> Did you get "never have to work again rich" through software?

It feels pretty stupid to reply to this as a "no", but to offset the incredibly depressing stories of random luck success, I figured I'd go ahead with it anyway.

No, I'm not rich. I'm 33 and dead broke, actually.

> How did you do it?

I started my first company (a video-related SaaS B2B product) at age 22 and it should have been a home run. The idea and timing were perfect and I found product-market fit almost immediately, cold-calling my way to paying customers 10 months after quitting my previous job.

But I fucked it up. I was too young. My engineering was shitty (wasted all my time putting out fires), but more damningly, I tried to grow the business organically. I'd never been exposed to "real" entrepreneurship before and didn't know anything about venture funding. By the time I realized I needed to raise money (and actually going as far as signing a $1M+ term sheet with a group of shitty investors), it was already too late.

The old guard companies in the space I set out to bankrupt did, indeed, go bankrupt, but it was another startup with the same idea and technology as mine that put the screws to them. While I was trying to turn a profit and make payroll, these other startups just passed me by like I was standing still.

>What did it feel like when you first realised it was going to be true that you would never have to work again if you didn't want to?

Re-interpreted as "what did it feel like when success slipped through your fingers?"

The business was doomed by 2006, but I "stuck with it" (following bad advice) and pivoted (more bad advice) until 2010 when I finally gave up. I wasn't exposed to the concept of failing fast until later.

There was no real moment in time I knew the dream was over, but I fell into a deep depression. Thinking funding was imminent, I'd borrowed money and found myself $75k in debt after all the work and sacrifice.

I finally pulled myself out of the depression and was able to pay back most of my debt within 2 years of being in the "working world".

> How old were you?

Company started at 22, on life support by 27, ended at 30. 2 jobs and 2-3 more startup attempts since then (one was a pivot, really). Now I'm 34.

> What was it specifically that made the cash that ended up in your pocket?

Like I said, I found product-market fit. Had I executed properly, as my competitors did, I'd be a multi-millionaire today.

I've tried to start 3 more companies since then, each better engineered and executed than the last, but none of them found the beginner's luck "fit" of the first.

What was different about the first? I experienced a pain point first hand in an obscure occupation. I don't want to get into specifics, but my first job out of college was as a peon in a non-tech industry. I saw a glaring inefficiency in one of the business processes and knew I could fix it with software.

Of my 3 product/usiness attempts since then, 2 solved problems I perceived from outside an industry that weren't really that problematic after all and 1 was/is a consumer product. For the consumer product, the problem I'm trying to solve is really a problem, but it's visible to many, many more people.

When you have a unique vantage point on an obscure problem, your chances of being the guy to solve it are much better.

> Do you feel happy in your life?

No. It gets really dark sometimes.

When I was running my first company, I was energetic and blissfully self-confident. Now I'm a heap of bitter frustration and anxiety with crippling sleep problems.

After I finally gave up pivoting and "persevering" on that first business, I had a 2-year "working world" tenure that was so painful I can't even talk about it under an anon account.

Entrepreneurship courses through my veins and I can't turn it off. But I've gone through my Rolodex of acquaintances a thousand times and can't find a viable co-founder for a new business. No cofounder = no accelerator = constantly stuck in neutral. The thought of going back to a cube job makes me break out into a sweat -- literally. (Echoing an above poster.)

All I can do at this point is try to start new businesses on my own and get traction like I did the first time. There is no other viable path for me.

TL;DR I was a 22-year-old wunderkind whose company crashed, career melted and am now a 34-year-old has-been.

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Epilogue: A friend of mine went to a state university and applied to his dream job at Microsoft upon graduating. He got rejected and ended up taking a position at his backup, Google... in 2002. Made a boatload (but not retirement money) in the IPO, was heavily recruited by the most hyped startup of the late 2000s (he admitted it was only because of the Google name), and is now an angel investor.

Life is fucked up and random, my friends. Signal and noise.