Ten years ago, Andy Dunn was at Stanford’s Graduate School of Business. He was torn between taking a high paying job and following the lead of Brian Spaly– a classmate who was selling better-fitting pants out of the back of his car.

That company would become Bonobos, a promising survivor in an otherwise graveyard of so-called “ecommerce 2.0” upstarts.

Spaly and Dunn had a contentious falling out; with Dunn keeping Bonobos and Spaly going on to build (and sell) TrunkClub. Dunn is still plugging away with Bonobos, hoping to reinvent the way brands are built in an online world.

He says he’s now confident that Bonobos will survive. But continuing to build it into a stand-alone ecommerce company is another matter. An even bigger challenge: Maki...