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

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.

Connect with Adam Dailey:

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

Connect with Mike and Nate:

Instagram: @the_hotel_investor_playbook

Website: www.hotelinvestorplaybook.com

Contact Us: info@hotelinvestorplaybook.com

Interested in investing with Mike and Nate? Visit Malama-Capital.com for more information.