Welcome FINTECHTALKERS!

In this episode, I sat down with Roey Dor, co-founder and CEO of Obligo, to explore how his fintech is transforming the rental experience. From his days as a fighter pilot to launching a PropTech company that has already partnered with AppFolio and Yardi — leaders in property management cloud software. Roy shares his journey and how military lessons translated into entrepreneurship.

Obligo is tackling one of real estate’s most stubborn inefficiencies: the $50 billion trapped in rental deposits. By reimagining the process with bank-linked preauthorizations, proprietary underwriting, and embedded finance, Obligo is helping renters keep more liquidity while giving property managers a frictionless way to manage risk.

We dive into Roy’s origin story, how trust-tech powers the platform, why verticalized embedded finance is the next wave for fintech, and what the arrival of AI agents in real estate means for the future of renting.

Key Takeaways From the Episode

* The $50B problem: Security deposits tie up renter cash while creating admin burdens for landlords.

* Deposit-free renting: Obligo’s hotel-style preauthorization model unlocks liquidity without added risk.

* Trust-tech underwriting: Predicts both property charge risk and renter repayment risk.

* Embedded finance distribution: Integrations with property management software embed Obligo at scale.

* The renter journey reimagined: One app, one sign-up, frictionless move-in to key handoff.

* AI in PropTech: Agentic AI will soon manage discovery, leasing, and payments for renters.

* From cockpit to startup: Lessons from air combat—awareness, pivots, and resilience—apply directly to building Obligo.

If you’re a fintech founder, investor, or just someone curious about the future of PropTech and embedded finance, this conversation is packed with insights.

www.obligo.com

Timestamp Table

0:00 – 2:30 – Meet Roy Dorr — From fighter pilot to bar owner to real estate developer to fintech founder.

2:31 – 5:00 – Entrepreneurship Lessons from the Air Force — Why reacting to external factors is the key to resilience.

5:01 – 9:00 – Air Combat Rules for Startups — Lessons from dogfights that apply to pivots, competitors, and risk management.

9:01 – 14:30 – The $50B Problem: Rental Deposits — Why deposits are inefficient for both renters and landlords.

14:31 – 18:00 – How Obligo Works — Deposit-free renting modeled after hotel pre-authorizations and powered by Plaid.

18:01 – 23:00 – Embedded Finance in Property Software — Why partnerships with AppFolio, Yardi, and others unlock massive scale.

23:01 – 27:00 – The Future of Renting — One app, one flow, frictionless check-in to key handoff.

27:01 – 30:30 – Verticalized Embedded Finance — Why industry-specific SaaS + fintech is the next decacorn wave.

30:31 – 32:00 – AI Agents in Real Estate — The future of renting with embedded AI copilots.

32:01 – 36:00 – Shifts in PropTech Economics — From landlords paying SaaS fees to renters as the monetized customer.

36:01 – 38:00 – Raising the Next Round — Roy’s journey from pre-seed to C-stage and his outlook for investors.

38:01 – 40:00 – Who Roy Wants to Connect With — Property tech partners, banks, and fintech investors.

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Enjoy and always be in the know,

Paddy RamanathanFounder of iValley and Host of the FINTECHTALK™ Show (on Substack, Apple Podcast, YouTube, and Spotify)

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Thanks to ChatGPT for suggestions.

(Violin piece in podcast, courtesy of my daughter Ilina)

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