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The Hotel Investor Playbook

Michael Russell & Nathan St Cyr

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Weekly
 
Welcome to The Hotel Investor Playbook, hosted by real estate investors and hospitality experts Michael Russell and Nathan St Cyr. As the founders of Malama Capital and Howzit Hostels, Michael and Nathan have a wealth of experience in owning and operating boutique hotels, hostels, and other experiential lodging properties. With over $30 million in real estate investments, including short-term rentals, long-term rentals, commercial retail, and hospitality properties, they bring a unique persp ...
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Smart Friends

Eric Jorgenson

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Monthly
 
Casual conversations with founders, technologists, investors, and artists about building a brighter future, together. Welcome to our digital living room. With science, technology and entrepreneurship we can *continue* to create unfathomable leaps in quality of life. We show you how to find, apply, build, and invest in technologies to change your life and the world. When we have smart friends, we do smart things. When we do smart things, we save the world. No matter who, where, or when you ar ...
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Hear the stories, learn the proven methods, and accelerate your growth and future through entrepreneurship. Welcome to The Foundr Podcast with Nathan Chan. About the show: For over a decade, The Foundr Podcast with Nathan Chan has been a leading entrepreneurship podcast for open-book conversations with, by, and for founders. Whether you're starting, building, or dreaming about your business, The Foundr Podcast is where you can access experienced founders who've been in your shoes to learn th ...
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On a mission to drive positive change in the golf industry for a greener future! Host John Failla focuses on advancing the sustainability of both the environment and the game of golf for generations to come through valuable insights, meaningful connections, and inspiring stories. This passionate golfer, who has already played on 39 of the World’s Top 100 Golf Courses, brings together industry leaders and organizations: Greg Nathan, the President and Chief Executive Officer of the National Go ...
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David Heath and Randy Goldberg turned Bombas from a scrappy Indiegogo campaign into the most successful Shark Tank investment of all time—now valued at $3.4 billion. In this interview, the Bombas co-founders share how a simple insight about homelessness sparked a mission-driven sock company, how they bootstrapped their way to product-market fit, an…
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It's been five years since the Almanack of Naval Ravikant was published. I spent the day with Naval expanding on key ideas from the book. We recorded hours of that conversation to share with you. This episode is a portion of that long conversation that talks about Building Judgement You can purchase the new expanded edition with nearly 4 hours of n…
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It's been five years since the Almanack of Naval Ravikant was published. I spent the day with Naval expanding on key ideas from the book. We recorded hours of that conversation to share with you. This episode is a portion of that long conversation that talks about Saving Yourself You can purchase the new expanded edition with nearly 4 hours of new …
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It's been five years since the Almanack of Naval Ravikant was published. I spent the day with Naval expanding on key ideas from the book. We recorded hours of that conversation to share with you. This episode is a portion of that long conversation that talks about Learning Happiness You can purchase the new expanded edition with nearly 4 hours of n…
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It's been five years since the Almanack of Naval Ravikant was published. I spent the day with Naval expanding on key ideas from the book. We recorded hours of that conversation to share with you. This episode is a portion of that long conversation that talks about Philosophy You can purchase the new expanded edition with nearly 4 hours of new mater…
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Naval Ravikant on Building Wealth It's been five years since the Almanack of Naval Ravikant was published. I spent the day with Naval expanding on key ideas from the book. We recorded hours of that conversation to share with you. This episode is a portion of that long conversation that talks about Building Wealth You can purchase the new expanded e…
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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…
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When you’re just starting out, the fastest way to grow isn’t automation, ads, or scaling systems — it’s doing things that don’t scale. In this episode, I share why the most successful founders — from billion-dollar startups to small ecommerce brands — all begin by leaning into the unscalable. From replying personally to every email, to sending hund…
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Brian Littlefield is the co-founder and Chief Product Officer of Jocko Fuel—one of the fastest-growing supplement brands in America. But his story didn’t start in a boardroom. It started with a life-changing health wake-up call. In this episode, Brian shares how he went from overweight and directionless to building a trusted supplement empire backe…
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Topics: (00:00:00) - Intro(00:03:26) - Marathon misadventures(00:06:15) - The failed acquisition(00:13:47) - Lessons from the deal(00:29:31) - The future of retail(00:33:44) - Empathy for founders(00:35:23) - The grind of capitalism(00:35:37) - Challenges for young founders(00:36:10) - The importance of peer support(00:37:17) - Scaling and growth p…
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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 share…
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Most ecommerce founders think the only way to grow is to get more traffic — but often, the fastest way to increase sales is by making more from the traffic you already have. In this episode, I share a proven “second sale” strategy you can use to increase your conversion rate, average order value (AOV), and customer lifetime value (CLV) without spen…
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Julie Wainwright, founder of The RealReal, reveals how she built a billion-dollar resale marketplace that transformed luxury fashion. In this exclusive Foundr Podcast interview, Julie shares how she scaled The RealReal to over $1B in revenue, reached 38 million members, and took the company public on the Nasdaq. From her early lessons at Pets.com t…
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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’…
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Every business has one major constraint holding it back from the next stage of growth — and solving it is the fastest way to scale. In this episode, I share the exact formula I use to identify the biggest problem in my business, find the right person who’s already solved it, and get the solution faster than years of trial and error. This is the sam…
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Kian Golzari is one of the world’s leading experts in sourcing and product manufacturing—developing over 2,500 products and visiting 500+ factories. In this episode, he shares how to go from idea to product without getting burned by bad suppliers or poor-quality manufacturing. Whether you're working with Alibaba or building a custom product from sc…
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Topics: (00:00:00) - Intro (00:01:46) - Personal updates and new ventures (00:04:06) - The youth sports complex project (00:05:21) - Challenges and strategies in youth sports business (00:09:09) - Community impact and future vision (00:19:00) - Reflections on education and parenting (00:34:05) - The magic of holding a newborn (00:34:32) - The joys …
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Few people have left a mark on hospitality like Richard Kessler. He started his hospitality career by helping scale Days Inn into a household name as the early CEO Then he founded the Kessler Collection, one of the leading boutique hotel portfolios in the U.S., which ultimately helped launch Marriott’s Autograph Collection. In this episode, Richard…
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After 12 years building Foundr, I finally committed to something I should have done a decade ago — posting online every single day for 90 days straight to grow my personal brand. In this episode, I share what that commitment taught me about building trust, deepening connections with my audience, and why your personal brand is one of the most powerf…
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In this episode of the Foundr Podcast, Nathan Chan sits down with Camille Moore — widely known as the internet’s favorite creative director and the strategist behind some of today’s most iconic brand transformations. Camille has built a reputation for taking founders from forgettable to unforgettable, crafting brand strategies that don’t just look …
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What if your first hotel deal could be funded almost entirely through Instagram? This week’s guest, Soli Cayetano AKA lattes.and.leases on Instagram, went from barista to building a $13M real estate portfolio in just four years. After exiting her residential investing business, she turned to hospitality and now co-owns a 13-key boutique wellness ho…
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After interviewing over 100 billionaires and ultra-successful entrepreneurs, I’ve spotted three lessons that come up every single time — no matter the industry, background, or business model. In this episode, I break down exactly what I’ve learned from these conversations so you can model the same habits, mindsets, and strategies that separate the …
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Alicia Yoon is the founder of Peach & Lily—the pioneering brand that brought Korean skincare to the U.S. before “K-Beauty” was a buzzword. In this episode, she shares how her personal skin struggles turned into a lifelong mission, how she went from finance to esthetician school, and why she took the slow, principled path to build a category-definin…
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***This is a Replay Episode*** Links for Matt’s stuff: ⁠Aalo.com⁠ ⁠Matt on Twitter⁠ ⁠Aalo on Twitter⁠ ⁠Aalo Job Board⁠ Link to invest alongside Eric in deals like Aalo: rolling.fun Links to stuff mentioned: ⁠Decouple Podcast⁠ ⁠Titans of Nuclear Podcast⁠ ⁠Nuclear Barbarian Substack⁠ ⁠Atomic Awakening by James Mahaffey⁠ ⁠Why Nuclear Power Has Been a …
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Four months into starting Foundr, I landed an interview with billionaire entrepreneur Richard Branson — without connections, without experience, and while building my very first business from scratch. In this episode, I break down the exact networking and outreach strategy I used to connect with one of the world’s most famous founders, plus how you…
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Most hotel investors default to syndication — raising capital from dozens of limited partners and layering in complex waterfalls. But what if there’s a smarter, simpler path? This week’s guest, Brandon Gore, is building The Outlier Hotel, a 10-cabin luxury retreat in Arkansas designed to last 100 years. Instead of chasing the traditional syndicatio…
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In this episode, Toni Ko, founder of NYX Cosmetics, shares how she built one of the fastest-growing cosmetics brands in the world—scaling from a $250,000 investment to a $500M exit to L’Oréal. She reveals: • How she turned 18 SKUs into millions of units sold in year one • The simple packaging strategy that disrupted the beauty industry • Why she av…
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I almost walked away from Foundr. Not because the business wasn’t working—but because I wasn’t. In this episode, I’m sharing the truth about burnout. After seven years of building nonstop, I hit a wall—mentally, emotionally, and physically. What followed was one of the hardest seasons of my entrepreneurial journey. But it also forced me to change e…
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Think great marketing is only for big hotels with big budgets? Think again. In this episode, we talk with Steph Weber, a marketing and branding expert who helps boutique hotel and STR owners drive direct bookings. She breaks down how she finds her audience, tells a compelling brand story, and uses limited resources to drive big results. You’ll lear…
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Brittany Stewart turned toothbrushes into a breakout DTC success story—co-founding one of America’s fastest-growing eCommerce brands: Burst Oral Care. In this episode, she shares how Burst launched at dental conventions, scaled through hygienist word-of-mouth, and partnered with A-list influencers like Khloé & Kim Kardashian—all while keeping produ…
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Topics: (00:00:00) - Intro (00:01:37) - The Netflix documentary: Misrepresentation and struggles (00:03:19) - Writing the memoir (00:08:47) - The challenges of independent publishing (00:12:40) - The creative process and future plans (00:35:23) - Impact of the book on readers (00:36:04) - Scripted series and unused content (00:36:36) - New docuseri…
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I got sued just a few months into starting Foundr—and it nearly crushed everything I was building. In this short episode, I’m sharing the full story behind how I was forced to change the name of my business, the legal mistakes I made, and the surprising reasons it turned out to be the best thing that ever happened to me. If you’re launching a brand…
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Think you need a perfect plan to start investing in hospitality? Think again. In this episode, we sit down with Jonathan Mueller, an everyday investor who went from zero experience and a failed multifamily deal to buying a $250K roadside motel and building a growing hospitality portfolio. He didn’t have a background in hotels, didn’t have much of a…
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In this episode, Ty Haney, founder of Outdoor Voices, shares how she turned her public downfall into the blueprint for an even bigger comeback—building multiple new brands and redefining how community drives growth. She reveals: • How she built Outdoor Voices into a $100M cult brand by age 30 • Why the DTC playbook failed—and what she’s doing diffe…
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Is your marketing helping your hotel or just draining your budget? In this episode, we sit down with Anthony Chiaravallo, founder of Vallo Media, who has managed over $100M in ad spend for brands like Nike, Resorts World, and boutique hotels across the country. Whether you're trying to fill beds or scale a brand, Anthony breaks down how to think ab…
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In this episode, Andrew Lacy, founder of Prenuvo, shares how he went from two startup exits to building one of the fastest-growing health tech companies in the world—revolutionizing preventative healthcare with full-body MRI scans. He reveals: • Why most healthcare systems are reactive and backwards—and how Prenuvo flips it • How Prenuvo scaled fro…
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Topics: (00:00:00) - Intro (00:03:14) - The magic of code (00:05:30) - The wonder of early computing (00:11:13) - The evolution of computing: From analog to digital (00:18:45) - The personal computer revolution (00:32:36) - The future of computing: Beyond silicon (00:36:59) - The importance of computing history (00:40:53) - AI and human uniqueness …
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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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In this episode, Trinny Woodall, founder of Trinny London, shares how she turned her mission to help women feel confident into a multi-million dollar global beauty brand. She reveals: • Why she focused on the overlooked 35+ market and won their loyalty • How she started with just £150,000 and her own wardrobe to fund the dream • The retention-first…
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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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Worried someone’s going to steal your business idea? You’re not alone — and you’re not powerless. In this short episode, I’m sharing exactly what to do when copycats come for your product — because they will. I’ll break down why fear of being copied holds so many founders back, how I learned this lesson the hard way, and the real strategies that pr…
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Topics: (00:00:00) - Intro (00:04:19) - Entering the VC space (00:08:38) - Pilot-fund theories (00:12:50) - Risk tracking (00:19:56) - Finding LP alignment (00:22:39) - Arkady’s fund thesis (00:47:12) - Creating the index of solutions to problems (00:57:18) - The TAM for VC in 2025 (01:00:29) - How founders can increase the odds of being funded by …
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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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In this episode, Christina Stembel, founder of Farmgirl Flowers, reveals how she built a $65M+ floral business from her dining room—with no funding, no degree, and no industry experience. She reveals: • Why she chose a perishable, logistics-heavy product in a recession • How she scaled with no marketing budget and $411 left in the bank • The scrapp…
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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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In this episode, Mark Rushmore and Gyve Safavi, co-founders of SURI (Sustainable Rituals), share how they turned a simple personal care item into a sustainable, design-led movement—challenging legacy players like Oral-B and Philips. They share: • Why the electric toothbrush was overdue for disruption • The intentional product and packaging design t…
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Topics: (00:00:00) - Intro (00:03:52) - The Founder's book project (00:04:06) - Effort and building relationships (00:11:20) - The value of self-publishing (00:24:00) - Bootstrapping a HoldCo (00:46:05) - Finding natural fit in business (00:47:48) - The role of trust in business (00:49:07) - AI and changing perspectives (00:50:26) - Daily use of AI…
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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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In this episode, Rytis Lauris, co-founder of Omnisend, shares how he bootstrapped a leading email and SMS marketing platform used by over 125,000 eCommerce brands worldwide. He shares:• Why most ecommerce founders start email marketing too late• How to convert more website traffic into high-intent subscribers• The 2% of automations that drive 40% o…
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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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