Zillow’s CEO Is Ready for Another Slow Year in the US Housing Market

On his Zillow account, Jeremy Wacksman has “favorited” every home he’s ever lived in, just to keep tabs. Among them: a two-story, 2,500-square-foot house with four bedrooms, 2½ bathrooms and a sprawling front yard in the Cincinnati suburbs where he grew up. “The doors weren’t red when we lived there,” the chief executive officer of Zillow Group Inc. notes, squinting at a “street view” image on his iPhone. In 1997, when Wacksman was in college, his father sold the house for $227,000. These days his company’s proprietary algorithmic valuation, or Zestimate, calculates it’s worth around $700,000.

Zillow is to homebuying what Uber Technologies Inc. is to taxis, a tech disrupter that’s come to redefine its market. (Others have called it “the Google of real estate.”) Every month about 243 million users scour its house-hunting portal via desktop or app for listings in the US—quadruple the reach of its closest competitor, according to Zillow. Mindlessly perusing Zillow is so enticingly common, especially for aging millennials, that Saturday Night Live in 2021 likened it to internet porn. “Our listings are just standing by waiting for you to browse them,” quipped the voice-over of a faux-erotic ad. That spoof was “a marketer’s dream,” says Wacksman, 48.