Work a high salary job and buy lottery tickets or 0DTE options instead. Half joking. Look at the success rate of outlier comp through liquidity as an early startup employee. If professional stock pickers can’t pick better than index funds, what makes you think you can do better picking startups, spending non renewable time, working for years vesting common shares that you might get liquidity for eventually, assuming they have any positive value.
If you want to get wealthy, there are more efficient, less effort ways. If you want to suffer with low chances of success based on all available data, well, help yourself to the firehose of startup jobs.
You're not just "picking a startup". That early, you're also a big factor in whether it succeeds. Betting on yourself is different than buying a lottery ticket. (Maybe just as irrational for a lot of people, but still.)
Advanced sports stats have the notion of "contribution above replacement value", the idea being it isn't just what you do, it's what you do relative to whoever they could (relatively easily) replace you with.
The startup failure/success rate already have some level of "smart, motivated staff" baked in. So you're really making a bet on how much better you are than the average early stage startup employee.
You (not “you”, but the persona for this discussion) are not special and will likely fail, based on startup failure rates. Certainly, you will put effort forth, but that is only tangential to odds of success. If you enjoy the experience and don’t need monetary resources, sure, knock yourself out. Just recognize the opportunity cost, that the odds are stacked against you, and if you succeed, you were as lucky as you were skilled.
I’ll take the lottery ticket over me any day, not because I suck, but because I am human. Even exceptional humans fail. I don’t drink the exceptionalism koolaid.
People, especially sw devs, love this narative but it's just not true. It's not all luck like the lottery but the combination of things outside your control might as well make it so for early employees at a startup. But hey, you did get that vp of whatever title...
When you work for a startup you have a ton of insider information not available to outsiders, even investors. If you think your startup won’t be successful then obviously just find a different job.
If you want to get wealthy, there are more efficient, less effort ways. If you want to suffer with low chances of success based on all available data, well, help yourself to the firehose of startup jobs.