I regret selling my startup

All good points here. For those reading just the title, the article asks to critically examine what values you hold and whether selling is compatible with those values. For me, I see selling as just another step to growing the hoard, as you state in the article, but I don't think it becomes draconic in practice.

The key in my opinion and experience is making and selling micro projects, not banking on any one taking off. That way, you can have cash flow and a hoard. Throw the hoard into VTI and let it grow while living off the cash flow (and/or reinvesting it into the business), until the investments become enough to live off of entirely, ie the 4% rule. Pieter Levels or Daniel Vassallo are good examples of this.

Just keep trying, don't be saddened by another startup failure, at least you already have one sold which is a lot more than most founders can say.

I'm also in NYC, let me know if you want to chat, as you stated at the end of the post.

I am kind of, have the same flow of thoughts. I have never worked on the project for more than 4 years. Now I have a product that I have built and live on, for the last 7 years. I don't have that much passion about this product anymore. But at the same time it allows me right now to work only 4 hours a week on average, and spend 2 months a year to build new versions of the product. I am making good Google Principal Software Total compensation.

Selling a company means I can probably get 4-6x of my annual income. But I am afraid to become that dragon on the pile of money. Draining money will be terrifying for me. And I am not good with managing money.

At the same time, I am afraid that company can slowly disappear, customers choose alternatives. And maybe 4-6 years that is how much I can get from it. But at the same time I will have opportunity to fix things, adjust my life based on the income.

This seems a little 'grass is greener' to me. Not sure if this is glib, but:

You can build the business again from scratch (ok, maybe you have a non compete for a while...) But you can't magic the $ you just got, out of thin air.

So he's been paid for the hard work he has done, and now if he so chooses he can do the same again, or different.

So seems like Boris is standing on the greener grass right now, to me at least. I think the post-sale reflection is naturally something that will make people question their decisions... It may be possible for Boris to Stoically rearrange his view here. There's definitely a bright shiny alternative to regret/second-guessing.

I don't know why people are so negative in the comments or overthinking what the author wanted to say, when it's pretty clear. Running the company is what made him tick, made him feel alive, and ultimately made him happy. He's cashed out, but sitting around thumb twiddling and maintaining the pile of cash might be an ok life, might make some people happy, but it's not making him happy. There's nothing wrong with any of that. The advice you can get from that is, figure out what it is that makes you enjoy life. If it's feeling secure because you have a pile of cash, then you will do the same as him, but be satisfied with the decision.

Sometimes I feel like people who sell their startup for a modest sum (hundreds of thousands to low millions) get put in a box of 'not ambitious enough' and this makes it hard to get new opportunities later as investors are seemingly all looking for unicorn founders who want to become billionaires and then achieve world domination...

I feel like any signal that you are a rational human being with well-defined, limited needs is going to be a huge turn off for investors. I don't think it's rational at all but I guess that's what decades of low interest rates does to them.