Five. Hundred. Million. Dollars.

Biz Stone
9 min readNov 15, 2023
A white shirt.

The year was 2008, about one year after officially founding Twitter. It was a Monday. I woke up in our little place in Berkeley and, for some strange reason, decided to wear a pressed white dress shirt for the day. I never wear a shirt like that because I always wear something comfortable like a t-shirt and jacket, but I saw it in my closet and put it on, and my wife, Livia, said I should wear it. So I did.

I walked the thirty minutes it took to get from our house to the downtown Berkeley BART station, swiped my card through the turnstile, sat down on a bench, and waited for the train. It takes twenty-three minutes to get from downtown Berkeley to the Montgomery Street station in San Francisco, and the train travels in a tube strapped to the bottom of the San Francisco Bay. It always made me a bit nervous, which made my questionable white shirt a bit sweaty. I knew the shirt was a mistake.

Carrying my Apple PowerBook in my backpack, I walked the thirty minutes it took to get from Montgomery Station to Twitter’s office, then on Bryant Street. By the time I got into the office, approximately two hours after waking up, I was shvitzing a little.

As soon as I walked into the office my friend and Twitter’s fearless Product Manager, Jason Goldman told me that Ev was waiting for me in his car downstairs. It wasn’t normal for me to show up at…

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