STR Global Unlocked with Simon Lehmann
Simon Lehmann talks to the people running short-term rental at scale.
Operators, platform CEOs and investors, on the decisions that separate
businesses that scale from ones that plateau.
No panel-discussion politeness and no vendor pitches. Guests have included
the co-founder of Vacasa, the president and CEO of Booking Holdings, and the
founder of Holidu. The conversations go where the operating problems actually
are: unit economics, distribution, AI, capital, and what breaks when you grow.
Simon is a former CEO of Interhome, co-founder and chairman of Vacasa Europe,
past president of Phocuswright, and sat on the HomeAway board before the IPO.
He now advises operators, investors and hospitality technology vendors.
New episodes every Tuesday.
simonlehmann.net
STR Global Unlocked with Simon Lehmann
015: Is Raising Capital Like Ecommerce the Answer to Real Estate’s Funding Problem? Insights From DealMaker Co-Founder and CEO Rebecca Kacaba
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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:
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