Talk to other founders

Chris Savage, co-founder and CEO of Wistia, which is based in Cambridge, Massachusetts, was inspired to buy back his company when he got calls from acquirers—three of them at once. He says other founders, some of whom had sold their startups, were instrumental in helping him decide to try to regain control of his company. He realized he loved running Wistia—or he had before he and his co-founder had driven it into the red with a growth-at-all-costs mentality.

Now, since they’ve announced their buybacks, both Gascoigne and Savage say lots of startup founders in similar situations call and ask for advice. The critical factors are often how much money has been raised, in how many rounds, what the rights are on those shares, and what the board structure is. “Based on all those things, you can get an idea of how possible it might be,” Gascoigne says. Mostly, he adds, take some time off to think. “Especially if you’re in Silicon Valley, get away for a week, go somewhere else,” he says. “Just to think. Read about companies that do things differently.”