Influencers, Community and IRL: Growth Strategies Behind Our New Favorite App

0:00Hey, business besties. Welcome back to the Female Founder World Podcast. I'm Jasmine Garnsworthy. I'm the creator of the Female Founder World universe and the host of this show. Today, I'm chatting with Julia O'Mara, the co-founder of Pickle. Welcome to the show. Thank you so much for having me. You are now entering Female Founder World with your host, Jasmine Garnsworthy. For people that don't know Pickle, tell us about what you're building. Yes, Pickle is a peer-to-peer fashion rental app where women are renting their clothes to and from each other. You can kind of think of it like Airbnb, but for your closet.

0:31and it's a great way to be able to wear something one time in a super circular sustainable way and then monetize the pieces in your closet that you aren't ready to sell or donate. So the idea first kind of like came to you a few years ago 2020. Talk me through what that time was like and how you thought that the world needed something like Pickle. Yes the idea came in a bit of a roundabout way. We actually had a different company before we pivoted to this rental marketplace So the long story short is I met my co-founder, Brian McMahon, when we were working back at Blackstone as product manager, business analyst with their fundraising team.

1:09So doing a bunch of data analytics and working with their fundraising teams on different analysis for investing decisions. And we left Blackstone in spring. It was April 2021 to start the first version of Pickle. It was actually called Pickle Poll. It was a social polling app where people were crowdsourcing opinions to make better purchase decisions. So if you were in the market to buy something new, you would post a poll to your community and they would vote on it and help you de-risk that purchase. So if you were deciding between buying a dress, you might say, should I buy option A, option B, option C, etc.?

1:45And what we saw was that people were using those polls in a bit of a unique way. They were commenting and recommending items from their own closets and even commenting and saying, oh, you don't need to buy that. You could just borrow it. And that was really interesting. We were not expecting that from a polling app, but it gave us a lot of conviction to look in the rental space. And obviously, borrowing items from people is not something that's not new. We've done it with our sisters, our siblings, our sorority friends, girls in college. but it isn't something that has really translated in the professional world.

2:19And so we saw that gap in the rental space where no one's really tackled that peer-to-peer model where you're literally circulating items that are already existing in your community. So we had a lot of conviction in that. And so then we pivoted over in May of 2022 and have now been building it since then. Wow. Okay. So you ended up raising some money from friends and family to like get this started. Was that when you were doing the polling idea or once you pivoted? Yes, we raised around$250K from friends and family, which was an interesting process. It's interesting to ask people in your network for money, but we took that process very seriously with a full pitch deck.

2:55And what was really important about that time of fundraising, what I would recommend is thinking about the people that you are going to be raising from in that kind of round are people that are like, it's okay if this money doesn't go anywhere or if this is potentially lost. they're investing at the end of the day of course they have to have some conviction in your idea and everything but they're investing in you as founders and so that's definitely where we found the most comfort that our friends and family the people that believed in us then were investing in us as founders first and that we would be you know resilient enough to get to that business that was gonna be working okay so talk me through the pivot and how you how you kind of like executed did that relaunch?

3:36$250 ,000 to get started. Like it sounds like a lot, but when you build one product and then you're, you know, pivoting and building something else, like that money's going to go really fast. Yeah. We ended up spreading out that 250K for almost two and a half years. So that was a very, we thought we were scrappy when we first got started with the polling app. But then when we were doing the pivot, we had already used a good amount of that capital on that first version. So we were really tightening our belts. But we had also had so many learnings from that first app that we were working on. I think a big fallacy that we had at first was build it and they will come.

4:15Both of us are product people. We are data driven, but we have been learning all of our growth and marketing skills on the job. And that's really in my side of the house. And so I've fully learned some different strategies and techniques there. And that's definitely something that we tackled much better when we did the pivot. So when we pivoted in May of 2022, we had shut down the first version of the app, retooled the platform really, really quickly and launched a new version of it in like three weeks. And we did that because we wanted to get something in the market immediately so that we could start learning.

4:48When you are going through a light beta version or you're going through something where you can't test it at a large enough scale, it's really hard to learn. and so we had to get something out there and we had to figure out how are people even going to think about using this new rental app that we were working on and so when we launched it then we had three key things that we were focusing on one looking to build really high quality supply on the marketplace so like great clothes great clothes for people to rent exactly we can't tell people to come rent unless there are items for them to rent on the platform so that was the first thing we were focusing on we had a really interesting creator and influencer strategy that we started off with we were also focusing on convenience even from the early days of the rental marketplace we thought people need to be able to have access to these items at their door we want to pickle to feel like a true extension of their closet so brian and i of course we're like we have to have door-to-door delivery or else people won't be able to get these items fast enough but we didn't have any money to be able to build out the technology to integrate couriers or to pay other couriers so brian and i were the first Pickle delivery people.

5:54We were the couriers, which was a very interesting time, but we were hands-on meeting our customers at their doors. And then the last thing and the third pillar that we really focus on is community. And that's just the whole building of trust and reliability with Pickle. Before we kind of had this interview, I was looking through your story and I read that you and your co-founder did like 4 ,000 Subway rides to deliver that product, which I just think like I love that it's just so relatable it was it was so challenging at the time because we were spending so much time doing deliveries so there's no wi-fi down there there's no wi-fi there are the New York people that are on the subways you are we would it was good because at the beginning when we would do the deliveries we'd get really excited because we were super low volume and be like oh my gosh we had our first customer that wasn't one of my friends you know then all of a sudden we were getting a few more deliveries a day.

6:49And then all of a sudden we had grown enough where we were doing deliveries from 7am to 9pm. And then you have to work on building your business outside of that, which is obviously challenging. And then you're physically drained from running around the city all day. I think my longest day I was, I had 22 miles marked on my, on my phone for how many things, how many miles I've walked. It's a marathon. Almost a marathon. So didn't run that last weekend, but maybe next year. But it was the best part of the delivery experience was meeting our customers at their doors, literally. So we would go and talk to them and you're picking up an item from a lender and bringing it to a renter.

7:27So at both doors, I would introduce myself and they would be very surprised to see me. You are not a courier. Yes. Well, I am one of the founders of Bickle and I'm your courier today, but hopefully not in the future. and I would ask how they heard about pickle and then any feedback that they might have and then on when we were doing that would be on like the delivery side of course on a return asking about their experience and how they how they liked it and what they were wearing their rental to and what they were doing with it and then it was helpful to also understand the way that pickle was starting to spread amongst the community so we would start to see the network effects in action because we would go and I would meet somebody and I would talk to them and they'd say, oh, my friend Hannah referred me or talked to me about it.

8:11And I would know who Hannah was because I had done a delivery with Hannah maybe like a few days before and realized that these circles of friend groups were starting to really talk about their experience and loving their access to these items. Last minute. Okay, business besties, I want to just pause for a second. I've got Natalie here on the Female Founder World team. And I want to ask, Nat, are you ready for the holidays? Honestly, no. And I feel like it's coming up so quickly. It's coming up so quickly and that's why I wanted to take a second to chat about this season's presenting sponsor, Vistaprint.

8:44It's honestly the best place to start holiday shopping and right now Vistaprint is giving all female Founderboard listeners an early holiday gift, up to 50 % off holiday cards, wall calendars and more. Oh wow, 50 % is a pretty good deal. How do you even have time though for all this holiday shopping? I know, honestly, like I'm usually pretty disorganized, but I've been quite on it this year. And we've also been sending out these really cute thank you packs to different founders who have been on the podcast, speakers who have been at the events. We've printed really cute, like little fleece blankets.

9:20We have embroidered caps and also stuff for my family as well, because you know, everyone's going to be wearing the female founder world merch. Oh, of course. You got to bring the family into it. And I personally love a branded tote bag, but I also didn't know that they did embroidery. That's pretty cool. The embroidered caps are particularly cute. Oh, I love that. Highly recommend. So everyone, go and get your holiday shopping buttoned up with up to 50 % off custom holiday cards, wall calendars, and more at vistaprint.com. Use the code HOLIDAY50 at checkout. Okay, let's get back into the show.

9:52You mentioned before like a micro-influencer strategy and you've been following this, I think, kind of like the whole time since you made this pivot. What is that? And what advice do you have for anyone else who wants to tap micro-influencers to build their brand? When we were thinking about the creator and influencer strategy, that was a very big supply play for the marketplace. So obviously getting the best quality items onto the app, we had to think about who has really great closets, who has maybe a little bit of excess pieces of clothing, and who is really obsessed with fashion and style.

10:25and those are the fashion creators that are in New York City. People are literally following them for inspiration on what to wear and what to buy. And so that was the very first strategy of getting people to upload items onto the marketplace. It's very manual, very not scalable at the beginning. And that is definitely a piece of advice I would give. A lot of things that you have to do at the beginning are not going to scale, like doing deliveries yourself or like manually working with each creator that's getting onto your app. So there would be a few of the first girls. I would FaceTime with them and help them upload their first items, walk them through every single step.

10:59We had a creative idea that was piggybacked off of Airbnb's playbook where we wanted to make sure that there were really high quality photos on the app. So that when people were shopping the different Pickle rentals, they would see people in beautiful UGC. These pictures that would basically be translated from Instagram to Pickle. And so we would host these scrappy photo shoots in Soho. we would invite any micro nano influencer that would respond to a dm and i would stand on a corner with an intern who was kindly volunteering and with a green balloon and a photographer and people would show up and say all right we're going to do some street style photos in soho bring an outfit bring in a change of clothes so that you can have two different instagram photos and then also have two items that we're going to help you upload on pickle and so that was a supply strategy that we started with.

11:49The nano and micro creators seen in New York is also pretty tight knit. They go to a lot of different, a lot of similar events. They're friends with each other. And so word of mouth also started spreading amongst that community. And then kind of the final point on that was these creators also are going to tons of events. They need to wear a lot of different outfits. So they were very interested in, of course, monetizing their closet on the lender side of the platform, but they also had a ton of rental use cases. So they would need a last minute outfit to go to a red carpet event or to go to a last minute birthday party or a brand activation.

12:23And Pickle was now a solution for them too. So we use them or worked with them on both sides. Then in December, 2022, so you're still not a very old brand, but you tapped your first like macro influencer, your first big influencer. What was that experience? That was an amazing experience. It was Audrey Challenger and we had been doing a lot of outbound outreach. Now we get a lot. So you're just DMing. We were DMing a ton of people. The response rate was very low, but that's what's expected at the beginning. And I would say, don't be discouraged by that. That's very normal. My tip would be to play around with your hook of your first four words that you get people to actually read your DM that you're sending.

13:03What do you say? Usually we'll say something like keep the intro not like hi this is julia from pickle and say hi exclamation point saw you're connected with or saw and try to just introduce something that would hook them into reading the rest of the message yeah and it might be from one of the first micro influencers that we were working with that they were friends with or followed on instagram and just wanted to build that mutual connection and a bit of social proof we're trying to build that social proof with the app in the early days. But working with Audrey and we she kindly, you know, got coffee with me in the in Midtown East, where one of her first apartments was in New York.

13:41And I think she was just super open to a new idea and very receptive to something that could be pretty game changing for her closet. She had some really cool pieces that she said, OK, these could be cool to share with some people and make some money off of them. And then I remember she was talking about a few different brands that she was interested in accessing. And she said, oh, just let me know if you guys get some of this on your platform. And so then I started to see some of the demand of really cool, unique items or brands that these influencers would want access to and not have to spend$800 to be able to wear that item.

14:11So was that a paid partnership or totally organic? No, that was organic. She had kindly responded to one of our DMs. And our entire strategy with creators is working with them in a strategic lens and with something that basically adds value without us paying them. And so their value is they make money on pickle by lending out their pieces. And they also see direct return when you put a little bit more investment into your pickle closet, whether that's uploading some additional items to your closet, whether that's sharing with your followers that, oh, I just wore this outfit out to this last event and now you can rent it on pickle they'll see that result in rentals and they'll see that result in followers of their closet on pickle and so there is this nice positive reinforcement mechanism where the more they put in the more they get out of it on pickle so that's what we focus on we work on hey let's make your closet amazing let's do a closet drop let's do a campaign we're going to tell our audience about it you should tell your audience about it and before you know it you'll be paying your new york rent with your with your closet that's amazing and and i was looking through some of the stats that you and your team sent through before we had this conversation.

15:21And like people are paying their rent with through Pickle, like they people are making true serious money by being suppliers on this app. Yes, it's, it's something that I mean, when you're building something like this, you're not sure how invested people are going to get. And obviously, there are some of these creators and influencers that have access to amazing pieces. And they're where they have to wear a lot of items for these different events and occasions, but they make up a very small portion of the inventory on the app. It's less than 2 % of the items on Pickle are in influencer closets.

15:54And they aren't, most of our top lenders are not influencers, the large majority of them. And so these are women that are really passionate about fashion. They've invested in some high quality pieces. They are almost ahead of the trends. They know when something is going to sell out. They know when, they know that Miracle-A is going to be trending for the holidays and they're on top of those drops ready to invest in that piece of inventory and then start circulating it and they actually profit off of that item. Amazing. I want to talk a little bit about the tech piece of this because your background, you're not an engineer and you were pretty scrappy when you started.

16:31You've raised more money now. We'll talk about that soon. But how does someone go about building a product like this? Yes. Brian and I, when we were starting, there were a few different options of how we would actually build the technology. And a few of them, one, we could have tried to find a third technical co-founder. Two, we could have used all of our money to hire a software engineer and build out and develop our app. Or three, we could have tried to use a no-code platform and build it that way without as much flexibility as when you are custom coding something. Fortunately, Brian was very excited to be a self-taught Pickle developer.

17:09and so he actually learned how to code specifically for Pickle. So he is not a trained software engineer, but he is a Pickle engineer and I would say still knows our code base better than anyone else on the team. That will change as our engineering team is growing and evolving. But that was something that we made a very pointed decision of we wanted to be super flexible and iterative and so we decided to be the self-taught developers and I was a self-taught designer and we built that app together ourselves. I think that is definitely a challenging route to take. Obviously, you're building from scratch and you're learning as you go, but we were so quick and scrappy with iterations.

17:49That's why we could retool that platform, our first app, in three weeks. And it's why when we have a really good feature idea, we could think about it today, design it this morning and then release it tonight because we can be super agile that way. What are some of those no-code tools that people should check out if they want to build something? do you know them or should I actually be asking you a crowd founder or you're in it as well we don't use any of them is my problem there's I want to look it up on my phone I think there's one like it's called like bubble oh yeah yeah yeah um we have not used it yeah because we have been able to use our own custom code we use AWS um for our back end and our front ends built on react native but we haven't used the no code platforms I've heard great wonderful things about it.

18:35And I think it allows people to get something into the market really quickly. But we I can't personally vouch for them. Okay, good to know. I want to fast forward to the middle of like 2023 last year, you raised your seed round. How much did you raise? And what was that process like? We raised$8 million, which was a lot we basically went from zero to 8 million. Wow. The process for that was definitely challenging. Before we went out to go and raise that seed round of capital, we were looking to raise a pre-seed round. Most people don't go from raising a family and friends to then raising a pretty large seed round.

19:12But we had a really hard time in the market raising a pre-seed round. We were going out and trying to raise one to two million dollars. We were going out and talking to investors and they would say, all right, here, hit this level of traction, hit these numbers and come back to us. And either that was the answer or we would get a ton of no's of we're not interested in your space. People have tried this before. It doesn't work, whatever it might be. And so we got a ton of those no's immediately. That's normal, by the way, in case anyone was wondering. And when we were going back out and we were starting to build traction, we had seen some amazing organic growth.

19:46We were starting to see, we were seeing consistent double digit growth numbers month over month. And we were seeing this all amplified organically on socials or through network effects within our own community. And that was very promising. When we were going back out with some of this additional traction, then we weren't at the right stage for some of these pre-seed firms. We were almost a bit further than that in the sense of how much we had grown at that point. So then we just thought, well, let's just go try to see if we have any reception for raising a seed round. And so we ended up kind of reformatting our pitch check a bit and went out for that and had some success there, which is great.

20:23We've raised from Kraft Ventures and Firstmark as well as Burst Capital. Those are our three main investors. I want to know what's in that deck. What's in that deck? Tell me. I mean, mostly a lot of numbers and graphs and then a bit about our story, of course, and all the things that we've been doing to build the momentum and kind of that product market fit that they're seeing. I think our investors were really, really excited about the retention that they saw. So that was something that we didn't have on the first app that we built. You can get you can get people to download an app, but if they don't come back and consistently use it, you're clearly not providing enough utility there.

20:59And so that was a big learning that we saw within our polling app, but that was entirely different on Pickle. And it was interesting because even the early days, we saw that kind of retention. We might've had our first 100 customers, but they were coming back and they would be renting again and they were consistently using the app. And that is where it was pretty clear that we had something a bit special there because people found it sticky and they were excited to come in and try the rental process again. And they were telling their friends about it. And that's where we started to have that early indication of product market fit that we had not seen with the previous app.

21:37I want to talk about community building because you mentioned that that was kind of, you know, that's one of the pillars that has helped you grow Pickle in a really tactical way. Like what are some of those things that you're doing boots on the ground, like build community? Because you're also, you're in this like very different kind of space where it's location based, right? So like I'm guessing IRL and having a physical presence is important for that. Absolutely. And it's definitely something that we have been investing in. And it's something that is sometimes hard to immediately measure that ROI, but it's something that pays off in dividends as you are growing your community and learning about the way that people are talking about your brand and spreading the word for you.

22:20When you're, when you invest in that community, people become your organic ambassadors. And those are the best people to be talking about your app. Paid ads and paid channels are never going to have the same return as a best friend referring their friend to go and use your platform. And so we've definitely invested in community. We invested early days, obviously talking to our customers at their door. That was a very important part of the process. We also, were incredibly hands-on with every single one of our customer support cases. Brian and I also did all of our customer support at the beginning.

22:50So we heard every single problem and every single qualm that somebody had with the app that allowed us to be very iterative and improve, of course. We also met our community in another form there and made a lot of remedies if something would go wrong at the beginning to improve the app and also just to mitigate that situation. But since raising capital, we've also continued to invest in community. And one of the first things that we did for that was we actually opened a storefront in the West Village. And you can find it 21 8th app. We had a little meet up there. Yes, had a meet up. So fun. And it is a great place, of course, to be able to go and rent in person.

23:27You still use the app. You just use the handoff method. So instead of having something delivered to your door, you can just pick it up from the store and then bring it back to the store or have it delivered back to the store. That location is an investment in our community. It is a place where we meet people in person. We have panel events. We have different community activations. We work with other brands collaboratively there. We host some cool creator closets there. They'll do some meet and greets there. But that is number one, first and foremost, an investment in our community and marketing and meeting people in real life.

24:00Something that we have seen at the store is that we are able to learn and receive feedback from people that we would never have access to just going through the app. At the store, there are tons of people that come in and they've never heard about Pickle before, or they might've heard about us, but they didn't have enough conviction to download the app yet, or they haven't tried a rental yet. And we get to ask them why they haven't, or what was their hesitation, or what were their questions that they have. And that is not something that we would have access to without that physical space, because on the app, someone has already broken that barrier and decided to actually download and sign up.

24:34When we did our event there, I met your team. And I'm guessing before you raised that$8 million, you didn't really have a team, right? Right. So what do you do? Like, you know, the money hits your bank account. What's the first thing that you spend on? And who did you hire? First thing we spent on were a few employees. We had kindly had some people. So yes, it was Brian and I for a long time, just us two as our full-time employees. but we had some people along the way that were really passionate about our brand and kind of put in that sweat equity when we couldn't really afford to pay them and so two of our first employees were interns that were working with us and were putting in that sweat equity and had kind of invested in pickle along the way even though we unfortunately didn't have the funds to be able to bring them on as a full-time employee or really compensate them the way that we wanted to and And they had been people that were sourced from our community, which was cool.

25:34So our first hire, Susan, who has worked on the growth marketing side of things, she is now kind of our TikTok guru and working within our paid ad strategy and performance marketing. That has been a really great supplemental way to boost our organic growth that makes up 80 % of our growth. And then Madeline, we brought on as our first customer experience. And now she does customer experience hire. She now does some product management with us as well, but she has fully helped build out and scale our support team Which has been an amazing amazing value add. How many people are on the pickle team now?