I spent 15 years trying to make it work, and it was a bad idea from the first day. Losses were well into six figures, without taking into account the opportunity costs of working a regular software developer job. Which is what I'm doing now, and am very happy. There is no way I would ever do it again.

The list of lessons learned is very long, much of it having to do with sunk cost fallacies and the "winners never quit" theory. I was able to keep at it so long because I had a lot of money saved up. "Fail fast" would obviously have been smarter, but I believed in the idea. (Still do, sorta, though the world went in a very different direction, high flexibility rather than high data quality.)

I have never been good at selling things. I made a million mistakes, but the main lesson learned is "just don't". Trying and failing leaves scars that "fail fast" doesn't take into account, and I'm less resilient than I had been.

Wow that shows a whole new perspective of how things can be. The line that resonates with me a lot is "working a regular software developer job. Which is what I'm doing now, and am very happy."

I've been trying to make it on my own (actually me and my best friend and also my business partner) for approximately the same amount of time and last year he said enough and left everything to me. He is now a full time employee and looks quite happy.

Me on the other hand is still waiting for the light at the end of this tunnel.

I've put so much time and effort into this and have very little to show for it. Had I taken the old tested job route maybe i would have been better off too I think.

My mistake definitely boils down to one thing which I've learned the hard way:

There are only two roles in a company: Sales and sales support. So if you aren't doing sales directly you better be doing something to support it and every dept including product dev, customer support, etc must work from that angle.

I went down a rabbit hole for several years, probably "wasted" $10,000 on AWS, wound up with $80k on my home equity line. I've done two years of regular work since and I expect to have the HELOC paid in the next few months.

It was stressful on me and my family but we kept it together.

Since those events I worked a year for a "startup" company in the data analytics and AI field slinging Python and now I do Java and Javascript for a non-profit/academic organization, entirely focused on getting data out of a database and in front of customers.

I am focused on doing application programming well on my day job but I do side projects involving printing, arduino, embedding Java inside itself as a Lisp-like DSL, etc. Practically those things line up: in the process of understanding handicapped accessibility for work i learned to think in terms of "value", Ansel Adams, and how to generate random color schemes that are always legible. jooq which I was using for work got me thinking in a mathematical way about what is possible to express as a java internal dsl, etc.

Do it again?

That's out of the time horizon I am thinking in today but I wouldn't rule it out.

Thanks for sharing. That must haven't been easy to share. The big silver lining is always that you gain a lot in experience and broaden your horizons even when you don't make it financially.