Pickle Co-Founder Julia O’Mara on Reinventing How We Get Dressed & Betting on Herself at 23
Today, I’m sitting down with Julia O’Mara, the co-founder and COO of Pickle. Pickle is the peer-to-peer fashion rental app changing how women get dressed for everything from sorority formals and vacations to weddings and nights out. Before Pickle, Julia studied Materials Science and Engineering at the University of Pennsylvania, played Division I lacrosse, and began her career at Blackstone. At just 23 years old, she left Wall Street to bet on herself and build a company of her own.
In this episode, we talk about her college and early career years, the evolution of Pickle’s business model, and the difficulties of getting a marketplace off the ground. She also shares some of her most memorable unconventional milestones with the company, and the importance of “ruthless prioritization” during hectic times. She and I connect about both being identical twins and growing up with a shared closet. Plus, Julia tells us about the Pickle rental that earned her a compliment from Alix Earle.
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My Conversation with Julia
This transcript has been edited for written clarity.
Lauren Stenger: Welcome back to another episode of Double Take. On today's episode, I'm sitting down with Julia O'Mara, the co-founder and the COO of the peer-to-peer fashion rental app, Pickle. So I'm really excited to hear all about her career journey today.
Julia O'Mara: Thanks Lauren, super excited to be here.
Lauren Stenger: Yeah, thank you so much for being here. So for those who are new, do you mind giving a brief overview on yourself?
For those who are new, do you mind giving a brief overview on yourself?
Julia O'Mara: Sure. I can go and give my little career background if that's helpful. I am Julia O'Mara, currently at Pickle. I have been working on this company for over five years now, and I originally started it with my co-founder Brian McMahon. Let me take a step back on how I even got into the startup world. I guess my original background- I grew up in Bel Air, Maryland, and I went to school in Philly. I went to the University of Pennsylvania, and I studied Materials Science Engineering there, which is a completely different background than what I'm currently doing today. I had a pivot kind of out of that career, and I started to get into more of the technology side of business. I did a few internships during college in the consulting world and finance world, and then ended up landing my first job in New York City at Blackstone. I was working there as a product manager / data analyst, and that's where I met my co-founder, Brian McMahon, for Pickle.
I worked at Blackstone for around just under two years, and while we were working there together, that's when Brian and I had been talking about the very first version of Pickle. It was the spring of 2021 when we finally had enough conviction to jump ship and go start to work on this first company. And it's a completely different concept than what we are today. We started out by building this social polling platform, and it was basically like a place where you could crowdsource opinions, decide what to wear, what to buy. Basically, think of like Instagram polls, but in its own app. We were working on that for around a year and learned a lot of things as first-time founders.
“It was the spring of 2021 when we finally had enough conviction to jump ship and go start to work on this first company.”
We saw some things that were going pretty well. We saw a lot of things that weren't going as well, but we did get some really interesting insights from that platform where we saw that people that were commenting on these fashion polls when someone was asking, What do I wear? What do I buy? Here are these options, we saw that people were commenting and recommending items from their own closets. Even some comments here and there that would say, like, “You don't need to go buy that, you can just borrow that from me.” Which was super interesting to see. That wasn't the intention of what we were building, but it also wasn't a net new concept.
You know, we've all shared clothes with our sisters and our sorority friends and peers in college, but it wasn't something that was used or done as frequently when you got into the professional world. Also at that time, you know, companies in the sharing economy like Uber and Airbnb were allowing you to monetize your home and your car, but nothing like that existed for peers to actually share their closets to and from each other in that rental model.
“You know, we’ve all shared clothes with our sisters and our sorority friends and peers in college, but it wasn’t something that was used or done as frequently when you got into the professional world.”
So heavy pivot in May of 2022 to the fashion rental marketplace that we are today. And yeah, we've been now working on it for over four years. We have hit some amazing milestones of growth. We've raised a bunch of capital. We now have a full twenty plus person team, which has been super exciting, but lots to chat through. So I'm really excited to be here.
Lauren Stenger: That's an awesome overview. The concept of Pickle, it's just one of those concepts that makes so much sense. It really is like a win-win-win, because the person who's selling their clothes, it's a nice little side hustle, and then you're helping someone who just has a one-off special occasion, and then also it's really good for the environment because you're reducing waste. So it's just one of those concepts that's brilliant.
Julia O'Mara: A hundred percent. Thank you. The circularity piece is awesome and I love that you're, both sides of that community that you're referencing already within this two sided marketplace is very cool to see, of course, from the demand side when someone needs that last minute outfit, or they want something new to wear and feel really confident in, whatever use case that might be. We see it across the gamut, right? Girls are renting for their college sorority formals, people are renting for weddings that they're going to, people are renting for their actual weddings where they want their second dress or after party dress to be something really special that they don't need to spend $3,000 on. So we see all these really cool use cases.
One of my favorite things that I think about when I'm renting is whenever I'm renting from someone else I'm like, I'm probably paying for her night of drinks or something like that. It's like a fun little play on community as well on both sides.
Lauren Stenger: Yeah, and I also love how the business model revolves around people's celebratory moments and holidays and events, and it's a very optimistic business model. If you're on Pickle you're probably shopping for a vacation or a nice wedding or a graduation or something. So seems like kind of a nice energy, I guess I would say.
Julia O'Mara: Yeah, definitely. We talk about this a lot where there's a few different ways that we're seeing people using Pickle, and there's everything from more of like the evergreen use cases of you're going out to dinner or you have a birthday party this weekend or something that's like more frequently happening. And often people, especially after they've rented for the first time on Pickle, are coming back to rent for those more frequent occasions. But then we see the special occasion attire like the weddings and vacations and the life moments that I've kind of already referenced, but even the prom dress that we're getting rented from the seniors this past spring, and seeing engagement parties and bridal showers and baby showers, it's all of these celebratory moments where we’re almost part of these different milestones that are in your life.
“Even the prom dress that we’re getting rented from the seniors this past spring, and seeing engagement parties and bridal showers and baby showers, it’s all of these celebratory moments where we’re almost part of these different milestones that are in your life. ”
Lauren Stenger: Yeah. It's like different stages of girlhood also. So going back to your earlier years when you were in college, what did you kind of envision for your career? I know you did internships, and did you work at Blackstone right out of college?
When you were in college, what did you envision for your career?
Julia O'Mara: Yes, Blackstone was right out of college. I mean I was definitely on more of this traditional Penn path, and anyone that went to Penn would laugh because the pipeline of Penn to finance in some form, or Penn to consulting, or finance or accounting, is quite heavy. So I was definitely following some of those more traditional footsteps and it was an amazing place to start. I am absolutely so happy that I was there for a couple years. I developed most of my basic professional skills, of course, there. It was a really good base foundation.
It's funny now that our company is getting bigger, there are certain things I reflect on even my first year at Blackstone where I'm starting to see, yeah, we used to follow this type of meeting structure, or this was a really good process that now we're implementing within our startup where you start to need more structure, and we're no longer a team of two co-founders running around New York City. We now have 20 plus people that we're working with, and it really helped build that great professional setting for myself.
I didn't always know that I wanted to be a founder or an entrepreneur. I would say that's quite different from my co-founder Brian. Brian always knew he wanted to start a business. His mom has built businesses, and he knew that he was going to. He was one of those people that just thinks about business ideas all the time. I would say that wasn't necessarily me. I think I knew that I probably wouldn't want to follow as traditional of a path as the corporate ladder, but I wasn't sure what that looked like.
So the opportunity of taking the leap from Blackstone and going to start the company was obviously something that people were like, “My gosh, are you crazy?” A little bit, but it was such a good opportunity that doesn't come along very often. And I had a lot of belief in Brian and I as a really strong co-founding partnership, and we both had a lot of similarities in how we think about building a business and things that we value around things like work ethic. We were both college athletes which definitely gave us very similar mindsets on how to win and persevere during some of the tough times that happen when you're building a business, so that was definitely a great way that set me up for success at Pickle without me really knowing about it in the earliest days.
Lauren Stenger: Looking back to the period where you were kind of transitioning out of Blackstone into Pickle, what did that timeline look like? Was it a quick kind of like you and Brian realized we need to go in all in on this right now because there's a need in the market? Did it take a lot of conviction? How did that transition look for you?
When was the moment you went all in on Pickle? When did you realize it was feasible to pivot out of Blackstone into a new venture?
Julia O'Mara: Yeah, it definitely wasn't an overnight let's quit and go. Part of when you are leaving a very stable corporate job is you're thinking about, all right, I'm not gonna have salary and that's a big, big decision that people are often making when they're making the jump to actually go and and start a business. Some good advice from people is to really think about what is your personal runway. How many months are you going to give yourself and you're committing to, “I'm gonna go X number of months salary free and I am comfortable with that financially, I am good to go on that.” How do you think about your next steps if this thing doesn't work out? Because odds are high that it doesn't. That's just the name of the game in the startup world.
“Some good advice is to really think about what is your personal runway... How do you think about your next steps if this thing doesn’t work out? Because odds are high that it doesn’t. That’s just the name of the game in the startup world.”
When we had been building and starting to work on the polling app for a bit, there was definitely a little bit of overlap while we were at Blackstone. Obviously, we were only working on this on nights and weekends when we were outside of working hours. This was also during COVID. So we weren't in the office anymore which did give us a little bit more flexibility. You can close your work laptop and open up your personal one, and you're not commuting from the office or whatever is happening there. So that did give a little bit more flexibility of starting to build something on the side. The jump was something that I was very confident in Brian, and I loved the idea of this polling app. But Brian definitely was helpful and reassuring because he is a few years older than me, and I was twenty three at the time. I was very young, so it was a big jump and big kind of bet. He was really, really confident in this. I was super confident in us, in the idea, and more importantly, really in us as founders, we have this winner kind of like mentality that you have to have. We can pivot, we can make something happen here.
And that's something that was the right way to think about going and making the jump for a business that I would give recommendation to anybody about is do you have the conviction in yourself and your business partner over anything else, over the idea because there's a very great chance that it's gonna change or evolve or whatever that might be. It was definitely some months of time, eventually made that jump, had very serious conversations with ourselves of what is my personal runway of going no salary, and you know, we are very fortunate. I had a lot of support from my family and friends in the sense that they were very encouraging of this. I definitely had the mentality of if it doesn't work out and I give it my all, this would be a very good interview story and I'll go back to another job in corporate America, hopefully.
Lauren Stenger: The thing about this marketplace is it seems like it's relatively asset light. Like you don't have to buy a ton of infrastructure to get going and all these fixed costs. But also I don't know what's harder though because then the thing about marketplaces it's like if you don't have a buyer and a seller, then you're not going to have any transactions so I feel like it was probably hard to like get off the ground because if no one's willing to lend or borrow, then nothing exists. So I'm sure that was scary too.
Julia O'Mara: You're one hundred percent correct. That is the hardest part of building a marketplace, especially one that's asset light, where we don't have control of anything. Especially when you're first getting started and the answer isn't to buy the inventory and then rent it out because that wasn't our business model. We want to help the trendiest, coolest people with these fantastic closets circulate and monetize them. Then you don't have any customers yet, so how do you get the closets on first? So it is very hard at the beginning and even as we're expanding geographically, you're always thinking about that balance of supply and demand.
“Especially when you’re first getting started and the answer isn’t to buy the inventory and then rent it out because that wasn’t our business model. We want to help the trendiest, coolest people with these fantastic closets circulate and monetize them. Then you don’t have any customers yet, so how do you get the closets on first? So it is very hard at the beginning and even as we’re expanding geographically, you’re always thinking about that balance of supply and demand.”
But in the earliest days, the way that we kind of hacked that or worked on it was we handheld each part of creating the marketplace. So you know, the very first thing to do is you have to build supply and start from somewhere. So I would run over to my girlfriends’ apartments and just upload their closets for them in New York. Or we would host these like really scrappy photo shoots in SoHo with with nano-influencers, like the girls that do all the SoHo fit checks. I remember DMing like a hundred of them, I probably got like three responses or whatever, and inviting them to this professional photo shoot of like, “Hey, you can come get some free professional pictures. I'm gonna tell you all about Pickle.” They had no idea what Pickle was, but they were down to get some cool photos in SoHo. It's funny, I even like think about those girls, and some of them in our photo shoots are still on Pickle today and avidly using it.
Lauren Stenger: I'm sure they love telling people that they were one of the first customers.
Julia O'Mara: Yeah, some of the OGs. Yeah, like the very first closet, it's kind of insane. It was a good way that we were able to think about, and this is what you always have to think about when you're starting a business, if you don't have any money or resources, what value can you add to somebody if you're looking to hopefully onboard them to your platform or get them to start to use it. Our hack in this case was like, “Hey, we'll give you really cool photos that we know you'll use for Instagram for free.” We worked with an FIT student photographer who was building out her portfolio, I think our budget was like $150. We had no money, but those were some of the first closets that we got onto the platform.
Those micro-influencers were very great first time customers on the platform, as owners, but they also always had all these events to go to, so they were already thinking about how this could be a helpful platform for them on the other side. So the overlap of our customer is actually really helpful for our acquisition strategies. A lot of marketplaces don't have the same luxury of having so much overlap with both sides. When you think about Uber, the drivers and riders are often very different personas. But on Pickle, 67% of our owners are also customers, so we have a ton of overlap there where people are using it on both sides.
“A lot of marketplaces don’t have the same luxury of having so much overlap with both sides. When you think about Uber, the drivers and riders are often very different personas. But on Pickle, 67% of our owners are also customers, so we have a ton of overlap there where people are using it on both sides.”
So we did some of that at the beginning, and then in order to hack the demand side to make sure that the rentals started to go, we literally helped fulfill all of the rentals, and in the the first like 2,000 of them, we did the deliveries. Brian and I were the couriers, so we wanted there to be that door-to-door delivery option that is so amazingly available today through professional courier networks that we integrate with. But the first Pickle couriers were Brian and I helping make sure that those rentals happened, making sure that was a really good experience. And that's what we did, day in and day out. You remember the days of, “Okay, last week we got nine orders. Let's get ten this week” You just get one more at a time and you start to compound and grow from there, but you start with these really, really, really small numbers.
“You remember the days of, “Okay, last week we got nine orders. Let’s get ten this week” You just get one more at a time and you start to compound and grow from there, but you start with these really, really, really small numbers.”
Lauren Stenger: Yeah, and over the past few years since then, Pickle has achieved so many amazing milestones and accomplishments. So reflecting on these past few years, what has been an especially meaningful milestone for you personally? It doesn't have to be like a conventional, we hit this many sales or whatever, just looking at your time with Pickle, like what really stands out for you?
What has been an especially meaningful milestone for you with Pickle?
Julia O'Mara: There are so many milestones that you think of that are so traditional, like you're saying for your business, the first time we had an external investor believe in us, because we had so many no's, so many rejections. And the first time an institutional investor came in and gave us capital was like two and a half years into building, like you're so far into the process. That was a crazy awesome, a three million dollar check, that was amazing to get that, and then you open an office and you you hire your first employee, or we opened a store in the West Village, like these very, very cool moments.
But one of my favorite milestones or moments, I think, was this turning point of. I remember the first time, this is a couple years ago, where I heard people talking about Pickle in the wild without me going and talking to them about it. Because I was personally using myself as like a marketing billboard. I would always wear something that I rented on Pickle, and I would try to wear something that was kind of extra, so hopefully, if somebody liked it or thought it was nice, like they would say, “I like that, where'd you get it?” And then I would tell them, “Have you ever heard of this company called Pickle? It's like so great”, shameless plug for the company at all times. But I remember hearing about it one time, in the wild, and I wasn't even the person that had brought it up or anything. I was Whoa, this is real this is really cool. People are actually starting to talk about this, and it wasn't one of my friends, it was a stranger at a bar or something.
Then in probably like the same year, there started to be this turning point of for the first couple years of building the business, every time I talk about Pickle, I'm explaining it and I'm talking to people and I'm saying, “I’m building this company called Pickle, here's what it is.” And then there was a turning point where now when I go, “Yeah, I'm one of the founders of Pickle.” I don't have to explain what it is because people know already, which is a which is definitely a huge turning point of brand awareness and the way that people are starting to use it so much more regularly or hearing it used as a verb of like, “Yeah, I Pickled my dress tonight.” I'm like, Whoa, that's so cool that you're referring to it as the rental and not just like the onion food. It's so good.
Lauren Stenger: Even for me, like I've been in college the past four years and I've kind of seen the evolution too. I feel like my freshman year people weren't talking talking about it, but I feel like more so last year or something, I’ve noticed a lot more of the girls in my sorority at SMU being like, “Are you gonna Pickle a dress for the jungle party this weekend”, or whatever. So it's cool to see that evolution too through a user's perspective.
Julia O'Mara: Yeah, I love to hear that. No SMU is popping off, so that's that's awesome.
Lauren Stenger: Okay, so now I'm gonna switch gears a little. Looking at your career trajectory from the outside, it looks like you are a super ambitious person and you've done a lot, you know, being a student athlete in college, studying engineering, Blackstone, starting your own company. Very impressive and admirable, but I'm sure at times things get a little hectic inevitably with just having a very busy schedule. So are there any kind of practical tips or things you do in your own life to manage those stressful or unusually busy periods?
What are some practical tips that help you stay grounded during hectic times?
Julia O'Mara: Great question. I am continuously learning about best ways to balance all of these crazy things in life, and I'm open to tips as well if you have any about the the best things to do there. I think one theme aside from like ruthless prioritization in my life of figuring out, and this is something that happens within work all the time. You have to ruthlessly prioritize and figure out, you have very limited resources, you only have so many engineers with things to work on, or whatever that might be. You're always trying to figure out like what's the most important thing that's gonna move the business forward.
It's kind of similar in your life, and often certain things are gonna stack rank higher than others. You have to sit down with yourself and think about where does this sit in importance and making that extra effort. Last night I had a friend who's had a goodbye party, and it's a Wednesday night and I had so much work to do, but I really wanted to go and and say bye to her before she's leaving New York. That was something that was like a top priority for me, even though things are a bit crazy at work. But it's something that you do even if it's not always ideal.
And then you do have to make sure that you're thinking about who are the important people in your life that you can spend a lot of time with because you won't have as much time for massive groups of friends and spending a ton of social hours while building the business. You make a lot of social sacrifices for sure, and the friends that are sticking by you and understanding that your schedule is crazy are like the ones that you should really keep and invest back into.
One of the things I try to remind myself every day, and something that my grandmother would always say to me is, her quote was, “You are the most important person in the world to you, and you have to make sure you prioritize that.” So that for me is like if I can do one thing every day that's just about me, I have to make it happen. For me a lot of times that's like movement of some form, whether it's a walk, or right now I'm training for the New York Marathon, which is really fun and and exciting. So I'm gonna run that in November. Every time I'm prioritizing and doing one of those workouts, I'm like this is for me. If I can make myself a little bit better, then I'm gonna be better in all these other functions that I'm doing throughout the day.
Lauren Stenger: So now I'm gonna pivot to a little bit more personal. I saw that you have a twin sister, and I also am a twin. So I just had to bring that up. Something I was thinking about in regard to Pickle and being a twin, it's growing up, borrowing stuff from people is just second nature. My twin and I are the same size, we're identical. So our whole lives we shared a closet, we've borrowed everything. So I feel like that's kind of a natural progression. So what was it like growing up with a twin?
What’s it like being an identical twin?
Julia O'Mara: Love that you have a twin. I love being a twin. Love my twin sister. She is my absolute best friend. It's funny that you say the the sharing the clothes and everything. It's so fun because you're like, double the closet. We went to school together. Did you guys go to school together?
Lauren Stenger: Yeah, so Kate and I went to boarding school together and then SMU for two years.
Julia O'Mara: Okay, cool. We went to school together and I remember at the end, because she moved to Philly and I moved to New York right after school, the separation of the closet was like a war, you know? So you're like figuring out where these clothes are going to which person and everything. Because alternatively we'd just be sharing them all the time. Now we are in two different cities.
I'm so grateful that that is how I grew up and having a built-in best friend. I said this at her wedding, having a built in maid of honor of knowing that that's gonna be your person is so cool and very fortunate that we're so close that way. We are very similar, so we really did like everything together, we played all of our sports together, we both played lacrosse at Penn, and our main divergence started to be when we were thinking about what we were doing professionally. So she's resident right now as an orthopedic surgeon at Jefferson in Philadelphia, so she's gonna be a foot and ankle surgeon. That is a very different thing that she is working on compared to what I'm doing right now with Pickle, but we have a lot of commonalities and similarities in work ethic and the ways that we love being really busy and having a lot of things going on and everything and we definitely are each other's number one fans. I'm sure that's the same with you and your sister. And it's actually really funny because my twin's name is Lauren.
Lauren Stenger: Really? That's so cute, I love that. Yeah, that's exactly how it is with my sister Kate. Growing up, we did everything together: sports, same friend groups, everything. But then I feel like we kind of experienced what you experienced in post grad a little earlier because when I transferred to Cornell, that was the first time that we were apart from each other. So that was kind of a hard transition. But now she's moving to New York, so it'll be really fun. And she's pursuing fashion and data science. So we're also kinda doing separate things, like you and your sister.
Lauren Stenger: Is there a particular Pickle rental that has been your favorite or most memorable, or maybe a recent one?
What is your most memorable Pickle rental?
Julia O'Mara: So many good rentals, and I'm actually wearing a Pickle top right now because I had to get a headshot done earlier. I rent all the time. I'm obsessed with it. One rental that it was just the coolest piece that I've ever worn was, Pickle was partnering with Gorgie. Gorgie was hosting this really fun Alix Earle community event in Miami, and we were working with them as their dressing partners. So we made a really fun lookbook and everything for people to be able to rent their clothes for that night. It was this really cool casino themed party.
And I remember I was like, “I have to wear something really cool. Alix Earle’s gonna be here.” I rented this very sick, vintage, one-of-a-kind Ema Savahl dress from a lender in Miami. Her name's Elaine. She has the sickest closet ever. And I wore it that night to the party, and it was so awesome because I was getting so many compliments. But most importantly, Alix Earle gave me a compliment on my dress, and I got to talk to her about Pickle. And I was like, this is very cool. My dream of getting her closet on Pickle is coming hopefully to fruition at some point. But yeah, that was a that was a fun one because I was like, if you get a compliment from her, I feel like it's a good dress.
“But most importantly, Alix Earle gave me a compliment on my dress, and I got to talk to her about Pickle... My dream of getting her closet on Pickle is coming hopefully to fruition at some point.”
