Mikey Taylor spent his early career earning a living on a skateboard, then rebuilt his identity around a very different kind of risk-taking: real estate private equity. When Mikey Taylor joined Sean Kelly on the Digital Social Hour, he walked through exactly how that transition happened, from the financial realities of pro skating to the strategy behind a fund now managing a quarter of a billion dollars.
The conversation moves through the identity crisis that came with stepping away from competitive skating, the mechanics of starting a fund, and the specific financial habits Taylor credits with getting him there.
About Mikey Taylor
Mikey Taylor built a name for himself as a professional skateboarder before shifting his focus to real estate investing. That shift has since grown into a private equity fund built around real estate, including storage facilities and multifamily development projects, now managing roughly $250 million in assets.
Taylor has become known for pairing hands-on investing experience with a distinct philosophy around personal finance, including his approach to credit, debt, and building multiple income streams rather than relying on a single source of wealth. His path from athlete to fund manager has made him a frequent voice in conversations about turning a passion into a lasting business.
What Mikey Taylor and Sean Kelly Talked About
- How a professional skateboarding career became the foundation for a $250 million real estate fund
- The identity crisis that came with stepping away from competitive skating
- Why Mikey Taylor avoids debit cards and relies on credit strategically instead
- What it actually takes to legally start and operate an investment fund
- His approach to building multiple income streams instead of depending on one
- How storage facilities and multifamily development fit into his investment strategy
- Where artificial intelligence is starting to show up in his day-to-day business decisions
- The tax strategies he uses to help protect and grow his real estate returns
Why This Conversation Matters
Mikey Taylor's story is a useful reminder that a career built on one skill doesn't have to end when that skill does. His path from professional skateboarding to managing a nine-figure fund offers real, specific detail for anyone trying to turn a passion into a lasting business, not just a motivational headline.
▶ Watch the full episode on YouTube
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About Sean Kelly & the Digital Social Hour
Sean Kelly is an entrepreneur and the host of the Digital Social Hour, one of the fastest-growing interview podcasts in the world, where he sits down with entrepreneurs, athletes, creators, and cultural voices for candid, long-form conversations. The show draws over 100 million views a month across platforms. Explore more guest features on SeanKelly.io.
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