Former Zillow Execs Discuss Startups and Trends

The housing affordability crisis continues to affect buyers, with some industry leaders focusing on the debate over private listings, a topic that one former Zillow executive finds discouraging.

Zillow, known for its real estate home search portal, has also served as a launchpad for its former executives to found and lead other companies in the space.

Greg Schwartz, co-founder of Tomo Mortgage and former Zillow president of media and marketplace, noted that moving from a publicly traded company to a small startup was a new experience.

“When you work at a company like Zillow or any of these great corporations, you have incredible scale and power,” Schwartz said during a panel discussion at the 2026 T3 Leadership Summit.

However, “when you start something from scratch, no one cares — except for you, hopefully your teammates and your mom,” he added, highlighting the challenges of building a new company from the ground up.

After leaving Zillow, Schwartz had to adjust his approach, taking “some years” to figure out how to lead a company where newly implemented ideas would only be seen by a handful of people.

Luis Poggi, co-founder and CEO of HouseWhisper, also shared his experiences, recalling a lesson he learned early in his career at Zillow about the importance of hiring the right people.

Poggi, who closed out his decade at Zillow as VP of product and engineering, said he was reminded to strive for better than just “OK” employees, a lesson that “changed how I hire forever”.

With the emergence of AI, they now look for curiosity in new tech as a key aspect in candidate interviews, noting that “a person who uses AI today can do the work of three or four or five people”.

“I think the biggest constraint today is your imagination,” he explained.

Competing with Incumbents

Greg Schwartz emphasized the importance of speed for smaller companies to compete with incumbents, saying “Learn, test, try, fail” is the only way to succeed.

Poggi shared a lesson from his time at Zillow, where he tried to create a home improvement product before quickly killing it, realizing that home improvement is “a completely different industry”.

“Most startups die for lack of focus, for distraction; not for competition,” he said, highlighting the importance of staying focused on the core business.

Schwartz expressed his disappointment with the industry’s focus on exclusive listings, calling it “selfish” given the current housing affordability crisis in America.

“People are really suffering. Our kids are suffering,” Schwartz said, emphasizing the need for the industry to shift its focus.

Philosophies for Success

Jay Thompson, founder of Jay.Life Consulting and former Zillow director of industry outreach, 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, noting that implementing this philosophy has had a significant impact on his personal and professional life.

Greg Schwartz also shared a motto that has guided him, saying “Be kind and be decent — to your teammates, your family, to your partners, your customers — rather than exercise conflict and power”.

The panel discussion at the 2026 T3 Leadership Summit highlighted the importance of learning from experiences, staying focused, and adapting to the changing landscape of the real estate industry, and understanding the difference between a short sale and other options.