STR Global Unlocked with Simon Lehmann: Unfiltered knowledge for the short term rental industry

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The short-term rental industry is evolving fast, and Simon Lehmann isn’t afraid to say what others won’t.STR Global Unlocked is where property managers, STR tech founders, vacation rental investors, and hospitality leaders get real about the business. Each episode breaks down what’s working, what’s broken, and what’s coming next: property management operations, direct bookings, vacation rental software, pricing strategies, mergers and acquisitions in real estate, professional host challenges, and the future of automation, AI, and tech stacks. Hosted by Simon Lehmann, CEO of AJL Atelier and one of the most trusted voices in the global STR space, the show delivers unfiltered conversations with the people shaping the industry. Simon has decades of experience in vacation rentals, travel tech, and hospitality, including leadership roles at Vacasa Europe, PhocusWright and HomeAway. If you’re scaling a property management company, building short-term rental technology, investing in vacation rentals, or entering this fast-moving market, this podcast is your seat at the table. 

  1. 016: Flexible Living Is Reshaping STR: An Institutional Capital Perspective with Jaja Jackson of ICONIQ Capital

    1D AGO

    016: Flexible Living Is Reshaping STR: An Institutional Capital Perspective with Jaja Jackson of ICONIQ Capital

    Short-term rentals, flexible living, and multifamily are no longer separate conversations. For institutional capital, they are converging into a single question around risk, yield, and long-term durability. In this episode, Simon Lehmann sits down with Jaja Jackson, Senior Vice President of Real Assets at ICONIQ Capital and Corporate Development Officer at Sentral, to unpack how large-scale investors evaluate short-term rentals, midterm stays, and flexible living models. This conversation cuts through platform narratives and focuses on underwriting logic, operational discipline, and why integration matters more than experimentation. In this conversation, we discuss: Why Jaja Jackson sees STR as both an asset class and an operating strategy, depending on how risk and operations are structured.How institutional investors assess STR, mid-term stays, and unfurnished rentals through one core lens: predictable income, controlled risk, and lasting upside.Why flexible living works only when it is fully integrated into Class A multifamily operations, not treated as an add-on.What billions in deployed capital reveal about returns, and why mixed-length stay models outperform unfurnished-only strategies.How lessons from Airbnb shaped institutional thinking, and why early lease-arbitrage models broke down without deep operational integration.Why brand, transparent reporting, and operational discipline matter more to institutional capital than short-term yield spikes, drawing on perspectives from ICONIQ Capital and Sentral.Disclaimer: The opinions expressed in this podcast solely represent the views of the respective speaker. Nothing expressed in this podcast should be viewed as investment advice or a recommendation to buy or sell any security, nor creates an advisory relationship with ICONIQ Capital. Nothing in this podcast constitutes accounting, legal, regulatory, tax, or other advice.   Explore more: Connect with Jaja Jackson on LinkedIn [https://www.linkedin.com/in/jaja-jackson-36832a57] to learn more about ICONIQ [https://www.iconiqcapital.com/real-assets] and Sentral [https://sentral.com/] Resources AJL Atelier – Global STR Consulting [https://www.ajlatelier.com]. Led by our host Simon Lehmann, AJL Atelier is a boutique advisory firm helping professional hosts, property managers, and investors succeed in the short-term rental industry. Connect with Simon Lehmann on LinkedIn [https://www.linkedin.com/in/simon-lehmann-8375753b/] Stay connected: Apple Podcasts: https://podcasts.apple.com/us/podcast/str-global-unlocked-with-simon-lehmann-unfiltered/id1842946960 Spotify: https://open.spotify.com/show/3kke4wOx0tNv0duq9MMWtO Youtube: https://www.youtube.com/playlist?list=PLWVkmUOkmhSHcFjzi28AhaQNR98vaG65O Website: https://www.ajlatelier.com/podcasts Newsletter: https://str-global-unlocked.beehiiv.com/

    55 min
  2. 015: Is Raising Capital Like Ecommerce the Answer to Real Estate’s Funding Problem? Insights From DealMaker Co-Founder and CEO Rebecca Kacaba

    JAN 13

    015: Is Raising Capital Like Ecommerce the Answer to Real Estate’s Funding Problem? Insights From DealMaker Co-Founder and CEO Rebecca Kacaba

    In this episode of STR Global Unlocked, Rebecca Kacaba, Co-Founder and CEO of DealMaker, joins Simon Lehmann for a candid conversation on why traditional capital raising no longer works for most founders and what a modern alternative looks like. Rebecca is a former capital markets attorney who left Big Law to build one of North America’s leading online capital raising platforms. DealMaker has helped companies raise more than $2 billion online and has become a key infrastructure layer for founders operating outside the traditional venture capital funnel. This is not a fintech pitch. It is a practical breakdown of how capital markets are changing and what that means for founders in short-term rentals, hospitality, and real estate. In this conversation, we discuss: Why capital raising remains slow, opaque, and founder-unfriendly, and how moving it online shifts leverage back to operators.How DealMaker approaches fundraising like an e-commerce checkout, turning supporters into investors and long-term community members.The most common mistakes founders make when raising early capital, from unrealistic valuations to choosing capital that limits flexibility.Why community-driven capital can complement venture capital, especially as companies stay private longer and need alternative growth paths.How AI is reshaping capital markets by reducing friction in compliance, verification, and investor onboarding.Rebecca’s lessons from scaling DealMaker, including how to build a high-performance culture while staying close to customers as the company grows. Explore more: Connect with Rebecca Kacaba on LinkedIn [https://www.linkedin.com/in/rebeccakacaba/] to learn more about DealMaker [https://www.deaDlmaker.tech/]  Resources AJL Atelier – Global STR Consulting [https://www.ajlatelier.com]. Led by our host Simon Lehmann, AJL Atelier is a boutique advisory firm helping professional hosts, property managers, and investors succeed in the short-term rental industry. Connect with Simon Lehmann on LinkedIn [https://www.linkedin.com/in/simon-lehmann-8375753b/] Stay connected: Apple Podcasts: https://podcasts.apple.com/us/podcast/str-global-unlocked-with-simon-lehmann-unfiltered/id1842946960 Spotify: https://open.spotify.com/show/3kke4wOx0tNv0duq9MMWtO Youtube: https://www.youtube.com/playlist?list=PLWVkmUOkmhSHcFjzi28AhaQNR98vaG65O Website: https://www.ajlatelier.com/podcasts Newsletter: https://str-global-unlocked.beehiiv.com/

    45 min
  3. 014: From Road to Air: How Drone Delivery Is Reshaping Last-Mile Economics and Guest Experience

    JAN 6

    014: From Road to Air: How Drone Delivery Is Reshaping Last-Mile Economics and Guest Experience

    In this episode of STR Global Unlocked, Bobby Healy, Founder and CEO of Manna Drone Delivery, joins Simon Lehmann for a grounded discussion on why last-mile delivery is structurally broken and how autonomous aerial delivery could reshape logistics, cities, and the short-term rental guest experience. Bobby brings decades of experience building travel and infrastructure businesses. Today, he leads Europe’s largest commercial drone delivery operator, running real operations at scale across Europe and the United States in dense urban environments. From airline software to car rental distribution and now drone delivery, his perspective cuts across regulation, economics, and operational reality. In this conversation, we discuss: ● Why last-mile delivery is structurally broken and constrained by road-based economics ● How drone delivery changes the unit economics of logistics at scale ● Why regulation is required infrastructure, not a blocker to innovation ● Where payload limits, flight availability, and use cases define what drones can realistically deliver ● Why drone delivery only works if it replaces road delivery rather than supplementing it ● How autonomous delivery intersects with hospitality and short-term rental guest experience Explore more: Connect with Bobby Healy on LinkedIn [https://www.linkedin.com/in/bhealy] to learn more about Manna Drone Delivery [https://manna.aero/]  Resources AJL Atelier – Global STR Consulting [https://www.ajlatelier.com]. Led by our host Simon Lehmann, AJL Atelier is a boutique advisory firm helping professional hosts, property managers, and investors succeed in the short-term rental industry. Connect with Simon Lehmann on LinkedIn [https://www.linkedin.com/in/simon-lehmann-8375753b/] Stay connected: Apple Podcasts: https://podcasts.apple.com/us/podcast/str-global-unlocked-with-simon-lehmann-unfiltered/id1842946960 Spotify: https://open.spotify.com/show/3kke4wOx0tNv0duq9MMWtO Youtube: https://www.youtube.com/playlist?list=PLWVkmUOkmhSHcFjzi28AhaQNR98vaG65O Website: https://www.ajlatelier.com/podcasts Newsletter: https://str-global-unlocked.beehiiv.com/

    48 min
  4. 013: 2025 Holiday Special - A Year That Changed the STR Conversation

    12/30/2025

    013: 2025 Holiday Special - A Year That Changed the STR Conversation

    2025 marked a turning point for the short-term rental industry. Not a year of hype or breakout growth, but a year of recalibration. In this Holiday Special of STR Global Unlocked, Simon Lehmann reflects on the conversations, tensions, and signals that defined the industry throughout the year. These insights are from the podcast, but also from in-person events, operator discussions, and real-world industry dialogue across global markets. This episode captures where short-term rentals stand today, shaped by operators facing tighter margins and more regulation. In this episode, we discuss: How industry conversations shifted throughout 2025Why margins, operations, and disciplined growth moved back to the forefrontHow technology discussions became more grounded in operational realityWhere AI entered the conversation in non-theoretical waysWhy professionalization continues to separate operators across regionsWhat remains unresolved as the industry looks aheadFOUNDING SPONSORS Founding PMS Partner, eviivo. eviivo Suite centralizes booking management, payments, automation, and OTA connectivity for 28,000 accommodation providers. 👉 Access the exclusive offer from eviivo here Founding Operations Partner, Breezeway. Breezeway brings operational workflows, service execution, and standards together in one platform for hospitality operators. 👉 Get started with Breezeway here Founding RMS Partner, PriceLabs. PriceLabs centralizes automated pricing and market intelligence for property managers operating at scale 👉 Start your 30-day free trial with Pricelabs here Founding Insurance Partner, Pikl. Pikl enables insurance-powered flexible cancellation and new revenue models for short-term rental operators. 👉 Know more about Pikl here Resources AJL Atelier – Global STR Consulting [https://www.ajlatelier.com]. Led by our host Simon Lehmann, AJL Atelier is a boutique advisory firm helping professional hosts, property managers, and investors succeed in the short-term rental industry. Connect with Simon Lehmann on LinkedIn [https://www.linkedin.com/in/simon-lehmann-8375753b/] Stay connected: Apple Podcasts: https://podcasts.apple.com/us/podcast/str-global-unlocked-with-simon-lehmann-unfiltered/id1842946960 Spotify: https://open.spotify.com/show/3kke4wOx0tNv0duq9MMWtO Youtube: https://www.youtube.com/playlist?list=PLWVkmUOkmhSHcFjzi28AhaQNR98vaG65O Website: https://www.ajlatelier.com/podcasts Newsletter: https://str-global-unlocked.beehiiv.com/

    17 min
  5. 012: Europe's STR Growth Challenge: Fragmentation, Regulation, and Execution - Panel with GuestReady, COCOONR, and Happy.Rentals

    12/23/2025

    012: Europe's STR Growth Challenge: Fragmentation, Regulation, and Execution - Panel with GuestReady, COCOONR, and Happy.Rentals

    Europe is often discussed as a single market. This panel makes clear why it is not. In this panel, Simon Lehmann brings together three leaders navigating growth across Europe’s most fragmented markets: Alexander Limpert (GuestReady and RentalReady), Antoine Serrurier (COCOONR), and Harold Lubberdink (Happy.Rentals). Together they break down what sustainable growth really looks like when regulation, local execution, and trust change country by country. You’ll hear why there is no single European playbook, how operators balance centralized systems with hyper-local operations, and why technology only works when it supports operational excellence on the ground. In this conversation, we discuss: Why short-term rental growth in Europe looks different market by marketHow STR regulation in Europe shapes scaling strategies and operating modelsWhy trust and local operations matter more than brand when scaling STR in EuropeHow European STR operators balance centralized systems with local executionWhere technology actually helps scale STR operations and where it falls shortWhy there is no single business model for scaling short-term rentals in Europe Learn more about our guests: Connect with Alexander Limpert on LinkedIn [https://www.linkedin.com/in/alexanderlimpert/] to learn more about GuestReady [https://www.guestready.com] & RentalReady [https://www.rentalready.com/].  Connect with Antoine Serrurier on LinkedIn [https://www.linkedin.com/in/antoine-serrurier-6a505917/] to learn more about COCOONR [https://cocoonr.fr/].  Connect with Harold Lubberdink on LinkedIn [https://www.linkedin.com/in/harold-lubberdink-b9a67113/] to learn more about Happy.Rentals [http://happy.rentals/].  Resources AJL Atelier – Global STR Consulting [https://www.ajlatelier.com]. Led by our host Simon Lehmann, AJL Atelier is a boutique advisory firm helping professional hosts, property managers, and investors succeed in the short-term rental industry. Connect with Simon Lehmann on LinkedIn [https://www.linkedin.com/in/simon-lehmann-8375753b/] Stay connected: Apple Podcasts: https://podcasts.apple.com/us/podcast/str-global-unlocked-with-simon-lehmann-unfiltered/id1842946960 Spotify: https://open.spotify.com/show/3kke4wOx0tNv0duq9MMWtO Youtube: https://www.youtube.com/playlist?list=PLWVkmUOkmhSHcFjzi28AhaQNR98vaG65O Website: https://www.ajlatelier.com/podcasts Newsletter: https://str-global-unlocked.beehiiv.com/

    1h 1m
  6. 011: What VCs Really Look For in STR Tech: Insights from TCV’s Woody Marshall

    12/16/2025

    011: What VCs Really Look For in STR Tech: Insights from TCV’s Woody Marshall

    Woody Marshall is a General Partner at TCV, one of the most influential investment firms in global technology and a long-standing backer of travel companies including Expedia, Airbnb, HomeAway and TripAdvisor. With more than two decades of experience investing in category-defining platforms, Woody brings a unique view of how technology evolves and what it takes for a company to break through in fragmented markets. In this episode, Simon Lehmann speaks with Woody about the state of short-term rental technology, why investor appetite has shifted and how AI, consolidation and new competitive pressures are reshaping the landscape. Woody explains how TCV evaluates opportunity, why STR technology has different valuation dynamics than traditional SaaS and what founders should understand as they build in an increasingly crowded space. This conversation offers an unfiltered look at how top-tier investors see the market and what it will take for the next generation of STR technology companies to stand out. In this conversation, we discuss: How TCV approaches travel technology and why STR platforms require a distinct investment lens.Why fragmentation across PMS, operations, revenue tools and distribution makes scale difficult to achieve.How AI is reshaping search, personalization and product experience and what this means for STR platforms.Why consolidation is likely and where the market may converge as the tech stack evolves.How competitive dynamics with incumbents and AI-first entrants affect valuation, defensibility and long-term strategy.What founders must demonstrate today to compete, differentiate and attract institutional investment. Explore more: Connect with Woody Marshall on LinkedIn [https://www.linkedin.com/in/woodymarshall/]  to learn more about TCV [https://www.tcv.com/]  Resources AJL Atelier – Global STR Consulting [https://www.ajlatelier.com]. Led by our host Simon Lehmann, AJL Atelier is a boutique advisory firm helping professional hosts, property managers, and investors succeed in the short-term rental industry. Connect with Simon Lehmann on LinkedIn [https://www.linkedin.com/in/simon-lehmann-8375753b/] Stay connected: Apple Podcasts: https://podcasts.apple.com/us/podcast/str-global-unlocked-with-simon-lehmann-unfiltered/id1842946960 Spotify: https://open.spotify.com/show/3kke4wOx0tNv0duq9MMWtO Youtube: https://www.youtube.com/playlist?list=PLWVkmUOkmhSHcFjzi28AhaQNR98vaG65O Website: https://www.ajlatelier.com/podcasts Newsletter: https://str-global-unlocked.beehiiv.com/

    45 min
  7. 010: The Midterm Rental Shift with Furnished Finder’s Jeff Hurst and Cami Narino

    12/09/2025

    010: The Midterm Rental Shift with Furnished Finder’s Jeff Hurst and Cami Narino

    Cami Narino, Chief Operating Officer, and Jeff Hurst, Chief Executive Officer at Furnished Finder, join Simon Lehmann to analyze one of the most important shifts happening in housing and hospitality today: the rise of midterm rentals. Over the past decade, Furnished Finder has grown from zero to more than 300,000 listings, powered by independent landlords, changing mobility patterns and a growing need for flexible housing across the United States. In this episode, Cami and Jeff explain why midterm rentals are gaining momentum, what supply looks like in practice and how the needs of monthly renters differ from short-term guests. They break down the economics of the category, the operational cadence behind longer stays and the technology required to screen guests, reduce fraud and deliver safer outcomes for both sides of the marketplace. This conversation shows how midterm rentals are evolving, what is driving demand and why operators and landlords should pay attention as the category matures. In this conversation, we discuss: Why midterm rentals are becoming a meaningful category in housing and hospitality and how demand has shifted beyond short stays.How independent landlords drive the majority of midterm rental supply and why their inventory behaves differently from STR.What sets midterm rentals apart from short-term stays, including operational cadence, guest expectations and pricing stability.How Furnished Finder scaled from 20,000 to more than 300,000 listings and why the marketplace model, not instant booking, works for monthly stays.How screening, verification and trust and safety have become essential to creating safer outcomes for guests and property owners.How regulation, supply trends and capital cycles are shaping the future of midterm rentals as the category matures. Explore more: Connect with CEO Jeff Hurst [https://www.linkedin.com/in/jeff-hurst-atx/] and COO Cami Narino on LinkedIn [https://www.linkedin.com/in/cami-narino/] to learn more about Furnished Finder [www.furnishedfinder.com].   Exclusive offer for STR Global Unlocked listeners: Use code UNLOCKED10 for 10 percent off a new Furnished Finder listing through 12/31/2025.Resources AJL Atelier – Global STR Consulting [https://www.ajlatelier.com]. Led by our host Simon Lehmann, AJL Atelier is a boutique advisory firm helping professional hosts, property managers, and investors succeed in the short-term rental industry. Connect with Simon Lehmann on LinkedIn [https://www.linkedin.com/in/simon-lehmann-8375753b/] Stay connected: Apple Podcasts: https://podcasts.apple.com/us/podcast/str-global-unlocked-with-simon-lehmann-unfiltered/id1842946960 Spotify: https://open.spotify.com/show/3kke4wOx0tNv0duq9MMWtO Youtube: https://www.youtube.com/playlist?list=PLWVkmUOkmhSHcFjzi28AhaQNR98vaG65O Website: https://www.ajlatelier.com/podcasts Newsletter: https://str-global-unlocked.beehiiv.com/

    51 min
  8. 009: Booking Holdings President and CEO Glenn Fogel on AI and Why STR Is the Next Big Travel Shift

    12/02/2025

    009: Booking Holdings President and CEO Glenn Fogel on AI and Why STR Is the Next Big Travel Shift

    Glenn Fogel is the President and CEO of Booking Holdings, the parent company of Booking.com, Priceline, Kayak and other global brands that shape how the world travels. With more than two decades at the forefront of online travel, he has guided Booking through major industry shifts, emerging technologies and changing traveler behavior. In this episode, Simon Lehmann speaks with Glenn about how AI, search and short-term rentals are redefining the future of travel. Glenn explains why STR is now central to Booking’s long-term strategy, how traveler expectations are evolving, and why the Connected Trip vision depends on both technology and human judgment. This conversation offers a clear view of how one of the most influential leaders in travel sees the road ahead and what operators need to understand as the industry moves into a new phase. In this conversation, we discuss: How AI is reshaping travel search through natural-language queries, proactive trip planning and Booking’s early work with OpenAI, Google Gemini and other models.Why short-term rentals are now a core growth engine for Booking.com, representing 36% of room nights and outpacing hotel inventory growth globally.What the Connected Trip means for travelers and how Booking plans to reduce friction with predictive tools, better timing, automated fixes and personalized recommendations.The strategic challenges in the US and Asia and how Booking is rebuilding its STR product to win listings, improve quality and meet rising market expectations.The rising role of FinTech in travel including payments, fraud prevention, cancellations, insurance and cross-border settlement designed to reduce friction for partners and guests.How regulation, consumer behavior and post-pandemic trends are reshaping STR supply, demand patterns and the long-term future of global travel. Explore more: Connect with Glenn Fogel on LinkedIn [https://www.linkedin.com/in/glennfogel/] to learn more about Booking Holdings [https://www.bookingholdings.com/].  Resources AJL Atelier – Global STR Consulting [https://www.ajlatelier.com]. Led by our host Simon Lehmann, AJL Atelier is a boutique advisory firm helping professional hosts, property managers, and investors succeed in the short-term rental industry. Connect with Simon Lehmann on LinkedIn [https://www.linkedin.com/in/simon-lehmann-8375753b/] Stay connected: Apple Podcasts: https://podcasts.apple.com/us/podcast/str-global-unlocked-with-simon-lehmann-unfiltered/id1842946960 Spotify: https://open.spotify.com/show/3kke4wOx0tNv0duq9MMWtO Youtube: https://www.youtube.com/playlist?list=PLWVkmUOkmhSHcFjzi28AhaQNR98vaG65O Website: https://www.ajlatelier.com/podcasts Newsletter: https://str-global-unlocked.beehiiv.com/

    51 min

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5
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About

The short-term rental industry is evolving fast, and Simon Lehmann isn’t afraid to say what others won’t.STR Global Unlocked is where property managers, STR tech founders, vacation rental investors, and hospitality leaders get real about the business. Each episode breaks down what’s working, what’s broken, and what’s coming next: property management operations, direct bookings, vacation rental software, pricing strategies, mergers and acquisitions in real estate, professional host challenges, and the future of automation, AI, and tech stacks. Hosted by Simon Lehmann, CEO of AJL Atelier and one of the most trusted voices in the global STR space, the show delivers unfiltered conversations with the people shaping the industry. Simon has decades of experience in vacation rentals, travel tech, and hospitality, including leadership roles at Vacasa Europe, PhocusWright and HomeAway. If you’re scaling a property management company, building short-term rental technology, investing in vacation rentals, or entering this fast-moving market, this podcast is your seat at the table.