Meet Julia O’Mara of Pickle

Today we’d like to introduce you to Julia O’Mara.

Julia, we appreciate you taking the time to share your story with us today. Where does your story begin?
My story really began when I met Brian McMahon, my co-founder, while we were both working at Blackstone. We were on the tech side of finance, working as product managers and collaborating closely with the fundraising and real estate asset management teams. Our role was to integrate third-party and internal data to help drive better investment decisions.

I landed at Blackstone straight out of college. I studied Materials Science and Engineering at the University of Pennsylvania, but pretty quickly realized I wanted to be at the intersection of technology and business. After a consulting internship during college, I moved to New York City and started my first job at Blackstone.

Brian and I overlapped quite a bit, especially with the investor relations and fundraising teams. We built data analytics tools and prospecting solutions to help those teams operate more efficiently. Then, in the spring of 2021, we decided to leave Blackstone to start the first version of Pickle.

We had a lot of conviction around crowdsourcing opinions—specifically helping people decide what to wear and what to buy through social polling. Both of us were notoriously indecisive when it came to fashion and shopping. We thought: why send a million texts or ask in a bunch of group chats when you could just tap into your community and get real-time feedback from people with similar tastes?

We worked on that concept for about a year and started noticing something interesting: people weren’t just voting—they were recommending items from their own closets. They’d say things like “this is my favorite brand” or “this is the best piece I own,” and sometimes even offered to lend it out. A few people literally said, “you don’t need to buy that—I can loan it to you.”

That insight led to the current version of Pickle: a peer-to-peer fashion rental app where women rent clothes to and from each other.

We officially pivoted to that model in May 2022. We essentially started from scratch—rebuilding the platform, brand, and experience around this new vision. It was a huge challenge to balance supply and demand in a new marketplace. On one side, you have lenders—women turning their closets into side hustles. On the other side, you have renters—people looking for that perfect outfit for an event, trip, or night out.

So our first move in 2022 was building supply. We got scrappy—working with nano and micro influencers and tastemakers in New York. We hosted DIY photo shoots in SoHo with volunteer student photographers and fulfilled all the early orders ourselves. Brian and I were literally the first Pickle couriers, running all over the city to deliver and return items.

We ended up personally fulfilling the first 1,500 Pickle orders—taking over 4,000 subway rides in the process. That scrappy approach is what helped us kickstart liquidity in the marketplace and start building real network effects.

By spring 2023, we’d built enough traction to raise our seed round, led by Craft Ventures and FirstMark. With that, we expanded the team to about 12 full-time employees, opened a storefront in the West Village, and kept growing from there.

Most recently, in 2025, we raised our Series A—a $12 million round. Now, we’re expanding the team, hiring across functions, and focusing on scaling to new markets. We launched in New York City, expanded to LA in 2024, and now, in 2025, we’re actively building out our presence in Miami.

Would you say it’s been a smooth road, and if not what are some of the biggest challenges you’ve faced along the way?
It has definitely not been a smooth road. I’d describe it more as a winding one—with plenty of ups and downs—but an amazing roller coaster nonetheless.

There were so many challenges along the way. One of the first was learning to adapt from our initial idea: a social polling app. We had a lot of conviction in it. When we looked at the data and insights, there were definitely some bright spots—but it became clear over time that certain things, like retention, weren’t where we needed them to be.

Still, that experience led us to our next idea: the rental marketplace. And while it’s been far more successful, making the pivot was not easy.

Pivoting—especially as a first-time founder—can be scary. We were starting from scratch. We had around 10,000 users, and we made the decision to shut down the app and relaunch with an entirely different focus. That meant walking away from most of those users to concentrate on building a local market in New York. At the same time, we had already spent a good chunk of capital on the first idea. So even though we had been lean and scrappy before, we were now working with a lot less runway—and rebuilding from the ground up.

Marketplaces are their own unique challenge. You have to build both the supply and the demand—and in those early days, that meant doing a lot of things that didn’t scale. We ran around the streets of New York personally fulfilling orders. I begged friends to list their closets—and would even go to their apartments, pull pieces off hangers, style them, and photograph them myself. Those were some of the first Pickle closets where people could start borrowing clothes.

At that point, we were doing maybe a handful of rentals a week. But we celebrated any sign of growth. If we went from 9 to 10 rentals in a week, that was a win. For context, the number of rentals we did in our entire first year is now what we do in a day—or even half a day. It’s surreal to see how far we’ve come in just three years.

Still, at the beginning, there’s no light at the end of the tunnel. You have to believe in your idea. You have to believe in your earliest sticky users. That belief is what keeps you going, because you’re not going to get external validation at that point—you haven’t hit any major milestones yet.

Fundraising was another major challenge. When we started looking to raise our pre-seed round—after we had some initial traction and revenue—we were rejected constantly. It was a million no’s. But we stayed persistent. We brute-forced growth and built the traction ourselves, which eventually led to the numbers that allowed us to raise our seed round in 2023: $8 million from Craft Ventures and FirstMark Capital.

Thanks – so what else should our readers know about Pickle?
Pickle is a peer-to-peer fashion rental app where women rent clothing to and from each other.
Think of it like Airbnb—but for your closet. It’s an incredible way to earn a side hustle from pieces you already own—statement dresses, wedding guest outfits, designer bags, or sets you love but don’t wear every day. With Pickle, you can rotate those items with people in your city and beyond.

Renters come to Pickle looking for something new at an affordable price.
Typically, they rent items for just 10–20% of the retail value. It’s not only affordable—it’s circular, sustainable, and super convenient.

We offer multiple delivery methods:

Local rentals: Use our door-to-door courier service—an Uber driver picks up the item from the lender and delivers it to the renter within two hours.

Self-pickup: Renters can also arrange to pick up the item themselves.

Non-local rentals: We offer USPS prepaid shipping labels, so items can be rented between cities.

Why peer-to-peer?
Because it gives us the most dynamic, trend-driven supply.
Many of our users invest in a special piece for an event—a dinner, night out, or wedding—and after wearing it and/or posting it on social media, they may not want to wear it again right away. But someone else absolutely does. So instead of buying that $400 dress, someone can rent it for $50–$60. This model provides a stylish, sustainable, and affordable alternative to fast fashion.

We’re also completely asset-light—just like Airbnb. We don’t own the inventory. We simply facilitate rentals between members of our community. It lets women shop smarter, wear something “new to them” as often as they want, and avoid wasteful one-time purchases.

Pickle is a two-sided marketplace.
Not only can you rent from others, you can earn by lending out your own wardrobe. Some of our top lenders make thousands of dollars a month. One of my favorite things I’ve heard is: “Women in New York are paying their rent with their Pickle earnings.”

We hear from users all the time that Pickle has changed their lives—not just financially, but by giving them the freedom to pursue a passion or hobby they couldn’t afford before.

Here’s how it works:

Download the free Pickle app—there are no subscriptions.

Browse items available for the exact dates you need.

Choose delivery (courier, pickup, or shipping).

Wear it. Return it. That’s it.

Lenders act like small business owners of their own “closets.” They manage listings, send out clean, ready-to-wear items, and handle cleaning upon return (whether that’s dry cleaning or hand washing). It’s simple, streamlined, and empowering.

What I’m most proud of is how community-driven Pickle is.
About 85% of our growth is organic. Our users are our greatest advocates. They share their experiences—whether it’s getting an outfit delivered an hour before an event (yes, that’s why we’re called “Pickle”), receiving amazing support from our customer service team, or using Pickle to support themselves financially.

This community fuels our entire product. They help us improve the platform, give us feedback, and spread the word. They’re our brand evangelists—and the backbone of our company. That kind of brand love is rare, and it’s something I’m incredibly proud of.

Where is Pickle available?
The app is free to download and available across the U.S., but we’re focused on building local communities in our core cities:

New York City

Los Angeles

Miami (launched in 2025)

Even if you’re outside those cities, you can still use Pickle—especially with our shipping option.

Our LA community has been especially exciting to watch grow.
It’s now our second-largest market. We’ve learned so much from them—whether it’s seeing spikes in demand during festival season or understanding what styles are trending for summer and fall weddings.

We’ve done tons of IRL activations in West Hollywood and Santa Monica, and it’s been amazing to see how organically the community has spread the word.

The women renting in LA have a distinct style—from renting for a Monday night movie premiere to a beach picnic in Malibu. It’s a bit more casual than NYC, with vibrant colors, less seasonality, and consistent demand for wedding guest dresses, brunch looks, and designer pieces.

Top brands we’re seeing in LA include:

Réalisation Par

Cult Gaia

Christopher Esber

Alexis

How do you think about luck?
I love the question about how luck has played a role in life and business. I think a lot of founders and entrepreneurs would agree—there’s always some element of luck and timing. But I also really believe that if you work hard enough and put yourself in front of enough opportunities, you can create your own luck.

There were definitely moments of building Pickle where timing played a role—like Brian and I meeting at Blackstone, or COVID sending us home to work remotely. That shift gave us the space and flexibility to think beyond corporate America and start exploring new ideas.

At the same time, the way we executed on building Pickle had a huge impact. We didn’t have funding or resources in the beginning—we had to do everything ourselves. That meant delivering items to customers at their doors, building the technology from scratch, teaching ourselves to code and design, and handling every part of the business firsthand.

All of that gave us invaluable experience and put us directly in front of our users. I think those moments—where we put in the work and got our hands dirty—created the conditions where luck could find us. So yes, there’s always some luck involved, but I think we made a lot of our own.

Contact Info:

• Website: https://www.shoponpickle.com/
• Instagram: https://www.instagram.com/shoponpickle/?hl=en
• LinkedIn: https://www.linkedin.com/company/shop-on-pickle/
• Other: https://www.tiktok.com/@shoponpickle?lang=en

Image Credits
courtesty of Pickle