I did, twice, and I'm about to go on a third run (though this time it's not because of any particular run of back luck with the job market). I have a weird-looking resume that doesn't look quite right at first blush, and most of the hiring decisions that brought me on board I later found out were someone "taking a chance" on me. I was in the Guard for many years, and deployed a lot (<i>a lot</i>). Even though it's against the law, startups just don't have the resources to give up a team member and save their spot while they deploy. I actually completely grok this. But for most of my adult life, it looks like I've jumped from job to job with weird breaks in between, which is a huge red flag. I'm actually pretty good at what I do, if you'll pardon me for saying so, and so I have a pretty good network to lean on <i>now</i>, but throughout my 20s I didn't truly understand the power of one's network and so didn't cultivate relationships that I should have. No problem, life lesson. We aren't all jumping out of our mother's womb in full armor swinging a chain.<p>Anyway, I have had both success and failure when I started my own businesses. The first time was a failure, but I saw it at the time as a success, because I had to make rent, and it paid the rent. I literally sat there with a notepad thinking of things I could do in less than 60 days to make rent. Incidentally, I have always paid rent one month ahead of time. It's just something I started doing by chance when I was 16, and it turned out to be the difference between having a place to sleep and living in my car or out on the street.<p>Anyway, that paid the rent but wasn't sustainable. Everything was wrong with it, since I thought I was smarter than everyone hah! But that was another life lesson, that the world is full of way smarter people, and history even fuller. The second time I started a business I was much older, late-20s, and by then had worked at a bunch of startups and a network full of sensors (the army says "every soldier is a sensor" and likewise your friends and professional network are like your sensors) and also had been taking notes the entire time. I still take notes every day on the things I learn, the decisions I make, or people around me are making and why, if I can discern it, or if they'll tell me when I ask (another life lesson about taking notes). That time I consider it a success, because the people I started the business with are still running it today, and I was able to sell out of my share of the business. I went back into working at startups (because that's where the action is yolo), and now I'm feeling the itch <i>really</i> badly. This time around I've got solid business partners / cofounders on board, and few "green leaderbooks" full of notes and ideas (another army thing) and a couple servers full of prototyped side projects. I've got enough saved to bootstrap whatever we do and most importantly, as a lifelong transient with wanderlust, I feel that same comfortable feeling of "going places and doing things and taking risks" that won't let me put down roots in one place for too long. Sorry for all the text, but that's my story.