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. “They’ve been in a house for a long time and they need to figure out the best strategy for how to sell their house and maximize their equity so they can move to wherever they’ve got to go, to be near their kids.”

The second group doesn’t have an industry-standard name yet. Liss offered “first-time sellers” — underbought millennials “bursting at the seams,” squeezed by high mortgage rates into starter homes they can no longer fit. “Maybe they had that third kid and they need to get out of their house,” he said. “They’ve never sold a house before. It’s a confusing process. There’s a lot of landmines.”

The NAR puts the median first-time buyer age at a record 40, and an April 2026 Fortune analysis found older millennials increasingly behaving like boomers in the market — flush with cash, highly competitive buyers — even as boomers themselves continued to dominate transactions on the strength of decades of accumulated home equity.

True Footage says its TrueTracts appraisal engine can land a valuation within 3% of a home’s eventual sale price — a claim drawn from KBB’s own early test markets and not yet independently verified. In those markets, more than 17% of homeowners who received a valuation ended up listing on the MLS within 90 days, though the company has not disclosed a comparison baseline.

Liss, who runs the company from Austin, points to his home city as a working example of the platform’s core argument. Citywide headlines call the Austin market “doom and gloom,” he said, but block-by-block data tells a more complicated story, with renovated homes in supply-constrained neighborhoods holding value even as broader averages fall.

Austin is also, he notes, one of the country’s top destination markets for baby chasers — which makes it as close to a natural test market as the company is likely to find.

The independence question

On the industry fight consuming the housing market, Liss positions KBB as neutral. “We’re Switzerland on that issue.” The dispute he’s referencing has moved through several rounds: Compass sued Zillow in June 2025 over rules restricting access to privately marketed listings; a judge denied Compass’s bid for an injunction in February 2026; and Compass voluntarily dropped that suit in March after Zillow agreed to loosen the restrictions.

A separate fight is now underway — Zillow sued Compass and the Chicago listings service MRED in May, alleging a conspiracy to hide listings from competing brokers and consumers. Liss noted Sen. Elizabeth Warren’s warnings on industry consolidation — first over the Compass-Anywhere merger in December, then this week warning that Compass’s private-listings network risks creating a “two-tiered housing market.”

The independence claim is both KBB Homes’ strongest asset and its most complicated one. The company sells real-estate agents subscriptions to “own” a share of a ZIP code — 25%, 50%, or exclusive rights to the whole territory — giving them first access to the leads that KBB’s valuations generate.

An agent who has paid for exclusive rights to a ZIP code has a direct financial interest in the homeowners in that territory transacting. Liss said it has generated “millions of dollars of monthly revenue” after roughly a month selling those subscriptions (a figure not yet independently verified).

There is also a technical distinction the company’s marketing does not emphasize. KBB Homes’ valuations are legally classified as broker price opinions under industry licensing standards — not certified appraisals — a meaningful difference for a product whose pitch leans heavily on appraisal-grade credibility.

“I think tools like this are the future, where software can help sort through hard problems,” Liss said. “Making sure that sellers get in front of the right agents is kind of the cornerstone of what we’re doing, in addition to the values.” Whether the brand promise of independence survives a business model built on agent territory sales is one of the next riddles for the housing market to solve.

This story was originally featured on Fortune.com