#128 - Banking to Real Estate Tech: Scalable Income with Kevin Shtofman

2026-03-06

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Send a textWhat if AI could finally make real estate data actually useful instead of overwhelming? In this episode of Path to Passive, Steven Arita sits down with Kevin Shtofman, Global Head of Alliances and Corporate Development at Cherre, a real estate data warehouse platform serving insurance companies, sovereign wealth funds, and REITs. Kevin brings over 20 years of experience from investment banking, Morgan Stanley, EY, and Deloitte, and he's now helping real estate companies turn fragmented data f...

Send a text

What if AI could finally make real estate data actually useful instead of overwhelming?

In this episode of Path to Passive, Steven Arita sits down with Kevin Shtofman, Global Head of Alliances and Corporate Development at Cherre, a real estate data warehouse platform serving insurance companies, sovereign wealth funds, and REITs.

Kevin brings over 20 years of experience from investment banking, Morgan Stanley, EY, and Deloitte, and he's now helping real estate companies turn fragmented data from acquisitions, leasing, accounting, and reporting into actionable intelligence.

You'll learn how AI agents are screening deals in seconds, comparing actual performance to underwriting models, and even helping solo property managers prioritize emergency maintenance requests based on tenant value and calendar availability.

Kevin shares a fascinating story about validation rules like why some leases show zero rent (hint: concession periods) and explains why bad data for reports is merely "not good," but bad data for AI automation is "very, very dangerous."

He breaks down the three-tier environment system (dev, QC, production) that prevents AI from acting on garbage data, and reveals how tech professionals building side portfolios can use Claude or Gemini as thought partners to draft lease agreements and financial models before paying attorneys.

Kevin also opens up about his leap from a 100,000-employee consulting firm to employee number nine at a start-up, the "intuitive fence" concept that helped him make the jump, and his biggest career skill: learning when and how to say no.

Whether you're a W-2 tech professional managing three rental properties or dreaming of scaling to institutional size, this episode shows you exactly how data pipelines, validation rules, and AI collaboration are reshaping real estate investing and how to apply these lessons at any portfolio size.

By the end, you'll understand why connecting actuals to underwriting to benchmark data isn't just about better reports—it's your business case for raising the next fund or fixing what's broken before investors notice.

Connect with Kevin:
LinkedIn: https://www.linkedin.com/in/kevinshtofman/
Website: https://cherre.com/

Episode Highlights:
0:00] – Intro
[9:06] – What Cherry does: Real estate data warehouse connecting all your systems into one standardized model
[17:36] – Why data lineage matters: How to prove your dashboard is right when executives say "this can't be correct"
[20:50] – The three-environment system: Dev, QC, and production prevent AI from acting on bad data
[26:22] – Why tech and business teams must collaborate: One plus one equals seven with AI in the mix
[29:43] – AI as your executive assistant: Prioritizing maintenance tickets, drafting communications, and syncing with your day job calendar
[33:10] – The ideal Cherry client: Why 2,000 units or 1M sq ft is the sweet spot, plus free tools for smaller portfolios
[39:24] – Actuals vs underwriting vs benchmark: The ROI-driven use case that either ra