February 2000. The stock market was partying like there was no tomorrow.
But Jason knew tomorrow was a bloodbath waiting to happen.
Everyone was drunk on IPO fever. Companies with zero revenue and paper-thin ideas were being valued in the hundreds of millions. Venture capitalists were throwing money at anything with a ".com" in its name.
Jason, meanwhile, was watching from the sidelines like a sniper waiting for the exact moment to pull the trigger.
He flew to San Francisco on a Greyhound budget and walked into a real estate office in Mountain View like he owned the place.
The receptionist looked at his thrift store blazer and raised an eyebrow. "Can I help you?"
"I'm looking for commercial properties. Office space. Cheap and flexible lease terms."
"Start-up founder?"
Jason smirked. "Investor."
The agent, a balding man in his fifties named Carl, took him around town in a dented Ford Taurus.
"This area's hot," Carl said, pointing at a cluster of low-rise buildings near Castro Street. "Bunch of start-ups renting out. Could be a great time to jump in."
"Or a great time to wait for them to implode," Jason muttered.
Carl blinked. "Come again?"
Jason smiled. "Nothing. Just talking to myself."
He took note of three properties in particular—one of which, he knew, would be Google's HQ in 2004. He didn't have the capital yet, but if he locked in an option-to-buy agreement now? He'd clean up.
Back at the motel that night, he wired Benny an extra $1,000—winnings from the Super Bowl bet had doubled his stake. And he told Benny to prepare for a Patriots game the next weekend.
Every correct bet gave him runway.
And every bit of runway got him closer to Phase 2.
Seed-stage investing.
Google was still in its infancy. PayPal was in beta. Facebook didn't even exist yet.
But Jason knew who to find, what to say, and how to plant the seeds before the world ever saw the tree.
His phone buzzed.
Amy: Still on for Friday. Bring proof you're not crazy.
Jason smiled.
Oh, he was crazy.
Crazy enough to break history in half.