Last week I gave a talk at MIT for a great group of students.
One of the questions was “which startups do you regret not investing in the most?”
I have heard this question before and certainly there are a number of successful companies where we had the opportunity to invest in the early days but we chose not to.
But I don’t feel regret when I think about those things.
My regret is more about startups we back and work with that don’t make it. They have to sell as an aquihire or shut down because the company didn’t work despite all the blood, sweat and tears. It’s not a regret of the investment. Rather I regret that we couldn’t make it work and feel for everyone involved given their sacrifice over a long period of time.
That is by far the hardest part of this job.