One former Zillow leader says buyers are still suffering from a housing affordability crisis, but that’s being ignored in discussions about private listings.
Although Zillow is best known for launching the real estate industry’s leading home search portal, it has also served as a launching pad of another kind, creating opportunities for many of its former executives to found and lead other companies in the space.
For some, moving from a publicly traded company to a small startup was a completely new experience.
“When you work for a company like Zillow and these great companies, you have incredible scale and power,” Tomo Mortgage co-founder Greg Schwartz said during a panel discussion at the 2026 T3 Leadership Summit last month. But, “When you start something from scratch, no one cares about you but you. Preferably your teammates and your mom.”
After departure At Zillow, where Schwartz was president of media and marketplaces, he “had to recalculate” his approach from a company that was already leading a large enterprise to one where newly implemented ideas were only seen by a small number of people. “It took several years” to understand the change, he said.
Don’t settle for an “OK” hire. Luis Poggi, co-founder and CEO of AI real estate brokerage assistant HouseWhisper, who wrapped up a decade at the home search giant as vice president of product and engineering, recalled interviewing candidates during his first month at Zillow and thinking he was “okay” for the role. But he was reminded that he should strive to get better employees, not just “OK” ones, a lesson that “changed the way I hire forever.”
With the advent of AI, curiosity about new technology has become a “very important factor” for him when interviewing candidates.
“People using AI today can do the work of three, four or five people,” he said, adding, “I think the biggest limitation today is imagination.”
How small businesses can compete: “Learn, test, try and fail. The only way young, small businesses can compete with the larger incumbents is to be faster,” Schwartz said.
Another lesson from his time at Zillow, Poggi recalled, was the company’s attempt to create a home improvement product before quickly discontinuing it. One of the biggest lessons from this experience was that home renovation, even real estate, is “a completely different industry,” and repurposing didn’t work for his team.
“Most startups die not because of competition, but because of lack of focus and distractions,” he said. “There was a huge learning curve about how we can quickly stop doing things that are too much and focus on our core business.”
“Selfish” industry trends: Mr. Schwartz suggested that the industry as a whole has a distracting problem related to the debate over private listings.
He said he was “a little disappointed” that industry leaders were “still talking about exclusive properties in the midst of the U.S. home affordability crisis.”
“People are really suffering. Our children are suffering,” Schwartz said. “I think it’s pretty selfish for the industry to focus on this.”
Philosophy for living: Jay Thompson, founder of Jay.Life Consulting, who served as Zillow’s director of industry support for about seven years, said he developed what he calls a “royal philosophy” during his time at the company.
“It’s a conscious thought process that you go through when you deal with a problem, whether it’s a person or a relationship,” Thompson explained.
He added that implementing the same philosophy in his personal life has “made a big difference in how I approach things, how I approach things, my attitude.”
Mr. Schwartz also shared his motto: “Stay true to yourself.”
“Be kind and courteous to your teammates, family, partners, and customers instead of being confrontational or assertive.”
Editor’s note: Real Estate News is an editorially independent division of T3 Sixty.
