STR GLOBAL
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Simon Lehmann

Learn from STR Experts

Simon Lehmann sits down with industry leaders, operators, and innovators to uncover the trends and strategies driving short-term rentals. Each conversation offers sharp insights and real lessons from inside the market.

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Rethinking Real Estate Capital With Ecommerce Models

Episode #
15
|
Rebecca Kacaba

How Drones Transform Last-Mile Delivery

Episode #
14
|

The Year STR Changed

Episode #
13
|
Simon Lehmann

Other Episodes

View All Episodes

Rethinking Real Estate Capital With Ecommerce Models

Episode #
15
|
Rebecca Kacaba

How Drones Transform Last-Mile Delivery

Episode #
14
|

The Year STR Changed

Episode #
13
|
Simon Lehmann
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Episode
16

How Institutional Capital Is Rethinking Short-Term Rentals

Institutional capital is reshaping short-term rentals and flexible living. In this episode, Jaja Jackson of ICONIQ Capital shares how investors assess STR, mid-term stays, risk, returns, and operational integration at scale.
January 20, 2026
Jaja Jackson
Episode
15

Rethinking Real Estate Capital With Ecommerce Models

This episode explores how capital raising is shifting from traditional, opaque models to more open, ecommerce-like platforms. DealMaker CEO Rebecca Kacaba shares why online, community-driven fundraising is giving founders more control, flexibility, and access to capital—especially in real estate, hospitality, and short-term rentals—while AI helps reduce friction across the process.
January 13, 2026
Rebecca Kacaba
Episode
14

How Drones Transform Last-Mile Delivery

Bobby Healy, Founder and CEO of Manna Drone Delivery, joins STR Global Unlocked to explain why last-mile delivery is fundamentally broken and how autonomous drones can transform logistics, urban operations, and the short-term rental guest experience. Drawing on decades of travel and infrastructure expertise, he breaks down the real economics, regulatory realities, and operational limits shaping drone delivery at scale.
January 6, 2026
Episode
13

The Year STR Changed

A reflective Holiday Special where Simon Lehmann breaks down how 2025 reshaped the STR industry—shifting the focus from rapid growth to margins, execution, regulation, and operational reality. A grounded look at the conversations, tensions, and signals defining where short-term rentals stand today and what lies ahead.
December 30, 2025
Simon Lehmann
Episode
12

Scaling STR in Europe

Europe’s STR market isn’t one-size-fits-all. This panel unpacks how leading operators scale across fragmented European markets—balancing regulation, trust, and hyper-local execution with centralized systems—while showing why technology only works when grounded in strong on-the-ground operations.
December 23, 2025
Simon Lehmann
Episode
11

Inside VC Thinking on STR

Woody Marshall is a General Partner at TCV, where he has invested since 2008 across fintech, mobile, and digital media. He currently serves on the boards of companies such as Spotify, GoFundMe, Payeroneer, and Newsela, and has backed category leaders including Airbnb, Netflix, and Nubank. With nearly three decades in venture capital, he brings deep experience in scaling global technology businesses.
December 16, 2025
Woody Marshall
Episode
10

The Midterm Rental Shift

Jeff Hurst and Cami Narino from Furnished Finder join Simon Lehmann to break down why midterm rentals are rising, how independent landlords built more than 300,000 listings, and what operators need to understand as monthly stays reshape housing and hospitality.
December 9, 2025
Simon Lehmann
Episode
9

Inside Booking’s View on AI and STR

Simon Lehmann speaks with Glenn Fogel, President and CEO of Booking Holdings, about how AI, search and short term rentals are shaping Booking.com’s strategy and the next phase of global travel.
December 2, 2025
Simon Lehmann
Episode
8

Tech vs Hospitality in STR

Sean Breuner from AvantStay shares how the company built a hospitality model focused on consistency, strong operations, and group travel. He explains the thinking behind their tech platform and what shaped their growth strategy in a volatile STR market.
November 25, 2025
Simon Lehmann
Episode
7

Inside Vacasa’s Lessons for STR Founders

Cliff Johnson, Co Founder of Vacasa and President of PadSplit, reflects on rapid growth, operational pressure, and the decisions that shaped Vacasa’s journey.
November 18, 2025
Cliff Johnson
Episode
6

When Revenue Meets Operations in STR

Revenue and operations have long worked in silos. In this episode, Simon Lehmann sits down with Jeremy Gall, CEO of Breezeway, and Richie Khandelwal, Co-founder of PriceLabs, to discuss how data-driven integration is reshaping profitability for professional STR operators.
November 11, 2025
Simon Lehmann
Episode
5

How Guesty Became a Global PMS

Amiad Soto, co-founder and CEO of Guesty, shares how he turned a side project in Tel Aviv into one of the world’s leading property management platforms. He opens up about scaling globally, adapting to fragmented markets, and building tech that empowers real-world operators.
November 4, 2025
Simon Lehmann
Episode
4

Inside the OTA Playbook Explained

Carl Shepherd, co-founder of HomeAway, joins to share the inside story of building a $3.9B short-term rental empire, the lessons behind Expedia’s acquisition, and what he thinks Airbnb and Booking got wrong in today’s OTA landscape.
October 28, 2025
Simon Lehmann
Episode
3

Global STR Scale Challenges

Graham Donoghue (Forge Group), Steve Schwab (Casago), and Quirin Schwaighofer (MadeComfy) join Simon Lehmann to explain why no one has built a truly global STR operator and what it really takes to scale across markets.
October 21, 2025
Simon Lehmann
Episode
1

Building a Profitable STR Business

Brian Egan, Co-Founder and CEO of Evolve, reveals how he turned a small vacation rental startup into a $5B business with 35,000+ properties. He shares lessons on scaling trust, balancing tech with hospitality, and the future of short-term rentals.
October 14, 2025
Simon Lehmann
Episode
1

6 Trends Defining Short-Term Rentals

The short-term rental industry is entering a decisive moment. Regulation is rising, OTAs are shifting power, and AI is changing the game. Simon Lehmann unpacks the six trends defining STR in 2025, sharing sharp insights from decades in the global market.
October 6, 2025
Simon Lehmann
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Host - Simon Lehmann

Simon is one of the leading voices in the short-term and vacation rental world. He runs AJL Atelier, a specialized consultancy, and advises multiple companies as a Board Member and Executive Chairman.

He’s a sought-after speaker and loves diving into everything from big-picture industry trends to the nitty-gritty of online distribution across the top OTAs.

Before that, Simon co-founded and chaired Vacasa Europe, led PhocusWright as President, and sat on HomeAway’s board. He’s also held top executive roles at Interhome, Hotelplan Group, and Swissport.

Work with Simon

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Episode #

16

Jaja Jackson

Senior Vice President of Real Assets

Jaja Jackson

Jaja Jackson is Senior Vice President of Real Assets at ICONIQ Capital, where he focuses on institutional investment strategies across short-term rentals, flexible living, and multifamily real estate.

Episode #

15

Rebecca Kacaba

Co-Founder & CEO

Rebecca Kacaba

Rebecca Kacaba is the Co-Founder and CEO of DealMaker, a leading online capital-raising platform transforming how companies raise and manage investment. A former capital markets lawyer, she brings deep regulatory expertise to building modern, community-driven fundraising infrastructure for founders across real estate, hospitality, and beyond.

Episode #

13

Simon Lehmann

Simon Lehmann

Simon Lehmann is a global STR leader and CEO of AJL Atelier. He’s advised hundreds of operators, startups, and investors, and is a frequent speaker at top industry events worldwide.

Episode #

12

Simon Lehmann

Simon Lehmann

Simon Lehmann is a global STR leader and CEO of AJL Atelier. He’s advised hundreds of operators, startups, and investors, and is a frequent speaker at top industry events worldwide.

Episode #

11

Woody Marshall

General Partner

Woody Marshall

Woody Marshall is a General Partner at TCV, where he has invested since 2008 across fintech, mobile, and digital media. He currently serves on the boards of companies such as Spotify, GoFundMe, Payeroneer, and Newsela, and has backed category leaders including Airbnb, Netflix, and Nubank. With nearly three decades in venture capital, he brings deep experience in scaling global technology businesses.

Episode #

10

Simon Lehmann

Simon Lehmann

Simon Lehmann is a global STR leader and CEO of AJL Atelier. He’s advised hundreds of operators, startups, and investors, and is a frequent speaker at top industry events worldwide.

Episode #

9

Simon Lehmann

Simon Lehmann

Simon Lehmann is a global STR leader and CEO of AJL Atelier. He’s advised hundreds of operators, startups, and investors, and is a frequent speaker at top industry events worldwide.

Episode #

8

Simon Lehmann

Simon Lehmann

Simon Lehmann is a global STR leader and CEO of AJL Atelier. He’s advised hundreds of operators, startups, and investors, and is a frequent speaker at top industry events worldwide.

Episode #

6

Simon Lehmann

Simon Lehmann

Simon Lehmann is a global STR leader and CEO of AJL Atelier. He’s advised hundreds of operators, startups, and investors, and is a frequent speaker at top industry events worldwide.

Episode #

5

Simon Lehmann

Simon Lehmann

Simon Lehmann is a global STR leader and CEO of AJL Atelier. He’s advised hundreds of operators, startups, and investors, and is a frequent speaker at top industry events worldwide.

Episode #

4

Simon Lehmann

Simon Lehmann

Simon Lehmann is a global STR leader and CEO of AJL Atelier. He’s advised hundreds of operators, startups, and investors, and is a frequent speaker at top industry events worldwide.

Episode #

3

Simon Lehmann

Simon Lehmann

Simon Lehmann is a global STR leader and CEO of AJL Atelier. He’s advised hundreds of operators, startups, and investors, and is a frequent speaker at top industry events worldwide.

Episode #

1

Simon Lehmann

Simon Lehmann

Simon Lehmann is a global STR leader and CEO of AJL Atelier. He’s advised hundreds of operators, startups, and investors, and is a frequent speaker at top industry events worldwide.

Episode #

1

Simon Lehmann

Simon Lehmann

Simon Lehmann is a global STR leader and CEO of AJL Atelier. He’s advised hundreds of operators, startups, and investors, and is a frequent speaker at top industry events worldwide.