Ep #97 | Build Incrementally



Jackie was shocked at the cost of wedding dresses. She quickly realized the wedding she imagined on Pinterest would cost a small fortune. So, like any resourceful girl with designer taste, she looked for another way. She found there were other girls trying to buy and sell their wedding gowns and save money. Jackie wore a Vera Wang gown that was worn by a bride in Atlanta. She resold it to another bride in NYC after her wedding, and that bride sold it to another bride in London. 4+ brides wearing a $7K dress instead of 4 new dresses at $7K each.

Jackie started Nearly Newlywed with the money she got from reselling her wedding dress and the little money left after her own wedding a few months before. NearlyNewlywed.com was launched out of her living room with the support of her husband, family and of women all over the country who sent her their gowns and believed in what she wanted to build. Every dress they help sell or bride they help get a gown she loves for less is a building block to a bridal revolution.



Shantel: Hi, Jackie. Welcome to the podcast.

Jackie: Hello, thank you for having me.

Shantel: Of course. We're excited to learn more about your journey in entrepreneurship and what makes you imagine more. And I'd love to share with our listeners a little bit more about Nearly Newlywed.

Jackie: Sure, so Nearly Newlywed is my company. I started it actually out of my bedroom with 50 used wedding dresses in 2012, based on my wedding and experience in dress-finding and selling adventures, I guess. And it's grown over the last seven years to be a global marketplace for new and pre-owned wedding items that range from wedding dresses to engagement rings to gifts to accessories. So that's kind of it, I guess, in a nutshell.

Shantel: That's amazing. I mean, first and foremost, seven years is outstanding. We just reached our six-year company anniversary, and it goes by so fast, but it's like "Holy cow, we're chugging along." Congratulations on seven years.


Jackie: Well, six years is a lot. I mean, I feel like there was a time when I used to be like, "Oh my goodness, we're getting ..." As a business and personally, but as a business, we're getting old, it's getting older for the startup world. There used to be a little more fudging I think on the ages, and now I'm just very much like, "Yeah, we're seven." Some easy, some hard years, and so I'm very proud to be an aging, I guess, business here.

Shantel: Yeah. I wonder what that threshold of when you can stop calling yourself a startup, what it is. Is it a year or…

Jackie: I don't know. I'm not sure. I think ... I don't know if I ever will, I guess. Maybe when you ... I don't know. IPO? I have no idea.

Shantel: I still very much ...

Jackie: Maybe 10 years. I think that's what they say. I've been living in New York now for, I don't know, 17 or 18 years, and when people ask where I'm from, my initial reaction is like I'm not quite sure what to say because I'm from Iowa, but I've lived in New York just as long basically, almost I guess. Anyway, and I think they say 10 years maybe for New York. They're like, "If you live here more than 10 years, you're a New Yorker." So maybe after 10 years, you're not a startup anymore. I'm not sure.

Shantel: Okay, we can use that metric. I do remember, we reached some big financial milestones that we were really excited about, but then the wheels started falling off because the process or lack of process we had before wouldn't work at this new level. So that kind of felt like, "Okay, now we have to have a handbook and a standard operating procedure for this one thing." So it did start to feel a little bit more real, like, "Okay, now just refer your handbook for that."

Jackie: That's true.

Shantel: Yeah, I don't know. Okay, I'll go with 10 years though.

Jackie: …because it's also like, you know ... I think I used to think once a company had an HR department, like a full HR department or something, that was when. I have no idea. I think that the other thing with like a business is that it's like this living, breathing thing, and so it's not this one linear path, I don't think. There's all these ups and downs. So, when you have financial or goal benchmarks, it's like now we're not a startup, but then if you kind of back-roll a little bit ... so I don't know. I think also the term, you kind of ... when you think of a startup, you think of a company that's growing and knows what they're doing potentially and has hit a stride but is also continuing to innovate and capitalize on new opportunities and is, in essence, somewhat nimble and exploratory in how they approach scaling the business. So, in that way, I'm like, I don't know, maybe we'll always be a startup. I'm not sure.

Shantel: Yeah. No, I love that. Okay, quick question. This was top of mind when you were telling the story. It started with 50 dresses. So were you purchasing dresses and then just reselling them, and it hadn't come into this ... like you were taking used dresses from other people. Can you talk about the 50 dresses? So one was your own, and then where did the other ones come from?

Jackie: So I actually ... when I ... So it was on consignment. I guess that's the easiest way to say it. But when I had the idea for my own process, I really just started kind of reaching out to people, generally that I found on sort of like large, mass-market places that didn't feel like a great place to shop for a wedding dress, but there they were, these $5,000, $10,000 wedding dresses, so particularly like Craigslist and eBay. I just emailed the sellers and was like, "Hey, my name's Jackie. I want to start this company that makes it easier to buy and sell especially pre-owned wedding dresses and creates more sustainability and transparency in this industry. And I also want to elevate it so that we can kind of de-stigmatize the idea of wearing or selling your dress." And the women ... I really targeted very, very high-end gowns, and the women for the most part really were like all really excited to hear from me. I think that a wedding in general is something that is ... if you've experienced it, it's something you want to share with someone else that's experienced it or wants to listen and hear about it, so that was part of it. I chatted with them on the phone and heard about their wedding and their experience getting their dress and then their frustrations in trying to sell it or why they were doing that. And then they just sent their dresses to me. I mean, we didn't have any startup capital. I had just quit my job, and these women from really all around the United States just shipped me their dresses in kind of the promise that we were going to kind of create this business together. And then I had, yeah, 50 wedding dresses, a lot of dollar-value of inventory, and these 50 women behind me that were supporting me in that way, and that's how we got it off the ground.

Shantel: That's amazing. So you kind of hear sometimes of the situations where it's like you have to get ... or the chicken before the egg, so you had to get the dresses, and you also had to find the customers. But it sounds like you started with a great base of inventory, so then it was maybe initially just trying to find customers.


Jackie: Yeah. I think that that's the challenge in terms of any marketplace especially. You need to have this good resource of product, and it's generally unique products, especially when you're talking about things like resale and stuff. So you have this limited product that's specific, but then you also need to be able to move that product to the buyer and facilitate that transaction in order to kind of increase the funnel and keep the sellers happy. So that was definitely something that I think really takes a long time to build that. So, yeah, at first, it was like, "Oh my goodness, we have all these wedding dresses," and "Now, how do we do this thing?" And then we did, and then it's like, "Okay, is anyone ever going to buy one? How are we going to sell these?" This was also seven years ago, and so not only did we have the idea that we were selling used wedding dresses, we were selling them on the internet when there was quite a lot less happening in the digital space for weddings. So I think a lot of people told me and also thought we were crazy. And I remember being like, "We're not ..." Like a couple weeks in or something, "We're not going to sell a wedding dress. Are we ever going to sell one?" And then you have to remember that it's the beginning. You have very little traffic, and also we had 50 wedding dresses on the internet. But eventually they started to sell, and we started to get more, and we got the word out, and it was predominantly grassroots. Yeah, so then it just kind of ... the machine started to chug, and the funnel started to build. We just kind of kept trying to incrementally build that little by little.

Shantel: Now, were there any competitors in the space when you first started? Or you did a ton of research trying to maybe find your own dress, and you were like, "There's nothing out there"?

Jackie: So there were, and there weren't, I guess. There definitely were. So eBay and Craigslist, that's how I found the first dresses anyway, and then there were a few specifically wedding companies, but they were just peer-to-peer, so they were like Craigslist and eBay but for just wedding items that had predated, that had really started in more like '06, '07. But they were ... That's actually where I found one of my dresses on one of them, PreownedWeddingDresses.com actually. But they were peer-to-peer marketplaces, so there was no way to try the dresses on. There was no quality control. There was no authentication. There was no payment processing, so the entire experience was just very challenging, especially for something like a wedding dress. So if you get it, and you just hate it, or you can't get it altered to fit you, most things were final sale. My experience actually was that a few people tried to scam me, so there were, and I think that they are in their own way great resources. What I was trying to do was create more of a shopping experience and something that really appealed to the buyer. So it's a space where there definitely are more sellers than buyers, and that's changing. But the current platforms or the platforms that did exist really made all of their money and their business model was around having as many sellers as possible because they just made money on listing fees and advertising. And so, when we built the business, I was like, "Well, that's great, but what I want to do is create ..." It doesn't matter if everyone's trying to sell their dresses if no one is going to buy them. So how do we elevate the experience and create services and content touchpoints so that we can appeal to more and more women to make them feel comfortable both buying a dress online and considering a pre-owned product?" And so that's kind of what we formulated, so some of our core promises are that we either have everything in stock or we get it in before. There's no peer-to-peer chatting. We authenticate everything. We do all the payment processing, and you can return the dress, which were really big things and initially really did impede us from working with a lot of sellers. There was a lot of anxiety from then with this type of item that, if they allowed returns, someone would wear it or something would happen, but being sort of an intermediary there, I think ... And now, through the years, we've been able to create enough awareness. But that was ... it's a very long answer, I guess. But there were, and they were great in their own way, but they had some big shortcomings and I felt were not really built to best serve the customer. So I tried to take what existed and create what I had wished existed when I was doing it.

Shantel: I think that's great. I do think, as far as differentiator, that you allow people to try it on first and then return it is something that I had never seen before. But if I was going to be a shopper, that's the exact experience I would want, so I think that's great.

Jackie: Yeah, we definitely ... I mean, it's kind of like ... I think that's also why you see success in other, with a lot of resell in general. When you're talking about resell and consignment, that's why you see companies now, like the RealReal, having such an impact. Certainly, some of it's the product mix and how slick the tech is, but a lot of it is that you can return the product and that you know it's authentic. I used to do a ton of just like personal buying and selling on eBay, and I really do most of it now on places like the RealReal, just because I did find that, even when I thought I was sure about something, just having the ability to actually return it in case it's not right makes a huge difference. And for something like a wedding dress, yeah, I was like ... I mean, when I was looking, I remember thinking there were a few dresses on sites that I wanted to try and I think could have maybe been my wedding dress, but I couldn't find them in stores to try on, and they were all final sale, so I was like, "I can't give these dresses a shot." So yeah. And then I think that it also appeals to markets that are underserved, that don't have a lot of designers, and we have a fair amount of international buyers also, which opens up the buying pool as well.

Shantel: You talked initially about being out of your apartment, so I can just imagine these huge dresses.

Jackie: Yeah.

Shantel: Dresses take up a lot of room in your apartment. Have you shifted out of your home?

Jackie: Yes, yes, yes. Yes.

Shantel: So are you in a ... When was that transition, and what type of space are you in now?

Jackie: Well, we had a few I guess. In the beginning, we held every dress. Now we don't hold every dress. We get some dresses in only when they sell to then authenticate/repack, so that minimizes some of our storage needs. But eventually, we have a small office in New York, and then we also have a fulfillment and logistics center in Iowa, and that is where all the dresses kind of go in and out. But we went through a few iterations. I think you don't totally know exactly what you need until you need it. We actually partnered with a cleaner for a while in the West Village in the earlier days when we had a fair amount of dresses, but maybe like, I don't know, 400 or 500. Then I worked with Rent the Runway in their earlier days, and that was great, but then we kind of outgrew that, and that also ended up being kind of clunky in terms of we thought we were going to do more appointments, and that didn't really work. And then we had a larger space in Brooklyn for a while, and then finally we just kind of outgrew it. And now we have two offices.

Shantel: Well, that's an exciting spot. So you outgrew the other one. So let's dive a little bit into the team, how you built the team, the size of the team, and kind of the main functions.

Jackie: So the main functions of the team are we have the most ... sort of like the core is our customer service and tech and logistics. That's the team that's based in Iowa. We have a lead tech person and a lead customer service, and then they have a few people each on their teams, and they lead that part of the business. And then content and partnerships and development is based out of New York, which I lead, and then we have a few women here on that team, and then we also have a few freelance resources that help us in terms of creative content and design, depending as needed.

Shantel: Has it been challenging leading a remote team out of Iowa?

Jackie: No. I mean, having a business is challenging. I would say ... no, I feel like the harder part is deciding when and how to scale. If everyone had unlimited funds, they could have unlimited teams, but in general, as you're growing a business, you have to be selective about where and what you staff. It isn't so much ... I guess it seems like a long time ago now that we kind of made those shifts, so I'm sure I'm just glossing over setting them up and getting them functioning. But no, in terms of the challenges, I don't think the remote ... I mean, I go back a fair amount, and we have very open communication, so I don't think that's actually one of the bigger challenges. At least, that's not how I feel today.

Shantel: Yeah, no, that's fair. Are there tools that you use though to communicate frequently, like Slack or any task management programs to just help that communication gap?

Jackie: Yep, we use Slack. We have a few. We use one for just the tech projects and stuff, for that team, that is really great, and then in general otherwise, yeah, Slack, email, phone calls. It's not a super huge team, and it's only over a couple of ... we only have two offices, so it's not too difficult to kind of check in and see what's going on.

Shantel: We love Slack. I was just joking with a colleague, we use it internally, but then we also set up a channel for every marketing partner we bring on, so there's a client-facing channel and an internal channel. It almost feels like part of our pitch every time is selling this amazing program we love and how we can't live without. We couldn't imagine life without it.

Jackie: Yeah. Actually, I've heard a lot ... in large companies too. There's a lot of large companies that use them and use them for inter-department stuff and all kinds of ... I feel like you hear all kinds of things go down on Slack sometimes.

Shantel: Oh, for sure. At one point, we were just communicating on Google Chat and via email and then just knowing kind of the lack of efficiency in that and looking back, it's like, "Goodness, how did we not hear about it? I wish we would've heard about it sooner." It's been pretty amazing. Is there any seasonality in your business with kind of like wedding and proposal season? Or have you been able to stabilize that in any way? Is that much of a challenge?

Jackie: There definitely is. I would say that, through no direct function of us, it's really started to level out. I think that that's just larger changes that are happening in the industry. People are getting married all around, increasingly in different months and at different times and in different ways. There's a lot less like rules and things surrounding weddings. And so they really have started to flatten out. In general, Q4 is the quietest, but it's started to really ... I think actually, when we started the business, and this could be completely wrong, but it was something like June I think was the biggest wedding month of the year, and now I want to say it's actually maybe like September or October. But there's still seasonality for sure, but a lot less than there was in the beginning. I think that that's a little bit more of an issue for brick and mortar businesses than it is for a business like ours, just because of the nature of the business. And I think that, because our product ships for the most part within two weeks, and it's a quicker fulfillment timeline and stuff like that, some of the seasonality doesn't affect us in as large of a way as it does someone that has four-to-six-month production windows. We have some people that are shopping ... Most people are shopping in a fairly traditional manner in terms of looking for that dress, six to nine months, let's say, before their wedding or more. But we definitely have a good amount of customers that are buying the dress one month before, two months before, and so that also I think allays some of the seasonality that you find in maybe more traditional production-heavy wedding companies.

Shantel: And I also saw really great accessories and engagement rings and totes and things, so has that helped kind of fill in some things or create repeat customers?

Jackie: Yes. I mean, some of them are very new. We launched a lot of those categories about a month ago, but yes, that really is something that we've been doing a little bit of in some categories for a little bit, and then we really launched about a month ago, based predominantly on feedback from customers. "We wish we could find this new or pre-owned" or asking for our feedback about designers, especially for things like veils and wedding bands and stuff. So that's definitely something that is increasing our repeat visitors, as well as creating more conversions on our visitors, since there's a little bit ... maybe someone is going to come and browse and look at dresses but ultimately buy one in store, but then they'll buy a wedding band and a veil and a couple T-shirts from us. So that's been a really exciting expansion, for sure.

Shantel: Definitely. Do you ever have customers try to purchase five dresses, knowing that they just want to try on a few and kind of have that experience maybe at home? Or do you have any limitations for that?


Jackie: We generally try to limit it to three at a time, but we do have a lot of people. We've done certain things in the past too to like kind of even facilitate that, like the idea of this at-home fitting. We actually love when people get three dresses because it means ... In the beginning, most people were coming to the website. They had gone to a store, they found the dress they want, they were going to try to find it online used, cheaper. That was really the very beginning, the vast amount of visitors. What I was talking about earlier about trying to create more of a browsing and buying pool and appeal to buyers, not just try to aggregate and make a lot of money on sellers, that's something else that was like a poor thing. How do we empower people to want to buy dresses online and consider this behavior? And two, how do we empower them to shop more and consider a dress that either they don't have access to or wasn't produced or was custom or all these other things? And so, when I see someone ordering three dresses, in general, unless they're all the same style or something, that's really great because that means that we're one of their earlier stops and that they are interested in what our promise is and the product in general, and maybe they have some idea of what they want, but they are looking at the shopping and buying experience as part of their discovery as well. So it's something that we really try to help facilitate. Certainly, we don't want people trying on 10 dresses at once. That can be overwhelming. But in general, we say three is a great number, and then all of our customer service and everything is in-house, so we also often are on the phone or emailing, also recommending things.

Shantel: That's great. I wish I would have heard of you guys before we got married.

Jackie: I know. Maybe down the line. I kind of tell people that vow renewals is going to be the next thing but not like a big vow renewal, but this idea of a smaller re-upping sort of thing, in the five-to-15-year mark, trying to make that more and more talked about and done, since now, having been married for a while and been in the space, I think that weddings are amazing, but we also need to come up with ways to celebrate and reinvest in love and marriages before you've been married for like 50 years. So maybe when you do that vow renewal at like five or six years, we can hook you up.

Shantel: Okay, I'm in. I also was just thinking ... I mean, now I have probably seven white ... like rehearsal dinner and bridal shower and ... I mean, I went a little ham looking back, but it's like, "I'm not going to wear all of these white dresses again." Do you guys have a spot for some of those pre-wedding type of events?

Jackie: Yes, and we're working on building out more on the shopping tools, but you definitely can. Yeah, I think that's something that we ... because I think that's the thing about weddings, and that's why I also think people are going to want to do more vow renewals. It's fun to get dressed up and have an excuse to wear a pretty dress, talk about happy things, so you're not alone with having multiple dresses.

Shantel: Okay. Well, Jackie, I just have a couple more questions to wrap things up for you. This is maybe a little bit more personal one for our listeners. But a barrier of entry, so the only thing that I can't seem to get by, and I would love kind of your hard pitch on this, is this thought of maybe one day, hopefully I'll have children, hopefully one will be a girl, and maybe she'll want to wear my dress. So oh no, what if I give it up? Do you ever have kind of that question, and how do you help brides that want to sell their dress get over that hump? Or is that just a personal thing that I just need to work through?

Jackie: Oh, no, no, definitely. I mean, I remember even when I was going to sell it, when I was about to sell mine, I was like, "But should I?" My husband's like, "Yes. It's taking up like a third of the bedroom." I guess I would say, if you have a strong feeling, selling your dress is not for everyone. Maybe you should keep it. For me, I think that one of the things I ask is "Well, did you consider or would you have worn your mother's? What was the reason that you bought a new dress now?" The other thing that I think is that the truth is that they do ... not only do styles change and stuff, but over the years, sometimes the years are not kind to the fabrics. They do kind of age, and so my thing is I think the idea of passing down something and having that is a really beautiful thing, but it's potentially easier to do with a veil or a piece of jewelry or something. Because I think that the dress has sort of existed as this talisman of the day and as a way to kind of hold on to that and then pass that down, which I think is beautiful and amazing. I just think that probably the dress is not the best thing. It would be better to, like I said, do something like a piece of jewelry that is easier to pass down, that doesn't depreciate and get worn in the same way and that also would be easier for your future daughter to integrate into her looks, since she will probably have her own idea of what that is. Generally, when I talk to people that have worn dresses that are passed down, they usually alter them pretty substantially but not always. And so it also depends on the dress and how you feel about it. We do kind of see that there's a lot of people that kind of know or even now a lot of times, when people are shopping for dresses, they'll ask us even like, "Well, I want to buy a new dress, but these are the three dresses I'm considering" at wherever, Kleinfeld. "Can you tell me which of the three I should buy that will have the best chance of reselling and get me the most money back?" And so we have a lot of that now, and we're working on tools to also have things that recommend those things, that designers and stores that do resell better. But then there's the other group of people that are not sure, and that's one of the reasons we also do, for new and used, we do resale rather than rental because it's something that I don't think you totally know how you feel about it a lot of the times until after. But we do see a lot of people after they get their photos back and start to kind of disengage from the planning process and settle into their newlywed life, like the four-to-six-month mark, then they're kind of like, "Okay, I'm ready." It's just sort of sitting there, and now I'm on to what my next things are going to be. But I feel like it's not a hard sell. If you want to keep it, you should keep it.

Shantel: Thank you for sharing that. I think that put a lot in perspective and all great, valid points. I was going to ask what's next on the horizon, but it sounds like you've got a lot of cool integrations and new tools in the pipeline. So switching up the last question to more of a fun one, have you listened to a good podcast or read a good book? That's kind of one angle we could take, or the other like what's maybe been the biggest lesson or takeaway you've learned so far in the seven years?


Jackie: Oh, geez. Let's do number 2, I guess. I would say some of it's just, I think ... like if I was to look back at where I'm at now and think about how I would get here, I would just in the beginning would have thought it was just impossible, and that would've paralyzed me. So it's important to have these big goals and like a roadmap, but to be able to kind of break it down and look at the pieces and really recognize that it's all these tiny, smaller, incremental things, that's what really builds your business and gets you where you're going. So I guess that, just the ability to realize that things take time, and all of these really small things you do are actually what end up to be the big things. Because there's some really shiny things that we've done, and they've definitely helped propel the business. I was on "Shark Tank," and we had a few big pieces in the New York Times, and some of those things really made large upticks. But the things that actually have brought us to where we are are the much more mundane, kind of day in and day out incremental things. So remembering that, especially in the times between the shiny moments, because there are some of those, the big press article, the big sale, the big expansion, and those things carry you through, and you need to pat yourself on the back. But I think that sort of the un-sexy truth about success and building a business is that it really is all of the smaller things and waking up and continuing to chip away at it, day in and day out, that really make the difference, I guess. Is that good advice, boring advice? I don't know.

Shantel: No, that's I think fabulous advice. I just heard from a mentor today, just like you don't want to dig too deep in the really lows, and you don't want to get too high in the highs. You just got to keep going, continue to look at the vision, and move forward. So I think that's great advice. And last is just how can people learn more about your company, get in touch with you if they have additional questions?

Jackie: Sure, so NearlyNewlywed.com is the business, and you can find us also on Pinterest, on Instagram @NearlyNewlywed. I am also on Instagram. It's @jac_courtney. Feel free to shoot me a note or DM me. And, yeah, thank you for taking the time to listen to my story and ramblings.

Shantel: No, this was great. Thanks so much for being on the show.

Jackie: Thank you.