👗Pickle: Series A fashion marketplace playbook

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A little-known fact about me: back in college, a few friends and I built a social bartering app called Clipp. It was my very first attempt at building a startup.

The idea was to create a "Tinder for secondhand items", making it fun for college students to swap stuff they owned and reduce waste along the way.

Well… let’s just say it was quite a FLOP. We shut it down a couple of months after launch.

We made every startup mistake in the book, from taking forever to develop the MVP to building a massive team from day one.

Pickle is like the product Clipp could’ve become in an alternate universe.

In simple terms, Pickle is a peer-to-peer rental marketplace for things people own, starting with women’s clothing and accessories.

Pickle now has tens of thousands of monthly active users and recently raised a $12M Series A from Craft and FirstMark.

We will dive into their growth playbook today.

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From social polling to peer-to-peer rental

Brian McMahon and Julia O’Mara met while working at Blackstone. They quickly realized they made a great team. Both were college athletes — Brian played football at Maryland, Julia played lacrosse at Penn — and shared the same competitive spirit and drive to push boundaries.

In 2021, they left Blackstone to build Pickle.

They initially started with a social polling app. Users could post outfit options, whether a new suit or a dress, and friends (especially those with similar style) could vote on what looked best.

It introduced social proof into the shopping process.

But it didn’t take off the way they hoped. However, they noticed something interesting — in the comments of polls, people were often recommending (and sometimes offering) items they already owned.

That sparked a lightbulb moment: what if people could rent or lend items directly to each other?

After whiteboarding it out, they realized they had an opportunity to create a true peer-to-peer rental marketplace and reshape how people consume and share in their communities.

Market timing

To be clear, peer-to-peer rental isn’t a brand new idea. Many startups have tried (like Rentah) — but most never scaled.

What’s different this time? Market timing.

Pickle is riding three big waves:

• Courier Convenience: Same-day delivery platforms like DoorDash, Uber, and Relay make logistics seamless. Pickle can build on top of that infrastructure.

• Social Trends: Fashion moves fast, driven by social media. People want new looks without the long-term commitment of owning.

• P2P Familiarity: Platforms like Airbnb and Poshmark have made peer-to-peer transactions feel safe and normal.

Product positioning

Pickle is a hyperlocal peer-to-peer rental marketplace, starting with women’s fashion — especially trendy or high-end items.

Value for renters:

• Access: Rent expensive or sold-out items.

• Convenience: Get last-minute outfits thanks to same-day delivery (if you are in a pickle).

Value for lenders:

• Income: Earn money from underused items; top lenders make tens of thousands per year.

There are also social features. You can follow fashionable people in your neighborhood.

Strong value props on both sides (often the same user!) + sticky social features = high engagement.

In fact, 50% of Pickle’s monthly active users are also weekly active users.

As Brian puts it:

Average order value: $70. 

Pickle takes a 20% service fee from the lender.

Pickle’s growth playbook

1/ Solving the cold start problem

No one wants to use a marketplace with no inventory, just like no one wants to party in an empty club.

Fortunately for Pickle, supply and demand can be the same person. That makes the chicken-and-egg problem easier to solve. You don’t need to build both sides from scratch independently.

Their first market was NYC.

To seed the first 1,000 items, Julia personally recruited her most stylish friends in the city. She went to their homes, helped photograph items, and uploaded them herself.

She also DMed stylish strangers on the internet to get them on the app.

To understand their users better, Brian and Julia personally delivered the first 2,000 orders.

2/ Free UGC cheat code

To get the next 10K users, Pickle tapped into NYC’s micro-influencer scene.

Instead of offering traditional sponsorships, they invited influencers to use the platform, turning them into both lenders and renters.

Micro-influencers are a perfect fit: they want extra income, need clothes for content, and love engaging with fans (who can now rent their outfits).

To sweeten the deal, Pickle offered free photoshoots with professional photographers. Influencers received high-quality assets for their content, along with beautiful images they could use on Pickle. In a way, micro-influencers were setting the standard for the quality of photos users should have on the platform.

(A clever trick Airbnb also used in its early days.)

This strategy worked. Influencers like Madi Khan (20K+ followers) and Megan Crean (22K followers) joined and started posting organically about Pickle. Word of mouth spread fast in NYC’s tight-knit creator circles. The initial group of micro-influencers attracted their influencer friends, who in turn brought their fans onto the platform.

Here’s one video that went viral:

3/ Market expansion

Pickle takes a bottom-up market expansion approach.

Although it’s hyperlocal, users can rent across cities (items just get shipped).

The team watches organic shipping trends to spot potential new markets.

For example, in LA, they noticed lots of users renting NYC-based items. Over time, those renters became lenders, which attracted more renters.

Once 8,000+ items were listed in LA, Pickle doubled down, investing in community activations and relationship building with local micro-influencers.

4/ Traction today

• Tens of thousands of MAUs

• 200K+ products from 2K+ brands

• Several thousand orders per week

My analysis of Pickle

What excites me most about Pickle is the team—Brian and Julia have worked together before and have the kind of scrappy relentlessness I love in early-stage founders. From personally delivering the first 2,000 orders to Brian teaching himself to code and building the platform from scratch, their grit is unmatched.

They also have a brilliant growth unlock with micro-influencers, who are perfectly incentivized to promote Pickle organically because they earn money, get free content, and create value by using the product itself.

In addition, the hyperlocal nature of the platform makes it incredibly sticky. It has the engagement of a social app and the monetization of a marketplace. Starting with women’s clothing, they’re already seeing demand for categories like ski gear, and even growing interest from men.

That said, as they scale, maintaining high-quality inventory and user trust will be crucial. Challenges like counterfeit items, fraud, and returns are classic marketplace growing pains, but hard ones nonetheless.

Still, Pickle is growing fast, executing with real focus, and I love their long-term vision of reshaping how communities sustainably share what they own.

Super excited to see how the story unfolds. Big shoutout to Brian for sharing Pickle’s story with me!

See you next week 🫡,

Leo

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