How Pickle’s Brian McMahon and Julia O’Mara Are Building the Airbnb of Clothing

In Pickle’s early days, founders Brian McMahon and Julia O'Mara racked up more than 4,000 subway rides across New York City, hand-delivering rented clothes to early users of their peer-to-peer fashion app. The grind paid off. Today, Pickle says one in four female Manhattan residents aged 18 to 25 has used the platform, which has gained traction among both social media influencers and everyday renters.

The company has long since moved beyond those hand-delivered orders. Pickle’s hundreds...