She won more lotteries than that. She won the lottery of being born rich, white, and connected. And in a country like the US. She won the lottery of being beautiful, of having an excellent voice and musical talent, of having parents willing to use their money and power to further her career of choice. She won the lottery of not having any crippling mental illnesses or learning disabilities, of not being sexually assaulted, and more lotteries besides.
But Bo Burnham’s quote really isn’t about that, he’s talking about getting lucky and having your career take off. The truth is that many many lotteries typically need to be won before you can even enter that lottery. My point was that Taylor Swift didn’t just “take a chance” on music, she used all of her existing wins to stack the deck in her favor. If you look at a lot of CEO’s the same is true of them, and it’s not just the luck of their career taking off, but the luck of ever being in a position to have that happen.
Nitpick, but this isn't actually true (see lawsuit she won), and we don't really have any way to know if it was true even before she became famous. I agree with your general point, though.
But Bo Burnham’s quote really isn’t about that, he’s talking about getting lucky and having your career take off. The truth is that many many lotteries typically need to be won before you can even enter that lottery. My point was that Taylor Swift didn’t just “take a chance” on music, she used all of her existing wins to stack the deck in her favor. If you look at a lot of CEO’s the same is true of them, and it’s not just the luck of their career taking off, but the luck of ever being in a position to have that happen.