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David Okonkwo
I started in commercial real estate at CBRE in 2014 as an analyst in the capital markets group. My job was to build financial models for office and multifamily acquisitions. I learned DCF modeling, cap rate analysis, and the particular art of making a 40-year-old building look like a good investment in a PowerPoint deck. I also learned that commercial real estate is one of the most relationship-driven industries in the world: deals worth hundreds of millions of dollars happen because two people played golf together in 1998.
After CBRE, I joined Zillow in 2018 as a product manager. I worked on the Zillow Offers (iBuying) program, which was Zillow's attempt to use algorithms to buy and resell homes. This was, in hindsight, one of the most instructive failures in recent tech history. The model worked in theory: use a Zestimate-like algorithm to price homes, buy them below market, do light renovations, and resell. In practice, the algorithm couldn't account for local market dynamics, renovation costs were unpredictable, and the holding costs during a market downturn were devastating. Zillow lost $881M and shut down the program in 2021. I had a front-row seat.
I stayed at Zillow and moved to the rentals team, eventually becoming a product director. The rental market is less sexy than home buying but far more interesting from a technology perspective. The workflows are fragmented, the data is worse, and the participants (landlords, property managers, tenants, brokers) all have different incentives. I spent three years building products for this market and developed a deep appreciation for how hard it is to digitize an industry where the underlying asset is physical and local.
The piece that got me writing for Signal was a postmortem of the iBuying era that I published on Medium in 2024. It went viral in real estate and tech circles because I had actual numbers and actual context, not just "algorithm bad." The thesis was that iBuying failed not because algorithms can't price homes, but because the margin of error in home pricing is wider than the margin of profit in home flipping. That's a math problem, not a technology problem.
I cover the full spectrum of proptech: commercial and residential, buying and renting, software and hardware. The industry is massive ($50T+ in US real estate assets), technologically backward, and ripe for disruption, but only by companies that understand that real estate is a local, relationship-driven, highly regulated business. Most proptech startups learn this lesson the expensive way.
I live in Chicago. I own a three-flat in Logan Square that I manage myself, which keeps me honest about the landlord experience. I play jazz piano at a bar in Wicker Park on Thursday nights, and I think the condo association is the most underrated power structure in America.
Experience
- Product Director, Zillow (Rentals)
- Product Manager, Zillow Offers (iBuying)
- Capital Markets Analyst, CBRE