He's an almost 44-year-old never-married man, worth almost $10 billion, who lives in San Francisco – which I already knew. All red flags, but inconclusive. What I didn't know are these tidbits mentioned in a recent WSJ profile (free link below btw):
"As it happens, this is Chesky’s home. He shares it with Sophie and Chloe—his golden retrievers. It has Aesop products in the bathrooms, tastefully curated bookshelves around a fully stocked bar and spectacularly panoramic views of the city."
"Chesky applies the same analytical rigor and maniacal attention to every detail in his life, including the black shirts in his closet. On the day we met, he wore a black shirt with frayed sleeves that looked almost as though the beefy former competitive bodybuilder had ripped them himself. ('No, this comes ripped,' he clarified. 'It’s a Rick Owens.'")
"'There’s going to be a really big decision I have to make: short sleeve or long sleeve?' he says. 'And then the second decision is what shade of black. And then the third decision is what sheen of black. And then the fourth decision is how thick….'”
"Like many CEOs, he sets aside time to work out every day. Unlike most CEOs, he works out from 8 p.m. till 9:30 p.m. Then he keeps working. 'If I had a girlfriend, that would probably change,' he says. 'But I don’t, so I’ll enjoy this.'”
And the coup de grace:
"He’s also one of the few CEOs who picked up a roommate during the pandemic: his mother. She was already planning to move across the country in March 2020. Then she moved in with him."
It's only on rare occasions that my gaydar goes into full-tilt "MARY!!!" mode solely from reading a single article, but this is Helen Keller obvious. I'm assuming his eventual autobiography will contain mentions of dialing the phone with a pencil as a child, and probably blowing Peter Thiel – repeatedly – in exchange for a cash infusion.