“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

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

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

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

Luxury glamping—game-changing investment or overhyped trend?

In this episode of The Hotel Investor Playbook, we sit down with Edward Haynes, a specialist in unique stays and experiential lodging, to unpack the massive growth in luxury outdoor hospitality.

We cover:

✅ Why glamping demand is skyrocketing (and if it’s sustainable)

✅ How unique stays can outperform traditional hotels in revenue

✅ What it really takes to develop a profitable glamping site

✅ The biggest mistakes investors make in this space

✅ How major hospitality brands are eyeing this market

If you’re an investor, operator, or just fascinated by the future of hospitality, this episode is packed with insights you won’t want to miss!

🔗 Connect with Edward & Learn More:

👉 EJH Distribution: www.ejhdistribution.com

👉 Posh Outdoors: https://posh.dealpage.io/

Connect with Mike and Nate:

Instagram: @the_hotel_investor_playbook
Website: www.hotelinvestorplaybook.com

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

Do you feel like you’re always busy but never really making progress? In this episode of The Hotel Investor Playbook, we explore how to transform your vision into reality by cutting through the noise and focusing on what truly matters.

Join Mike and Nate as they share their proven four-step process for executing your 2025 goals: from crafting a clear and compelling vision to creating accountability structures, setting measurable objectives, and tracking progress with a weekly scorecard.

Whether you’re just starting out or scaling your hospitality business, these practical strategies will help you eliminate bottlenecks, empower your team, and move forward with confidence. Stop working harder and start working smarter—tune in now!

Get our company structure by clicking this link here.

Connect with Mike and Nate:

Instagram: @the_hotel_investor_playbook
Website: www.hotelinvestorplaybook.com

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

What happens when a hotel investment doesn't go as planned?

In this candid episode of the Hotel Investor Playbook, we chat with Tanya Rooney about the ups and downs of buying and operating a roadside motel. From discovering hidden challenges in partnerships and revenue projections to navigating the nuances of small-town hospitality, Tanya's story is packed with invaluable lessons.

You'll learn:

• How to spot red flags during underwriting and due diligence.
• The differences between short-term rental investing and hotel operations.
• Why partnerships are like marriages - and how to choose the right one.
• Actionable steps to prepare for success in hospitality investing.

Whether you're new to hotel investing or looking to avoid costly mistakes, this episode will give you insights and strategies to help you level up.

🎧 Listen now and uncover the ultimate hotel investing hack: learning from the mistakes others have made.

Connect with Tanya:
Instagram: @tanyamn
Website: Tanya Rooney
Podcast: Tribe Builders Podcast

Connect with Mike and Nate:

Instagram: @the_hotel_investor_playbook
Website: www.hotelinvestorplaybook.com

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

What does it take to transform $400,000 into $10 million in hospitality assets while building a brand that wins awards in just a few years? In this special crossover episode, we’re featuring a conversation we had as guests on Direct Bookings Simplified, hosted by Gil Chan.

In this episode, we reveal:

•How we tackled fear and failure to seize opportunities others missed.

•The strategies behind our 12% increase in direct bookings—adding $600K+ to our property valuation.

•Why obsessing over guest experience, systems, and culture is the ultimate hospitality growth formula.

Whether you’re an investor, operator, or someone with big dreams in hospitality, this episode is packed with actionable advice and real-world insights.

Connect with Mike and Nate:

Instagram: @the_hotel_investor_playbook
Website: www.hotelinvestorplaybook.com

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