Former Zillow execs talk startups, AI and a ‘discouraging’ trend 

Zillow is best known for launching the real estate industry's leading home search portal — but it has also served as a different sort of launchpad, creating opportunities for many of its former executives to found and lead other companies in the space.

For some, the move from a publicly traded company to a small startup was a whole new experience.

"When you work at a company like Zillow or any of these great corporations, 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 — except for you, hopefully your teammates and your mom."

After leaving Zillow, where Schwartz was president of media and marketplace, he "had to recalculate" his approach from leading a company already at scale to one where any newly implemented idea would only be seen by a handful of people. That shift "took some years" to figure out, he said.

Don't settle for 'OK' hires: Luis Poggi, co-founder and CEO of the AI real estate agent assistant HouseWhisper, closed out his decade at the home search giant as VP of product and engineering, recalled interviewing a job candidate in his first month at Zillow that he thought would be "OK" for the role. But he was reminded that he should be striving to add better than just "OK" employees — a lesson that "changed how I hire forever."

With the emergence of AI, curiosity in new tech has become "a very important aspect" for him in candidate interviews.

"A person who uses AI today can do the work of three or four or five people," he explained, adding, "I think the biggest constraint today is your imagination."

How smaller companies can compete: "Learn, test, try, fail. The only way a young, smaller company can compete with incumbents that have massive scale is to be faster," Schwartz said.

In another lesson from his time at Zillow, Poggi recalled trying to create a home improvement product before swiftly moving to nix it. One of his biggest takeaways from the experience was that home improvement — even in real estate — is "a completely different industry" — and the diversion wasn't helpful for his team.

"Most startups die for lack of focus, for distraction; not for competition," he said. "There was a big learning in how quickly we tried to do something too far — and then quickly killed it and focused on the core business."

A 'selfish' industry trend: Schwartz suggested the industry as a whole has a distraction problem tied to the debate over private listings.

He was "a little discouraged" that industry leaders are "still talking about exclusive listings in the middle of the housing affordability crisis in America."

"People are really suffering. Our kids are suffering," Schwartz said. "I think it's pretty selfish that the industry is focused on this."

Philosophies to live by: Jay.Life Consulting Founder Jay Thompson, who worked as Zillow's director of industry outreach for about seven years, said he developed what he calls "The High Road Philosophy" during his time at the company.

"It's a conscious thought process to go through when I deal with problems — whether they're people or relationships," Thompson explained.

Implementing that same philosophy in his personal life has had "a tremendous difference in how I approach things, how I do things, my attitude," he added.

Schwartz also shared a motto that he said "kept me true to myself."

"Be kind and be decent — to your teammates, your family, to your partners, your customers — rather than exercise conflict and power."

Editor's note: Real Estate News is an editorially independent division of T3 Sixty.