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. 019: Travel Marketplaces That Endure: Lessons from HomeAway to RVshare with Jon Gray

    1D AGO

    019: Travel Marketplaces That Endure: Lessons from HomeAway to RVshare with Jon Gray

    Some platforms optimize for growth. Others optimize for survival. Very few manage both. In this episode of STR Global Unlocked, Simon Lehmann sits down with Jon Gray, CEO of RVshare and former executive at HomeAway (now VRBO), for a grounded conversation on what actually makes marketplaces last. Jon has seen multiple cycles from the early days of short-term rentals, through the $3.9B sale of HomeAway to Expedia, to scaling the largest RV rental marketplace in the world. This is not a discussion about categories, labels, or hype. It is about discipline, tradeoffs, and building platforms that hold up when demand shifts. Throughout the conversation, Jon returns to one core idea. Marketplaces exist to remove friction and expand real choice. Everything else follows from that. In this conversation, we discuss: Why the true job of a marketplace is removing friction and delivering meaningful consumer choice, regardless of category.What felt uncertain in the early HomeAway days but later proved obvious, including instant booking and inventory neutrality.Why guests prioritize experience quality over who manages the inventory, and what that means for professional operators.How RVshare translated STR marketplace fundamentals into a higher-friction, mobile asset class.Why pushing supply sophistication faster than feels comfortable protects long-term experience and reputation.Why resilience, unit economics, and survivability matter more than valuation narratives during growth cycles. Resources and links: Connect with Jon Gray on LinkedIn [https://www.linkedin.com/in/jonathangray/] to learn more about RVshare [https://rvshare.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. 018: Where Real Estate Models Are Converging: Lavanda CEO Fred Lerche-Lerchenborg on Flexible Living, STR, and Multifamily

    FEB 3

    018: Where Real Estate Models Are Converging: Lavanda CEO Fred Lerche-Lerchenborg on Flexible Living, STR, and Multifamily

    In this episode of STR Global Unlocked, Simon Lehmann speaks with Fred Lerche-Lerchenborg, CEO of Lavanda, about how short-term rentals, mid-term stays, and multifamily are converging inside the same assets. This is not a tech pitch. It is a practical discussion on institutional real estate, operating risk, and why flexible living is becoming a core strategy for owners and investors. Fred breaks down why legacy long-term rental systems fail at daily pricing and mixed inventory, why lease-arbitrage collapsed at scale, and how investor psychology, cap rates, compliance, and risk transfer shape real decisions. The conversation also explores why Europe is moving faster than the US in flexible living, and what operators must get right before blending STR into multifamily creates value instead of backlash. In this conversation, we discuss: Why residential real estate systems were never designed for flexibility, and how changing living patterns are forcing new operating models.Where traditional PMS platforms fail when short-term, mid-term, and long-term stays coexist in the same building.Why institutional capital evaluates flexible living through asset value protection, not revenue upside alone.How lease arbitrage broke down at scale, and when selective leasing can still work for smaller STR operators.What flexible living unlocks for student housing, build-to-rent, and urban development in regulated markets.Why risk, liability, insurance, and guest vetting become non-negotiable when STR enters multifamily environments.Explore more: Connect with Fred Lerche-Lerchenborg on LinkedIn [https://www.linkedin.com/in/fred-lerche-lerchenborg] to learn more about Lavanda [http://getlavanda.com]   . . . Podcast supported by Breezeway. Breezeway brings operational workflows, service execution, and standards together in one platform for hospitality operators. 👉 Get started with Breezeway 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/

    53 min
  3. 017: Decisions, Not Forecasts: How Professional STR Operators Win in 2026 with Simon Lehmann

    JAN 27

    017: Decisions, Not Forecasts: How Professional STR Operators Win in 2026 with Simon Lehmann

    The short-term rental industry is entering a more demanding phase. In 2026, performance will be defined by execution, discipline, and decision-making under pressure. In this solo episode, Simon Lehmann outlines what professional operators must change, what they must stop doing, and where time and capital should be focused to protect margin and build durable businesses. The 6 Decisions Shaping STR Performance in 2026 Quality of earnings – Why unit-level profitability matters more than portfolio growth.Pricing – How pricing shifts from a tactical tool to a leadership strategy.Operations – Why friction, not branding, defines trust and long-term value.Regulation – The transition from headline risk to enforcement and professionalism.Risk and insurance – How liability, safety, and preparedness are being repriced.Distribution – Why controlled exposure replaces maximum exposure in a changing discovery landscape. FOUNDING 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/

    29 min
  4. 016: Flexible Living Is Reshaping STR: An Institutional Capital Perspective with Jaja Jackson of ICONIQ Capital

    JAN 20

    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
  5. 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
  6. 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
  7. 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
  8. 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

Trailer

5
out of 5
11 Ratings

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.