Why We Invested in Pickle

Jeff Fluhr
Craft Ventures
Published in
2 min readOct 11, 2023

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Craft is excited to co-lead Pickle’s $8 million seed round.

Pickle is a peer-to-peer rental marketplace that makes it easy and affordable for people to rent high-quality clothing and accessories from other people. The product is interactive and social, allowing users to create their own profile pages, post pictures wearing their favorite outfits, generate wish lists, and share listings and outfit suggestions with others in their community. This creates a delightful experience for users which in turn drives strong retention and viral growth. Because Pickle tries to match renters with owners who live within a close radius, the company facilitates same-day rentals, which is a magical experience (and incredibly valuable for procrastinators who might be in a pickle!).

Pickle cofounders Julia O’Mara and Brian McMahon.

Pickle’s early traction was particularly impressive for a company that had previously raised less than $400k of outside capital. We saw growing volumes, loyal customers, and lots of social media buzz. We were even more impressed to learn that the product, engineering, marketing, customer acquisition, supply acquisition and customer support were entirely built and managed by only two people: co-founders Brian and Julia. This dynamic duo clearly understands their target users, knows how to build fast, and appreciates the importance of being scrappy.

Pickle also struck a personal chord for me because my family has been in the consignment clothing business in New York City for many decades. I’m a big believer in the power of the sharing economy and the sustainability of circular fashion. I’m always intrigued by businesses that give people a way to make money from an underutilized asset they already own. Everyone has a closet full of clothing but only wears one outfit at a time, leaving 98% of their closet idle at any given time. Pickle creates the perfect opportunity for people to monetize their idle clothing.

We’re excited for the journey ahead and are honored to be a partner.

Congrats to the Pickle team!

Written by Jenny Sui and Jeff Fluhr

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Jeff Fluhr
Craft Ventures

Now: General Partner of Craft Ventures. Former: Co-Founder/CEO of StubHub. Angel investor in Twilio, Houzz, Warby Parker, Trulia and others.