Measure of AI

Measure of AI

Case Study: Zillow's $500M Mistake in Trusting Their Model

When you let the model's make decisions with money, you better have strong guardrails in place.

Azmain Hossain's avatar
Azmain Hossain
Jun 16, 2026
∙ Paid

Open Zillow right now and type in your own address. A number comes up - the Zestimate. It’s Zillow’s guess at what your home is worth, and it is almost certainly a little wrong. By Zillow’s own accounting it misses by about 2% on homes that are actually for sale, and by 7%+ on the ones that aren’t. It’s been doing this since 2006, and it’s never cost an…

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