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. Although he’s usually in Seattle, where he and the company are based—he lives in a mid-century modern house with a pool and hot tub, Zestimate not shared—today Wacksman is strolling the floor of Unlock, a conference put on by Zillow at the Fontainebleau Las Vegas. Boyish and of medium height, he’s dressed almost aggressively business casual, in a navy cardigan with black Zegna sneakers. The day before, he’d delivered a keynote address; tonight there’s a private concert by country singer Kacey Musgraves. Giddy attendees, mostly real estate agents, grin knowingly in his wake. Not everyone agrees Zillow is good. Like Uber, the company has weathered a barrage of industry resistance, naysayers and litigation in its conquest. But its dominance is unquestionable. Arizona’s Kris Mayes, one of five state attorneys general suing Zillow over alleged anticompetitive practices, has called it “a gorilla-sized company.” In 2024, Zillow reported annual revenue of $2.2 billion; analysts estimate it will be even higher in 2025 and 2026. People associate Zillow with homebuyers, but it actually makes around 70% of its revenue from agents, who pay the company for customer leads. Wacksman thinks a lot about how to keep the agents happy (hence tonight’s Musgraves concert). He knows many of them have reason to loathe Zillow, which has empowered consumers with market data and property history previously known only to licensed agents. Many of these “information arbiters,” as Wacksman describes pre-internet agents, were ruined during Zillow’s rise. “Our original mission statement was ‘power to the people,’ because it was about giving the nonprofessional access to data that only the professionals had,” he says. “It obviously worked.” When Wacksman joined Zillow in 2009, leaving a cushy marketing job at Microsoft Corp., the real estate market was in a similar state as it is now: poor. “Headlines were being written about how no one can sell their house and home values are plummeting,” says Wacksman, who studied both computer engineering and marketing. Today homebuying has stalled for the opposite reason: Prices are too high. But the outcome is the same—seemingly no one is able to move. A freshly married Wacksman bought his own first home in 2003—“what newlyweds used to do, when there were affordable starter homes,” he says. He and his wife had moved to Austin, where they found an agent through a friend and toured properties. They eventually bought a 2,500-square-foot house for $280,000. But Wacksman found the experience pointlessly cumbersome, especially being shepherded from house to house without having any sense of a property before visiting. “You felt completely clueless and completely at the behest of the professional you’d hired,” he recalls. Rich Barton and Lloyd Frink, former Microsoft executives and Expedia founders, looked to change that experience when they launched Zillow in 2006. “We were trying to answer a simple question,” Barton has said of his motivation. “What is that house worth? What should we offer if we wanted to buy it?” In addition to Zestimates, Zillow provides users with a property’s sales history, estimated costs for the seller, projected repair costs and a list of comparable homes. It recently stopped displaying its climate risk scores following a complaint from the real estate industry. (Zillow maintains they are still accessible by clicking a link to a third-party site.) In 2011 the company made its first acquisition: Postlets, a digital property-listing platform. Four years later, Zillow bought a major competitor, Trulia, for $2.5 billion. But the emergence of smartphones is what really propelled the onetime startup to dominance. Soon after Wacksman joined, as a marketer-cum-product leader, he was tasked with helping develop a mobile platform for the iPhone, a still fairly new invention. (Zillow also had one of the first apps on the iPad, “which was huge for us,” he says, and on the Apple Vision Pro, which was less so.) The company went public in July 2011 at a valuation of almost $540 million. Now it’s worth about $16 billion. There were major bumps along the way, such as Zillow Offers, an iBuying house-flipping program in which the company tried buying and selling houses itself. It scrapped the poor-performing idea in late 2021, forcing it to offload properties at a loss and fire 25% of its workforce. “You’re not always going to be right,” Wacksman says, reflecting on the episode. “But if you’re not willing to take a big swing, then you risk missing whatever the next wave is.” The Zestimate offering has also been criticized for inaccuracy, spurring a class action from a group of Illinois homeowners in 2017 who claimed erroneous numbers were misleading buyers. (The case was dismissed.) Over the years, Wacksman rose from chief marketing officer to chief operating officer to president. In August 2024 he succeeded Barton as CEO. A self-described introvert, whatever all those conference-floor handshakes would lead you to believe, the married father of two is now the one taking big swings. Under Wacksman, Zillow has continued its push into the transaction side of homebuying—not just introducing buyers and sellers but also facilitating sales. “It’s a better business to be in,” he says. “The way the internet is moving, you don’t just want to be a lead-generation site. You want to actually help with transactions.” Using software to coordinate the myriad parties involved in closing a house—agents, loan officers, title and escrow providers—is maddeningly tricky. To solve that, Zillow acquired one of the largest customer relationship management systems in the industry, Follow Up Boss, for about $500 million in 2023. Zillow has also added a home tour reservation system and an agent-buyer messaging platform. And its business model is shifting accordingly. Although its platform boasts a large “audience” of visitors, Zillow is involved only in a single-digit percentage of real estate transactions, through either select agents or its mortgage company, Zillow Home Loans. To boost the number of transactions Zillow is involved in, it has introduced a “success fee,” wherein the company receives 15% to 40% of an agent’s commission. Known as the Flex program, this incentivizes Zillow to help agents close deals. The more homes sold, the more money Zillow makes. Of course, all that depends on people actually buying houses. In 2024 a little more than 4 million properties sold in the US, according to the National Association of Realtors—an almost 30-year low. The future doesn’t look much brighter. In 2026, Zillow’s economists are expecting “very modest” growth, Wacksman says, citing “affordability challenges” caused by a lack of housing supply. The company has been lobbying in Washington for housing policy reforms it says would encourage more building. Meanwhile, Zillow is facing intense scrutiny from regulators. Joining the state attorneys general, the Federal Trade Commission sued Zillow in September for alleged anticompetitive practices. The FTC is accusing the company of coordinating with competitor Redfin in a way that will ultimately raise prices for renters. (“Redfin strongly disagrees with the FTC’s allegations and is confident we will be vindicated by a court of law,” says a company spokesperson. Zillow, too, remains “confident in our partnership with Redfin and also in our listing access standards which benefit sellers, buyers and agents,” says a company representative.) Compass Inc., the residential real estate brokerage, also sued Zillow, in June, for alleged antitrust violations. Although Wacksman’s company is facing nine-figure judgments, he appears unfazed. “As you succeed in a category, as you’re an innovator and changing, there’s naturally a sharper focus on you,” he says, flashing a smile. “There’s a lot of folks poking at us right now. But we feel really good about what we’re doing.” He continues his stroll along the sleek conference floor of the newest major casino resort on the Las Vegas Strip. Amid this sea of real estate agents, Wacksman seems perfectly at home.