From Olympic Trials to Losing Millions—And Bouncing Back With a Boutique Hotel Empire

In this episode of Hotel Investor Playbook, Mike and Nate are joined by Adam Dailey, a former 5x All-American athlete turned hospitality investor. Adam shares his wild journey—from building a multimillion-dollar business, losing it all in a matter of weeks, to bouncing back stronger with a growing portfolio of boutique hotels, hostels, and STRs.

We unpack:

•How championship-level discipline translates to high-performing hotel operations

•The mindset shift from solo business owner to team-driven investor

•Tactical ways to spot hidden value in underperforming hospitality assets

•Why your exit plan needs a backup plan

•What it really takes to raise capital from friends, family, and investors

•The future of self-check-in models vs high-touch hospitality

This one’s honest, gritty, and packed with lessons you won’t find in a textbook.

About Adam Dailey:

Adam Dailey is a serial entrepreneur, real estate investor, and former elite athlete with a passion for adventure and business. As the CEO of Bronco Surf Capital, he specializes in boutique hotels, hostels, and mixed-use projects in San Diego.

Adam founded Ludus Sports, a multimillion-dollar company that catered to sports tourism at global events like the Olympics, landing on the Inc. 500 list before facing a major financial setback. He later sold the business and wrote a book about his experience and about his travels: How to Run Away From Home (and Take Your Family With You).

A former five-time NCAA All-American and SEC Champion at the University of Arkansas, Adam also competed in the 2000 U.S. Olympic Trials in the 10,000 meters. Today, he balances real estate, coaching his kids’ sports teams, and leading the San Diego chapter of Entrepreneur Organization (EO).

Connect with Adam Dailey:

Linkedin: https://www.linkedin.com/in/adamdailey/

Connect with Michael on Instagram or LinkedIn.

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