This always sounded intuitively correct to me, but looking back over the past two decades basically all of the successful entrepreneurs and business owners I know didn’t come from families with a lot of resources and didn’t have much of a safety net. They just went all in on their goals when they were young and had many years ahead of them to start over if it all went wrong.

Contrast this with some of the people I grew up who came from wealthy families: A lot of their parents pushed them toward entrepreneurship and funded their ventures, but to date I can only think of one business from this cluster of friends that went anywhere. When you come from such resources and wealth that you don’t need to succeed and you can drop the business as soon as it becomes difficult, it’s a different situation.

I don’t know exactly what to make of this, other than to remind myself to keep pushing through the difficult times for things I really want even when I could fall back to an easy path and give up.

It's like a baseball game. Most people are benched their whole lives. They never get a chance at the plate. More privileged people with a lucky combination of the right family, the right education, the right timing, and the right opportunity get an at-bat, and they'll either strike out, or hit the ball. A few very lucky people will get to stand at the plate maybe once or twice more.

The wealthy get infinite at-bats. They get to stand at the plate for however long they want, and swing and swing until they get their home run. I worked with a founder like this. He would always talk about his business's humble beginnings, starting from a garage and so on--you know the story. What he would neglect to admit was this was like his 7th try. Every time he failed, he'd just chill on his family's couch, dreaming up his next startup idea.

This is not true. No matter how many different teams I try out for, I as a 51 year old short male with a limp will never be a star basketball player or ever make it to even the D leagues.

There are plenty of people who tried repeatedly to “succeed” in their own company and failed. Let’s say I did try to start my own company at 22 10x and spent 3 years at each one. I’m now 52 and would have been better off just working those 30 years and saving and investing with a lot less stress

Out of curiosity (not accusation, I promise) how did you make it?

Well said, this is the real game to pursue. Best of continued luck.

That sounds good, but with a safety net, are you really going to be hungry enough to make sure your one shot at getting out of the ghetto doesn't fail? The entrepreneur that says to themselves, if this doesn't work, I'll just ask mom for another $300k at St Barts over Christmas doesn't sound like the one sleeping under the desk at the office to get the demo ready for TechCrunch Disrupt. Or maybe they are (to prove daddy wrong). The human condition contains multitudes.

That's a cliche and it sucks. A safety net and family resources correlate with nothing related to entrepeneurship and risk taking.