The (un)bearable heaviness of being (a founder)
I often doubt if having been a founder makes me a better investor - I hope it at least makes me more empathetic
The worst conversations are the ones where a founder calls full of self-doubt, wanting to check if some feedback they got is reasonable - if the doubts that are welling up around them like so many hot waves are justified.
My answer is usually to suggest that they should lower their expectations of their own performance - at least that usually lightens the mood.
The doubts are usually about things that have not gone according to plan. That pit-of-the-stomach nausea when it seems like you are at, or maybe past, the point of no return (it is often so hard to know).
Most people don't experience these feelings because they don't try to do unreasonable things.
If you are doing unreasonable things, then you will spend a lot of time teetering on the edge of failure - that false step in the darkness.
It seems like empathy as I listen and feel the well of similar feelings - visceral memories of existential dread.
Then I wonder if it is something else. Some sort of perverse pride at the sheer insanity of the founder's journey. A recognition of that ability to withstand superhuman levels of stress and risk. The utterly unreasonable and, to most, unfounded belief that there is a path through - a better way.
This is the point where being on the other side of the table (a phrase I love & hate) brings its own doubt. How responsible am I for calling a halt, for intervening, for ending this hopeless undertaking?
These doubts always fade and I remember that I too have work that needs to be done.
A lot of people want outcomes, but far fewer people are frustrated when they can't do the work that is needed to achieve them - an unreasonable commitment to doing hard things.
Society moves ahead when mission-driven people keep at things that others gave up long ago. I am constantly in awe of the founders we partner with and love doing the work required to help them succeed.