Both my parents are entrepreneurs as well. My father a couple times over. My older brother also set out that way, and had a couple businesses, and I actually worked for his IT company for a few years, until he shut it down (and he now works for at tech company in SF).
There was always the idea that being my own boss would be cool, but also a lot of angst about what if I succeed and have to deal with the stress of not knowing how things will be month to month if it's not a breakout success? Most businesses I've seen are not startups that get huge investments. They're small businesses where people struggle much the time, even if they have comfortable stretches.
Eventually I settled on what I would want for any business of my own, which would be a side business or lifestyle business to supplement or maybe supplant my day job. I mostly stopped pursuing that, but am always open to the idea. Through introspection I've realized that were I even to somehow have become the founder of some startup, I probably would have wanted to exit with money ASAP as it grew, because that level of instability is just not what I'm looking for, and not what I think I should be subjecting my family to.
Now, I'm fairly happy with a good job and more free time. I don't necessarily regret all of my attempts at side businesses, but I also feel like I missed more of the youth of some of my children than I should have. That doesn't feel like it was the right trade to make, and that's without even missing a huge amount. That's just not something you can get back, so it doesn't take too many nights a week of being absent for a couple years to add up. But there's freedom in dropping expectations for yourself to be doing more, and trying to make it for yourself. There's a reason people lament the loss of the middle class factory jobs of the last century, there's immense freedom in leaving work at work and having that provide enough money to live somewhat comfortably. There's no shame in that, nor in letting go of dreams of making it big yourself, if you decide that you're happier doing something else.