The Loneliness of an Entrepreneur

This showed up in my inbox the other day from a friend of 20 years. He’s been involved in a number of companies that we’ve invested in over the years in different senior and/or co-founder roles, including CEO. It was short and sweet but captured the essence of something I often talk about with founders.

Heard you and Jerry on CPR this morning, nice job!

What struck me was your point about the gap between expectations in the role of CEO or startup founder, or investor — and the reality of depressive events/emotions that are often present — but no one gets to expose or relinquish.

I felt this first hand in my experience, both as co-founder and later as CEO. I used to *hate* seeing people around town or whatever because they’d ask “how’s the startup going?” and usually extra commentary like “oh startup rockstar, and you must be killing it, etc…” and my answer was always “no, it’s fucking unbelievable hard, and anxious, and trying, and most of the time shit is more fucked up than you could ever imagine”. You live with that veil and it always made it worse when people wanted to interact with you but position it as only successful sounding answers would work.

I learned to approach others the way I wanted to be approached:

1. I recognize everyone has a “bag of despair” they carry — you can’t see it, and anything can be in there, work, home, friends, family — serious shit is wrong somewhere for everyone at most points in time. So know it’s there, don’t assume and ask questions from ridiculously positive framing, but rather in a way that lets folks share honestly and is then actually helpful dialog to them (if they do want to take the opportunity to disclose challenges and discuss)

2. when someone asks “how’s it going” be honest — share the good and the bad, but don’t feel like you have to fulfill the stereotype and give them the sugar coated answer

Originally published at Feld Thoughts.