He expects a Starship successful orbit in 6 +- 3 months. Demonstrating human capability with non-reusable hardware means building and throwing away hardware 10 times. A rocket capable of rapid reuse would be able to do about 3 flights a day (due to orbit time + needing to align to landing site again + some downtime) Even at the "low" rate of 1 a day, that's less than two weeks of flights. If they're way off their mark, one launch a week is 2.3 months.

Not that I would take your bet, but it's not unthinkable.

The Boeing Starliner was supposed to fly uncrewed in 2018, then October 2019, and now Boeing is shipping it to the launch site but not giving a date.

Are there others where you don't have to put money into predicting?