From Stocks to Short-Term Rentals: Josh Meisel’s CEO Shift and Investment Diversification

In this episode of the Built For This Podcast, hosts Alissa Bickar and Andrea Lane sit down with real estate investor and entrepreneur Josh Meisel to uncover his unique journey from corporate employee and stock market investor to real estate owner and CEO of a short-term rental property management business.

Josh shares how he started out diversifying investments through real estate after getting burned by rising HOA fees on his first condo purchases. Learn how those early lessons shaped his pivot into multifamily and single-family rentals, and why long-term rentals became his investment of choice—even while building a thriving short-term rental business managing over 35 properties in Austin.

This episode is packed with real talk about building systems, making mistakes, and balancing passive income with the hard realities of running your own business. Josh opens up about the importance of discipline with tenants, the challenge of scaling a new business, and why choosing your role inside your company can be your greatest superpower.

 

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