Leader of the Rack

As sacred as her maternity leaves were, there was at least one professional event exciting enough to take Jennifer Hyman away from her second baby: a gathering of other women founders of “unicorns,” privately held companies valued at over $1 billion. But Jenn and her family—which includes husband Ben Stauffer and daughters, 3-year-old Aurora and infant Selene—were living at the beach for the summer, a long way from the Manhattan apartment of the event’s host. Rather than attempt to breast-pump while driving, Jenn took an hours long bus ride to the city. When the time came, she did what any nursing mom would do: She pumped in the back seat. “I was like, ‘Oh, my god, if anyone took a photo of this, it would be on the front page of the New York Post.’ It was insanity.”

It wasn’t any more insane than the leap she and Rent the Runway co-founder and fellow Harvard Business School ’09 grad Jenny Fleiss took a little over a decade ago. As their oft-repeated origin story goes, they cold-emailed legendary fashion designer Diane Von Furstenberg. She invited them to her office