The Revenue Expert Managing $125M Says You're Leaving 40% on the Table | Jasper Ribbers E74 episode artwork

EPISODE · Mar 17, 2026 · 39 MIN

The Revenue Expert Managing $125M Says You're Leaving 40% on the Table | Jasper Ribbers E74

from The Hotel Investor Playbook

Jasper Ribbers went from trading equities on Wall Street to traveling to 100 countries as a digital nomad, funding it all from a single Airbnb apartment in Amsterdam. Today, he manages pricing strategy for over $125 million in annual short-term rental bookings and co-founded Freewyld, a micro-resort brand in Idyllwild, California that's pulling $190 RevPAR against a $97 market average. In this episode, Jasper reveals which STR markets worldwide are generating the best returns right now, why 99% of operators are leaving up to 40% of their revenue on the table with "set it and forget it" pricing, and breaks down the exact financials behind his micro-resort. Whether you're scaling a short-term rental portfolio or looking to break into hospitality investing, this episode is loaded with real data, real numbers, and real strategies you can use this week.About Jasper RibbersJasper Ribbers is a former corporate equity trader turned hospitality entrepreneur, currently serving as the Co-Founder of Freewyld and the Head of Revenue Management at Freewyld Foundry. As a pioneer in short-term rental revenue optimization, he leverages his background in econometrics to actively oversee pricing strategies for over $125 million in annual bookings globally. He is widely recognized as the author of the foundational industry book Get Paid for Your Pad and host of its accompanying podcast, which has amassed nearly 2 million downloads across more than 700 episodes. Today, Jasper is dedicated to helping property operators maximize their profits through dynamic pricing routines and scale their portfolios from single-family units to commercial boutique micro-resorts.Connect with Jasper RibbersConnect with Jasper on LinkedIn.Follow Jasper on Instagram.Visit their website, Freewyld and Freewyld Foundry.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 [email protected] the Hotel Investor Playbook InstagramInvest with Malama CapitalSubmit a deal

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Jasper Ribbers went from trading equities on Wall Street to traveling to 100 countries as a digital nomad, funding it all from a single Airbnb apartment in Amsterdam. Today, he manages pricing strategy for over $125 million in annual short-term rental bookings and co-founded Freewyld, a micro-resort brand in Idyllwild, California that's pulling $190 RevPAR against a $97 market average. In this episode, Jasper reveals which STR markets worldwide are generating the best returns right now, why 9...

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The Revenue Expert Managing $125M Says You're Leaving 40% on the Table | Jasper Ribbers E74

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