How Wearloom simplifies secondhand shopping

Wearloom co-founders, CEO Samuel Spitz (right) and CTO Kunal Rai (left) worked together in Tahoe, California over the summer of 2021 after graduating from Rice and receiving initial funding, Courtesy of Wearloom.

Philly investment partner Jasman Singh recently led Dorm Room Fund’s investment in Wearloom, a startup founded by two recent Rice University grads who want to make shopping secondhand just as easy as Amazon shopping. We spoke with Wearloom’s founders, Samuel Spitz and Kunal Rai, about how they came to found Wearloom, their mission in simplifying the secondhand buying experience and the challenges they’ve faced.  

Where did the idea for Wearloom come from, and why are you guys excited about the space?

Samuel: I’ve been interested in fashion, as a consumer, since middle school. I was always shopping the sales at the high-end department stores for items I would never buy if they weren’t 80% off. It’s just always been something that appealed to me. Freshman year of college onwards, I started shopping secondhand and noticed a few consumer pain points that stuck out to me.

First was this fragmentation. When I was looking for something secondhand, the odds that it was on any one site for something specific in my size were pretty low. Even if it was in one place, on Poshmark for instance, the odds that it was on one of the other dozen major resale sites for a better price was really high. I would be jumping between four to five different sites to try to find what I wanted.  

The second problem was around categorization in search. Once I’d get to any one of these sites, the experience still felt akin to digging through the bins at Goodwill. The data secondhand is very unstructured and inconsistent. Listing details are different from listing to listing, even for the same exact item, because they’re entered by different people. What that means is the search process is not intuitive, it takes time to learn how to use these platforms, and even for me now if I go to Poshmark and type in what I’m looking for, eight out of the ten things that I get in my results aren’t going to be quite what I’m looking for. 

The last problem is just around the quantity of stuff that gets posted – hundreds of thousands to millions of listings per day, the best of which tend to sell within days of being posted. I noticed in order to keep up with the good deals, I was spending hours every week doing this rote searching across these different sites.

I saw an opportunity to come into the market, aggregate the supply from across the internet to one central place, use the order of magnitude more product data that we would have to fix search and recommendations with machine learning, and ultimately not only become the primary way that the 100 million people plus that are already shopping for secondhand clothing. I wanted to build an e-commerce giant to rival Amazon by making secondhand commerce the primary way people shop. If we can make shopping secondhand as easy as shopping on Amazon, secondhand becomes the better option. At that point, it’s just as easy, less expensive and more sustainable.

How did you find your first 100 customers?

Samuel: We launched with a Typeform the same week we had this idea. People would tell me what they were looking for, and while Kunal was building the product, I would manually go out and type in on Poshmark what that person wanted, go through the results, handpick the best ones and email the items to them. We did this super-lean launch, which is definitely the proper way to launch a company. 

It took us three days to get anyone to sign up, banging our heads on the table, mostly just me because Kunal was busy building stuff. He was keeping my spirits up, but I was just like, I’m spending hours every day marketing this, and literally not a single soul has signed up for our product, not even our friends, nobody had signed up.

Kunal: Samuel was tweaking the copy, day after day, then something clicked on that third day when we changed a couple words. I think we made it more casual, and in that moment, someone started signing up. We ran with it, and Samuel went full throttle on that script.

How did you meet Jason (Calacanis), and how did he come to invest in Wearloom?

Samuel: We were getting started with Wearloom, about a month in, with hundreds of users, products in the market, etc. I spent a lot of time on Twitter, and I ended up seeing Jason posting one day, “Moving my community for my This Week in Startups podcast from Slack to Discord, just downloaded Discord. It’s so cool.” And I saw that he had tweeted it three minutes ago, and it had two likes. I had already at that point DM’d him five different times and he hadn’t opened any of them, so I was like, “Ok, Twitter’s not gonna work. Maybe if I message him right now on Discord, he will see it at the very least.”  

As fast as I could, I typed up a message about Wearloom and sent it to him on Discord. Sure enough, he saw it and wrote back, “Email this person from my team.” I was able to email that person from his team with the subject line “Jason told me to email you.” We got that first meeting, it went pretty well, and then we got a meeting with the whole team and they ended up saying that they wanted to invest on the day of our graduation. 

So Kunal and I were on the field, in Houston, with our caps and gowns on, as we received the email saying that Jason was going to be our first check through his accelerator. It was top-to-bottom a crazy story to get there. We literally got funded because I sent a DM on Discord. That’s one of the things throughout the startup that’s definitely stuck out. If other people are trying all these other avenues, whether that’s marketing or fundraising or whatever else, find some other angle where you’re not just in a sea of other people doing the exact same thing.

What were some of the challenges you’ve faced, so far, with Wearloom, that you never saw coming?

Kunal: What I didn’t expect were the complexities in handling the data from these websites, either from the API or from scraping, but also just secondhand data itself. You think of a traditional product page, where it’s just a Nike shoe or something. Everything’s very laid out and consistent. On these secondhand sites, all these listings are made by someone like you or me. You can describe the shoe however you want. Handling that data, and being able to provide the user with exactly what they’re looking for, was a challenge definitely off the bat. But it’s also a challenge going forward to get it to the point where it’s like shopping on Amazon.

Samuel: It made the opportunity much bigger. We knew secondhand wasn’t as easy as retail, but it took us actually building the first version of the product to realize that if we don’t do anything to these results, and you just see them in this email format, and you remove the UI layer, it’s like “Oh, these aren’t actually very good results.” We have to figure out how to make them better.

How do you guys think about the long-term vision of Wearloom?

Samuel: We want to make secondhand the primary way that most people buy most things. Secondhand becomes the better way to shop as soon as it’s as easy as shopping retail because it’s less expensive and more sustainable. We’re starting with clothing, and the goal is to grow the secondhand clothing market 10x by making it that much easier to shop secondhand clothing. eBay’s been around for more than 20 years at this point, and that product experience still pales in comparison to a retail store like Neiman Marcus. But we’re changing that. 

After we build a multibillion dollar company in secondhand clothing, we’re going to expand next to home goods, and then to electronics, sporting goods, musical instruments, and every other physical thing. Over the long-term, we see ourselves as the primary platform people use to shop (with most commerce shifting to circular). At scale, we’re a $100B+ business and the most important sustainability company outside of energy & carbon removal.

Written by DRF content associate Casey Kline. Reach him at More updates on our TwitterMedium, and newsletter. Founders, apply for an investment from us. 🚀

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