I've had two very different experiences starting a company. The first time I was two years out of school with $12k in the bank, had a partner with a ton of exp

I've had two very different experiences starting a company. The first time I was two years out of school with $12k in the bank, had a partner with a ton of experience, and a decent idea. We crunched for six months, launched, failed, and then tried to pivot. I ran out of cash a few months before the iPhone launched and had I had a longer runway we could have ported our app to the iPhone and potentially seen success. A year ago and nine years later than that attempt, I've started a small video game company with another friend (justintimegame.com). Despite my life situation being more complicated and expensive to maintain, the prior nine years success combined with my wife's income basically lets me try and fail until I get sick of it instead of when the money would run out. Obviously I'm aiming for success, but the massively reduced stress from barely worrying about money let's me be much more open to experimentation while also being resilient to failure. I don't regret starting and failing my first company however. It set me up for having a higher risk threshold and an interest in startups that ended up working out quite well for me.