The Painful Failure That Pushed Me to Pivot (and Made Me Millions) w/Joe Downs episode artwork

EPISODE · Dec 15, 2025 · 39 MIN

The Painful Failure That Pushed Me to Pivot (and Made Me Millions) w/Joe Downs

from Real Estate Investing for Cash Flow with Kevin Bupp

The fear of failure stops many from ever getting into real estate. But what if it's the failures that actually make you wealthy? Today's guest woke up in his 30s, broke and burned out, having traded years of his life for a business that went belly up. What looked like a failure to everyone else was the start of a multimillion-dollar business empire for Joe Downs. Joe has invested in it all—rental properties, flips, self-storage, mortgage notes, industrial warehouses, and more—but his newest obsession is one much of the market knows nothing about: pro storage. This new wave of self-storage has high demand, greater revenue, and a growing need in an increasingly entrepreneurial economy.  Joe breaks down why he's so excited about this new type of storage and shares the returns he's making from running an incredibly lucrative "distressed debt" company. Plus, why investors are overlooking the wide open opportunity in small "mom and pop" real estate investments and how to "reinvent" yourself after failure puts you back at the starting line.   Insights from today's episode: The pivots that helped Joe build multiple million-dollar real estate businesses Surprisingly high returns in the second mortgage note market (big investors can't get in!) Is everyone wrong about self-storage? Why this asset is actually undersupplied in much of the country  Pro storage: the newest investing opportunity that is seeing a wave of demand  Think you can't start over in your 30s, 40s, or 50s? Joe will prove you wrong—and get you fired up — Connect with Joe on LinkedIn Email Joe: [email protected] Are you a high-net-worth investor with capital to deploy in the next 12 months? Build passive income and wealth by investing in real estate projects alongside Kevin and his team!  Grab a copy of my latest book, The Cash Flow Investor!  Listen to past podcast episodes! 

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The Painful Failure That Pushed Me to Pivot (and Made Me Millions) w/Joe Downs

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This episode was published on December 15, 2025.

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