxury apartments in his small town of Roseburg, Oregon. We start with something almost everyone asks me at bootcamps: lead gen. Trevor breaks down what he calls evergreen marketing, online lead systems that work for you 24/7 instead of keeping you on the hamster wheel of cold calling and direct mail. Then we go deep on AI search visibility, how Google's AI overviews and tools like ChatGPT are changing SEO, and what you can do right now to win in that new world. From there we shift into entrepreneur mindset: breaking through revenue "pain lines," designing your calendar around energy instead of just money, and building a business that actually funds your life vision instead of trapping you. Trevor shares exactly how he scaled Carrot to an eight-figure company, the role coaching and masterminds played, and why your business should give you energy, income, and impact, not just revenue. Key Talking Points of the Episode 00:00 Introduction 01:04 Who is Trevor Mauch? 03:02 Trevor's background: Growing Carrot and investing in real estate 04:55 The problem with "hamster wheel" marketing 06:56 How evergreen marketing generates inbound online leads 07:57 The impact of AI in how SEO works today 09:15 Practical AI SEO tips you can implement today 12:26 Taking advantage of hyperlocal links to build credibility online 15:56 Where to find Trevor and the AI Search Visibility Challenge 17:20 Business growth in 3s and 10s: The "Pain Lines" 19:50 Avoiding the "shiny object" churn through 12-month contracts 21:02 Optimizing for revenue vs optimizing for energy 22:01 The Quarterly Energy Audit: Identifying top energy-drainers 23:07 Redefining success and the purpose of being in business 27:09 Business game-changers: Coaching programs and masterminds 31:21 Fitness, faith, and proximity 34:04 What's next: EPIC Coaching, AI, and expanding Carrot Quotables "Business should give us work that interests and energizes us, it should fund our vision, and it should help us deliver an impact we're proud of." "Evergreen marketing might take a little bit longer to get going, but it builds this foundation and it builds amazing momentum." "You're the best person to mentor the person you used to be." Links Carrot https://carrot.com Trevor Mauch https://instagram.com/trevor.mauch QLS 4.0 - Use coupon code for 50% off https://smartrealestatecoach.com/qls Coupon code: pod Apprentice Program https://3paydaysapprentice.com Coupon code: Podcast Masterclass https://smartrealestatecoach.com/actionpodcast 3 Paydays Books https://3paydaysbooks.com/podcast Strategy Session https://smartrealestatecoach.com/actionpodcast Partners https://smartrealestatecoach.com/podcastresources
undefined
Nov 26, 2025 • 29min

Episode 535: Design A Cashflowing Real Estate Business with Asher Cohen

In this episode of the Smart Real Estate Coach Podcast, I sit down with Arizona real estate advisor and coach Asher Cohen to talk about building a real estate career and portfolio you actually enjoy. We cover how he went from marketing and commercial real estate through the 2008 crash to closing nearly 1,000 deals, focusing on buy-and-hold rentals, high-demand markets, and turning your current home into your first investment property. We also dive into leaving the W-2, using coaching the right way, working with investor-savvy agents, and Asher's core value of "love where you live." If you're an investor, agent, or aspiring full-time real estate entrepreneur, this episode will help you design a values-driven, cash-flowing real estate business. Key Talking Points of the Episode 00:00 Introduction 01:06 Who is Asher Cohen? 03:04 From marketing to commercial real estate before the 2008 crash 04:02 Pivot to residential: buy-and-hold, fix-and-flip, and hedge funds 05:08 Personal investing strategy: long-term buy-and-hold & "monopoly boards" 06:10 Arizona market shifts & why cash flow is harder today 07:55 Getting out of your W-2: Take the plunge & have faith 09:28 The role of coaching in making big transitions 10:44 Beware the gimmick coaches: 12:02 Ethics, values & the whole-life approach to coaching 16:09 Asher's three pillars: team, coaching, and transaction management 18:45 How investors should leverage relationships with investor-savvy agents 20:18 The difference between having a dedicated agent vs "whoever brings me a deal" 21:53 Primary transaction markets: Phoenix Metro, plus northern Arizona 23:24 How to get in touch with Asher and his team 24:10 Upcoming episode on The Real Deal with Asher Cohen Quotables "The best investment property is probably the one they own already." "You have to just take the plunge.You have to have the faith in yourself to make that leap." "Everyone should have a coach. The coach should have a coach, the coaches' coach should have a coach." Links Asher Cohen (480) 650-2995 BUYAZRE https://buyazre.com QLS 4.0 - Use coupon code for 50% off https://smartrealestatecoach.com/qls Coupon code: pod Apprentice Program https://3paydaysapprentice.com Coupon code: Podcast Masterclass https://smartrealestatecoach.com/masterspodcast 3 Paydays Books https://3paydaysbooks.com/podcast Strategy Session https://smartrealestatecoach.com/actionpodcast Partners https://smartrealestatecoach.com/podcastresources
undefined
Nov 19, 2025 • 30min

Episode 534: How I Went From Broke, Stuck, and Downsized to 10 Deals a Month

In this solo episode of the Smart Real Estate Coach Podcast, I pull back the curtain on my early days of investing and the messy transition from the 2008 crash into creative real estate. I walk you through the "dead zone" years, the IRS and creditor headaches, the move from a waterfront home into a 900-square-foot apartment, and how those experiences forced me to design what eventually became our Three Paydays™ system. If you're sitting in a W2 you don't love, stuck in analysis paralysis, or wondering how to actually replace your job with creative real estate deals, this one is for you. I'll share the exact sequence: hiring a coach when I had no money, raising $25K for a mastermind, doing my first 12+ deals out of a tiny office, building the team around me, and scaling from zero to 10 properties a month under contract. You'll hear the mindset shifts, the tactical steps, and the hard-won lessons that took me from "completely stuck in my head" to building a business and community that now has 95+ years of combined experience helping students all over North America. The goal is simple: shorten your learning curve, help you avoid my mistakes, and challenge you to ask, "Why not me?" Key Talking Points of the Episode 00:00 Introduction 01:24 The value of getting "a decade worth of lessons" handed to you 03:05 The difference between knowing the path vs. walking it 04:24 30/60/120-second decisions & the cost of indecision 05:47 What your real risk is: Gut check for anyone with a W2 07:13 Goals vs. a real plan with accountability 08:17 Why you don't need the full "how" before you commit to a clear beacon 09:31 IRS, creditors, repossessions, and downsizing to a 900-square-foot apartment 10:10 The birth of the Three Paydays system 11:08 How that "you're done" moment forced me back into the trenches making calls 12:03 Lesson: doubters, weather, circumstances, and past failures can't stop you 14:10 The difference between "crap debt" for toys and investing in yourself 15:34 Proximity, association & eliminating money stress 16:31 How thinking about money 24/7 chokes your creativity 17:20 Why you only need a phone and leads—no fancy tech required 18:13 How 13 deals stacked up between August and December 2013 19:08 Building the team: VAs, Nick, and qualifying buyers 20:23 Why good team members create revenue, not expense 21:29 Lesson: everyone is bad at first—that's normal and fixable 23:53 Tax refund season & stacking big checks 25:05 Future pacing: who are you in 3–5 years? 26:41 Start/stop list & aligning your calendar 28:01 Free resources to help you get on the right track Quotables "There is an enormous difference between knowing the right path and walking it, actually doing it in the trenches." "Only you can stop you." "Good team members will create more revenue, not expense." Links QLS 4.0 - Use coupon code for 50% off https://smartrealestatecoach.com/qls Coupon code: pod Apprentice Program https://3paydaysapprentice.com Coupon code: Podcast Masterclass https://smartrealestatecoach.com/masterspodcast 3 Paydays Books 3paydaysbooks.com/podcast Strategy Session https://smartrealestatecoach.com/actionpodcast Partners https://smartrealestatecoach.com/podcastresources
undefined
Nov 12, 2025 • 30min

Episode 533: Building a 1,500-Unit Portfolio Across Two Continents with Mike Stohler

In this episode of The Smart Real Estate Coach Podcast, I sit down with Mike Stohler—Navy veteran, former airline pilot, and now co-founder of Gateway Private Equity Group to talk about the highs, lows, and pivots that shaped his real estate journey. Mike's story is a masterclass in perseverance and reinvention. He went from losing everything in his early 20s to owning and managing over 1,500 multifamily units and expanding into hotel investing across the U.S. and Spain. We cover how he turned failure into fuel, built confidence through education and mentorship, and made the leap from W-2 employment to full-time investing. Mike also shares his transition from multifamily to hospitality and how partnering with experienced operators helped him scale internationally. If you've ever struggled with fear, self-doubt, or analysis paralysis, this episode will show you what's possible when you commit to learning, surround yourself with the right people, and take calculated risks toward financial freedom. Key Talking Points of the Episode 00:00 Introduction 01:06 Refocusing before the new year and setting goals for 2026 02:02 Meet Mike Stohler: Navy vet, former airline pilot, and real estate entrepreneur 04:01 Buying properties with no experience and losing everything 05:29 Learning resilience through military discipline and rebuilding after failure 07:27 The mindset shift from fear to action—"Just make the move" 09:28 The biggest fears holding investors back and how to overcome them 11:05 Why mentors and proximity are the ultimate accelerators for success 12:06 The power of partnership: how to shadow and learn from experienced investors 17:01 Balancing family, business, and burnout while making the transition from W-2 19:42 "Apartments are not hotels"—why hospitality is a completely different game 21:14 Building partnerships with experienced operators and profit-sharing structures 23:38 Why Spain? Expanding internationally through strong local networks 24:45 Managing hotel investments remotely: systems, teams, and automation 25:13 Turning travel into a business expense: living and investing internationally 26:21 How to get in touch with Mike and his team Quotables "All of the fears that are inside your head are real inside your head—but that's not the truth." "Hotels aren't real estate. They're businesses that sit on real estate." "I'm still learning every day. Warren Buffett's 90 and still reading 10 books a week." Links Mike Stohler https://www.linkedin.com/in/michaelstohler Gateway Private Equity https://gatewaype.com/ The Richer Geek Podcast https://www.therichergeek.com/ QLS 4.0 - Use coupon code for 50% off https://smartrealestatecoach.com/qls Coupon code: pod Apprentice Program https://3paydaysapprentice.com Coupon code: Podcast Masterclass https://smartrealestatecoach.com/masterspodcast Wicked Smart Books https://wickedsmartbooks.com/podcast Strategy Session https://smartrealestatecoach.com/actionpodcast Partners https://smartrealestatecoach.com/podcastresources
undefined
Nov 5, 2025 • 32min

Episode 532: How to Use Content, Coaching, and Connections to Scale Faster with Evan Carmichael

In this episode of The Smart Real Estate Coach Podcast, I welcome back Evan Carmichael—entrepreneur, author, YouTube powerhouse, and global speaker—to share powerful insights on belief, content creation, and taking bold action. Evan first joined us way back in Episode 241, before the world changed. Since then, his YouTube channel has exploded to over 4 million subscribers and hundreds of millions of views, and he's helped entrepreneurs and investors across the world grow their influence, impact, and income through content and consistency. In this conversation, we unpack how to overcome limiting beliefs, surround yourself with the right people, and use platforms like YouTube strategically, not just for views, but for real business growth. Evan also shares a practical framework he calls the "Money 50", plus his approach to using podcasts and interviews to build the right relationships and scale faster. If you're ready to take bold action, build belief, and start showing up more powerfully in business and life, this episode will give you the tools and mindset to do it. Key Talking Points of the Episode 00:00 Introduction 01:10 From biotech to YouTube: how Evan went from startup founder to global thought leader 03:43 Why belief and not resources is the biggest barrier for most entrepreneurs 06:21 Surrounding yourself with the right circle of influence and mentorship 07:24 How Evan structures his week around "extrovert days" to stay energized and focused 09:04 Success leaves clues: Learning daily from aspirational mentors 10:40 Repurposing content and collaborating ethically 13:48 What Evan would do if he started a real estate investing business today 15:35 The "Money 50" method: How to identify the 50 relationships that could change your business 16:04 The Biz Dev Show strategy: Interviewing your way into meaningful connections 18:08 Turning small podcasts into big opportunities 20:08 How to get in touch with Evan and his team 21:15 The biggest unlock in Evan's business: Learning to ask for help and seek coaching 22:09 Why most people's circles hold them back and how to find real mentorship 26:20 Acting on bold decisions and why waiting kills momentum Quotables "Every major breakthrough I've had has come after I asked for help. The unlock is on the other side of humility." "If you're in a job and everyone around you is stuck, remember—most people are cheering against you, not because they hate you, but because they're afraid to grow." "You are one great relationship away from your entire career changing." Links QLS 4.0 - Use coupon code for 50% off https://smartrealestatecoach.com/qls Coupon code: pod Apprentice Program https://3paydaysapprentice.com Coupon code: Podcast Masterclass https://smartrealestatecoach.com/masterspodcast Wicked Smart Books https://wickedsmartbooks.com/podcast Strategy Session https://smartrealestatecoach.com/actionpodcast Partners https://smartrealestatecoach.com/podcastresources
undefined
Oct 29, 2025 • 33min

Episode 531: After $200M Raised & Why Real Estate Still Beats the S&P 500 with Mike Zlotnik

In this episode of The Smart Real Estate Coach Podcast, I sit down with Mike "Big Mike" Zlotnik, CEO of TF Management Group and host of The Big Mike Fund Podcast. Mike's journey from tech executive to full-time investor and fund manager is a masterclass in timing, risk management, and courage. We unpack what it takes to transition from a corporate career to real estate, why masterminds are the fastest way to collapse your learning curve, and how today's commercial market offers one of the best entry points we've seen in years. Mike also shares his expert take on market cycles, cap rates, AI's growing impact on real estate operations, and why "fear in the market" often signals opportunity for disciplined investors. If you're serious about learning how to analyze risk, find predictable cash flow, and invest strategically in a changing economy, this episode is your blueprint. Key Talking Points of the Episode 00:00 Introduction 01:03 Who is Mike Zlotnik? 02:20 From IT to investing: how Mike went from VP in tech to full-time investor 03:55 Are you investing to learn or learning to invest? 05:03 The power of masterminds and how surrounding yourself with the right people changes everything 06:05 Networking, knowledge, and doing business with people you know, like, and trust 07:41 Why paying for access beats free advice: Value always outweighs cost 09:08 Making the leap in 2009 during market chaos: Burnout, courage, and timing 10:03 "Be greedy when others are fearful": Why the bottom of the market breeds opportunity 11:16 Why 2025 is shaping up like 2009: Commercial real estate values today 16:10 TF Management's current strategy: Precision over volume 17:43 Breaking down a commercial deal: cap rates, spreads, and downside protection 19:02 Why triple-net industrial is a hidden gem in today's market 20:35 Finding deals nationwide through trusted relationships and not by chasing markets 22:50 How to underwrite for safety: Positive spreads and conservative leverage 23:51 The impact of AI on real estate: Efficiency, deflation, and productivity 25:39 Why AI may push interest rates lower and create new tailwinds for real estate 28:05 Mike's interest rate forecast and why the next few years favor disciplined investors Quotables "Are you investing to learn or learning to invest? It's always both." "When the cycle is at the bottom and fear is high, that's when I get greedy. That's where wealth is built." "Success isn't ready, aim, fire—it's ready, fire, aim. You just keep adjusting until it works." Links BigMikeFund https://bigmikefund.com/ The BigMikeFund Podcast https://podcasts.apple.com/us/podcast/bigmikefund/id1333666009 QLS 4.0 - Use coupon code for 50% off https://smartrealestatecoach.com/qls Coupon code: pod Apprentice Program https://3paydaysapprentice.com Coupon code: Podcast Masterclass https://smartrealestatecoach.com/masterspodcast Wicked Smart Books https://wickedsmartbooks.com/podcast Strategy Session https://smartrealestatecoach.com/actionpodcast Partners https://smartrealestatecoach.com/podcastresources
undefined
Oct 22, 2025 • 25min

Episode 530: How $100M in Private Funds Is Navigating Today's Economy

In this episode of The Smart Real Estate Coach Podcast, I sit down with Lon Welsh, founder and CEO of Your Castle Real Estate and Ironton Capital, to unpack how investors can navigate today's economic climate with data, discipline, and diversification. Lon brings more than two decades of experience in commercial and residential real estate and now manages nearly $100 million in private funds through Ironton Capital. We talk about how market trends are shifting across regions, how private income funds compare to active investing, and why investor sentiment is near decade lows despite strong fundamentals. Lon also shares how his team is using AI and data analytics to gain an edge in decision-making, plus what investors should expect heading into 2025 and beyond. If you're ready to sharpen your macro understanding and learn how to balance active vs. passive investing, this episode will help you make smarter, calmer financial decisions in any market cycle. Key Talking Points of the Episode 00:00 Introduction 01:20 Who is Lon Welsh? 02:45 National housing slowdown: why the West and Southeast are softening faster 04:05 Comparing private funds vs. individual investing: pros, cons, and liquidity 05:17 Why investor sentiment is at a decade low and how media fear feeds it 06:35 Explaining Ironton's Short-Term and Medium-Term funds 08:26 The ideal investor profile: active landlords, busy professionals, and developers 09:29 How developers use Ironton's funds to earn while waiting on permits 13:16 The National Diversified Fund: balancing new builds with value-add multifamily 14:20 Using AI for analytics, underwriting, and even writing Lon's 14th book 15:32 How Lon tracks national real estate trends quarterly and why it matters 17:30 The regional outlook for 2025: where growth and appreciation are heading 18:56 How to get in touch with Lon and his team 19:54 Alternatives & diversification: making institutional-grade investing accessible 20:45 How the JOBS Act opened opportunities for accredited investors Quotables "Consumer sentiment right now is the lowest it's been in a decade, even though the economy is healthier than people think." "Don't panic. The media thrives on fear but markets reward patience and perspective." "At each phase of the market cycle, there's a different strategy that works best. Listen to the market, don't fight it." Links Ironton Capital https://irontoncapital.com FREE Guide to Passive Diversified Real Estate Investing https://irontoncapital.com/smartrecoach Lon Welsh lonwelsh@irontoncapital.com QLS 4.0 - Use coupon code for 50% off https://smartrealestatecoach.com/qls Coupon code: pod Apprentice Program https://3paydaysapprentice.com Coupon code: Podcast Masterclass https://smartrealestatecoach.com/masterspodcast Wicked Smart Books https://wickedsmartbooks.com/podcast Strategy Session https://smartrealestatecoach.com/actionpodcast Partners https://smartrealestatecoach.com/podcastresources
undefined
Oct 15, 2025 • 34min

Episode 529: How to Leave Your 9-5 Job By Investing in Real Estate with Lauren Keen Aumond

In this episode of the Smart Real Estate Coach Podcast, Chris is joined by Lauren Keen Aumond, a Florida-based real estate investor, podcast host, and personal finance educator who left her corporate sales job at age 33 thanks to her strategic investing. Lauren walks us through her journey from personal finance nerd to full-time investor, how she built her rental portfolio, and the importance of taking action before you're desperate to leave your job. She and her husband now manage a combination of short-term and long-term rentals, operate with financial freedom, and navigate the unique challenges of the Florida market—including tricky insurance issues and tenant laws. You'll also hear Lauren's best advice for escaping the 9-to-5 grind, how she and her husband split responsibilities in both life and business, and the behind-the-scenes evolution of her podcast Adulting Is Easy. This episode is a masterclass in intentional living, taking action, and building a life on your own terms. Key Talking Points of the Episode 00:00 Introduction and welcome 01:05 Meet Lauren Keen Aumond: real estate investor and content creator 01:52 Leaving her corporate job at 33—how she built her foundation early 02:40 Why you shouldn't wait until you hate your job to start investing 04:00 How Lauren bought her first house at 22 working at Toys "R" Us 06:10 House hacking and her first experience as a landlord 07:20 The role her dad played in keeping her first property as a rental 07:50 Meeting her husband and scaling their portfolio together 08:20 Why they moved from long-term to short-term rentals 08:53 Their current portfolio: apartment buildings, duplexes, ADUs 09:30 How her husband selling his engineering firm accelerated their progress 10:00 Advice for those stuck in a corporate job: "Don't give your best to someone else" 10:45 Set a goal, have a plan, and stick to it 11:50 The belief factor: "You already take more action than most" 12:50 The importance of setting a hard date for quitting 13:19 Details on the Wicked Smart Apprentice Program 15:00 Real examples of students who made the leap from corporate 15:50 How tenant laws led Lauren to shift toward short-term rentals 16:30 Florida's murky tenant laws and eviction moratoriums during COVID 17:58 Why short-term rentals offer more control over property access 18:32 Managing real estate with your spouse: the good, the bad, and the boundaries 20:10 How Lauren and her husband split responsibilities—and why they had to redefine their roles 21:49 The challenges of being romantic and business partners 22:32 Florida market analysis: insurance costs, flood zones, and climate concerns 24:00 What properties are likely to appreciate—and which won't 25:19 Lauren's podcast Adulting Is Easy—teaching finance through storytelling 26:12 Her #1 takeaway from hundreds of podcast interviews 26:41 Avoiding "self-help porn": why action matters more than knowledge 27:27 Tying your action to a strong "why" 28:55 Lauren's why: freedom from alarms, business trips, and limitations 29:46 Final thoughts and how to connect with Lauren Quotables "Don't wait until you hate your job to build your exit plan. Start while you're still happy." "Why would you give the best of yourself to someone else, day after day, instead of to your own dream?" "Have a goal—and when you hit it, do the thing. Leave the job." "Action is what makes you an investor. Not podcasts. Not books. Action." "The confidence boost from taking action will make the rest of life easier. Everything changes." Links QLS 4.0 - Use coupon code for 50% off https://smartrealestatecoach.com/qls Coupon code: podApprentice Program https://3paydaysapprentice.com Coupon code: PodcastMasterclass https://smartrealestatecoach.com/masterspodcast Wicked Smart Books https://wickedsmartbooks.com/podcast Strategy Session https://smartrealestatecoach.com/actionpodcast Partners https://smartrealestatecoach.com/podcastresources
undefined
Oct 8, 2025 • 27min

Episode 528: The 4 Pillars of Powerful Negotiation with Derek Dombeck

In this episode of The Smart Real Estate Coach Podcast, I'm joined by our newest team member and longtime friend of the community—Derek Dombeck. Derek has completed thousands of creative real estate deals, built multiple successful businesses, and is now stepping into a coaching and mentorship role here at Smart Real Estate Coach. In this episode, we unpack Derek's negotiation training, explore how he's helping our associates refine their people skills, and dive into the art of controlling the conversation, overcoming objections, and closing more deals. Derek also shares recent transactions he's working on, including a divorce scenario turned win-win lease purchase, and a seller-financed duplex bought with private money, showing exactly how creativity and strong communication turn challenges into profits. Whether you're a new investor learning the ropes or a seasoned dealmaker looking to sharpen your edge, this episode will level up the way you negotiate, close, and grow. Key Talking Points of the Episode 00:00 Introduction 02:45 Recap of Derek's live negotiation training at QLS Live Boston 03:24 Why most investors learn strategies but never master communication 05:02 Personality profiling: identifying who you're talking to in the first few minutes 06:12 The driver vs. analytical personality and how to adjust your communication style 07:33 Frame control: leading conversations even from a "beta" position 09:10 Storytelling as a negotiation tool: overcoming objections before they appear 10:26 The four pillars of powerful negotiation: personality, control, storytelling, and closing 11:50 Introducing the "No Means Not Now" negotiation course 13:19 Derek's first impressions as a coach inside the Wicked Smart community 17:19 Derek's recent deal: divorce property turned lease purchase success 20:56 Second deal: seller-financed duplex using private capital with equity share 21:51 Negotiating with private lenders and structuring long-term terms 23:47 Take action: Get in the room, learn, and do deals together Quotables "People spend a lot of time learning strategies, but almost no time learning how to actually talk to people." "Negotiations are nothing more than social interactions—and you can learn to control every one of them." "If you can control the frame, you can control the outcome." Links No Means Not Now Negotiation Course https://smartrealestatecoach.com/NoMeansNotNow QLS 4.0 - Use coupon code for 50% off https://smartrealestatecoach.com/qls Coupon code: pod Apprentice Program https://3paydaysapprentice.com Coupon code: Podcast Masterclass https://smartrealestatecoach.com/masterspodcast Wicked Smart Books https://wickedsmartbooks.com/podcast Strategy Session https://smartrealestatecoach.com/actionpodcast Partners https://smartrealestatecoach.com/podcastresources
undefined
Oct 1, 2025 • 36min

Episode 527: What $500M in Real Estate Transactions Taught Him About Investing with Kevin Bupp

In this episode of The Smart Real Estate Coach Podcast, I sit down with Kevin Bupp—real estate investor, bestselling author of The Cash Flow Investor, and host of the Real Estate Investing for Cash Flow Podcast. With more than $500 million in transactions and a portfolio spanning 14 states, Kevin has seen the highs, the lows, and everything in between. Kevin shares how he got his start tending bar at 19 before finding his first mentor, how the 2008 crash forced him to rebuild from scratch, and why mobile home parks and parking lots are his favorite asset classes today. We also dive into proximity, coaching, and the power of association—why surrounding yourself with the right people can completely change your trajectory. This is a masterclass in resilience, creative deal-making, and niche investing. Key Talking Points of the Episode 00:00 Introduction 02:26 Kevin's entrepreneurial start and early mentorship at 19 05:47 First property deal at 20 and building a single-family portfolio 07:50 The power of proximity and association: why who you know matters 09:43 How Kevin's mentors helped him get to where he is today 12:25 Coaching, ROI, and why investing in yourself pays off 14:07 "Get comfortable with being uncomfortable" – growth mindset in action 15:15 Surviving the 2008 crash, losing it all, and starting over 16:56 Discovering mobile home parks accidentally at first, then by conviction 21:33 Creative financing in mobile home parks—seller finance and bank debt 23:20 Parking lot investments: how Kevin evaluates demand drivers 27:11 Advice for new investors: pick one niche, go deep, and avoid overwhelm 30:15 Sunrise Capital and Kevin's current portfolio Quotables "If you could do one thing in life, get incredibly comfortable with being uncomfortable." "Private money is not easy to find, but once you have it, it can change everything." "We don't want to dilute our focus. It's really difficult to be an expert at many different types of real estate." Links Episode 52: From Broke to Mobile Home Parks in 8 States https://smartrealestatecoach.com/post/episode-52-from-broke-to-mobile-home-parks-in-8-states Real Estate Investing for Cash Flow https://podcasts.apple.com/ph/podcast/real-estate-investing-for-cash-flow-with-kevin-bupp/id791316884 QLS Live Ticket for $199 (Bonus: QLS 4.0 Program Included) https://smartrealestatecoach.com/qlspodcast QLS 4.0 - Use coupon code for 50% off https://smartrealestatecoach.com/qls Coupon code: pod Apprentice Program https://3paydaysapprentice.com Coupon code: Podcast Masterclass https://smartrealestatecoach.com/masterspodcast Wicked Smart Books https://wickedsmartbooks.com/podcast Strategy Session https://smartrealestatecoach.com/actionpodcast Partners https://smartrealestatecoach.com/podcastresources

The AI-powered Podcast Player

Save insights by tapping your headphones, chat with episodes, discover the best highlights - and more!
App store bannerPlay store banner
Get the app