Circular Chic: Pickle Raises $8M Seed Led By FirstMark and Craft for Fashion Rental Marketplace

5 min readOct 11, 2023


credit: TechCrunch

Written by FirstMark’s Rick Heitzmann (Founder & Partner) and Derek Chu (Principal)

We are thrilled to announce that FirstMark and Craft have led an $8 million seed round in Pickle, a pioneering peer-to-peer fashion rental marketplace with shared roots in NYC, the fashion and finance capital of the world.

We’re proud to partner with Co-Founders Brian McMahon and Julia O’Mara, who have built a thriving peer-to-peer marketplace and community that makes exclusive fashions accessible, affordable, and available on demand.

FirstMark is proud to be an investor in iconic marketplaces like Pinterest, Airbnb, StubHub, DraftKings, and Discord. We’ve been honored to work alongside the visionary founders of these companies with network effects, organic growth, high retention, and marketplace liquidity that enables users to monetize underutilized assets. We see the same virtuous cycle in Pickle, to the tune of 55% MoM growth and 90% user retention after 12 months.

We look for organic viral growth and retention that’s driven by network effects and power usage. The common thread in recent marketplace IPO S-1s like DoorDash, Instacart, and Uber is 100%+ Annual Net Dollar Retention (i.e. for every $1 users spend in Year 1, they spend $1+ in Year 2). More than 90% of Pickle renters are still active after 12 months and spend repeatedly, which is a telltale sign that Brian & Julia have created something users truly want.

Chic-onomics: How Pickle Works

Pickle is a fashion rental marketplace that works by connecting Listers and Renters:

Listers monetize shared closets within their community via convenient delivery options for on-demand door-to-door delivery (integrated courier service, self-delivery, or standard shipping for non-local rentals).

Renters borrow trendy, high-quality items exactly when they need them, on demand, and only pay for the amount of time used. The platform enables renters to access high-quality items at fast-fashion prices.

Why Now? Creators, Community, and the Circular Economy

Fashion is a $395B marketing in the US alone, $107B of which is online. It’s a big, constantly changing, cyclical industry, what’s “cheugy” (Gen Z for passé) this season can make a big comeback in the future, like primary colors, art prints, pleated skirts, and elevated minimalism.

The rise of Influencers has intensified these cycles even more by aggregating long-tail demand/distribution with their audiences. Hot items like Hailey Bieber’s dress and Cult Gaia can go viral at the drop of a hat and create overwhelming demand that suppliers can’t produce fast enough. Like popular shoe drops, these items are too high-priced and sought-after for consumers to find anywhere else. Pieces fly off the shelves and the inventory restock delay can be months, which is an eternity in the world of viral trends and influencers. The only way to access them is peer-to-peer on Pickle.

The average consumer in 2023 buys ~70 items of clothing per year, compared to 40 items per year in 1990 (WSJ). 55% of the closet is not worn regularly, and 33% of women consider an outfit to be “old” after wearing it fewer than three times.

Fashionably Early to the Market

Brian and Julia met on the Blackstone product team and bonded as former D1 athletes. They brought their competitive streak to entrepreneurship in 2021 when they first launched a social polling app for sourcing opinions on purchasing decisions from focus groups. Despite facing bankruptcy three times in eight months, they discovered an immense untapped market — people want to borrow items from each other.

They built Pickle from the ground up by wearing every hat. Brian taught himself to code and built the app from scratch, and the two of them personally delivered items across 4,000 subway rides over 7 months to fully understand the user journey. “Do a Delivery” became part of the culture at Pickle, with team members doing deliveries in the same way that Airbnb employees host guests, Uber employees drive passengers, and DoorDash employees deliver meals.

Community Service and Customer Obsession

“Your customers are your marketing department.”

Brian and Julia learned from thousands of hand deliveries that if you obsess over your customers, they’ll obsess over you. We saw this firsthand at Pickle’s birthday event, where we met power users who rented 80x on the platform and made thousands of dollars a year from their closets. Many had never rented out their items before Pickle, and some even hand-delivered rentals to neighbors.

Now, they’re all part of a passionate community like Airbnb SuperHosts and eBay power sellers, which attracts other Listers and Renters, creating a “symmetric marketplace” and virtuous cycle, where buyers become sellers and more quality supply attracts more demand. This network effect grows stronger with scale — each new user makes Pickle more valuable to existing users.

Retention is a proxy for marketplace liquidity and customer obsession, which starts with early power users. Pickle caught on with popular circles in NYC and took off from there to other major markets like LA. Soon, word spread from trendsetters to the mainstream, and we started to hear rave reviews “in the wild” from friends of friends. We even did our part to acquire users by recruiting our team to try the product (many are now passionate Pickle users!).

Quality Listers become Renters, who attract more Listers. This creates more availability (50,000 items from 2,000+ unique brands) at lower prices (10–20% of MSRP) and access (65% same-day delivery) for Renters, and more earnings for Listers (up to five-figure incomes!)

Fashion Forward

Consumers prioritize sustainability when it is aligned with economic incentives. With Pickle, you can “look good while doing good.”

Brian and Julia saw an opportunity to build micro warehouses on every corner of every street in America, so that communities would be able to share and redistribute things they consume. Every rental is a step towards a more sustainable future, and every closet contributes to a greener economy and healthier environment.

If you are a Lister, Renter, talented candidate looking to make an impact, or just want to help, head to and the App Store to join the rental revolution.

Please click here to reach the full funding announcement on TechCrunch.