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

Oct 1, 2025

36:23

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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