PTSD and IPOs

One of the main reasons I left salesforce was my desire to take a company public. And with the news of DocuSign’s upcoming IPO, I have found myself reflecting on my experiences there.   Did I regret my decision to leave prematurely?  Was I happy with how things ended up?  How would life be if I stayed?

After surprisingly little reflection, I can honestly say that while I learned a ton and grew a bunch, leaving was the best decision I could have made… adding those three little letters to my resume was just not that important to me after all (Oskar and Martin definitely helped to refocus my priorities to where they belong)... Unfortunately while I didn’t leave with the coveted three letters of IPO, I did manage to leave DocuSign after two and a half years with four different letters - PTSD.

Blame the hours, blame the start-up culture or blame me trying to fit my round peg skills into a square-hole job. But it was stressful; and after being gone for over a year, while I don’t regret my decision to leave I still wonder every once in a while if I actually failed during my time there (which is the general feeling I left with) or if I am just being overly critical of myself. I probably will never know, but considering my old teammates (at least a handful of them) still reach out to catch up, share gossip or ask for career advice, I guess I couldn’t have been that terrible at my job.

And as for those other three little letters, you know, IPO, well I ended up getting those too. This past week, salesforce had its initial public debt offering and raised $2.5 billion. And I was one of the lucky few to be part of the event. We might not have rung the bell on Wall Street but we raised more in a day than DocuSign is worth, so there is that.