I second that. You regret the things you DON'T do more than the things you do. In 10-20 years' time you might get bitter wondering what could have been, and see

I second that. You regret the things you DON'T do more than the things you do. In 10-20 years' time you might get bitter wondering what could have been, and seeing another company succeed with "your idea". It also sounds like you can afford to make this bet. You are young, good savings, tech skills, and I'm assuming "asset light" life (no family or lots of bills weighing you down). If the startup fails you can get back to corporate life after a few years, which startup life experience under the belt. Another answer said that you should love the market you're in. I agree. You'll live and breathe this market for 7-10 years, so you better love it. That being said, most startups fail. You have to be fine with the fact that you might lose your savings and those years of your life. And if it does, fine, it's an investment that didn't pan out. What I did when we made the jump (8 years ago) was set aside a pile of money and a 1-year window to see if the company floated. If the time or money ended before we saw paying customers and some small traction, we'd stop. It all worked out fine but we were very lucky.