Ever dreamed of quitting your six-figure job to build real wealth through hotels? This episode shows you what it actually takes.

Tim Ensmann, founder of the T.C. Hotel Fund, shares how he went from tech sales to owning a multi-million-dollar boutique hotel portfolio in under five years. He reveals the sacrifices, systems, and strategies behind turning a $1.5M property into a $4.5M success story. He then shares how you can follow the same path without losing your sanity.

You’ll learn:

• The real moment he knew he couldn’t stay in corporate anymore
• How he used short-term rentals to bridge the gap from W2 to full-time investor
• What it costs (financially and emotionally) to leave a secure job for entrepreneurship
• How to identify the right first project for your goals

This is a step-by-step blueprint from someone who’s actually done what so many people dream of.

Follow and share the Hotel Investor Playbook so more people can learn how to invest in hospitality assets the right way.

About Tim

Tim Ensmann is the founder and managing partner of Boutique Hotel Fund, an investment platform that acquires and repositions boutique hotels across the United States. With a background in corporate sales and strategy, Tim transitioned from tech leadership roles into hospitality investing, where he now helps accredited investors build wealth through experiential real estate. His firm focuses on transforming underperforming properties into design-driven, story-led destinations that deliver both emotional impact and strong financial returns. Through his content and education platforms, Tim is redefining what modern hotel ownership looks like for a new generation of investors.

Connect with Tim

Email: tim@boutiquehotelfund.com

LinkedIn: www.linkedin.com/in/tim-ensmann/

Website: boutiquehotelfund.com/

Instagram: @tim_ensmann and @boutiquehotelguy

Connect with Michael:

Invest with Malama Capital: malama-capital.com/invest
Submit a deal: https://www.malama-capital.com/deal-submission
Instagram: @the_hotel_investor_playbook
Contact Us: info@hotelinvestorplaybook.com

Ever wonder where the money actually goes in a hotel deal?
In this episode, Michael Russell breaks down real estate syndications in plain English. How investors and operators really get paid, what fees are fair, and how to structure deals that build long-term trust.
Whether you’re looking to raise capital for your first project or invest passively, this is the playbook for understanding the math behind every syndication.
You’ll learn:

• The simple breakdown between LPs and GPs and how each gets paid
• How preferred returns, profit splits, and waterfalls actually work
• The most overlooked risk in syndications (and how to avoid it)
• How to structure deals that attract repeat investors
• Why clarity always beats complexity when raising capital

If you’ve ever wanted to peek behind the curtain of a hotel syndication, this episode will make everything finally click. Follow and share the Hotel Investor Playbook so more people can learn how to invest in hospitality assets the right way.

Connect with Michael:

Invest with Malama Capital: malama-capital.com/invest
Submit a deal: https://www.malama-capital.com/deal-submission
Instagram: @the_hotel_investor_playbook
Contact Us: info@hotelinvestorplaybook.com

When most people say they want to buy a hotel, it’s just talk.

Jacobo Hernandez sold his entire $10M short-term rental portfolio, packed his car, and hit the road for 90 days to find one.

He toured 35 hotels, underwrote 2,000 deals, and slept in random motels across the U.S. before discovering a hidden gem, a 59-room hotel on 10 acres in Eureka Springs, Arkansas, for just $1.2 million.

Now he’s turning it into Forest Springs Hotel & Spa, a wellness-focused retreat with saunas, cold plunges, and outdoor cinemas funded by investors who believed in his vision.

In this episode, you’ll learn:

• The exact framework he used to identify hot markets and good deals
• How storytelling and video marketing helped him raise $2.5M+ in capital in weeks
• Why focusing on unique, experiential assets can help investors stand out and command higher ADRs

This episode is super interesting and shows what can happen when you go all in!

About Jacobo

Jacobo Hernandez is the founder and CEO of FreedomVest Capital and managing partner at The Vesta Group, where he specializes in transforming undervalued real estate into high-performing boutique hotels and short-term rentals. With expertise in acquisitions, revenue management, and digital marketing, Jacobo has built multimillion-dollar portfolios that merge design-driven hospitality with investor-focused returns. He’s also the author of Short-Term Rental Secrets, a guide to scaling and exiting rental portfolios through data, SEO, and systems. Passionate about education and impact, Jacobo now teaches entrepreneurs how to build scalable hospitality businesses that generate both financial freedom and exceptional guest experiences.

Connect with Jacobo

Website: https://thespringsretreat.space/

LinkedIn: https://www.linkedin.com/in/jacobo-hernandez-747299128/

Instagram: @_jacobohernandez_

Tiktok: @jacobohernandez_official

Connect with Michael:

Invest with Malama Capital: malama-capital.com/invest
Submit a deal: https://www.malama-capital.com/deal-submission
Instagram: @the_hotel_investor_playbook
Contact Us: info@hotelinvestorplaybook.com

We’ve all dreamt of quitting our bland corporate jobs to buy a hotel in Costa Rica… well, today’s guest did that.

After leaving a private equity career in San Francisco, Bill Graf traded suits for surf towns and founded Onda, a hospitality brand in Costa Rica that blends the style of a boutique hotel with the social energy of a hostel.

You’ll learn:

• How to uncover hidden opportunities in small hotels that big players ignore
• What U.S. investors should know about buying real estate in Costa Rica
• His unique strategy for keeping his properties full year-round

This episode is a blueprint for spotting opportunities where others see risk… and will certainly have you daydreaming by the end of it!

Follow along with The Hotel Investor Playbook to discover how to invest in hospitality assets the right way.

About Bill

William “Bill” Graf is the founder and CEO of ONDA, a hospitality collective in Costa Rica that blends boutique hotel comforts with the social energy of a hostel. A former investment banker and private equity professional, Bill left Wall Street in 2016 to travel the world, visiting over 50 countries and experiencing firsthand the challenges of inconsistent accommodations. Inspired to create a better model, he launched ONDA to deliver reliable, community-driven stays in lifestyle destinations where major hotel brands won’t go. Today, Bill is building ONDA into a global hospitality brand focused on culture, connection, and transformational guest experiences.

Connect with Bill

Website: www.stayonda.com

LinkedIn: linkedin.com/in/williamgraf

Instagram: @billygoat_graf and @findyouronda

Connect with Michael:

Invest with Malama Capital: malama-capital.com/invest
Submit a deal: https://www.malama-capital.com/deal-submission
Instagram: @the_hotel_investor_playbook
Contact Us: info@hotelinvestorplaybook.com

The hotel industry is changing: costs are rising, AI is here, and investors are getting more selective.

This week on the Hotel Investor Playbook, we sat down with Bob Rauch, better known as The Hotel Guru. From starting out as a dishwasher to building and selling a 20-hotel management company, then launching Brick Hospitality and managing nearly 1,000 rooms, Bob has seen it all.

In this episode, you’ll learn:

• How to spot hot markets (and avoid the ones that eat your profits)
• The truth about using robots and AI inside hotels
• The 4 core skills Bob believes every investor must master

Bob has 45+ years in the trenches, and he’s sharing real stories, wins, and lessons that can change how you invest.

Follow and share the Hotel Investor Playbook so more people can learn how to invest in hospitality assets the right way.

About Bob

Robert A. Rauch, CHA, widely known as “The Hotel Guru,” is a nationally recognized hotelier, consultant, and strategist with over four decades of experience in the hospitality industry. He is the Chairman of Brick Hospitality, Managing Partner of the Hilton Garden Inn and Homewood Suites San Diego/Del Mar, and founder of Hotel Guru. This consulting firm advises hotel owners and investors on acquisitions, operations, finance, and marketing. A Certified Hotel Administrator, Rauch has also served as a faculty associate at Arizona State University, authored the industry newsletter Hospitality Innsights, and contributed regularly to leading hospitality publications. Through his leadership, market forecasts, and hands-on advisory, he has helped shape the future of hotel investment and management while mentoring the next generation of hospitality professionals.

Bob's Book

The Hotel Guru’s Journey: A Guide to Excellence in the Hotel Industry, launching October 2025, available on Amazon.

Connect with Bob

Website: hotelguru.com

LinkedIn: www.linkedin.com/in/robertrauch

X: x.com/truehotelguru

Facebook: facebook.com/hotelguru

Email: rauch.ra@gmail.com

Connect with Michael:

Invest with Malama Capital: malama-capital.com/invest
Submit a deal: https://www.malama-capital.com/deal-submission
Instagram: @the_hotel_investor_playbook
Contact Us: info@hotelinvestorplaybook.com

Where is the hotel market headed in 2026, and how can investors succeed in a challenging environment?

This week on the Hotel Investor Playbook, we sat down with Jan Freitag, National Director of Hospitality Analytics at CoStar. With over 30 years of experience analyzing hotel performance data, Jan is one of the most respected voices in the industry.

Here’s what you’ll learn:

• How to use data and analytics to spot opportunities others overlook
• Why conviction and strong operations can outperform market averages
• How investors can protect margins as costs continue to rise
• Why the sub-$10M space stays active and how to play in it wisely

If you want to understand how smart investors can win even in a challenging market, this is the episode you need.

Follow and share the Hotel Investor Playbook so more people can learn how to invest in hospitality assets the right way.

About Jan

Jan Freitag is the National Director of Hospitality Analytics at CoStar Group, where he provides industry-leading insights on hotel performance, market trends, and investment opportunities. With nearly two decades at STR as Senior Vice President of Lodging Insights, Jan has become one of the most trusted voices in hospitality analytics, frequently cited by outlets like The Wall Street Journal, New York Times, Bloomberg, and CNBC. His expertise helps investors, owners, and operators make data-driven decisions across acquisitions, funding, marketing, and operations. Jan is also a sought-after speaker and thought leader, known for translating complex data into actionable strategies for hospitality success.

Connect with Jan

LinkedIn: https://www.linkedin.com/in/janfreitag/

Podcast: Tell Me More: A Hospitality Data Podcast

Jan's non-CoStar data set: I-92/APIS data https://lnkd.in/g-faxadX

Connect with Michael:

Invest with Malama Capital: malama-capital.com/invest
Submit a deal: https://www.malama-capital.com/deal-submission
Instagram: @the_hotel_investor_playbook
Contact Us: info@hotelinvestorplaybook.com

The most powerful part of a hotel stay isn’t the design or the amenities, it’s the feeling guests take home.

That’s the philosophy of Bashar Wali, one of the most candid and creative voices in hospitality, who's spent 30+ years building, operating, and reinventing hotels around the world.

In this episode of the Hotel Investor Playbook, Bashar shares:

• Why “give-a-shit-ability” beats corporate playbooks
• The power of emotional intelligence in hotel teams
• The biggest mistakes first-time owners make
• The difference between the three types of hotel deals (core, value-add, and opportunistic)

Bashar doesn’t hold back. Whether you’re an operator, investor, or aspiring hotelier, this conversation will reshape how you think about hospitality.

Follow and share the Hotel Investor Playbook so more people can learn how to invest in hospitality assets the right way.

About Bashar

Bashar Wali is a seasoned hotelier, entrepreneur, and the founder of This Assembly and Practice Hospitality, with over 30 years of experience leading and scaling some of the industry’s most innovative hotel brands. In this episode, Bashar shares his playbook across acquisitions, funding, marketing, and operations, revealing how emotional intelligence, design, and culture are just as critical as deal structures and NOI. From building authentic guest loyalty without points, to structuring creative capital stacks, to “making the magic” in operations, his insights are both tactical and timeless. Whether you’re a first-time hotel investor or looking to scale your portfolio, this conversation will give you actionable lessons to apply in your own ventures.

Connect with Bashar

LinkedIn: https://www.linkedin.com/in/basharwali

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

Website: https://www.thisassembly.com

Connect with Michael:

Invest with Malama Capital: malama-capital.com/invest
Submit a deal: https://www.malama-capital.com/deal-submission
Instagram: @the_hotel_investor_playbook
Contact Us: info@hotelinvestorplaybook.com

How do you turn a struggling hotel into a profitable asset?

This week on the Hotel Investor Playbook, we sit down with Naveed Khan, co-founder of London Rock Partners, a hotel management and advisory firm that oversees everything from branded hotels like Holiday Inn to boutique independents and even a 650-bed hostel in London.

In this episode, you’ll learn:

• Why the first step in turning around a hotel always starts with people, not P&Ls
• The advantages (and risks) of branded vs. independent hotels for investors
• How management companies can become a true partner in value creation
• Why tech and automation are reshaping hospitality operations
• Tactical advice for first-time hotel investors on keeping it simple

If you want to understand how the right management partnership can transform your hotel investment, this episode is a must-listen.

Follow and share the Hotel Investor Playbook so more people can learn how to invest in hospitality assets the right way.

About Naveed

Naveed Khan is the Chief Operating Officer of London Rock Partners, a leading hospitality asset and hotel management firm based in the UK. With a career spanning revenue management, commercial strategy, and full-scale hotel operations, he has led both branded and boutique properties through transformation and growth. Naveed is known for his people-first leadership, tech-driven operational strategies, and ability to maximize asset performance for owners and investors. His journey from revenue manager to COO reflects both resilience and a deep commitment to reshaping the future of hospitality.

Connect with Naveed

Website: https://www.londonrockpartners.com/

LinkedIn: https://www.linkedin.com/in/naveed-khan-580ba179/

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

Connect with Michael:

Invest with Malama Capital: malama-capital.com/invest
Submit a deal: https://www.malama-capital.com/deal-submission
Instagram: @the_hotel_investor_playbook
Contact Us: info@hotelinvestorplaybook.com