By May 2022, Pickle re-emerged as a peer-to-peer fashion rental marketplace based in New York City, rebuilt in three weeks with no romance about the process. Brian McMahon and Julia O’Mara carried clothes on the subway. They hand-delivered more than four thousand orders. They photographed closets in apartments. They learned that inventory moves faster when it already lives next door. Pickle became less about fashion statements and more about asset velocity. Closets stopped sitting still, a shift now visible across the recommerce and sharing economy landscape.
That momentum compounds. By March 2025, Pickle closed a twelve million dollar Series A led by Craft Ventures and FirstMark Capital, both doubling down after leading the seed, a funding moment that briefly put the company in startup news. Inventory crossed two hundred thousand items. More than two thousand brands flowed through the platform. In Manhattan, one in four women aged eighteen to thirty five uses Pickle. Weekly rentals surpassed the company’s entire first year. Wedding rentals climbed five hundred nineteen percent year over year. Ski trips followed, up three hundred three percent. The closet kept paying rent.
On January 7, 2026, Brian McMahon posted something simple and loud. Pickle is entering a major growth phase. Six leadership roles opened at once. Head of Engineering. Head of Operations. Data Scientist. Director of Finance. Senior Growth Marketing Lead. More to follow. The language matters. This is not about headcount theater. It is about unlocking billions in underutilized assets, starting with clothing, then moving outward, a signal that returned Pickle to the startup news cycle. The pickle jar is opening wider.
This is where execution replaces novelty. Engineering to scale a marketplace that moves at street speed. Operations to keep same-day delivery tight with partners like Uber and DoorDash. Data to price taste, not guess it. Finance to protect unit economics while growth presses the gas. Marketing to grow without lighting money on fire. Julia O’Mara’s operational spine meets Brian McMahon’s product math. Investors like Rick Heitzmann and Jeff Fluhr have seen this movie before. They stay when the sequel has legs, and startup news tends to follow when discipline starts compounding.
