Episode
33. This One Thing Will Make or Break a Commercial Real Estate Deal w/Kevin Bupp
- Podcast
- AJ Osborne Podcast
- Published
- Oct 9, 2025
- Duration seconds
- 2554
- Processing state
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Summary
There’s one thing that separates a “good” commercial real estate deal from the rest —and you have complete control over it. Get it right, and your returns are much closer to being locked in. Get it wrong, and you could have a cash-draining property on your hands. Kevin Bupp , 20+ year investing veteran and mobile home park and parking lot expert, is here to help. He built a massive real estate portfolio from nothing , starting at the young age of 20, lost it all in the 2008 crash, and rebuilt it bigger, better, and (much) safer than before. He’s learned the lessons the hard way, so you don’t have to. In this episode, we’re talking about commercial real estate underwriting , how to separate the “good” deals from the BS, and the most crucial factor that makes or breaks a real estate investment. Kevin is buying multimillion-dollar deals, meaning his margin for error can only be tiny . This is the way he decides whether to buy or move on to the next opportunity. Insights from today’s episode: The most crucial factor of a “good” real estate investment that so many got wrong in 2020 - 2022 The best loan to use for commercial real estate investing that can save your deal during bad times What sets the successful real estate investors apart from the rest (99% of people can’t handle this) How Kevin built his portfolio, lost it all, and rebuilt it better and stronger than before How to filter out the BS when getting started in real estate investing — Sunrise Capital Investors: https://sunrisecapitalinvestors.com/fund-4/ Kevin’s Website: https://kevinbupp.com/ Kevin’s LinkedIn: https://www.linkedin.com/in/kevinbupp/ Sign Up for My Newsletter Here: https://ajosborne.com/newsletter