Ask HN: You were and entrepreneur and now you're not. Why?

I started Textfyre in 2007. At first I was just trying to build Interactive Fiction (text story games, also known as IF) games and sell them. Once I realized there was no captive audience for such things, I nearly quit. But then I noticed my kids elementary school textbooks. They sucked. I also noted how stressful the entire testing regiment had become.

So I thought maybe IF could solve the problem. So I pivoted to an ed-tech firm and though selling games to schools was a better model. This led to actually getting a team together. I had a CEO, CFO, teachers, marketing help, testing expert, and many supporters. We had the basics of an "embedded testing" web application built. We actually managed to get the attention of The Gates Foundation and talked with them for several months.

In the end, The Gates Foundation focused their efforts at the big players (like Pearson) and we were left out in the cold. My team disbanded and I gave up.

Of course now "embedded testing" is all the rage (there was just an NPR story about it), but unless you're one of the big players, you're not getting anywhere.

I have another idea I'm researching, but I'm much more pragmatic about it than I was with Textfyre. I'll build it on my own, spend as little money as possible, test it, and see what happens.

It's very hard to be a first-time unproven entrepreneur. If you manage to succeed and get one exit, you're golden and investors will hand over money without really asking any questions. Once they know you can "execute", they will support you 100%.

The trick is to learn how to execute. I'm still learning.

The grind is quite difficult and long. It can take 1-3 years for a good idea and a good product to gain traction. In the mean time, you have to reduce your spending and work crazy hours in order to stay afloat. The previous comment about it being lonely as a founder is very true. Typically founders and other corporate leaders have no one to discuss their problems with and few people who understand their unique challenges.

I can't speak for myself, but I've done quite a few one-off MVPs for people who stopped being entrepreneurs.

The most common reason is that they weren't willing to sacrifice the time/money involved in starting up, and then they quit. They typically had high-paying corporate jobs and weren't willing to give up the income.

A lot of people have an "if you build it, they will come" attitude about any good idea, not just the ones that people are truly clamoring for.

I am an entrepreneur still.

It is a hard long lonely slog. You spend most of your daylight hours working and most of your weekends working too. When your friends are all out partying you are catching up on sleep. BUT you obviously have a far greater chance of the big payout than they do...

My company is semi passive income so thinking of a "normal job" on the side just to interact with others.

It's lonely.

I'm looking for a job so I can have coworkers.

OP here. Personally, I came to believe that the expected payout of entrepreneurship is not anywhere near break even. Just like a roulette wheel is expected to pay out .97 for every dollar over that long haul (.03 house cut), accounting for all possible outcomes, including "jackpots", I started to feel like the expected payout of any given entrepreneurial effort wasnt worth the investment. Sure, some end up like Uber or Paypal. But the vast silent majority are failures.

There is some nonmonetary value in giving it a shot, I guess, but that value diminishes with each successive failure, even as the chance of success increases as a function of one's previous experience.

A friend and I were remarking recently that for all our entrepreneurial effort {10+ years each) and meeting with other entrepreneurs, we don't know anyone who has "made it". (A guy from my class in college sold a company for 170 mil, but I didn't know him before.) That's dozens or hundreds of people trying and zero successes.

In short, I think the odds are much longer than most are willing to believe, and that sapped my motivation to keep trying.