Yes, even if you only get 0.3-3% of that 100M exit it's going to completely change the equation if you ever try again. Or just do something else with the rest of your life. Further, if you have another exit of that size again your likely to end up with a much larger chunk of the second company. To the point where it's possible to be better off with 2 x 100M exits than 1 billion dollar exit.
Most startup fail. So though yes that's true, the chances of it happening twice are quite small. Even the first chance is quite small, so maybe... dunno have not seen numbers to back up hypothesizing.
The odds are much better that you can repeat after your first success. Most startups fail before gaining significant funding, if you have enough capital to skip the seed stage and a good relationship with investors and have experience with running a startup then you have much higher odds. To use some famous examples, Apple/Next/Pixar, Paypal/Tesla /Spacex/Solar City they both had a weaker startup such as Next and Solar City but leveraged past success to avoid failure.
Totally agree. My first company raised $300k and sold for between $2M and $10M. Started my second company and immediately raised $1M in a seed round. Having an exit is an excellent signal to future investors. And employees. And acquirers.