The main mechanism to become 'well-off' is through 'secondaries': founders sell some shares instead of the entire investment going to the company's bank account

The main mechanism to become 'well-off' is through 'secondaries': founders sell some shares instead of the entire investment going to the company's bank account. When a company gets to series A/B, VCs are incentivized to give founders enough money so they can focus solely on the company. From what I've seen, they give you enough money to be the poorest kind of rich (say, 1-5M depending on the raise). This keeps you hungry, arguably a bit more than before, as you now have peers who have net worths in the 10s-100s millions.