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Meet the 33-year-old CEO betting on boomers chasing their grandkids—and millennials selling their first house

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08.08.2026

Meet the 33-year-old CEO betting on boomers chasing their grandkids—and millennials selling their first house

Kelley Blue Book built its reputation on a promise: a number you could trust because the people giving it to you had no stake in whether you bought or sold. John Liss is betting that promise will travel from cars to houses.

Liss is the 33-year-old CEO of both True Footage, the appraisal-technology company he founded at 26, and its new joint venture with Cox Enterprises: Kelley Blue Book Homes, which launched nationally across 11 states on Aug. 3.

He was a real estate agent in high school. Fifteen years — and multiple Harvard degrees — later, he is persuading one of America’s most trusted consumer brands to put its name on a housing market where, by his own account, almost nobody trusts the numbers anymore.

“The available options are not accurate. They’re not interpretable. They’re not credible,” Liss told Fortune. “Consumers are starved for better tools to help make one of the biggest financial decisions of their life.”

Boomers and older millennials

The platform is built for two very different Americans converging on the housing market at the same moment. The first are what housing researchers call “baby chasers” — retirees relocating to be near grandchildren. Baby boomers are now the single largest cohort of both buyers and sellers nationally, accounting for roughly 42% of purchases and 55% of sales according to National Association of Realtors data.

“You have this sort of ‘baby chaser’ cohort,” Liss said.........

© Fortune