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