The Idea
In 2003, Spencer Rascoff, aged 27, sold Hotwire, the discount travel site he'd co-founded at 24 to Expedia for $685 million. He stayed on as VP, and watched Expedia do something that felt almost unfair: take the fares that insiders had hoarded and hand them out unwitting buyers. The lesson stuck. Find a market where ordinary people are locked out of something, tear down the wall, and a giant business falls out the other side.
Real estate was the obvious next wall. A home's value was a guess only an agent could "estimate", so in 2005 Rascoff, Rich Barton and Lloyd Frink put a free price on tens of millions of homes and called it the Zestimate.
The same pattern resurfaced years later in a different disguise. Austin Allison, a founder whose company Zillow had once acquired, owned a second home in Lake Tahoe that sat empty most of the year. Rascoff saw the identical locked door: something people wanted, walled off by cost. The fix was to split the house into eighths and sell co-ownership of it.
This was the beginning of Zillow, and, more than a decade later, of Pacaso.
The Execution
- 2005: Rascoff, Rich Barton and Lloyd Frink launch Zillow with the Zestimate on roughly 40 million homes. Rascoff runs COO, CFO and VP of Marketing before being named CEO in 2010.
- July 2011: At 35, Rascoff takes Zillow public. The stock rockets from $20 to $60 within minutes of opening, valuing the company at over $1 billion. He later called the size of that pop a "facepalm" moment, money left on the table.
- 2014: Zillow swallows its biggest rival, buying Trulia for $3.5 billion and folding it, StreetEasy and HotPads into Zillow Group.
- February 2019: Rascoff steps down after a decade as CEO. On his watch Zillow grew revenue from $30 million to $1.3 billion, headcount from 200 to roughly 4,000, and a market cap into the billions. One company built. He could have stopped there.
- October 2020: He doesn't. Rascoff co-founds Pacaso with Allison, launching the co-ownership marketplace.
- March 2021: Pacaso raises $75 million at a $1 billion valuation, becoming the fastest US company ever to hit unicorn status, roughly five months from launch.
- September 2021: SoftBank's Vision Fund 2 leads a $125 million round at a $1.5 billion valuation, as Pacaso pushes into Europe.
- October 2022: The music stops. Rates spike, luxury second-home demand craters (rate locks down 28% in a quarter), and Pacaso lays off about 30% of staff, roughly 100 people, back to 200. The second billion-dollar business nearly becomes a cautionary tale.
- Today: Pacaso survived by cutting burn and grinding. In 2025 it closed an oversubscribed $72.5 million Reg A+ raise from 17,500+ retail investors, the largest real estate crowdfunding round of the year, taking total equity past $300 million on more than $1.2 billion in lifetime transactions.
The lesson?
The best serial founders aren't lightning-strike visionaries with one perfect idea. They're pattern-matchers who spot the same flaw in a new market and run the same play. Rascoff's play never changed: find a market built on information the insiders hoard, and hand it to everyone. Hotwire did it to airfares. Zillow did it to home prices. Pacaso is doing it to the locked front door of a second home. Two of those became billion-dollar businesses, one of them after almost dying.