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