Beyond the Series B: When to quit, when to sell, and when to double down
So far on our podcast series, “Beyond the Series B: How the Giants of Silicon Valley Made It,” we’ve dealt with the topic of luck, we’ve dealt with rivalries, we’ve dealt with the money you shouldn’t take, and we’ve dealt with the chaos of holding your company together when things go too well.
In this episode, we deal with a universal question almost every entrepreneur faces, whether you company is exploding in the good way, the bad way, or is just kinda limping along: At what point do you give up, cash in, pull the plug, or refocus your capital, time and talent on something else?
The conventional entrepreneur wisdom is you never give up…. And as long as your site is growing, you don’t sell. But does that always make the most sense?
This month, we present several cases to the contrary, and examine how this question has changed in an age of runaway valuations, jaw-dropping mega rounds, and partial liquidations. This month’s podcast features interviews with Jerry Yang, Stewart Butterfield, Kevin Systrom, Max Levchin, Reid Hoffman, Dick Costolo, Al Gore and more.