Scaling SidelineSwap As A Leading Resale Marketplace With Brendan Candon | EM Group Chat #181

Welcome back to Everything Marketplaces, where we talk about founders and leaders from some of today's top marketplaces. So this is episode 181, which is really great group chat that we just had with Brendan Cannon, who's the CEO of Sideline Swap. Sideline Swap is a leading online marketplace for buying and selling sports gear. They've been mentioned on A16Z's Marketplace 100 list as one of the fastest growing marketplaces, and they've also raised over $18 million in capital from investors like 500 Startups, FJ Labs, and eBay Ventures. Brendan was also a past group chat guest. This is great to welcome back on. And we started off with a quick refresher on the founding story and first steps for starting Sideline Swap, what some of the early challenges were. We got to learn more about how it's evolved and scaled. We did a deep dive into it as a leading resale marketplace today. We got to learn more about the resale partnerships, recent growth. We discussed how they're leveraging AI, and we also had a great group Q&A. I really enjoyed this conversation. You're going to find it a great watch to the end. So, Baron, I mentioned it to you right before we started recording, but you've been highly requested as a guest again after our past group chat. So I'm really excited to have you join us here today. I want to start off by saying huge thanks for taking the time to do so in advance. So we have a lot that we're going to dive into with SidelineSwap and your recent growth. But before we do, I think it'd be great if you can start off with a quick refresher on your background and also for those that have just joined us here.

Thanks for having me back. I started SidelineSwap about 10 years ago now. For us, The, the idea came out of a personal problem. I grew up with a garage full of sports equipment, so I ended up going on playing lacrosse in college and coaching for a year. But after graduation, had to buy some new equipment. I'd forgot how expensive the equipment could cost, and rather than spend $500 on a new set of, of equipment for men's league, ended up buying some gear off a friend of mine. And the 2 of us started talking about why it wasn't easier for athletes to buy and sell their gear online. This is like 2012, 2013. And so at the time, we obviously some buying and selling was happening on eBay and on Craigslist. We felt like eBay was focused on professional sellers and really hadn't catered their experience to peer-to-peer. And then a lot of vertical marketplaces were starting to pop up. So Poshmark, Reverb, StockX were all starting to gain momentum. And we felt like it was a multi-billion dollar sporting goods or a multi-billion dollar category on eBay and that there should be a vertical marketplace in sports. We didn't have background in tech or ever worked at a startup, but we're excited about the idea. And so we ended up trying to just get it going and we kind of talk about how we went from like 0 to 1. But the, you know, the idea in the beginning was just to like address that personal pain point and go after an opportunity that we thought made a lot of sense and try to solve a problem for customers like us. So we could get into it from there. But that my background like is not your prototypical like drop a perfect marketplace founder. I didn't work at a big marketplace before this, but learned a ton along the way and find marketplaces fascinating. And obviously we've had a pretty good run so far.

No, that's, that's great. Thanks for sharing with us. And it's really cool to, you know, go back to the founding story as well. So, you know, when you, when you were just getting started, you know, what were some of those biggest challenges that you faced?

Yeah, I think like all marketplaces, we had to solve the chicken and the egg problem. So for us, we built, you know, a product, like an early version of the marketplace and, you know, people could list, they could message, they could buy. And you know, through the marketplace, although it got, that got a lot better over time. The, but to solve the initial chicken and the egg problem, what we did is we were pretty well connected in certain sports. And so, you know, having played college lacrosse, we basically went to our buddies who had just graduated from top programs and knew that that was highly desirable inventory. And so we basically used that to seed the marketplace. So we launched with like a dozen or so recently graduated college athletes from top programs, each listing like 10 to 20 items in their locker. And, and so that seeded with like initial set of supply. Then we took that inventory and there was a lot of the buying and selling was happening on Facebook groups and forums at the time. And so we would take those listings and basically go post them into the Facebook groups and forums where there was some existing demand. And we were kind of acting as the seller. So a little bit of catfishing of acting like these top college athletes saying like, hey, I'm selling my Maryland lacrosse gear on Sideline Swap. Like, and we would kind of basically have that chat on the forum and then pull them over to the marketplace. What happened was, as we started to pull in some of those really, you know, the people that were buying and selling on forums, were dealing with a really high level of friction in order to get access to the inventory that they were interested in. So we felt like we could get them into a more frictionless marketplace experience. We could really expand the pool of even that initial group of buyers and sellers. So we'd bring the buyers over, usually they're like high school athletes who were like following those college teams and they would say like, oh wow, this is where all the college players are selling their stuff. So the product then converted them from buyer to seller. And so a dozen or so sellers turned into hundreds and then thousands kind of over the course of the first summer listing tens of thousands of items. And the way we always thought about that was there's a huge pool of demand for high-quality used sports equipment. I think people are always looking for a good deal and are open to shopping used. There's a lot smaller group of people who are thinking explicitly about selling. So our marketing strategy is typically, as we've scaled, stayed consistent with let's go find people who would be interested in this as a buyer. And then once they get to the product, start converting them to seller. And so once you, you know, you make a purchase and you go through the chat, you're like, wow, this is pretty easy. You know, my item came quickly. Maybe I should try this too. I have a lot of gear in my garage that I could sell. So that was kind of how we got things going. And then over time we evolved from, you know, we went from really focusing on one sport, which was lacrosse, because that's where we had the connections to. But I think the concentration on one sport initially was important. If we had tried to build a marketplace for all sports on day one and had, you know, a couple hundred items spread out across every sport, you might come in and shop for hockey gear and see 3 items and be like, oh, this, this isn't a good marketplace. But we concentrated our efforts on supply and demand in a single category or like subcategory. So that way when, you know, we, it was always set up to be a sports marketplace and there was taxonomy set up for some of these other categories. But if you came in initially, we knew we were driving like 90+% buyers and sellers into a single category, which created a high level of liquidity for, for within that niche. And then as we got momentum going there and got that flywheel going, we went into and basically replayed the playbook in hockey and then baseball, golf, lacrosse, or golf, skiing, snowboarding. And we've continued to expand out. Now we have like a ton of inventory across all sporting goods categories. But it was a similar playbook. In some cases, we stayed with like the college athletes. In other cases, we found power sellers who had aggregated high-quality inventory and were still selling on Facebook or forums. But in almost all cases, we tried to find unique inventory. We weren't just moving inventory from eBay to Sideline. We felt like that wasn't a differentiator. And when we've tested that, it hasn't performed well. It's always been like, how do we go unlock inventory that otherwise isn't being sold and discoverable online, bring it into a marketplace experience, drive buyers to it, and then unlock more supply from peer-to-peer as we go. And we, we could explain how that's kind of evolved from peer-to-peer To, you know, eventually we did find more of those aggregators across other sports. And then more recently, we've kind of, we'll get into our trade initiative where we do some of that aggregation ourselves. But, you know, again, it's always the same playbook of how do we build a good experience of high-quality inventory from day one so we could drive buyers into that and then convert those buyers into sellers.

Yeah, there's lots of great points that we're gonna get into that you mentioned. I guess I wanted to, you know, highlight the point as far as like, you know, the importance of the unique supply right from the very beginning.

Yeah, I think I kept saying that, right? High quality, unique supply. It's not— yeah, we're saying that for a reason. I think what we've seen is if you just shift inventory from one marketplace to another, it's not that interesting and you're not really differentiating yourself from buyers. And we have a couple of categories where we're still trying to figure out how do we differentiate. Maybe there is more used supply from a competitor or or eBay has better aggregate, better supply there. If we are just offering the same type of supply at the same prices and the same experience, it's much harder to grow. But when you're competing, you know, against your, you know, your own, you're not competing against anyone because you're the only one who's aggregated the inventory. It's a much different ballgame. And we've also always tried to start with that high quality, like aspirational inventory the way we think about it. So like in sports, there's a franchise of stores called Play It Again Sports. They have about 300 stores. They're good big business. I shopped there a lot growing up and a lot of their sellers sell on our platform, but the inventory in their stores is typically the like lower tier. It's not like from the premium seller. And I think then you associate the whole experience with that type of inventory where if you can, you know, like I think Airbnb does a good job with this and Uber with their black cars, but Airbnb, like you want it to— people when they think about an Airbnb to think about like that treehouse in the woods, right? It's like that unique experience, even if like often it's maybe not that different from a hotel. For us, it's like high-quality inventory within each category, whether it's pro and college gear or some other like differentiated inventory in some way allows us to have an edge when it comes to marketing and building some momentum.

Yeah. And you also mentioned as far as, you know, categories quite a bit here. And if we think about like categories on like a sport, sports level, and, you know, you mentioned like initially kind of starting off, you know, focused on an initial sport, how did you think about, you know, if and when the right time to expand was?

Basically, I mean, it wasn't like a hard science to it, but it was when we felt like the peer-to-peer momentum was starting to build off itself. Like it gets to a point where you have enough supply where you can drive marketing, you could use marketing dollars to drive traffic efficiently and that converts to sellers. And so once we started to see that happening and we could basically just put marketing dollars into that category and that will drive supply and then we can kind of continue to grow the category from there. Our, my, one of my, my co-founder Anthony is like our head of sales and he works closely with stores and resellers all over the country. So he'd go like, all right, lacrosse is working, hockey's working, let's go to baseball. And he might go spend 3, 6 months a year getting to know that category deeply, building it and kind of getting it to the same point and then off to the next one. And we've basically replayed that playbook over and over over the course of the years.

Yeah, we'll probably get into as far as, you know, how you manage categories here a little bit later. But I did want to, you know, learn a little bit more about, you know, how is Sideline Swap as far as, you know, the marketplace experience? And maybe even kind of walking us through that, what that product experience is like, you know, how has it evolved? And then also the business as well, each kind of walk us through.

The V1 experience was you could list. We always focused on like creating the structured data that made sense so that way we could guide sellers through an experience, a peer-to-peer seller through an experience. So that way when the item became available for sale, it had all the details that you needed to make the purchase. I think there's always this balance of friction of like frictionless selling experience. You get the item listed with just a photo, but then no one can find it. And they, when they see it, they don't have any of the information that they need to make a purchase. So we will always try to find the right balance of like, what are the criteria? And it's pretty detailed. I think every category is more technical than you expect that we need in order to create a great shopping experience. Let's guide sellers through that. And then that feeds into the shopping experience. So in the beginning, it was a simple listing flow purchasing. I mean, this is back in the day when like Stripe didn't exist yet. And so you had to use PayPal and go click a PayPal link and go over. What we ended up seeing in the beginning was that messaging was really important. So like messaging kind of lived over here and people could chat between accounts, but they weren't chatting on like an item, right? So One of the big things we did when we relaunched the site in 2015 after the initial learnings was combine a couple of things, but we basically brought chat into the transaction, which is pretty typical what you see now. And the message thread happened within like make offer. You could like do all your swap actions directly within the message thread that allowed people to answer questions that they had to get comfortable buying used equipment. And then the, then there was all the marketplace mechanics in there that really prevented, like, reduced the incentive for you to go offsite, which obviously is something we think about too. Because like you already had the chat, you already negotiated, you make your offer, and now we, we provide prepaid shipping labels to every seller. And the payment sits in escrow with our buyer guarantee. So the payment is made by the buyer. Seller gets a prepaid shipping label, and then the seller can see that they've been paid. They don't actually receive access to the funds until the item's been delivered. So we track the item through shipment. That's our buyer guarantee. The buyer has 3 days to open a dispute if something's not as advertised, and then the funds are released to the seller, and that ensures buyers always get what they ordered and sellers always get paid with as little friction as possible around shipping. We do a lot of other stuff too. Like we, on the shipping side, obviously shipping things can be challenging. You think about shipping golf clubs or skis. And so we know like baseball bats fit in a certain size box. So like we map every category to a shipping parcel size. We kind of set those by default. We do a lot of things around pricing guidance because of all the structured data we have. We've gotten really smart around pricing and shipping. And so that streamlines a big lot, a lot of parts of the seller experience as well. From a buyer perspective, I'd say chat and the buyer guarantee are the big things on top of the basic one I started with, which is like really robust shopping experience. We want to build the best shopping experience in sports, which means shopping on Sideline should feel a lot like shopping on Dick's Sporting Goods or some other retail site. That's best in class. Like we have just as good of a taxonomy, if not better, where you can discover all the same product at the same level of detail that you need with, you know, without, and even though it's from peer to peer, right? Even though it's from an inexperienced seller. And that foundation allowed us to do a lot of things over time. But I'd say like those are the main things. I think now we'll get into some of the AI stuff, but we're doing more with personalization and reducing seller friction using some of the new tools, which I think are really exciting. But yeah, at the end of the day, it's like a lot of marketplace basics and I think it applies across kind of all verticals.

Yeah, that's really interesting to learn more about. And I guess it's worth noting as well, you mentioned the buyer guarantee and it sounds like that was kind of key from the very beginning as well.

Yeah, I think so. I mean, I think you, if you're gonna buy something online, you need to Check off the trust box, whatever that looks like for you. For us, that meant, am I gonna get what I ordered in as advertised condition? It doesn't, like, there's not, we don't have as much authenticity issues because people aren't making fake hockey skates for the most part, you know, like it's just we're in categories where there's not a ton of counterfeits. But I think for other marketplaces, there's different levels of trusts and safety that need to be put in place. And I think we, we did what we thought we've been doing, what we think is appropriate for our category, but that can vary quite a bit by category.

Yeah, no, it definitely can. And, you know, a lot of peer-to-peer marketplaces, you know, supply can tend to kind of professionalize over time. So is that something that you've seen with SidelineSwap as well?

We've definitely seen that. So we're still primarily a peer-to-peer marketplace and like 95% of our sellers are individuals selling from their homes. There's 5% of our sellers who are businesses and they do a higher share of total GMV. And I think that's good. It's a good thing for the marketplace. It allows us to grow faster because they can aggregate supply and supply is always a growth constraint. So yeah, we've seen it. They come in different shapes and sizes. We have, you know, in certain categories they aggregate inventory from golf courses or college teams. Played Again Sports are a big seller on our platform. So a lot of those stores sell through us and use us as their e-commerce platform. So, you know, we want to be the like engine behind e-commerce in sports and, you know, like a Shopify for resale in sports. So we're excited, but we want to enable that while still supporting our peer-to-peer community. And I think like We, we are very conscious of that. I think some marketplaces, and then I think eBay did this at points, like over-indexed to support, like chasing power sellers. And I think there's benefits to that, but then you kind of open the door to Poshmark and Sideline and Reverb because like they built experiences for peer-to-peer. And so we're always like, we want to be a peer-to-peer friendly marketplace. that also works well for power sellers. And at the end of the day, our goal is to provide the best selection of inventory at the best prices for shoppers, right? It's actually a service to the buy side. And so how do we then enable all the selling experiences that we need to be able to deliver that experience to the buyer? But, but yeah, pretty healthy mix. We've built some tools for power sellers over time. to make it easier for them to manage their inventory and get their inventory onto the platform. So that's kind of where things stand today. Yeah.

And I guess a related topic is the resale partnerships. And I know it was pretty early on your last group chat with that. And since then, you've, you know, announced a few new partnerships, you know. So could you maybe share more about, you know, how that's kind of played out as well?

Yeah. So In 2022, we, you know, up until that point, we'd basically been a pure play marketplace similar to eBay. We connected buyers and sellers, we took a fee, we never touched any inventory, but we always felt supply constrained. We always felt like there was more inventory, high quality inventory in people's homes that wasn't making its way onto a marketplace today. And so how could we go get it? And we felt like one of the biggest points of friction for that segment of sellers that wasn't participating was time, that they just didn't have the time to sell themselves and manage listings and go to the post office. So we felt like there was an opportunity to leverage what we built, leverage the pricing data and the taxonomy and all the marketplace foundation that we had built to go enable resale experiences for retail partners and brands in sports. So we approached a couple of those retailers. Dick's Sporting Goods is one of them. And we said like, hey, what if your customers could come into your store and get paid on the spot in a Dick's gift card for the resale value, for the trade-in value of their stuff? And so, you know, they were into that and we kind of formed this partnership where we started with pop-up events. And I think the last time we talked in 2020 was in the beginning of '23. So in '22, we ran like 70 of these events. Since then, we've run over 1,000. So we've like scaled this up super quickly. And the experience is customers can bring in anything in their garage. Usually it's like things purchased in the last 5 years worth more than $100 when they bought it new and still good working condition. We have tech that we've built to price all that stuff on the spot. So we have this like instant quoting tool where you can, we can with confidence decide what is this item gonna sell for based on our pricing data. How long is it gonna take to sell? And so what can we pay for it? Customer gets a gift card, we take the inventory, we resell it first party at higher margin. So we now have this like Poshmark, ThredUp hybrid with some unique twists that make sense for us where we own some inventory first party to pump more liquidity into the marketplace so that way the marketplace could grow faster. I think like the main goal at the end of the day is actually to just let the marketplace grow faster. And we've, we've actually built a premium, like a SidelineSwap Pro tier where sellers can get access to these tools if they want to run events in their community. We're like teaching them how to do it. We want them to compete with us and sell on the marketplace too. The goal is to get more inventory out of people's homes and onto the marketplace. We happen to be doing it as basically like because there wasn't anybody else to do it and we wanted to show they could work and like be really close to the problem and fine tune it. But over time, like if more sellers start to do this and we take a step back, like that's fine to us and we're competing on a level playing field on the marketplace. We're learning what pain points are sellers going through. And so we end up improving the marketplace experience as a result. That event experience has evolved to include a new version of the tech where our partners can offer it in store all the time. So it's like a point of sale integration where they could quote your items in certain product categories and do the trade-in for us. And then we get the inventory and resell it. And then there's a new version launching soon where it's online. So you could go onto like their .com, start your trade online, send it to us directly or drop it off at a store. But the goal is like within a couple of years, anywhere you shop for sports gear, you'll be able to trade in through a brand or retailer that you trust and Sideline Swap will power all those resale experiences in sports. The goal is for us to get all the inventory back onto the marketplace and then grow the marketplace faster as a result. So it's been cool. It's, it's been a really good thing for us, I think. We've partnered with Dick's Sporting Goods, Rawlings, Monkey Sports, Piranhas Hockey, and have a long list of other partners who are kind of eager to, to work with us. And so we're kind of just scaling it up year by year.

Yeah, no, that's really awesome to hear how it's scaled up since your past group chat. So, so you did mention as far as, you know, the kind of Poshmark, you know, connecting buyers and sellers directly or pure-play marketplace model versus kind of like the ThredUp and, you know, taking on inventory. And there's of course like pros and cons to each. But, you know, I guess like how is that kind of impacted Sideline Swap and maybe even just kind of breaking down like an example kind of transaction for each?

Yeah, I mean, I think the Poshmark model is great, right? Like, I think if you cannot touch inventory, take a fee and acquire customers cost effectively, you know, it's a beautiful business model. The managed marketplace owned inventory model or even consignment has a lot of challenges. And I think we've tried to learn from the challenges of some, like whether ThredUp or RealReal, and implement this in a unique way that makes sense for us. I'm not going to give away all of our secrets, but there's a few things I think we do well that I'll talk about. We screen inventory upfront, right? So we don't ship junk. We don't ship things that's not going to sell. I think there's a lot of operational challenges with the clean-out kit. People throw up a lot of, you know, probably I don't know what percent, but a high percent of stuff that ends up in those cleanout bags at ThredUp are things that aren't going to sell. And so they ship things and then have to deal with processing things that aren't going to sell. We screen all that stuff upfront. If it's not eligible for trade-in, it's eligible for donation or like being recycled responsibly, but we don't take it. And so we're only touching things we have high confidence are going to sell. Our sell-through rates speak to that. And then, you know, there's a couple other things, how we do payments and how we do our pricing on top of our secondary market data and how frequently that's updated. That allows us to, again, make sure we're only buying inventory that we have confidence is going to sell. And the payment terms, like there's, there's like things that we do with how we issue payments that help us not have too much inventory, how much money Too much money tied up in inventory. But yeah, I think like if you can have a pure play marketplace, it's great. I do think having a liquidity engine that gets more supply that you want on the marketplace onto the marketplace and doing that yourself does make sense in some cases. We capture, obviously we make a lot more on a first party sale than we do on a third party sale, which that means, let's say our standard take rate's 12%. Let's just say we make 60% on an item we sell first party. As the share of first party sales increases, our blended take rate increases, which then allows us to compete more aggressively in performance marketing channels to drive more traffic, which then can get more sellers onto the marketplace and gets more inventory on. So again, it's like trade-in is in service of the marketplace. The, that end goal is to have a large, you know, the largest and a very large marketplace for sports. And these are all means to an end.

That's great to learn more about. So another kind of topic on that is, you know, as far as like when it comes to partnerships, that's something that a lot of earlier stage founders in the community are always, you know, discussing. So do you have any maybe tips for, you know, early stage founders that might be thinking about, you know, how to approach similar partnerships?

So we did it late, later in our life cycle, right? Like we, we didn't do it on day one and I think it would have been hard. You know, we had built legitimacy, we had built a good standalone business in resale, we had built a trusted brand in our vertical and we were the leader in the space and we had the tech and data to that and brand to then go to these partners and enable it. I think The other, but so like that's where it's like hard to do on day one. I don't think we could have gone after someone like Dick's Sporting Goods, public company, 800 stores on day one. But some of the things that worked well is we found, we tried to create win-win-win scenarios, right? So it's like on the surface you might look at Sideline and Dick's Sporting Goods as competitors, right? We both sell sports gear. But the way we think about it is they sell new sports gear and we help people with new sports or used sports gear sell it so they can get more money to go buy more new sports gear. And we've proven that, that like the people who buy and shop at Dick's every year and spend $500 on a baseball bat honestly probably aren't buying a lot of used bats, but they have a lot of great bats to sell. And so like the trade-in allows them to turn that into cash. to then go spend more money at Dick's. So we try to position this as like, look, it's great for your customer, it's great for you, it works for us. It's a sustainable business model where we don't, they don't pay us, like we make money off our side of the business, they make money on their side of the business and it's a very symbiotic relationship. So I think like that's, that's the key is like where can you find opportunities to help someone achieve their goal, right? That they, they're focused on how do I get more people into my stores? And spend more money each time they're there. We have a tool for that. And so we just focus on giving them that. And then our business model works within that framework. We don't have to like get them to do anything different. And so I think like that's the way I think about partnerships is try to put yourself in their shoes. What is it that they want? And then how do you frame everything about what you do to help them achieve their goal? They don't really care about your goal as much, right? They're focused on themselves. And you need to make sure you think that way when you're communicating to partners.

It definitely sounds like a win-win, and those are going to be helpful tips for founders here. So, so kind of zooming out though, you know, you've definitely grown quite a bit since your past group chat, even though it's only been about a year. So, you know, what have been some of the more recent challenges, you know, with SidelineSwap and maybe even learnings?

For us, the big thing has been evolving from a pure-play marketplace with a small, you know, engineering, marketing, like Everybody working remote to, we have warehouses, we touch inventory and we're getting, we have to think like a retailer for that side of the business. And so we've spent a lot of time thinking about how to be great at that, how to be great at inventory management, leveraging our pricing data for unique advantage. And that's a new skill set. I think we're learning super fast and getting better every day, but that has been like a big focus and challenge. So yeah, I think then do all that with a small team delivering on the marketplace experience, right? It's like, how do we continue to drive the marketplace experience forward with, you know, especially some of the latest and greatest tools that are coming out? And so we've invested heavily in content in the last year as well, partially with the lens for SEO, but mostly like, how do we how do we create a library of content that makes Sideline the best destination to start and end your search for sports gear, right? You should be able to like come here, learn about product, find the product you want and, and buy with confidence kind of all in one spot. So we've written out a lot of content about top products and merchandise that better. So that's been another big focus for us this year is just like leveling up the shopping experience with, with more content.

I definitely noticed the content. I've been following along on social and then also to, you know, check out the site. So that's great. So we're going to get into the group Q&A here in a bit. Otherwise, you know, I just got to go talking about things here. But right before we do, though, so of course I couldn't have a conversation without talking about AI. So, you know, how are you leveraging AI at SidelineSwap?

Yeah, we're, we're excited. We're doing a lot on a couple of different fronts. The way I think about it is Starting point, like, I think there's just like operational efficiency stuff. So I think our engineering team's gotten more efficient. We, we use, you know, Copilot and Vercel and a lot of the— a lot of tools that you'd expect us to use to level up our engineering efficiency. And our team is using Claude or ChatGPT constantly to improve their workflow. We're also, we've been testing like a chatbot. So like a frontline customer support that can reduce our customer support overhead and allow us to respond to customers faster with more, to more questions faster with high quality answers. So that's another area on the op side. And then on the buy and sell side, I think there's, there's the main thing is personalization. We think there's a lot of opportunity to, you know, and I think there's been a lot of writing on this. I saw, I think Olivia Moore put out like a great post on how personalization will evolve with marketplace. But we're going from a wave of like unlock all the selection to then distill, like curate that selection to just the items that are most relevant to that person. And so we launched a for you, for you section on our homepage. Recently. And so we're surfacing highly personalized results. We're seeing a great revenue lift from that and are really doubling down on how do we continue to make the experience much more personalized so that way it's fun and everything, every explicit action you take to tell us what you're interested in is feeding a recommendation engine to get you more items like that, keep you on the site longer and discovering other items. So the discovery piece is super, super exciting and we're really focused on that right now. And there's some other big updates that are coming in the couple weeks on that front. The, on the sell side, I think it's about using AI to reduce friction. So like in the selling experience, I think what you could expect to see this year is that we're extracting more details out of a photo, right? So you start with photo, what is this item, you know, less taps for the user to go and complete all the details on the listing. Enhanced descriptions, enhanced titles, and even things on the account management side of, you know, the, the help me write stuff that you're seeing in Gmail. You know, there's a lot of time sellers spend chatting with buyers. Like, how can we give them tools to be able to respond better and faster within their account? So a lot of stuff that we're focused on there too. I think It, I think it's taken like a little bit to figure out, okay, what are, what's not like the shiny object, but what are the right applications for this? And then how do we incorporate that into the product in a meaningful way? And, you know, I think last year we did some experimentation and we figured a lot of it out. And now we're kind of moving full steam ahead with where we see the product going. And we want to stay on the frontier of like, like if we were building a marketplace today, what would that experience look like? And we wanna make sure that we're, we're doing that ourselves and not waiting for someone else to come along and build the next-gen experience.

No, it's all great to hear about even, you know, thinking like that even at the later stages. So cool. So we're gonna get into the group Q&A here. Hey, Dimitri, saw you raise your hand. Do you wanna jump on?

Yeah, I have a question for you about how you've sort of set up the product experience on your site. So you seem to have a listing experience where, you know, you have maybe the same item for multiple sellers. And that's what you present to the customer. Whereas you could also maybe have a, like a product-based experience where you have a product and then under that you have kind of the various listings from each customer. How did you think like about this choice about how to set that up and sort of what were you kind of the trade-offs for you and why did you land on, on the kind of the listing experience?

Great question. I think it's like, it's a, it's a really hard problem to, to deal with. And I think it's good to be thoughtful about it upfront. The sporting goods category, sporting goods is just super long tail. So you might look at like a Rawlings Icon bat and to the naked eye it's like, okay, that's a Rawlings Icon bat, that's the product. Well, there's BBCOR, USSSA, and USA certifications. And so gotta go at least one layer deeper within each of those. There's drop 5, drop 8, drop 12, right? Now there's all these colorways and unlike books or sneakers, and I don't know, maybe there's other categories, you can't just like scan the UPC on the back and boom, here's your title, right? Like it is really complicated. And so organizing that into products is really hard. So I think initially what we did was not try to solve that problem and just go with listings. We are working in the direction of backwards to organizing it. So like the way our value guide works for trade-in, we're creating, you know, manufacturer SKU might be like all the way down the tree to color drop, like all the criteria I talked about to a unique layer. Customers don't think that way. That's not the way anybody buys or sells. So we have to like create a, like a layer somewhere in between the Rawlings icon and like that UPC, that's the shoppable layer, right? And it's different by every category. So we're like basically doing that for our value guide and assigning val— like we basically pick like where's the value because at some point you get to too little data and too granular where it's actually not useful anymore. So we pick where's the value and then we, and we're now incorporating that into the shopping experience. So I think what you'll see is like all the work we're doing in trading actually helps us organize the catalog better to then build a better shopping experience. And I think over the next year, you'll start to see some of those product-based shopping experiences in certain parts of the site. They'll probably continue to coexist though. It's really hard to do. I think like Pango Books does a great job with it. If you want to look at like their experience where Titles and authors make it a little bit easier to do, and I think they've done a fantastic job of what that experience could look like.

Thank you. Awesome.

That was a great question. Actually, I had a question that a founder posted in the community in advance and wanted me to ask, and it's around increasing frequency as far as like on purchases. And are there any maybe specific, you know, ways that you've been able to do this, or maybe even kind of tips for others on how to think about You know, helping increase frequency?

I do think frequency is a little bit inherent to the category, right? Like, you know, you're only gonna travel so many times a year, right? So it's really hard for Airbnb. I mean, maybe they can move the needle a little bit, you know, like if you're ordering food, right, you can maybe get, you know, you can move the needle a little bit more or with Ubers. But in sports, you're probably somewhere in the middle, right, where we can get you to We think about it more of share of wallet, right? So like you can only purchase baseball bats so many times a year, although some people will buy a lot more than you expect. The, so like we want to make sure that, you know, we have a great experience, you could find good deals here. And if you're thinking about buying a baseball bat, it's here. And we want you to know like, okay, you need a glove, you need cleats, like, hey, that's all here too. But then like we're also trying to be intentional about, okay, What is baseball players? And like now it's getting more personalized. Like what are baseball players in certain geos? Like what is this profile of customer also likely to buy? How do we then surface that to them? And so I think it's enabling discovery across a broader range of categories and getting them to think of you for more things more frequently. So I think expanding share of wallet to more sports and being smart about that, understanding like, okay, you just bought a hockey stick, what's the next most likely thing you're gonna buy? Obviously, like there's both the skates and gloves, but there's also tape and laces. And so like merchandising checkout with high frequency purchases is another one. I'd say like those are the 2 main things. And I think you do have to do that throughout the shopping journey. You can't like wait till after and be like, hey, by the way, like we also sell all this stuff. They should like see it naturally through the experience so that way you're planting the seed for them when they come back and then you hammer it home with email push and other marketing. But it's hard. Like, I think it's as much as we, I'd like to say we've like really moved the needle on that. I think it's more incremental improvements. It's hard to go from like 2 purchases a year to 30 purchases a year. Like that just might not be possible in your category. I think that's where you have to make sure in the beginning your expectations are correct of like what is the purchase frequency in this category? What's the AOV and what's my take rate? And like, you kind of have to make sure that given that frequency, given that AOV and given your take rate, how big can your business get? You got to make sure like your take rate is appropriate for that because I think sometimes if your AOV is too low and your take rate is too low, purchase frequency is not high enough, it just gets really challenging to build like a good LTV to CAC ratio that you can scale on. So yeah, it's a tricky one, but those are some of the ways we've thought about it.

Definitely a lot of consideration. That's gonna be super helpful though. So, hey, Molly, do you want to come on? I saw you raise your hand.

Yeah, I had a question about early organic marketing strategies. And I've seen that you've got some press, of course. So were you, did you have an organic marketing strategy in the beginning? Were you going out and looking for PR or brand ambassadors to achieve virality? Yeah. Can you just walk us through kind of how you got that started?

Yeah. So press is great to post on LinkedIn, but like the, that is like pretty like spiky and really never, I don't think really moved the needle. Maybe like in the beginning with niche communities, like building some trust and awareness was helpful. So like less the Forbes headline and more like where's the blog that everybody, you know, or TikTok, you know, creator that everybody in your space follows. Like I do think that can help a little bit. But I think having your own content strategy is key. And like we've had that since day one. We, one of my co-founders leads marketing and we, yeah, I think he went like 5 years with posting on Instagram every single day. Like it's about consistency and we, we had to find a strategy that worked for us. So like if we just posted pictures of sports gear every day, that would've got really boring and no one would've followed us. So what we did was like we posted a lacrosse helmet, then we posted a lacrosse highlight. A lot of people watch the highlights. So you like come for the highlights, stay for the gear, right? Like, and that was kind of the philosophy of how do we create a content engine that reaches the audience that we want to reach? And then how do we insert our messaging into that? It has to be like relevant enough, but it can be a little bit disconnected. And if you look at our TikTok and Instagram, like we're kind of really reinvested in that over the last year. We'll do some collaborations with influencers. I think that's helpful in the beginning. But I think having your own engine is really important and has been key for us. We had, you know, we got to $1 million in GMV without any paid marketing. It was all social. I mean, it was a different time where You could, it was early days of Instagram. It was a lot easier to reach your full following. So we had 500,000 Instagram followers across multiple accounts. We had an account in lacrosse, baseball, hockey. And so we had like targeted content. But like there's no shortcuts on that stuff. You know, it's, think about like if you've watched Catch Me If You Can, I always think about this where they're like, how'd you pass the bar in Alabama or whatever the question is? And he is like, I studied. Like you just have to do the work sometimes. And like to us, that was the content strategy of, you know, you have to be consistent and put out high quality content. If you're not gonna be serious about it, you might wanna find a different channel. But for us, it was something we like really invested in and it worked. It worked well for us.

Awesome. That's a great question. So it's a great way to wrap up the group chat here. So we're almost out of time. Just realized that. You know, Brendan, really appreciate taking the time to join us here today. This is, you know, fun to kind of go back to the, to the early stages of SidelineSwap again and, you know, hear a little bit more about how it's evolved and, you know, even some of your kind of learnings here. So we also appreciate taking the time to answer some of the questions. So, you know, one last question for you, and this is my closing question. I know I asked it last time, you know, which is typically if you could go right back for you in the world of marketplaces, you know, what would you tell yourself about them? If we like slightly kind of reframe this and maybe to right before, you know, your past kind of group chat and, you know, the more recent kind of growth stages with Sideline Swap, you know, what would you tell yourself?

I think like going into this phase, it's like recognize where your risks are, like where's the flank, your exposed flank of like where can the things that could really hurt you, what are they? And like, because we're just getting to a bigger point, we're taking more risk with inventory and I think it's like understanding there are some things that like we kind of let go and small problems became a little bit bigger problems than maybe they needed to. And it's like now we're like super focused on like, okay, here are the risks. There's known risk and there's unknown risks, but like at least the risks that we know about, we try to be super thoughtful about how do we mitigate them as much as possible? How do we focus on them? So I think like That's just something we've been thinking a lot about over the last year of, you know, moving aggressively to mitigate those risks so that way we can then feel good about that and focus also on, on the growth side. But it's, it's kind of blocking and tackling of doing a little bit of both.

Well, it's gonna be great parting advice for the later stage founders and then also for the early stage of, you know, what to kind of look forward to. So we really appreciate you taking time to join us here again. And then last but not least, I know you shared it last time, but time for a quick plug again.

Where can we keep up with Uh, probably most active on LinkedIn, so you can find me Brendan Candon.

Also include a link to some of your previous posts. I know your hiring post and then the partnership post as well. So had those, want to make sure we could share them. So thanks again for joining us and thanks everyone for the great questions.