Best Nathan St Cyr Podcasts (2025)

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Syndication Simplified: The Strategy That Builds Generational Wealth | Desiree Doubrox E41 52:10

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2d ago52:10

52:10

Ever wondered how people raise millions to buy real estate without using their own money? In this episode, Desiree Doubrox breaks down the world of syndication and how she built an eight-figure fund while empowering hundreds of others to do the same. Whether you're new to investing or ready to raise capital for your first deal, this conversation si…

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A Masterclass In Experiential Hospitality With The Bolt Farm Treehouse Founders | Tori and Seth Bolt E40 54:26

9d ago54:26

54:26

Instead of chasing bookings, the founders behind Bolt Farm Treehouse create an obsession amongst their guests, and they do it with love at the center of everything. Their hospitality business heals relationships, attracts top-tier employees, and doesn't require the use of OTAs In this episode, Seth and Tori Bolt break their iconic hospitality busin…

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$187M Hotel Portfolio by Age 30: How to Choose the Right Deals, Brands, and Ops Model | Sujay Mehta E39 1:10:59

16d ago1:10:59

1:10:59

Thinking about buying or operating a hotel, but not sure where to start? Sujay Mehta built a $187M hospitality portfolio by betting on himself, starting lean, and learning through execution. In this episode, he breaks down what most people get wrong about hotel investing and how you can start smarter. You’ll learn: How to determine which hotel bran…

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Under Canvas Acquires The Fields! Irene Wood Exclusive 1:33:59

22d ago1:33:59

1:33:59

In huge news for the glamping industry, The Fields of Michigan has been acquired by glamping giants, Under Canvas. Irene Wood returns to the pod to give us the lowdown: How it all went down; the advice she'd give to operators looking for a similar exit; and what's next for her. Irene is always a blast. Give it a listen! Open Sky Glampitect North Am…

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Turning Passion into Profit in Rural Hospitality | Dave Cook E38 44:03

23d ago44:03

44:03

What does it take to build a successful hospitality business in a small rural town, with no outside investors? Dave Cook, founder of Barn Door Hostel in Rumney, New Hampshire, walks us through his journey from hostel volunteer to hostel owner. We dive into: How he used sweat equity and personal savings to convert an old chicken coop into a thriving…

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Bootstrapped Hospitality: Scaling Your Hotel Portfolio Without Major Capital | Austin Phippen E37 37:22

1M ago37:22

37:22

Today’s guest bought a roadside motel in a town of 900 people and turned it into a thriving hospitality brand. In this episode of the Hotel Investor Playbook, Mike and Nate sit down with Austin Phippen, a 26‑year‑old owner of Chama Trails Motel, a portfolio of 12 short-term rentals and a scenic wedding venue in Chama, New Mexico. What you’ll learn …

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Lessons from launching Paws Up, AutoCamp and Wildhavenn from 'Mr. Outdoor Hospitality' 1:55:10

1M ago1:55:10

1:55:10

In this episode we dive in with Scott Randall who helped launch Paws Up, AutoCamp and Wildhaven over his 25 year career in outdoor hospitality. There is no person on this continent with more experience growing prominent glamping brands. Hear about creating ice wall climbing, dog sledding, and hot air balloon rides in the Montana wilderness. Learn a…

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Building a Scalable Outdoor Hospitality Brand Through Franchising | Brian Linton E36 1:00:46

1M ago1:00:46

1:00:46

In this episode of the Hotel Investor Playbook, Mike and Nate sit down with Brian Linton, co-founder of Finding Promised Land, Camp Ferncrest, and The Rex Hotel. Brian shares how he transitioned from building a $20M apparel company to launching one of the fastest-growing outdoor hospitality brands in the U.S. Key Topics: How a rundown motel purchas…

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How to Know If Your CPA Is Helping You or Holding You Back | Kelly Tate E35 51:11

1M ago51:11

51:11

Not sure if your tax advisor is actually optimizing your returns, or just filing forms? In this episode of the Hotel Investor Playbook, we’re joined by Kelly Tate, a CPA with over two decades of experience helping real estate and hospitality investors navigate the tax code with confidence. We dive into key strategies like bonus depreciation, Sectio…

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What Does A Glamping GM Do? Wes McCloskey from Open Sky Reveals All 47:16

2M ago47:16

47:16

Familiar favourite Bygnal Dutson from Open Sky in Zion returns to the pod today, but this time he's joined by his General Manager, Wes McCloskey. Today's episode is all about the nitty gritty of running a glamping business as the GM. What roles and responsibilities does a GM carry out? What's the hardest part of the job? What's Wes' advice to prosp…

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Why Hostels Are an Untapped Investment Opportunity in the U.S. | Mike & Nate E34 36:54

2M ago36:54

36:54

We're proving why hostels are one of the most powerful investment models in real estate. In this episode, Mike and Nate break down exactly why they’re going all-in on hostels and how they turn underperforming assets into award-winning hospitality destinations. You’ll learn: Why the U.S. hostel market is ripe for disruption The revenue model that tu…

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The Strategic Power of Third-Party Hotel Management | Bryan Fish E33 45:22

2M ago45:22

45:22

You don’t need to be an expert in everything to scale in hospitality, just need to align with the right consultants, operators, and partners who’ve done it before. In this episode, we sit down with Bryan Fish, CEO of Reliance Hospitality, to unpack how third-party operators help investors go from scrappy operators to institutional-level players. Br…

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Glamping ON WATER at Sol Stay with Joe Lisa and Bill Nolan 1:26:57

2M ago1:26:57

1:26:57

Hear the story behind Sol Stay, one of America's only glamping resorts ON THE WATER. Find out how Joe Lisa and Bill Nolan built this unique property on the waters of Lake Erie in Ohio. In this episode you will learn how they: Found and reimagined this run down marina Raised the money to renovate into a floating glamping resort Built a floating saun…

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He Managed $320M for a Family Office - Then Walked Away to Build His Own Empire | Reilly Brennan E32 47:12

2M ago47:12

47:12

After helping scale a family office real estate portfolio from $3 million to over $320 million, Reilly Brennan walked away from the comfort of a W-2 job to carve his own path in boutique hospitality. In this episode, we sit down with Reilly to unpack how he sourced and acquired two independent hotels in Duluth, Minnesota, one through creative selle…

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Building a $6M Micro Resort with Only 3% Down Using a USDA Loan | Ian Joseph E31 47:42

2M ago47:42

47:42

In this episode, we dive into an uncommon but powerful financing strategy that could change how boutique hospitality projects get funded. Ian Joseph, founder of Branch, shares how he’s leveraging a USDA Rural Business Development loan to finance a $6M micro resort buildout in West Virginia - with just 3% down. We break down the entire capital stack…

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How to Execute a Successful Grand Opening with Quentin Incao of Q Hospitality 1:48:57

3M ago1:48:57

1:48:57

Learn the critical items you need to think about before your grand opening. Hear about pre-marketing, selecting a property management system, opening your booking calendar, OTA integrations, OS&E purchasing and more. Quentin Incao is the founder of Q Hospitality and has consulted on a dozen prominent glamping sites, landscape hotels, independent bo…

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The Ultimate Guide To Financing Your Next Hotel Deal | Suraj Desai E30 53:30

3M ago53:30

53:30

In this episode of the Hotel Investor Playbook, we sit down with Suraj Desai, a hospitality finance expert who has helped close hundreds of hotel deals, to unpack everything you need to know about financing your next acquisition, renovation, or ground-up development. Suraj breaks down the full capital stack, from SBA 7a and 504 loans to bridge, CMB…

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Buying Hotels Is Just the Start: How to Build a Lasting Hospitality Brand | Keir Weimer E29 48:10

3M ago48:10

48:10

In this episode of the Hotel Investor Playbook, we sit down with Keir Weimer, founder of Weekender Hotels, to unpack how he’s building a boutique hospitality brand designed for the long haul. Keir shares how he aligned his business with his personal lifestyle, his on-the-road strategy for sourcing deals, and the frameworks he’s using to scale Weeke…

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Nick Purslow's Story - From Small English Town to the Canadian Rockies 1:26:20

3M ago1:26:20

1:26:20

Some of you have been listening to him for more than 4 years, but you don't know his story. Nick got to where he is today through hard work, tenacity, and a whole lotta dreaming. As he prepares to open his first mirror cabins at Skyridge Glamping, we go all the way back to his childhood and explore his journey to the present day. It's a doozy. Posh…

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Hotel Investing Insights from the CEO of One of America’s Top Hotel Brokerage Firms | Suraj Bhakta E28 52:09

3M ago52:09

52:09

What does it really take to scale from your first hotel acquisition to managing a hospitality portfolio worth tens or even hundreds of millions? In this episode, Michael and Nate sit down with Suraj Bhakta, CEO of NewGen Advisory, a leading hospitality brokerage with offices across 12 states and transactions in 44. Suraj brings over two decades of …

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Saturday Special: Behind the Curtain at Malama Capital | Mike & Nate E27 25:33

3M ago25:33

25:33

In this special Saturday edition, we’re flipping the script. No guest today — just Mike and Nate giving you a behind-the-scenes look at what’s going on inside Malama Capital. After a listener reached out asking to hear more about our journey, we decided to hit record and share where we’re at, what we’re focused on, and how we’re thinking about the …

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How to Create a Sense of Community at Your Resort - With Nathan St Cyr of Howzit Hostels 1:09:17

3M ago1:09:17

1:09:17

We explored beyond the world of glamping this week and interviewed Nathan St Cyr of Howzit Hostels. He broke down the hostel business model; how Howzit obsesses over the guest experience; and how to create a sense of community at your resort. Nathan's Links: Howzit Hostels The Hotel Investor Playbook Posh Outdoors Links: WeFunder page Schedule a ca…

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How Sky McLean Built a $500M Hotel Brand from Scratch | Sky McLean E26 38:30

3M ago38:30

38:30

What do you do when you get fired from your job and get escorted out with a cardboard box? If you’re Sky McLean, you build one of the fastest-growing hospitality brands in Canada. In this episode, we sit down with Sky McLean, founder and CEO of Basecamp Resorts, owner of 14+ resorts, and operator of over half a billion in real estate. From bootstra…

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Glamping for Profit: Low Cost, High Cash Flow, Massive Upside | Zac Willms E25 51:44

4M ago51:44

51:44

What if you could double your money in one season with glamping tents? Zac Willms is pulling it off — and building a profitable outdoor brand in the process. In this episode, Mike and Nate talk with Zac Willms, co-owner of a thriving glamping resort in Tobermory, Ontario. Zac shares how he turned a neglected trailer park into a profitable outdoor h…

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How Hal Feinberg Became America's Biggest Glamping Dome Operator 1:09:33

4M ago1:09:33

1:09:33

Hal Feinberg is the founder of Clear Sky Resorts. Clear Sky is the largest dome operation in the US, with resorts in Utah and Arizona. Hal joins us to discuss his journey to this point, his special interior designs, how he scaled to a second location, and much more. Posh Outdoors Links WeFunder page Schedule a call Nick's email: nick@posh-outdoors.…

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Olympic Discipline, Million-Dollar Loss, and Building a Hospitality Portfolio | Adam G Dailey E24 1:07:10

4M ago1:07:10

1:07:10

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 bou…

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From Motel Renovation to 300K Followers: The Innvestors Story | Brett McManus E23 1:00:36

4M ago1:00:36

1:00:36

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 indu…

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What Is Your Outdoor Hospitality Business Worth? And How Can You Maximize Its Price In A Sale? 1:16:33

4M ago1:16:33

1:16:33

Learn what your outdoor hospitality business is worth and how you can maximize your value in a sale. In this episode Connor interviews experts Bob Kaplan of NAI Outdoor Hospitality Brokers and Shari Heilala of Sage Outdoor Advisory. Find out how your business is valued by appraisers and brokers in the current market. Learn the strategies about maxi…

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Ground-Up Boutique Hotel Development in San Francisco - High Risk, Higher Reward? | Mike Demson E22 53:12

4M ago53:12

53:12

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 …

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What It Takes to Build a Revolutionary Hospitality Business | Brian Meyer E21 48:31

4M ago48:31

48:31

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 vertica…

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How to Hire the Best Staff In Outdoor Hospitality 1:20:05

5M ago1:20:05

1:20:05

Jacob Halverson joins Connor and Nick to discuss all things recruitment. How do you find staff for your hospitality operation? What questions should you ask them in interviews? How does the process change according to job role? Links: Posh Outdoors Schedule a call re Posh Outdoors Glampitect North America The Glamping Insider (Nick's newsletter) Sa…

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Cost Segregation Made Simple: Unlock Massive Tax Savings in Real Estate | Brian Bigham E20 38:35

5M ago38:35

38:35

“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 …

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From First Responder to Ground-Up Developer: An Inspiring Journey | Andrew Owlett E19 50:24

5M ago50:24

50:24

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 scrat…

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How AI is Disrupting Hotels—And Why Small Operators Have the Advantage | Ari Smith E18 56:52

5M ago56:52

56:52

💡 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 mak…

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How Ken Barber Scaled His Californian Glamping Business | Wildhaven Glamping 1:26:58

5M ago1:26:58

1:26:58

In Connor's first solo-hosted episode, he speaks to Ken Barber of Wildhaven Glamping in California. Ken has pulled off the notoriously difficult task of starting and scaling a Californian glamping operation, and he dives into his initial capital raise, Wildhaven's mid-marketing positioning, and the art of scaling a glamping business. Links mentione…

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Buying, Financing & Operating a Seasonal Boutique Hotel | Ryan Edwards E17 53:26

5M ago53:26

53:26

🏨 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 $…

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The Glamping Boom: Hype, Profits, & Pitfalls | Edward Haynes E16 45:00

6M ago45:00

45:00

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 c…

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What Can American Operators Learn from Luxury African Safaris? 1:14:21

6M ago1:14:21

1:14:21

We're back! We hope everyone had a wonderful holiday season. Nick and Connor are excited to return with the first episode of the new year, and boy is it a good'un. We're joined by Michel Girardin and (rejoined by) Andrew Murphy to talk all things African glamping. This industry traces its roots back to that amazing continent, and there's a ton we c…

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From Vision to Execution: Our Framework for Hospitality Success | Mike & Nate E15 59:22

6M ago59:22

59:22

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 cle…

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Lessons Learned from a Failed Motel Deal | Tanya Rooney E14 47:34

6M ago47:34

47:34

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 i…

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Turning $400K into $10M: Lessons in Fear, Failure, and Direct Bookings | E13 1:03:45

6M ago1:03:45

1:03:45

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 opport…

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How a Property Manager Can Help You Maximize Your Hotel Profits | Bryan Tubaugh E12 52:27

7M ago52:27

52:27

Join us as we sit down with Bryan Tubaugh, a seasoned hotel management expert, to explore the common pitfalls of self-management, the benefits of bringing in a pro, and how to evaluate whether outsourcing management is right for you. Whether you’re buying or managing your first—or fiftieth—hotel, this conversation is packed with insights to help yo…

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Leveling Up: How To Turn STR Success into Boutique Hotel Ownership | Kim Herrlein E11 48:53

7M ago48:53

48:53

Are you ready to take your short-term rental success to the next level? In this episode of The Hotel Investor Playbook, we sit down with Kim Herrlein, an accomplished STR investor who transformed her success into hotel ownership. Kim’s story isn’t about leaving short-term rentals behind—it’s about using her knowledge to scale into an exciting new c…

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Christmas Special + An Update On the Future of the Podcast 1:17:22

7M ago1:17:22

1:17:22

Jacob Halverson joins Nick and Connor for a bumper Christmas special! We discuss our favorite glamping resorts, glamping naughty and nice lists, and our favorite Christmas movies. The podcast also begins with an update on our plans for the podcast in 2025. Thanks to all the listeners, and have a very merry Christmas! Links mentioned: The Glamping I…

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How to Drive 70% Direct Bookings: Strategies for Hotel Investors | Kerri Gibson E10 57:06

7M ago57:06

57:06

Are you tired of paying high fees to online travel agencies (OTAs)? Imagine driving 70% of your bookings directly—and keeping more of your revenue. In this episode of The Hotel Investor Playbook, we sit down with Kerri Gibson, founder of Chalets Hygge, who has built an incredible hospitality brand with six short-term rentals and a boutique motel. H…

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Why Winter Glamping Is a Hidden Goldmine, and How to Exploit It 50:35

7M ago50:35

50:35

Sorry for the delay on this week's episode - my laptop is broken! Everybody thinks of glamping as a summer activity, with the sun shining and the leaves in bloom. But have you ever considered glamping in minus 40 temperatures? The good people of Saskatchewan, Canada do, and we think winter glamping will become more and more common as the industry m…

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Building a Winning Investment Thesis for Hotel Success | Mike & Nate E9 43:44

8M ago43:44

43:44

Join Mike and Nate, founders of Malama Capital, as they explore the critical role of a well-defined investment thesis in the hospitality industry. With $30 million in current real estate assets and a goal to build a $400 million business, they share detailed insights on creating and refining an investment strategy. From understanding guest avatars …

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The Craziest Glamping Site We've Ever Seen 57:21

8M ago57:21

57:21

Today's guest is the opposite of every previous operator we've had on the show. And his counter-intuitive strategy may give you your next great idea. Introducing Travis Chambers, Founder of Outpost X. Travis isn't trying to create luxury at Outpost X. He's comfortable with 20% of his guests not enjoying their experience. To him, the goal is to tran…

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How to Build a Hotel: Expert Insights into Real Estate Development | Zeke Freeman E8 1:01:59

8M ago1:01:59

1:01:59

Ever wondered what it takes to transform an empty building or raw land into a thriving hotel? In this episode of The Hotel Investor Playbook, we’re diving deep into the real estate development process with architect and developer Zeke Freeman. With over 20 years of experience and a current ground-up hotel project near the iconic Red Rocks Amphithea…

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How to purchase your first hotel while working a full-time job | Alex Kang E7 1:03:15

8M ago1:03:15

1:03:15

In this episode, we dive deep into the inspiring journey of Alex Kang, who purchased his first boutique hotel with no prior experience while maintaining a full-time W2 job. Alex shares his step-by-step process, from leveraging his skills from his MBA and software tech job, to joining a mastermind group that accelerated his learning. He emphasizes t…