The latest number he posted, from July 3, was 6.5% [1]. This means roughly 1 in 15 people you come across in San Francisco is positive for Covid. If you're on a crowded bus or train car, there will be multiple Covid positive people on it, and likely one that is contagious. If you regularly take transit and aren't wearing a really excellent mask, it's pretty likely you'll catch it over the course of a month or two.
Back to anecdotes, about 70% of the people I know that fit this description and ride transit in a big city without a mask have gotten symptomatic Covid in the past 3 months. All of them boosted btw.
[1] https://twitter.com/Bob_Wachter/status/1543780608744165376