The Hotel Investor Playbook

Tim Hubbard, founder of Corzly and operator of 200+ short-term rentals, built a 20-unit boutique resort in Medellín. He walks through the ground-up build, rising costs and surprise licensing resets. He explains financing without banks, the 50/50 partnership that made it possible, and how his virtual management model runs 200+ properties across 40 cities.

Greg Emmert, founder of Vireo and 26-year campground operator with eight industry awards, explains why many buyers become overworked operators instead of owners. He covers the revenue threshold to hire real staff, why site count and guest mix matter, pitfalls of raw-land builds and prefab hype, and practical labor strategies like work-exchange.

Jasper Ribbers, former equity trader turned hospitality entrepreneur who runs revenue for $125M+ in STR bookings and co-founded Freewyld. He discusses which markets and niche experiences are outperforming, why 99% of operators leave up to 40% on the table with set-it-and-forget-it pricing, and how daily pacing, pricing tools, and product differentiation drive outsized returns.

Brent Bowers, a former US Army officer who built a passive-income land business with nearly 400 deals, shares practical real estate playbooks. He explains finding off-market sellers, a 3-step market selection framework, and why shifting to fewer high-margin deals changed everything. He also covers turning raw land into turnkey assets, essential due diligence, and designing strict work boundaries to protect time.

Ben Wolff, former McKinsey consultant turned hospitality developer and founder of Onera and Oasi, built scalable landscape resorts and a content-first marketing firm. He discusses choosing landscape hotels, a land-lease model that makes $7M deals work, achieving ~50% NOI with high direct-bookings, procurement lessons from a $300K mistake, and lean staffing and scaling strategies.

Ziggy Hallgarten, Co-founder and CEO of Broome and Cornell Hotel School grad who moved from hotel acquisitions to building AI tools. He discusses ALIS conference takeaways and which markets are heating up. He explains how Broome automates deal screening to slash time spent on pipelines. He shares how he prototyped without code and why focusing on one problem matters.

Sam Degenhard, founder and CEO of Campfire Ranch, builds outdoor lodges, huts, and campgrounds focused on small, high-touch stays. He explains scaling by leasing properties instead of buying, the OpCo-PropCo lease model, boots-on-the-ground due diligence, owner-operator staffing, and how unique amenities and pricing drive premium ADRs across varied outdoor assets.

Mark Podolsky, former investment banker turned land investor and author of Dirt Rich, built a multi-million automated land business. He shares a 3-step system: do it, document it, delegate it. Topics include systemizing acquisitions, using VAs and automation tools, direct-to-owner outreach for boutique hotels, deal arbitrage with minimal capital, and reclaiming time and focus.

Most hotel owners think the only way to reduce OTA dependency is to throw more money at Facebook ads or hire expensive marketing agencies. But the real solution isn't more budget, it's leveraging what you already have: authentic stories and staff who actually care about the guest experience.A hospitality marketing veteran who's advised VCs and built a 1.6 million social following reveals the direct booking playbook that independent hotels are using to reclaim revenue from OTAs. Scott Eddy has spoken at hundreds of conferences worldwide, doing the unexpected: giving away strategies that agencies charge thousands for.In this episode, you'll discover:Why rolling out the red carpet for OTA guests (instead of alienating them) converts 30%+ into direct bookersThe exact content categories that drive bookings and why shaky iPhone footage outperforms polished videosHow to make your front desk staff into content superstars without hiring an expensive agencyThe one Instagram metric (hint: it's not followers) that actually predicts revenueWhy "saves" and "comments" matter 10x more than likes for direct bookingsThe AI-discoverable scripting framework that's replacing traditional SEO for hotel discoveryHow long-form storytelling videos outperform short-form for brand discoverability (despite what Instagram tells you)The fatal mistake 80% of hotels make: posting beautiful property photos with promo text overlays that actively repel guestsIf you're serious about reducing OTA dependency and building a direct booking engine without a massive marketing budget, this episode will provide the roadmap. Don't make the expensive mistake of outsourcing what your in-house team can do better.About Scott EddyScott Eddy is a globally recognized hospitality brand strategist and digital pioneer who transitioned from a decade in investment banking to founding the first and largest digital agency in Southeast Asia. With a combined following of over 1.2 million, Scott has hosted the travel series Video Globetrotter on Lifetime Television and is consistently ranked among the top 15 hospitality influencers in the world. He now travels full-time as a consultant and keynote speaker, helping hotel brands convert authentic storytelling into measurable ROI while championing the "independent advantage" through raw, human-centered digital engagement. A genuine citizen of the world, Scott lives entirely out of hotels and cruise ships, leveraging his experiences in 85+ countries and 120+ cruises to provide a unique "perpetual guest" perspective on the evolving travel landscape.Connect with Scott EddyConnect with Scott on LinkedIn.Follow Scott on Instagram or visit his Website.Learn how to use AI to underwrite faster, streamline operations, automate the busy work, and make better decisions. Start your 7-day free trial of the AI for CRE Collective here.Connect with Michael on Instagram or LinkedIn.Email Us at info@hotelinvestorplaybook.comVisit the Hotel Investor Playbook InstagramInvest with Malama CapitalSubmit a deal

Jordan Malara, a former U.S. Space Force engineer, now co-founder of Springs Hospitality, shares his journey from engineering to hospitality. He reveals insights from purchasing a 27-key motel for $2.45M, emphasizing the importance of conservative underwriting and understanding hidden costs like CapEx. Jordan discusses effective financing strategies, the crucial upgrades that enhance guest experiences, and how he uses outsourced revenue management to streamline operations. His unique perspective blends creativity and analytics, perfect for aspiring hotel investors.