But I listened to him speak to the A16Z team about their $350M investment in his company, Flow, and I’ve got to say… I don’t hate it. The bet makes a ton of sense.
Was WeWork flawed? Absolutely. But let’s be honest, the biggest "mistake" Adam made was raising at a $47B valuation. He’s not in the same bucket as Elizabeth Holmes or SBF. He convinced SoftBank, Goldman, and Fidelity that his vision was worth backing at that number.
That’s not fraud. That’s a skill.
Because one of the most uncomfortable truths in startups is that success often comes down to how good you are at getting other people to do irrational things.
Convincing a developer making $500K at Stripe to join your idea-stage startup.
Convincing investors to give you $1M with nothing but a pitch deck.
Convincing the press to crown you “the next Steve Jobs” because your co-working company put kombucha on tap.
This industry is built on belief and hype. And belief and hype are irrational by nature.
What Adam did was tell a story big enough that they bought it. And like it or not, that ability matters. If you’ve ever tried to fundraise, you know how hard it is to get people to care. To believe. To say yes.
So when I see A16Z backing him, I understand the move.
A16Z is a massive fund. They have more capital than great companies to invest in, so when you have a unicorn founder building in residential real estate - the largest market on the planet, you make that bet when you’re managing $35B.
The common criticism is: why does this guy get all the cash while underrepresented founders never got a shot? And I get that. But those two things aren’t mutually exclusive.
Venture isn’t a finite pie. There’s way more capital than there are truly compelling opportunities. And if Adam’s play works, it doesn’t stop anyone else from getting funded, in fact more venture success = more dollars going into the ecosystem.
The truth is, most startups fail. Most founders never make it to the scale WeWork did, let alone get another shot at it. But if we say we believe in talent, in vision, in redemption, then we’ve got to believe in second chances too.
America believes in second chances. Three of the hottest companies in the Valley right now are Anduril, Flow, and Rippling, all led by founders with blowups at their previous companies.
Will it work? I have no idea.
But let the guy build.
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