It was the 2013 Met Ball where everything started to go wrong. The first Monday in May was to be the moment when the buzzy, three-year-old fashion start-up Moda Operandi would step out and become a Major Player in style and e-commerce. At least, that was the vision of its chief brand officer, lissome, ice-cold socialite and former Vogue editor Lauren Santo Domingo (“L.S.D.” to her friends), who was determined to serve as Anna Wintour’s co-chair, along with Rooney Mara and then Givenchy designer Riccardo Tisci.

There was only one problem: Moda Operandi wasn’t flush with cash. Like many Anna Wintour–related opportunities, Santo Domingo’s coveted co-chair role came at a steep price. In this case, $4.5 million, a fee that was shared with Samsung and amounted to a big chunk of the $36 million in funding that the company had just received. Inside the firm, a fierce debate erupted: wasn’t this a waste of money? For a start-up, there were much wiser—and more urgent—expenditures. Santo Domingo dug in her heels. “Do you know what it took me to be able to get you guys the chance to sponsor this?” she told the executive team, alluding to her Wintour ties. “You can’t just walk away!”