Like in most things, the odds are against you. But the game you play, and your skill playing it, dramatically influences the odds.
The “easiest” way to make $1m+ is to join the best pre-unicorn start-up you can at the moment in time when you can get the most risk-adjusted equity.
The thing is, at a very senior level … you basically get a similar amount of equity (at least dollar-weighted) no matter when you join. So the later you join, the less risk you take.
If you are a very seasoned executive, the best risk-adjusted time to join then is often just before an IPO, or just before a big Unicorn round. Get a ton of stock as SVP of XYZ at a “startup” worth $1b+ that is killing it is one “simple” way to book $1m+ on paper at least.
Assuming you aren’t That Guy, if you can reproduce that at an earlier stage, it’s the “easiest” way to potentially make $1m.
Join as a VP right after the latest venture round where you can still come in as a VP. If you can’t do that, join as a Director at the latest venture round you can. If you can’t do that, join as one of the first 10 or 20 employees, and one of the Most Important 5 or 6, at the best start-up you can.
Odds are still against you in all but the first scenario, but you can start to see the Math to A Million in any of these scenarios.
Most other scenarios, the odds of you making $1m unless the company ends up being worth $10b-$20b+ are relatively low. There just isn’t enough to go around, odd as that may sound, once there are 1000+ employees and 5+ venture rounds.