founder's mentality

I was at Amzn early '00s when we lost 95% of our market cap. Later at FB I negotiated a down-round in '09, and then in '12 our stock dropped 50% post-IPO. I was on the board of a public company that went bankrupt (Borders) and a start-up that went under (Hello). Some lessons:

One of the biggest reasons it gets harder to do new things as you get older is that new things are generally undignified at first (indeed, this is an excellent heuristic for discovering them) and the older you get, the more dignified you're expected to be.