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

Website: www.hotelinvestorplaybook.com

Contact Us: info@hotelinvestorplaybook.com

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

What happens when two young investors decide to buy a rundown motel, renovate it themselves, and document the entire journey online? For Brett and Casey McManus—creators of the viral Instagram account Innvestors—it led to a booming boutique hotel business and a wildly loyal following.

In this episode, Brett joins us to share how they went from industrial real estate to short-term rentals, and ultimately into purchasing a hotel—with a storytelling approach that’s as entertaining as it is effective. We dive into how they’ve built real brand equity through content, why they’ve avoided the traditional syndication path, and how SBA loans helped them get in the game.

We also get into the unsexy side of operations, what it really takes to run a hotel day to day, and how documenting the journey—flaws and all—turned into their biggest asset.

Whether you’re building a hotel brand, raising capital, or figuring out how to create content that actually connects, this one’s full of gems.

Connect with Brett:

Instagram: @innvestors

Website: https://apresinnkillington.com/

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.

Could you really buy a hotel development site in Fisherman’s Wharf, San Francisco—at a fire-sale price—and turn it into a boutique hotel with a projected value over $11 million?

That’s the plan today’s guest, Mike Demson, is working on. In this episode, Mike breaks down how he’s finding undervalued hotel opportunities, increasing density, reducing construction costs, and creating Instagram-worthy experiences with lean operations and smart design.

We challenge the assumptions, dig into the numbers, and talk about what it actually takes to pull off a project like this.

You’ll also hear about his second hotel project in Sonoma wine country—including a planned 67-unit expansion and brand partnership with IHG’s Vignette Collection.

If you’re thinking about hotel development—or you just want a behind-the-scenes look at a real-world deal—this one’s for you.

Connect with Mike:

Website: https://www.demsonconsulting.com

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

Instagram: https://www.instagram.com/mike.demson

Facebook: https://www.facebook.com/michael.demaria.1987

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.

What if your next hospitality investment didn’t sit on land?

In this episode, Mike and Nate sit down with Brian Meyer, founder and CEO of Flow Home—a luxury floating home rental business redefining waterfront living. We explore how Brian turned a niche concept into a scalable brand, how he raised capital, overcame regulatory barriers, built vertically integrated operations, and is now expanding into floating communities and resorts.

If you’re a hotel or STR investor looking for what’s next, you’ll love this conversation on innovation, scaling, and why the future of real estate might just be on the water.

Connect with Brian:

Linkedin: https://www.linkedin.com/in/brianmeyer5787/

Instagram: https://www.instagram.com/flohom_ofc/

Facebook: https://www.facebook.com/weareflohom

Website: https://flohom.com/

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.

“Do you enjoy paying taxes? Would you like to learn how to keep more of your hard earned money?

In this episode of The Hotel Investor Playbook, Mike and Nate sit down with Brian Bigham, Vice President at Madison Specs and also known as the Cost Seg Cowboy. Brian breaks down the powerful strategy of cost segregation, showing you how to legally keep more of your hard-earned money by accelerating depreciation on your real estate investments.

Listen in as Brian simplifies complex tax strategies using analogies like the “Pizza Method,” making it easy to understand how you can offset your gains, reduce your tax bill, and strategically plan for future investments. Plus, you’ll learn advanced loopholes that can help you avoid massive tax bills—even when selling a property.

If you’re a real estate investor looking to maximize your tax benefits and keep more cash in your pocket, you won’t want to miss this episode.

🔗 Connect with Brian:

Linkedin: http://linkedin.com/in/costsegcowboy

👉 Don’t forget to subscribe and leave a review!

Hotel Investor Playbook — The podcast where we talk story about how to make money investing in hotels.

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.

Ever dreamt of creating your luxury resort from scratch? In this episode, we’re diving deep into the world of ground-up hospitality development with Andrew Owlett, a visionary building a boutique wellness resort in Virginia— with plans to expand into three other states!

Here’s what you’ll learn:

🔥 The freedom and challenges of developing from scratch — Why Andrew chose to build rather than buy.

🔑 Critical first steps — From forming the right team to finding the perfect piece of land.

📍 Navigating zoning and special permitting — The do’s and don’ts of turning raw land into a thriving resort.

💡 Game-changing strategies — Including how Andrew funds his projects by acquiring small businesses to generate cash flow.

Andrew also gets real and personal, sharing how his experience as a first responder inspired him to create a wellness-focused retreat.

If you’re curious about ground-up development, and wellness resorts, or want to learn how to turn a vision into reality, this episode is a must-listen!

🔗 Connect with Andrew:

Instagram: @AndrewOwlett

👉 Don’t forget to subscribe and leave a review!

Hotel Investor Playbook — The podcast where we talk stories about how to make money investing in hotels.

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.

💡 AI is revolutionizing hospitality, but not how you think.

The big hotel chains? They’re struggling to adapt. The real advantage? It belongs to small, independent operators who know how to leverage AI the right way.

On this episode of The Hotel Investor Playbook, we sit down with Ari Smith, an AI scientist and futurist, to unpack:

✔️ How AI is making boutique hotels more profitable than ever

✔️ Where to automate—and where human service is irreplaceable

✔️ Why ultra-luxury stays will always demand a human touch

✔️ The AI-driven hospitality tech that’s leveling the playing field

✔️ How micro-communities could be the future of resilient real estate investing

Ari is building a 550-acre micro-community in Vermont, integrating AI with nature-driven experiences—AND developing next-gen tech that could change hotel operations forever. If you’re in hospitality or real estate investing, this is an episode you can’t afford to miss.

📍 Links & Resources:

•Connect with Ari: Balance Farm | FatRat.ai

•Follow us for more: The Hotel Investor Playbook

•Got questions? DM us on Instagram: @the_hotel_investor_playbook

🎧 Tune in now and get ahead of the curve in AI-driven hotel investing!

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.

🏨 How do you turn a seasonal boutique hotel into a $2M value-add opportunity?

In this episode of The Hotel Investor Playbook, we sit down with Ryan Edwards, owner of a 17-unit boutique hotel in Maine, to break down the real strategies that make a seasonal hotel thrive.


We cover:
✅ How he financed his $3.6M hotel deal with 75% bank financing
✅ The $100K revenue increase that added $1.4M in value
✅ How he built a 100% direct booking strategy (no OTAs!)
✅ Staffing challenges & using visa programs for seasonal workers
✅ Marketing strategies that fill rooms months in advance

If you’re considering investing in boutique hotels, seasonal markets, or direct booking strategies, this episode is packed with gold.

🔗 Connect with Ryan & Learn More:
👉 Instagram: @FiveGablesInn
👉 Website: https://fivegablesinn.com/

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.