I quit bootstrapping profitable businesses and got a job at Amazon

I sort of get what he is trying to say.

A personal anecdote. About 10 years ago, as a single man, I was in a similar position, having saved enough money through work and investments to enjoy "freedom" for a period of many years. And at first it was great, nirvana like even, traveling and dabbling about in various projects. Even though I wasn't driving around fancy cars or living a lavish lifestyle (these things have never really appealed to me anyway), I felt that this must be what it's like to be rich, not to want for anything and indulging every whim and fancy.

However, as time marched on and I checked things off my list, I began to encounter a problem I didn't see coming. I started to feel an ever increasing desire to do something with my time that felt worthwhile, but what should that be? As I found out, it's not so easy to answer. See, at the time, I had removed every hook society had put into me. No bills, no obligations, no responsibilities other than paying rent and feeding myself. I could literally move in any direction. Should I join the fight against climate change? Study robotics and AI? Start a (most assuredly successful /s) SaaS business? The possibilities were endless, and so was the worry that choosing one path meant I could not pursue the others, at least not in a meaningful way. Hence, I ran into a very real and unexpected problem with commitment, that would go on to keep me at unease for a period of several months.

So what did I do? Well, the only thing I could think of to get out of that episode of paralysis by analysis; went back home and started up with some contracting work to pass the time. I met my wife shortly thereafter and not too long after that we welcomed our first child into the world.

Funny thing is I no longer wish for total freedom (well maybe just a day or two here and there), but now that I've been down that path, I've seen how it plays out for me personally. Now I have all the direction I need. Happy trails everyone.

I think I can relate to the idea of quitting a profitable business to work for a large corporation. I've thought about that myself.

I have been running a one-person Saas business for the past 8 eight years. I make more money now than I did before the business and probably more than I would make if I took a job now at Amazon or Google. If I wanted to, I could also probably get away with working 2 hours a day. I also have 2 kids, and the business gives me the opportunity to be with them and my stay-at-home wife all the time (which I actually really like) and it gives me a platform to launch new businesses. So why have I thought about ditching it? It's definitely not the commitment that a corporation would provide, since a job can end easier than a business can. I've thought about it because I'm curious as to how successful I could be in that environment. I worked in large corporations for years, but I never worked in a large corporation after running my own business for 8 years. I have a completely different perspective now and I think that my opinions would carry a lot more weight and with the right type of infrastructure, I think I could make a real difference.

I don't have any plans to cut ties with my business, but I can at least say that I've thought about it.

I’m not sure I understand why people are struggling with how to interpret the post.

It reads very straightforward to me:

1. He went through bootstrapping several times, reached great profit at 2 hours a day of work and had a big exit, and achieved freedom to do whatever he wants for a bit.

2. He spent a lot of his newfound freedom filling the day with improving himself and keeping his options open to do anything he wants

3. Then he took a step back and thought about what it was he wanted in life, and that was spending time with family, stability, structure, and committing to a thing. So he went to work for a big corporation that would fill the part of his day that he had been spending on himself alone

4. And is now more fulfilled. The takeaway being that if what you know what you want to be fulfilled you don’t need to grind away at bootstrapping a startup to achieve “freedom” and that with all the freedom he has he ended up working in big tech because that fit his goals and still enabled all the things he wanted in life.

"For me the answer was clear. I wanted to take care of my children and give them opportunities I never had. I wanted to continue to enjoy my marriage. I wanted to take care of my health and I wanted to have a career where I could build and sell with autonomy."

So you then did the opposite of securing that, including the option to only work 2 hours a day, and went to work for Amazon? I mean, weird choice to be honest.

Someone else already said it, and I have been on a 12hr a day 6 day a week grind for a few months now, if I'm going to bust my ass I want to reap those rewards, which includes expanding the types of companies I can build, not giving it up to go work for Amazon.