Courting the Old Guard

The smartest entrepreneurs don’t only look ahead—they also check the rearview mirror. “Tech founders tend to assume that everybody in the past has done things badly. I think that’s a fatal flaw,” says Matthew Gross, founder of Newsela, an edtech startup. Whether they’re investors or board members, you can profit from former execs in the very industries you are taking on.

COMPANY AUNT FANNIE’S

In 2015, Caldrea founder Monica Nassif—who sold her company to S.C. Johnson in 2008—invested in Aunt Fannie’s and joined its board.

NASSIF Mat kept sending me all these messages on LinkedIn, and I was like, this guy is driving me crazy. He totally stalked me, and it was for several months. Finally, he asked if I would take a call, and I said, I have to get this jerk off my back. So I took it, and it was so persuasive that I said, you know, why not meet with him? I did, and I have to say I was really inspired.

FRANKEN As an entrepreneur, your board is the only entity that