Olympic Discipline, Million-Dollar Loss, and Building a Hospitality Portfolio | Adam G Dailey E24 Artwork

The Hotel Investor Playbook

Welcome to The Hotel Investor Playbook, hosted by real estate investors and hospitality experts Michael Russell and Nathan St Cyr. As the founders of Malama Capital and Howzit Hostels, Michael and Nathan have a wealth of experience in owning and operating boutique hotels, hostels, and other experiential lodging properties. With over $30 million in real estate investments, including short-term rentals, long-term rentals, commercial retail, and hospitality properties, they bring a unique perspective on how to turn passion-driven investments into financial freedom.

In this podcast, they share their roadmap for transitioning from traditional real estate investments to boutique hotels, offering listeners the insights and strategies needed to succeed in this niche market. Whether you're looking to learn about identifying the right property, managing operations, or understanding the financial complexities of boutique hotel ownership, The Hotel Investor Playbook has you covered.

Join Michael and Nathan each week as they document their journey towards building a $400 million real estate-based business and bring you along for the ride. Subscribe now and start turning your real estate investment dreams into reality.

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The Hotel Investor Playbook

Olympic Discipline, Million-Dollar Loss, and Building a Hospitality Portfolio | Adam G Dailey E24

April 01, 2025

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 Mike and Nate:

Instagram: @the_hotel_investor_playbook