Over the last couple of years there has been great wealth creation for operators. After years of hard work they have finally cashed out and made their bones. The novelty of cashing the big check eventually wears off for these entrepreneurs and the jones to find the next thing comes into effect. Now that they have comfort the majority of them do not want to start from the beginning – additionally they do not want to do the things that bothered them about operating – I.e. managing people, having to deal with repetition/boredom etc. What they want to is to take their street cred and capital and start working with younger companies. They get to work on new and different things as well as not being directly responsible for the P/L.

On the flip side venture capitalists (like myself) also get bored of the repetition. We see endless amounts of deals in order to find the ones we ultimately invest in. We also deal with constant rejection in pitching our funds and SPVs. We are surrounded with greatness with founders and naturally feel insecure and inadequate. So we want to “quasi-operate” or at least get “founder high.”

Where is the right middle ground in order to find career fulfillment as an operator and investor?