Capri Wheaton is the Founder & CEO of Dressd which is a peer-to-peer dress rental marketplace aimed at GenZs to help them make some cash off of their clothing without having to sell them! Her founding story is a clear depiction of how passion can turn into a thriving business.

Capri knew early on that she wanted to build a start-up and her drive for launching different projects on campus was proof of that. When Covid hit in 2020, Capri was still in her freshman year of college at UC Berkeley. Along with the lockdowns, Capri found her motivation for college slipping away so she decided to take time out of uni and pursue her startup dream.

I was always really passionate about business, but I was just too into school to think about starting a business earlier. But I think, the younger you can start a business, the better, because there’s just so much to learn at every stage!

Capri’s initial started Thyft started off as a software tool for people who are reselling clothing over Instagram to be able to build a fully-functional website within seconds. While it was a great tool to create, Capri soon realized that there was a better avenue for her startup. While staying true to their main vision of enabling sustainable fashion, Thyft, a software tool for reselling clothing, was pivoted to Dressd, a marketplace for clothing rentals.

Listen to the full podcast to learn all about Capri Wheaton’s building journey with Dressd.

Capri’s Book Recommendations:

The Cold Start Problem: How to Start and Scale Network Effects by Andrew Chen

Flow: The Psychology of Optimal Experience by Mihaly Csikszentmihalyi

Where to Find Capri:

Follow her on Twitter: @Capri_lynnn

Find her on LinkedIn: Capri Wheaton

Where to Find Dressd:

LinkedIn: Dressd

Instagram: shop.dressd

TikTok: shopdressd


Episode Transcript:

[00:00:00] Intro


In today’s episode, we have Capri, the woman behind Dressd. Capri, welcome to the show.

How are you doing today? 


I’m doing good. How are you?


I’m well, thank you. Can you briefly introduce yourself and what you are trying to build? 


Yeah. So I’m Capri, the founder, and CEO at Dressd. We are a peer-to-peer dress rental marketplace trying to build the next side hustle for Gen Z to turn their clothes into cash without having to sell them.


A quick question. I think you used to have another startup, probably the same one you pivoted. Could you tell us a bit about that initially so then we can come back to this? 


Yeah, totally. So I was previously the co-founder and CEO of a startup called Thryft. It’s the same overall company, but we essentially pivoted to Dressd. But previously we were building a software tool for people who are reselling clothing over Instagram. We actually built that with one of the fastest website builders out there.

So we would go from your Instagram page to a fully functional website with listings and everything in about 20 to 30 seconds. So that was a really great product. We were helping people sell over Instagram and Instagram lives but decided to shut it down in about December and pivot to Dressd.


So how is it different from Thryft to Dressd? What changes are there? 


Yeah. So with Thryft, we were doing more of a software business model. We had tiers of different plans. We were sort of more of a software tool, mainly a website builder, but also providing super easy checkout links for people selling second-hand clothing.

And we’re primarily working with resellers. So people who sell their clothing want to make money off at once and they get rid of it, versus Dressd is a marketplace, not a software tool. And we’re also clothing rental, not resale. So on our platform, people can make money off their items by renting them out over and over again as opposed to just selling them once. 


Right. Could you walk us through the process? Let’s say Desiree has a spare dress that she wants to rent it out. How will it work? Could you walk us through the process?


Yeah, it’s super easy. You can go to the Dressd website or the Dressd app. You can click the button that says sell. You upload a couple of pictures of your item, the size, the brand, and input a quick description of the item and how much you want to rent it out for.

And then the product essentially is uploaded onto our app at and website. And then when someone rents it out, you’ll get emailed two shipping labels, one shipping label to send the dress that you’re renting out to the person renting it out, and then one for the renter to return the dress back to you.

So if I’m renting out my dress, let’s say, I do have to print the shipping label and find the box to put it on and ship it. But on the person who’s renting it side, it’s even easier because you already have the box, you already have the return shipping label.

So you can just put the clothing item back in the box and then drop it off to be mailed. 


Superb. So I saw that you dropped out of Uni. Could you offer that? What made you drop out of Uni and start a startup?


Yeah, I did. When I was 18, I decided to drop out of UC Berkeley to start Thryft, and the first version of Thryft looked very different. We kind of morphed into the software tool over time, but, yeah, I think for me it was a difficult time because COVID had hit the end of my freshman year, so I had kind of wanted to do a start-up.

I was really passionate about launching different projects on campus. And then when Covid hit, kind of all my motivation for school went away, and a lot of my friends were taking gap years or taking time off to do work opportunities.

So I figured if I’m interested in doing a start-up, now is the perfect time. And at first it was just, oh, let me do this to take a year off school. And the plan was always kind of to go back to school. But everything changed when we actually got funded in the fall.

So in the fall of the next year, we got into Y Combinator. They invested 125 k, and then we also raised a small pre-seed after Y Combinator. So as soon as we raise money, we’re like, all right, we’re in it. We’re in this for the long haul.

So it turned out to be an incredible adventure, but it was a tough decision.


And how did you get the initial idea to build the initial product? Thrift.


Yeah. As with startups, things definitely morphed over time. We started out when Covid hit. We built a marketplace to try to bring Thryft stores and vintage stores online. So we would help them photograph their items, upload them on to an app and website, and then we’re helping them facilitate shipping and pick up so that they didn’t have to close their stores because of COVID.

So we’re doing that for a bit, and we realized that that was kind of a logistical nightmare, driving around selling all the stores manually in person, taking photos of their items. It was just so much work for obviously second-hand items that wouldn’t sell for very much. So for us, it was a huge logistical issue, and the unit economics weren’t really working.

So we were looking into different models, and we decided that we wanted to try something more in the software space while still, I guess, playing in the space of sustainable fashion that we loved and were familiar with. And so we sort of found this group of people who were reselling clothing over Instagram, and we decided that we could build much better tools for them.

After talking to them, we essentially learned that they were doing a lot of manual processes, like collecting payments completely manually over Venmo and PayPal. And shipping was awkward and they had no tracking for their customers, but they were doing a ton of sales.

So we were like, why don’t we build something for these people? And then it turned out to go pretty well while we’re doing it.


I think you go into Y Combinator as well, up to that point. How did you fund it?  Where did the funding come from to build it? 


Yeah. So it was actually a very short time frame. So I guess the timeline was school was ending in the summer, so I was still kind of living off of my student loans, student housing, money through the end of the year.

And then in the summer, I really was just doing a combination of living at home and living with my boyfriend at the time. So I was living pretty much for free, only had to really worry about food, and I was pretty cheap on that end.

So essentially we just kind of bootstrapped it. I had always nannied and did a lot of babysitting

in high school and in college as well, so I had some money saved up and thankfully that was kind of just enough to get us into Y Combinator.

I think my co-founder and I initially put in, I want to say, like a couple to a few thousand each,

probably no more than like 2 to 3 thousand each to sort of really get it off the ground, run some experiments and see some initial traction that helped us get into YC when we actually got our first, more legitimate round of funding.


Did you get into YC on your first application or you had to apply a couple of times? 


Great question. We got on our second application and same with most of my friends. Most people I talk to don’t get in until their second or third application. So our first application, we applied with an idea that is so bad, I’m almost embarrassed to tell you. But basically, we applied with the idea of a social network for thrift shoppers.

So like, you go thrifting you find something unique and you can post online and all your friends can like and comment and share whatever. And we really had no path to monetize

that we were just really passionate about thrifting we’re like, everyone’s going to love this.

But YC was like, ‘Nope’, we didn’t even get an interview.

And then on our second application, we got an interview. They wanted to kind of give us some more time to prove out a little bit more traction. So they did something very unconventional with us.

So they actually interviewed us once, and then they said, all right, we’re going to give you one month, and we’re going to see how much traction you can make in a month. And at the end of the month, we’re going to meet again. And essentially, if you impress us, you’re in.

If you don’t, you’re not.

So we had this kind of period where we really had to hustle hard and try to get more stores and more sales on board when we were doing the first marketplace. And yeah, we ended up getting in after the second interview, which was great.


Superb. Could you walk us through the process, how Thryft morphed into Dressd? How did that process go?


Yeah, great question. So when we were initially running Thryft, everything was looking great.

We were growing sometimes 100% every month. The sellers really loved us and we’re solving a real need. But I just don’t think the market was where we initially thought it was in terms of the amount of resellers who were already on a social media platform like Instagram and TikTok and doing their sales 100% there at the time that we’re building, most of the resellers are still on platforms like Deepop and Poshmark.

I do believe it will go a little bit more decentralized in the future. I just honestly think we’re a little bit too early because we got to a point where our growth plateaued and we were having trouble finding high value sellers who would really contribute a lot to our GMV and our revenue.

And that, combined with the SaaS model that we were doing, was very difficult for resellers because we had the typical marketplace dynamic of a few small number of sellers, sort of driving all the growth.

And then we had a bunch of casual sellers who were doing fewer transactions. But we’re doing a SaaS model, so we could only really charge the top power users of our product. We weren’t able to capture the rest of the users and their sales.

So I don’t think our business model was the most effective for what we were trying to do. And so through that, we kind of learned a lot about the secondhand space. And I personally believe that a marketplace model makes a lot more sense to sort of empower those people who want to be entrepreneurs and run their business because you can sort of capture everyone at every stage in their business, not just the top power sellers. 


Got it. I think you got quite a few competitors, from the top end. And how do you differentiate yourself from them? What makes you unique? 


Yeah. So at least from my perspective, there’s sort of three categories of players in the rental space right now. So first we have direct to consumer rental. So these are companies like Rent the Runway and Urban Outfitters rental company Newly, and they essentially own all of the inventory.

They keep it in these centralized warehouses and they ship from there and they handle all the logistics. And with that, really, there are tons of logistical issues, particularly with Rent the

Runway, which we’ve been seeing recently.

But there’s a lot of things that go into why that’s not an effective model for Gen Z or for consumers, mainly logistics, but also not enough variety of inventory. You can only rent a certain selection of brands and of items, so you’re kind of restricted to the inventory that they hold.

They also typically follow a subscription model, which isn’t really the best for Gen Z, because that’s not really how Gen Z manages their finances. I think Gen Z works a lot better with transaction-based model, seeing as Gen Z myself, it’s hard to get us to commit to subscriptions.

So that’s one thing I would say. The second player is really the peer to peer resale. So apps like Depot, Poshmark, Curtsy, Mercari, etc. etc. Where people are hopping on to the marketplace and just selling their clothes and only making money off of it once. And with that, of course, people regret selling their items a lot, which is something I’ve learned through this process.

So, for example, I’ve had friends who have sold their prom dresses, their homecoming dresses, because they needed to make a quick buck in college, and then immediately they regret it. They’re like, man, I could have worn that dress to this other event, or I could have saved that for my daughter, or it’s something I still want to have in my closet for whatever reason.

So Dressd sort of allows people to still make money off of their clothes but keep those items for the long term. And then we have, I think, the most interesting category, which is informal rental.

So this is the clothing rentals that we’re seeing happening on Instagram and TikTok without any platform and within sorority houses themselves. So sorority girls essentially just borrowing each other’s clothes or Venmo each other to borrow each other’s clothes.

And of course, there’s no platforms, there’s no tracking, no reputation checks, no way to facilitate payment really easily and do that at scale. So rental really could be the next side hustle for people if we just build a platform around it.


Cool. I mean, let’s walk me through the scenario. Let’s say Desiree rented a dress from somebody else through your platform, but she stamps it or damages it. What happens then? How do you handle that?


Yeah, great question. So whenever you upload an item to the Dressd app or the Dressd website, you put in the price that you’re going to rent it out for, but then you also put in another price. And that price is what we call the lost fee. So that fee is essentially the amount that if anything happens to the item, whether it’s lost, damaged, not returned, or anything else happens, we will essentially automatically charge the renters card the amount that the seller designates, and that sort of gives them room to sort of insure the item for whatever they think it’s worth to them because it’s their item.

So that kind of builds a layer of safety around the platform where unfortunately things might get damaged and things might get lost. But at least you’re sort of guaranteed to get an amount back for your items.


And what sort of percentage is that right now in your platform? Do you have a higher percentage? Is it like 2%, 3% where it does get damaged or lost?


Luckily, we haven’t actually encountered that yet, which is great. I’m sure we will, though.


And I saw that you are also a part of Launch House. You took part in it. Could you walk us through that as well? What was the experience like? 


Yeah. To be honest, I think Launch House was one of the best experiences of my life so far.

And I know that sounds like a big thing to say, but my background was I was living in San Francisco. I was literally living in a hacker house, of all guys, and it’s me and a bunch of just tech bros in a house together. And in San Francisco, the tech scene is very predominantly male. So a lot of my other founder friends were males.

And I think as a woman in tech, you encounter unique things, things unique to being a woman. And so when your entire scene is male founders, sometimes it can feel really isolating. It can feel like no one really understands what you’re going through.

And I saw this opportunity at Launch House. Actually, one of my friends told me about it and

then I looked online and saw that they were doing a female founders only cohort for the month of March. And so I was really nervous about doing it at first. But when I saw it was all female founders, I knew I had to do it.

And I think that was the first time I actually felt like I had a network of female founder friends where we could support each other. So it was really awesome. They did tons of fun events and stuff, too. Got to meet a lot of creators and investors and yeah, it was an awesome experience.


Cool maybe as a female founder did you face any special challenges, maybe with financing or at any other point? 


Yeah absolutely. Um I mean where do I even begin? It’s, it’s sort of everything from like the stuff that we do ourselves that’s kind of subconscious or wasting time so, for example, like when I hop on a call with an investor um I have to think about like what am I wearing what is my makeup convey what is my hair convey am I doing too much if I wear makeup and be my girly self as it can convey that I’m not as serious or I’m not spending as much time on my start-up and you know I think a lot of people will say that they’re not that they’re not sexist but I mean to be honest a lot of it is subconscious where I have to think about what message I’m conveying to the investor subconsciously and my male counterparts will never have to think about that. 

In addition, I face a lot of direct sexism when fundraising so, for example, I met with an investor the other day and I sent him my follow-up materials and he declined to join the round but in that email, he said thank you so much for your cute and sweet offer so I’m I’m pretty sure that’s a message that a male founder would never receive so it’s of course it varies but I would say every day we have to kind of battle with some level of that and it can be very difficult.


Right the young Capri, when you were like ten, who did you want to be?


I always wanted to be the president!






Right uhhuh ambitious, good


Yeah very much, it’s very funny but yeah I was always really passionate about policy and politics there was I didn’t really know how but I always knew there was a lot of change that I wanted to make in the world um and so I thought politics would sort of be the most direct way to do that. 

But yeah I think now as a founder though um you see yourself like impacting people’s lives impacting people’s businesses and it feels like you’re making a positive difference especially if you’re doing something in sustainability so it’s still very fulfilling although I do love politics and maybe someday I’ll get into it. 


Cool and what are the future plans for Dressd like your annual goals?


Yeah so I think the overall vision is really just to be the next side hustle for gen z essentially or the Depop for rental. So being the go-to biggest platform for event wear rentals whether that be dresses for weddings or dresses for proms or festival attire for things like Coachella, really the goal is to be like the go-to you know event wear or marketplace.


Cool and who inspires you especially entrepreneurs do you have any role models or you look up to who are they?


Yeah definitely Sarah Blakely the founder of Spanx and anyone who has sort of a well, of course, all women founders really inspire me but I think her story is particularly inspiring. As well as one of my mentors and angel investors from college, his name is Charles Huang he’s the co-founder of RedOctane which created a Guitar Hero so he’s been a great mentor to me over the years and I’ve just learned how much he sacrificed to build his business and it was really inspiring he kind of got to this point where i was like do or die and he laid everything on the line for his business took a huge risk and it paid off uh big time so that’s super inspiring. His dedication and everything he sacrificed to build his business.


Right, knowing what you know now if you had to give any advice to your younger self, what would that be?

I would say focus less on school and more on building businesses earlier on or building more unique hobbies. I was always such a nerd I was just completely focused on school that was my entire life and i think I could have um done a better job with sort of like having more balance in my life. I was always really passionate about business but I was just too um into school to think about starting a business earlier but I think the younger you can start a business the better because there’s just so much to learn at every stage.


Cool this is something we ask very much all our guests three books that inspired you or changed the way you think non-fiction books how would that be? 


Oh nonfiction books, oh I mean to be honest I don’t really read a lot of non-fiction most of the books I read are business and startup books 


Yeah, start-up books work as well, go for it.


Well what I’m reading right now is The Cold Start Problem by Andrew Chen. 

Yeah it’s a really really great book because it sort of breaks down how a lot of popular tech companies got started in the very early phases from Uber to Tinder and it’s really helpful as an early-stage founder because it talks about how to sort of get your initial user base and building what you want that to look like and then how to sort of think about scaling from there. 

So it gives a lot of really helpful you know stories and case studies such as Tinder starting off at universities and starting off with you know partnering with fraternities and doing parties and that type of thing and how one party kind of actually got them their initial user base that they kind of needed to achieve the critical mass of you know people on their dating app so I thought that was super interesting.

I’m also reading this book called Flow ah by I actually can’t pronounce the author’s name I’m not even gonna try but um it’s really interesting because it talks about well I guess one thing I learned from it recently was that it says hobbies where you let sort of passively consume things such as watching tv or eating actually drain your energy versus hobbies where you’re actively participating in something such as drawing or painting or learning a language actually give you more energy which can be really counterintuitive so from that I’m sort of doing this monthly challenge where I try to only do hobbies that I’m actively participating in and I’m going to see if that increases my energy levels and happiness overall so I think I don’t have more than that but those are two that I’ve been really into recently.


Super thanks Capri


Thank you for being here with us and sharing us your journey and that’s a wrap.

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