How Pickle’s Brian McMahon and Julia O’Mara Are Building the Airbnb of Clothing

In Pickle’s early days, founders Brian McMahon and Julia O'Mara racked up more than 4,000 subway rides across New York City, hand-delivering rented clothes to early users of their peer-to-peer fashion app. The grind paid off. Today, Pickle says one in four female Manhattan residents aged 18 to 25 has used the platform, which has gained traction among both social media influencers and everyday renters.

The company has long since moved beyond those hand-delivered orders. Pickle’s hundreds of thousands of users now exchange items in person, via couriers or by shipping. More than 350,000 items are listed on the app, which—unlike traditional rental services that hold inventory—rely on users lending items from their own closets and charge per rental rather than a subscription fee.

McMahon, 31, Pickle’s CEO, and O’Mara, 28, its chief operating officer, launched the venture five years ago after working at Blackstone as an assistant vice president and a product manager, respectively. Named for its usefulness when someone finds themselves “in a pickle,” the startup has emerged as a rising player in the fast-growing clothing rental market.

Last year, the founders raised $12 million in a funding round led by FirstMark and Craft Ventures, capital they plan to use to expand their 18-person team and take the platform beyond the U.S.

They’re also looking beyond women’s apparel. While Pickle’s most common rentals today revolve around vacations, weddings, birthdays and ski trips. Dresses, in particular, have proven popular. The most rented item last year was a green wedding-guest dress from Manning Cartell. Other categories are gaining traction, too. Pickle’s second-most-popular item last year was a Canon PowerShot G7 X Mark II camera. The founders say demand is rising for hair tools, luggage and other borrowable items.

Observer spoke with McMahon and O’Mara about their ambition to build an Airbnb-style marketplace for fashion while unlocking underused items in people’s closets and promoting a more circular approach to consumption.

The following interview has been edited for length and clarity.

Could you tell me about the origins of Pickle? The two of you met at Blackstone initially, right?

McMahon: Yes, we met at Blackstone. We were working together on a couple of different projects while there, and then we left in the spring of 2021 to start a company that was a different concept than what we are today. The original idea was to help people make better purchase decisions through social polling. So, if you were in the market shopping for something new—whether it was a new dress or some shoes or a suit—you could post a few options in the form of a poll to a community of users with similar style preferences, and they’d basically be able to recommend or vote on what you should buy.

We ran with that idea for about a year. We were looking at ways to make it a bit stickier and potential pivot opportunities. And what we noticed is that in the comments of a lot of those polls, people were recommending stuff that they already owned, and it just kind of set off this light bulb: what if we just let people rent, lend, borrow and buy from each other?

We were able to pivot the company in about a week and launched what we are today, which is Pickle, the rental and resale marketplace. We describe it as kind of an Airbnb for things that you own.

What makes Pickle stand out amongst its competitors?

O’Mara: When comparing some other players that are in the rental space, we are completely asset-light. We don’t own any of the inventory; it’s really that peer-to-peer model. And what the peer-to-peer aspect does is it allows the supply to be completely dynamic.

Someone will post something on Instagram—say it’s a creator, say it’s just a regular user—and their audience and followers are immediately like, ‘Hey, this is really great. I’d love to see it in your Pickle closet. I’d love to borrow it from you.’

How much of a role did social media influencers play in getting the word out?

O’Mara: You have to build a lot of supply before you can tell people to come on to Pickle and rent from other women there, and influencers have an excess of clothing in their closets. They’re on the forefront of fashion, they’re setting those trends, and they also are excellent at wearing a lot of clothes because they’re always going to events.

Right now, we are seeing influencers have a really strong push of sharing about their closets with their audience for a few different reasons: their monetization, of course, it’s a great extra income stream for them. And they have that kind of recurring feedback loop from their audience that is really excited to be able to wear that item that they just wore on their trip, whether it’s something that they got engaged in when they were in Paris, or something that they decided to wear to Aspen or for their own birthday party.

One caveat with influencers is that they are amazing at brand awareness and everything, but they make up a very small portion of the people who are actually using Pickle. Most people are kind of everyday women really interested in trends but who would like to participate in an affordable, circular way, rather than turning to fast fashion.

What are the biggest challenges you’ve had to navigate?

McMahon: The hardest thing has really just been helping people understand how this works, the value it provides. It’s definitely a new concept. While the sharing economy itself is not new—we get in the back of people’s cars, or we stay in people’s houses—using people’s things is pretty new, and helping people understand that concept is probably the most challenging part so far.

Is there a limit to where you’d expand beyond fashion?

McMahon: Houses and cars are probably where we’ll draw the limit. I think those are being done pretty well right now by some of the early pioneers of the sharing economy, like Airbnb, Uber, Turo, and we’ve learned a lot from them.

Around the holidays, especially, people wanted KitchenAid mixers to bake cookies, or blenders and things like that. If they’re hosting a party or a gathering, you don’t need to store several long tables and a bunch of chairs and coolers when other people around you have some, and you could borrow or leverage that supply. Ski wear is very popular on the platform, and a lot of people are like, Hey, I’d love to rent the skis and the snowboard as well. You can take it a step further and think, Oh, what if they were just waiting in their Airbnb when they get there?

I don’t think there’s a limit to the things that we can put on this marketplace. At the end of the day, it’s going to be driven just by that consumer demand. Our job is really to listen and understand what our customers want and then go out and make it happen from either the supply or the demand side.

How much does the average lender on Pickle stand to earn?

O’Mara: Some of our top lenders are making thousands of dollars a month. One of our favorite quotes is hearing someone say, “I’m paying for my rent with my Pickle earnings.” That’s always a good one.

What does the process of maintaining and cleaning items look like?

O’Mara: We have a few things to ensure that’s a seamless, great experience. One, we obviously have a full Pickle protection policy so that you’re protected on both sides as a lender or renter. When you’re lending out an item, you’re expected it to be treated with care, returned in a regular worn capacity, with no damage. And you’re fully protected: if something is to happen, the renter would pay for those damages. On the flip side, the renter is expected to be able to get an item that is clean, ready to wear, and as described on the marketplace.

And then within the app, we have looked at other marketplaces that have amazing review systems that hold people really accountable amongst the community. So every single person is reviewed on the platform, and if you don’t treat someone’s item with care, you’re going to get a bad review, and another lender isn’t going to accept your rental.

Where is Pickle most popular, and what accounts for its growth in certain cities?

O’Mara: New York was our first focus. Then LA, then Miami—all of these other communities were starting to grow, I think, because of the way that people were talking about Pickle. It’s a word-of-mouth product. You’re wearing a beautiful dress, I compliment you and ask you where you got it, and you’re telling me all about Pickle.

We’ll see some nice little pockets picking up, whether it’s sorority girls at SMU in Dallas or young professionals in Chicago doing their MBAs. And we’re seeing some of that density happen amongst the different programs that we’ve launched across growth fellows and ambassadors.

Would you ever expand beyond the U.S.?

McMahon: Absolutely. We’re planning for it in the future. I won’t say too much now, but we’re very excited about it. I think there’s a lot of markets within North America, as well as over in Europe and other areas as well. We’re very excited to do that, hopefully pretty soon.

What are your main goals for 2026?

McMahon: We’re working on a lot of cool new product features and just overall improving the speed, the personalization and the operations of the entire experience—both the shopping and discovery experiences, as well as the actual exchange process. We’re excited to continue to grow more and more in all of these different markets across the U.S., which we think will be really awesome.

I think the number one thing that we want to be doing this year is just really nailing the customer experience and making sure as many people are walking away saying, Wow, this was great, or this was nice, or this was really helpful, and raving about it to their friends. That’s our number one focus for this year, all in all.