She grew up rich, with the freedom to pursue her passion from the age of 10, when her mother would take her to karaoke contests. The ability to up stakes and move to Nashville, to have your father buy your way into a record label... well... it doesn’t overshadow her natural ability, but it helps to explain how she was able to leverage it so effectively.

Exactly - she won the lottery being born into a rich white family in the U.S.

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.

I think it was about both. Later in the clip he says to Conan O'Brien "We're tall white guys, we overcame nothing to get here."