Entrepreneurs who regret starting businesses

There aren't that many entrepreneurs who failed multiple times before succeeding at a business. If you look at the big businesses that dominate the US tech economy, they're all first time founders (Amazon, Apple, Google, Microsoft etc).

There are also very few entrepreneurs bootstrapping their own business. Even rich kids go to VC, they aren't usually risking their own funds.

Finally, if you try multiple times, learn something important from each failure, and then succeed, it seems reasonable to claim that this is now due to the skills you developed and not mere luck. You can't even claim it's privilege - it might be, but as this article argues, being an entrepreneur isn't being handed a nice life on a plate even if you're successful.

For sure there are counter-examples where some rich kid spent their parents money trying and failing over and over, then got lucky without learning anything, somehow had an incredibly easy life from that point on and then started talking about merit. But they're going to be the exceptions that prove the rule. The carnival analogy therefore feels like ideologically motivated reasoning of the most common Marxist kind (claiming hard work and risk taking don't matter, that all success in life is the inherited privilege of capital).

But i still came here for the comments!

I started a self-funded SaaS business fairly late (in my 40s). I was tired of being dependent on others, especially as others mostly failed me in the past. I wanted to be independent: no investors, no bosses, no employees. Just me.

It took five years of slow growth to get to a stage where I didn't have to worry about revenue.

Do I regret it? Hell no! It's the best decision I've ever taken in my life.

I am now very happy with where I am: I have a business that depends on very few external factors and runs well. I don't have to worry about investors doing crazy investory things. I don't have to worry about employees pulling crazy employee stunts (believe me, I've seen a good number of those in the past, and the entitlement of many employees is absolutely crazy). I don't have to worry about user numbers, only about paid subscribers and maintaining slow revenue growth. Nobody pushes me for crazy growth.

Most importantly, the business model is simple: my customers pay me because my software improves their workflows. That's it. There is no "monetization", no shove-it-down-your-throat marketing, no tracking, none of that unpleasantness that seems to be dominating today's world. If they like the software, they pay a subscription fee, if they don't, well, they don't, and I have a problem. But so far it seems they do :-)

The only thing I had to carefully manage was my engagement: it's easy to get pulled in and work crazy hours, because in a single-person business there is always much more to do than you can possibly ever do. You have to become good at prioritizing, which means identifying the single (ONE!) most important thing at this moment and focusing on that. But you also have to accept that most things will not get done and be OK with it. That was hard for me, but I learned, and I keep sane hours and a good work-life balance.

I'm posting this just to provide a counterpoint to many negative comments.

PS: if I were to provide one bit of advice to aspiring entrepreneurs, it would be: look for a business that delivers high value to customers with money. So don't start a B2C business that does something easily replicable with a low value. B2B is where it's at.