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Maybe the rational way to play the game then is to make that $200K, then stretch your reach and make $1M, and so on... until you've taken care of the money problem. Then that's when you're ready to start taking shots at the big opportunities, without being motivated by money or being held back by it.


The problem is by the time you've saved up $200k, most people are committed to a certain lifestyle based on their annual income. They're generally in their 30s or older, married, couple of cars, kids in school, mortgage, used to spending $X/yr on a vacation, etc etc. And, they've worked so hard to save up that $200k that it's unlikely they burn it to fund living expenses while they work on a startup.

Most entrepreneurs (generally, not just tech) are in fact in their 40s-50s. Well established professionals with good relationships and skills. Thing is they are usually doing it with Other People's Money, not their nest egg.


I don't think we're talking about "saving up $200K", at least I wasn't at all. Instead build and grow a profitable business to achieve that, not as ambitious as a "startup" but also nowhere near as risky. You're still an entrepreneur either way, just learning to crawl before you walk, so to speak.


I would argue it's easier to go all with a smaller hand.


Easy, but a lot higher-risk. It takes money, resources, and connections to actually do big things, and past wins improve your execution ability and chances of success.

But prescient market timing greatly skews the odds in your favor and gives you a huge edge too -- I think that's apparent in all the startup successes that started off with a small hand.




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