In Pickle’s early days, founders Brian McMahon and Julia O’Mara racked up 4,000 subway rides across New York City, delivering hand-picked clothes to the first users of their peer-to-peer fashion app. The grind paid off. Today, Pickle says one in four Manhattan women aged 18 to 25 have used the platform, which has gained popularity among social media influencers and everyday employers.
The company long ago moved beyond those hand-delivered orders. Hundreds of thousands of Pickle users now exchange items in person, by courier or by delivery. More than 350,000 items are listed on the app, which—unlike traditional rental services that maintain inventory—relies on users borrowing items from their closets and charges per rental rather than a subscription fee.
McMahon, 31, Pickle’s CEO, and O’Mara, 28, its chief operating officer, founded the business five years ago after working at Blackstone as an assistant vice president and product manager, respectively. Named for its usefulness when one finds oneself “on the beach,” the launcher has emerged as a growing 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 grow their team of 18 people and take the stage across the US.
They also look beyond women’s clothing. Although Pickle’s most common hires today are for tours, weddings, birthdays and ski trips. Clothing, in particular, has proven popular. Last year’s most sought-after item was a green Manning Cartell wedding-guest dress. Other categories benefit, too. Pickle’s second most popular item last year was the Canon PowerShot G7 X Mark II camera. The founders say that the demand for hair tools, luggage and other loanable items is increasing.
The Observer spoke to McMahon and O’Mara about their desire to create an Airbnb-style fashion marketplace while unlocking discarded items from people’s closets and promoting a circular approach to consumption.
The following interview is planned for length and clarity.
Can you tell me about the origin of Pickle? You two met at Blackstone originally, right?
McMahon: Yes, we met at Blackstone. We were working together on a few different projects while we were there, and then we left in the spring of 2021 to start a company that had a different mindset than what we are today. The original idea was to help people make better purchasing decisions through public voting. So, if you were in the market to buy something new—whether it’s a new dress or shoes or a suit—you can post a few options in the form of a poll to a community of users with similar style preferences, and they’ll actually be able to recommend or vote on what you should buy.
We ran with that idea for a year. We were looking for ways to make it a little more sticky and possible pivot opportunities. And what we noticed was that in many of the comments on those votes, people were praising the things they already have, and this light bulb just went off: what if we allowed people to rent, lend, borrow and buy from each other?
We were able to spin up the company in about a week and launched what we are today, which is Pickle, a rental and resale marketplace. We describe it as the Airbnb of your belongings.
What makes Pickle stand out among its competitors?
O’Mara: If you compare the other players in the rental space, it shines. We have no ownership of that; truly a peer-to-peer model. And what the peer-to-peer feature does is allow the offer to be completely dynamic.
Someone will post something on Instagram—say they’re a creator, say they’re a regular user—and their audience and followers immediately say, ‘Hey, this is really cool. I would love to see it in your Pickle Cabinet. I’d like 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 inventory before you can tell people to come to Pickle to rent from other women there, and the promoters have too much inventory in their rooms. They are at the forefront of fashion, they set those styles, and they are good at wearing a lot of clothes because they are always attending events.
Right now, we see promoters have a strong urge to share about their rooms with their audience for a few different reasons: their monetization, of course, is a great way to earn more money for them. And they have that kind of repetitive response from their audience who are so excited to be able to wear that thing they just wore on their trip, or that thing they got engaged to while they were in Paris, or that thing they decided to wear to Aspen or their birthday party.
Another caveat with influencers is that they are great at raising brand awareness and all, but they make up a very small percentage of the people who use Pickle. Most people are the kind of everyday women who are really interested in trends but would rather participate in an affordable, rounded way, rather than resorting to fast fashion.
What were the biggest challenges you had to navigate?
McMahon: The hardest thing was just helping people understand how this works, the value it provides. It is definitely a new concept. While the sharing economy itself isn’t new—we’re getting into the back of people’s cars, or living in people’s homes—using people’s stuff is very new, and getting people to understand that idea is probably the biggest challenge so far.
Is there a limit to where you can expand beyond fashion?
McMahon: Houses and cars are probably where we will reach the limit. I think those are done very well now by some of the early pioneers of the sharing economy, like Airbnb, Uber, Turo, and we’ve learned a lot from them.
For the holidays, especially, people wanted KitchenAid mixers to bake cookies, or mixers and stuff like that. If they are having a party or a gathering, you don’t need to keep several long tables and lots of chairs and coolers that other people around you have, and you can borrow or use that offer. Snowboarding is very popular on the platform, and a lot of people are like, Hey, I’d like to rent skis and a snowboard. You can go ahead and think, Oh, what if they were just waiting in their Airbnb when they got there?
I don’t think there is a limit to the things we can put in this marketplace. At the end of the day, it’s just going to be driven by that consumer demand. Our job is to listen and understand what our customers want and then go out and make it happen from the supply or demand side.
How much does the average lender in Pickle earn to profit?
O’Mara: Some of our top lenders make thousands of dollars a month. One of our favorite quotes is hearing someone say, “I pay my rent with my Pickle money.” That’s always good.
What does the maintenance and cleaning process look like?
O’Mara: We have a few things in place to make sure that’s a seamless, great experience. First of all, we obviously have a full Pickle protection policy so you are protected on both sides as a borrower or renter. When you borrow an item, you expect it to be handled with care, returned in unworn condition, with no damage. And you are fully protected: if something happens, the renter will pay for the damage. On the other hand, the renter is expected to be able to find something clean, ready to wear, and as described in the market.
And then within the app, we looked at other markets that have amazing review systems that hold people accountable within the community. So every single person is reviewed on the platform, and if you mistreat someone else’s property, you will get a bad review, and the other lender will not accept your rental.
Where is the most popular Pickle, and what causes its growth in certain cities?
O’Mara: New York was our first focus. Then LA, then Miami—all these other communities were starting to grow, I think, because of the way people were talking about Pickle. It is a product of the word. You are wearing a nice dress, I admire you and ask you where you got it, and you tell me all about Pickle.
We’re going to see good little pockets get picked up, whether it’s smart girls from SMU in Dallas or young professionals in Chicago doing their MBAs. And we’re seeing some of that overlap happening between the different programs that we’ve introduced across all races and embassies.
Can you expand beyond the US?
McMahon: Definitely. We are planning for the future. I won’t say too much now, but we’re very excited about it. I think there are a lot of markets in North America, as well as Europe and other places. We are very excited to do that, hopefully soon.
What are your top goals for 2026?
McMahon: We are working on many great new product features and improving the overall speed, personalization and functionality of the entire experience—both the buying and receiving experience, and the actual exchange process. We’re excited to continue to grow in all these different markets across the US, which we think are going to be really good.
I think the first thing we want to do this year is nail the customer experience and make sure more people walk away saying, Wow, this was great, or this was fun, or this was really helpful, and talking about it to their friends. That’s what we’re focusing on this year, collectively.
