Nathan: Hello, and welcome to the “Foundr Podcast.” My name is Nathan Chan, and I’m your host. And I am speaking with you from Melbourne, Australia. Happy 2015. I hope you guys have some big goals planned for the New Year. I certainly do. And for me, the start of the year is really, really exciting.

About today’s guest, her name is Nikki Durkin, and she was previously the founder of 99dresses. Nikki actually wrote a blog post that went viral on Medium a few months back. And it really touched me. It was about how her startup failed. She told a story that is not told that often. The media often glamorizes what it means to become an entrepreneur. And whenever you actually speak to anyone about, you know, how’s your business going, this and that, you don’t really, like, to talk about the struggle. You like to just talk about the stuff that’s working, because that’s people wanna hear. They don’t wanna hear about the hard times. And that’s actually one of the reasons I created Foundr, because I wanted to show what goes on behind the scenes. But enough about me.

Nikki is an incredible entrepreneur. I won’t go into the story too much, but pretty much, she got into one of the top incubators in the world, called Y Combinator. Yeah. After a couple of years, things didn’t really work out, and she had to close up her startup, 99dresses.  She has a really, really fascinating story, and I just thought it would be interesting to share with you her lessons learned from her startup, and what she would do differently. And yeah, it’s a really, really inspiring story, and it’s a really interesting interview.

So that’s it for me, guys. If you are enjoying these episodes, please make sure you leave us a review. Please get in touch with me. I’d love to hear from you, nathan@foundrmag.com. Make sure you subscribe to the podcast. Check out the magazine at foundrmag.com/itunes. Now, let’s jump into the show.

Can you tell us about how it all started? Like, can you give the listeners a bit of a run through on how your journey as an entrepreneur started and everything.

Nikki: Yeah. So for me, I think, the whole journey as an entrepreneur started pretty early. Like, my parents kind of raised us in a way where, you know, if we wanted something, we have to kind of, like, figure out how to get it and be a bit creative. So they tried not to hand us everything on a platter and that kind of…they’re all very encouraging of like, you know, entrepreneurial stuff when we were kids. Like, ever since I was young, I was always very creative. And I make stuff and go and sell it just like I make dresses, I paint portraits of people’s dogs or draw stuff, paintings, ceramics, like, all that kind of stuff. And I just loved kind of doing that and then selling it to people.

And then I started kind of…I was probably, like, 14 when this happened. I was at boarding school. My parents didn’t give me so much pocket money compared to… Like, I was in a school where, you know, it’s full of pretty much, like, rich kids who got a scholarship there. And I learned how to, like, screen print t-shirts in one of my design technology classes in school. So I actually bought some, like, really basic equipment and was starting to print stuff for, like, all the girls in the boarding house. And so they’d order design and I design it, and then I print it for them, and sell that.

Then I realized I was getting paid for my time. So I actually set up an eBay business with my…I was 15, my brother was 13. So we started Kultkandy. So basically, I design t-shirts. We have them printed and drop shipped from China, and sold them online. And that was kind of my first taste of, like, a proper business or entrepreneurship. And I was making, like, really good money for a schoolgirl compared to, you know, my friends who were just working on an hourly rate at Kohl’s. And that’s when I kinda fell in love with it, and I love kind of the aspect of…I don’t know, like, solving a problem, making people happy, and they’re actually paying money for it.

And so I had the idea for 99dresses when I was 16. And I just looked at my wardrobe, like, I don’t wear 80% to 90% of this stuff. You know, it’s perfectly good stuff. Solution in Australia for just like… like, designer stuff will sell on eBay, but I didn’t have designer stuff. I was more, like, fast fashion things. And so I’m like, “Oh, it’d be really cool to be able to trade stuff.” And then I thought of the virtual currency idea. And that kind of idea kept nagging me for a few years until I finished high school. And I’d actually entered a business planning competition as, like, an extra-curricular thing for my business studies class with that idea, and had won my age group, like, the nationals but my age group. So I’m like, “Oh, you know, maybe that has some merit.”

And then by the time, I, like, finished high school, I was, like, itching to do this. So literally the day I finished my last HSC exam, I was in the office of a company who did those technology stuff, and partnered with them. I pitched it to my parents and got some investment from them, and started that way. I was just like an 18-year-old girl trying to solve a problem for other, like, young girls. And I said that, like, on a… I started a Facebook event, and I said, “Hey. My name is Nikki. And I have this problem. I have a closet full of clothes, but nothing to wear. And here’s my idea on how we can solve this problem like a community, and I’ll do it. But you know, if other girls are interested in it… like, if you use a website like this, can you click “Attending the event”? And if not, can you click “Not attending”?

And I sent it to a few of my girlfriends. It got spread around to, like, 40,000 women in Australia.

Nathan: Oh, wow.

Nikki: So I had a few thousand fans of this nonexistent product. And then they’re all like, “Okay. When is it gonna… like, what’s happening?” And so I kinda collaboratively started it with them that way. So I was building up the products, and then we launched it. And you know, like, the first thing we did when we launched it, we said, “Okay. All you can do is log on, and upload dresses. And we’ll launched the trading site when we get 1,000 dresses on there. And people who upload dresses at first kind of get buttons to spend,” because that’s essentially how the system works. Like, stuff was traded using buttons.

And that worked well. And then from there, it started taking off in Australia. And yeah, that was really good, but, like, I came up with a lot of problems, like, technology problems. Like, we were growing faster and the technology wasn’t scaling with us, and trying to get the right people on board. And then it went through a period where, like, there were so many technology problems. I didn’t understand them. Yeah. It was, like, a really low period. Like, I thought the whole thing was gonna fail, but then a whole series of events worked out, and I ended up going to Y Combinator.

You know, and then I had the down period of the funding pulling through, like, trying to build that back up and get to America, and then the down and the up. And so that’s kinda, like, how it started. The rest of it is kinda, like, written.

Nathan: Yeah. No, that’s okay. I’m curious. Like, you just finished your HSC and you wanted to start this thing. Were you ever afraid that it might not work out or you just wanted to go for it?

Nikki: Honestly, I didn’t even… like, now, it’s kind of you talk about it like, “Oh, it’s a startup.” Back then, I didn’t even know what a startup was. I had no idea about the tech industry. Like, I didn’t have any connections. I guess I was just blissfully unaware, like, I was naïve to the point where, like, the idea of failure didn’t even cross my mind. I’m like, “I’ve been thinking about this for a few years. And if I don’t do it, I’m gonna be thinking about it.”

And so for me, I just like, if I have an idea, I just get really restless and I just wanna do something. And the thought of failure, like, it never really even crossed my mind. And maybe that’s the benefit of naivety. But you know, like, it’s harder now, like, I still have that kind of outlook. Like, if I was to start something else, I know a lot better, like, what opportunities I would look at, and how I’d, like, eliminate opportunities, and kind of decide on the right one. I’m not scarred now to the point where, like, I don’t think about failure. But I just think, like, when you’re young, you haven’t started anything, you don’t know how hard it’s gonna be. So, like, if I knew how hard it was gonna be, I’d probably, like, think twice. But when you actually go through it, it’s very character building. And so it looks intimidating upfront, but, like, once you actually have the experience, yes, it’s tough. But it also develops, like, emotional resilience and a lot of kind of good character traits, I think. So yeah.

Nathan: From what I’m hearing, it sounded like you had this idea and it was like an itch, and you just wanted it bad enough. It didn’t really matter, right? That’s something that’s different between, I guess, someone that wants to start a business and someone that actually does, is they just want it bad enough to a certain extent, right?

Nikki: Yeah. And I think just, for me, like, it wasn’t built up as this huge… like, I wasn’t planning on raising all this money, and building out a massive… All I wanted to do was solve my own problem, you know. To get together a whole bunch of girls online. We’ll trade stuff. And yeah, we’ll earn some money. I wasn’t thinking like, “Oh,  it’s gonna be a huge thing,” and like, “Let’s raise money, and expand, and grow,” you know, like, the whole Silicon Valley type thing. I didn’t even know about Silicon Valley. Like, I just wanted to solve my own problem, and I like doing that. Like, I like scratching my own itch, and kind of being productive, and doing it in a creative way. So that really appealed to me.

So yeah, for me, it was a fun kind of side project as well. And I was, like, studying at University at the time. I got scholarship there, so I was paying my living expenses. I was doing Uni full-time and starting this. But eventually, I love this so much that…especially when you’re on the high, like, it’s really good. It’s a really good feeling.

Nathan: Yeah. It is very addictive, right?

Nikki: It’s very addictive, like, especially when you get people who are like…you know, they love your product, and they’re, like, evangelists, and they’re kind of… like, I remember at one point, me and one of my friends had this, like, beau who was kind of…like he was a bit of a player. Not anymore. But we would go into clubs at night and have business cards. And then he would kind of, like, chat up the chicks. And he be like, “That’s a nice dress you’re wearing.” And then I’d come in and be like, “Oh,  dresses.” And we have this routine. And it goes to the point where, like, I’d be like, “Oh, have you heard of 99dresses?” And then they’re like, “Oh, yeah. I’ve actually signed up for that.” You don’t expect people to actually, like, know about your product. And we didn’t spend any money on marketing. It was just kind of, like, girls loved it because it solved their problem for them.

Nathan: Yeah. That’s where the real gold is, isn’t it? You know, the money is great if somebody is prepared to spend their hard earned cash on something that you’ve created. But yeah, you can’t put a price on somebody just… Yeah, like, you said, like finding somebody that’s an evangelist you’ve created or just, you know, having that kind of impact.

Nikki: Yeah. I remember, like, when 99dresses shut down, when I announced it to our community, they were like… like, they were posting stuff on our Facebook thing. It’s like, “I woke up today, and my boyfriend was like, ‘Why are you so sad?'” She was like, “Well, 99dresses lost their trading.” And they were trying so hard to keep us afloat, like, they literally… like, on our app, we’re posting what was supposed to be items, but they’d put up Textgrams, they’re called, and write out stuff to the community. And they’d be like, “Okay, ladies. I’ve emailed all the investors I know. Who else has, like, connections?” like, they were trying so hard to kind of, like, help us save it, and it was just heartbreaking. And then they’re like, “Oh. You have our credit cards on file. Can you just charge us, like, a monthly fee?” You know, like, they really wanted to save it.

Nathan: Wow.

Nikki: And then they were like, “Oh, we’ll put together, like, a crowdfunding campaign for you.” But, like, by the time this happened, the ship had already sailed. Like, we’d already started winding stuff down, and it was just kinda far gone. But it was just kind of, you know, that’s why I do it. Like, these people who are just so passionate about this product and the community and what you’ve built, and I think that was kind of, like, the saddest part about shutting the whole thing down because you…we really built something that worked. It was just kind of unfortunate, I guess.

Nathan: Are there any regrets?

Nikki: No. I don’t have any regret. I mean I don’t do regrets, really. Like, there’s things I would’ve done different, but I don’t regret necessarily not doing them. Like, I learned a lot of lessons, but I’m glad I learned the lessons because I’m not gonna repeat the same mistakes in my next business. So I don’t regret anything at all, but there are definitely things that, like, I’d probably do differently next time.

Nathan: Yeah. That’s a great attitude. And I’m curious. What can others learn from your mistakes when you said the things that you’d do differently? Can you give us at least three things?

Nikki: Three things. Raise money when you don’t need it, definitely, is number one. I think trying to get the right dynamics with the team is really hard, and I think I know better now, like, what qualities to look for, I guess, like, to find the right team. Like, I think that the team is kind of, like, just so important. And I think with pivoting as well, like, we made a pivot kinda, like, at the last minute. And I think that that was probably a bad decision. And I think approaching problems, like, with a sense of panic can lead you to do stuff, like, that. And I’ve talked to a lot of entrepreneurs who do the same thing. It’s kind of, like, you’re in a bad situation so you kind of invest a lot of time in something that you probably shouldn’t, as, like, a panic kind of…it’s approaching the problem from the wrong perspective, and I think that towards the end. And that probably, like, wasn’t good.

I think one of the most important things I kind of pulled out of it is knowing how to assess an opportunity, and what to look out for in different opportunities. Like, when I started 99dresses, I just wanted to solve my own problem. I didn’t think about it from business building or, like, a scalability perspective or, you know, like, economics and all that kind of stuff. And then now, when I’m looking at different opportunities, like, I can look at something and pretty much, like, have a really good idea of what the pitfalls are gonna be, and whether it would make a good business.

Because the problem with 99dresses was, like, even though it solved a problem that so many people have, from a business perspective, I think there were problems with the business model. One of the hard lessons I learned was, just because there’s a problem that needs solving, doesn’t mean that it…there might be a huge problem, huge market and it needs solving, it doesn’t mean that’s gonna make a good business. If I want to make money, there are, like, way better ways, I think, for me to make money than that one. But I did it because I was passionate about it. I didn’t know that from the beginning. I think that’s a really tough lesson to learn because it was something I was so passionate about, but realizing, like, if I break down the business model, I think there were flaws there from the scalability perspective  we solved a really good problem.

I think one of the takeaways as well is that if you have a good market and a good business model, you can work just as hard as someone who is in a bad market or has a bad business model, you can work just as hard as them, and you’ll have a much higher chance of success. If you start in the wrong market with that business model, you can work your butt off and work just as hard as someone and beat the system and everything, as someone who’s in a better market with a better model, and you’re not gonna be successful no matter how hard you work because of that.

And so I think, now, when I’m, like, assessing opportunities, looking at the market and the model, it’s, like, really important because when I started 99dresses, I didn’t even think about that. Really, it was just more, like, this problem I have.

Nathan: When you talked about models, the next thing that you start, what sort of business model do you like the sound of the most now?

Nikki: So the next thing, I would do something that I could bootstrap initially, at least to get some initial traction. And then I’d raise money for growth if I could. Maybe I’m a bit jaded with marketplaces. The problem with marketplaces is that you invest a lot upfront, like, they’re expensive to start because you’ve got to acquire users and then you don’t…it’s really hard to validate whether they’re gonna pay you. The technology is worth nothing without the community, so then you invest in getting the community together. And then you might find out after all that investment that they’re not willing to pay or, you know. I guess it’s like they can be really good if you have that capital and you wanna do that whole approach.

I think, for me, next time I’d rather do something where I sell… like, I, like ecommerce that, like, sell a product or software as a service or just something where, you know, kind of this concrete money changing hands from a market who’s willing to give you money. And I think one of the problems with the market we were targeting was that we were solving a problem which was in fast fashion. It was like a huge problem. Like, from an environmental point of view, from, like, a lot of different points of views, it’s a big problem. And it’s a really obvious problem women have. But part of the problem, I think, is that from an ease of use, like, people, no matter how environmentally responsible it is to trade and recycle stuff, you can still go down to H&M and buy a blouse for $15, or you can get one of 99dresses for, like, $4. But you have to give away your own thing and then you can get something that’s, like, secondhand.

So the point is, I guess, like, we were targeting a market that was a bit cash trap and almost thrifty. And so it’s hard to get money from them. They would spend money with us because we were, like, a really good solution for them. But, like, from a scalability point of view, it was just really hard to learn that even though our solution worked really well, the laziness factor of people and the, “Oh, it’s just easy to go to H&M to buy something new and chock out my old stuff, and throw it in the trash,” which is so inefficient and wasteful. You know, like, I think in the end that was, like, a big factor.

Nathan: I see. And there’s something else I’d, like, to unpack. And that was you said around you would have a better eye for building your team, and you know what qualities to look for. Can we go a bit more specific on those qualities?

Nikki: One thing that I realized is that when you’re working with someone new, it’s incredibly hard to suss them out straightaway. Like, you need to spend a decent period of time with them. You also need to see them under pressure. So I worked with people who were great when things were great, but just had no backbone and no, like, staying ability, and they just flaked, like, when things weren’t even getting tough. The co-founders that left pretty much, like, got the interview to YC. My other guy I’ve been working with got a really serious illness, had to drop out of the company, and I had, like, a few days to find new co-founders, so I put these guys on, which was, you know, a shotgun wedding which I would not recommend. But at the same time, it did kind of give me the opportunity to go to YC.

And I went through YC, told me they’re leaving right before we raise… like, I’d spent two months on this deal, and then they told me they were leaving. You know, it was just devastating and, like, a sense of betrayal. I pretty much, like, financed their whole adventure to the U.S. YC founders and move on with their life. And I was left to pick up the pieces.

So I think loyalty and just having good moral standards, like, my co-founder Marcin, who eventually stuck it out. He quit his corporate IT job because… I mean he dabbled with, like, some startup projects on the side, but he could never find the right team. And he was working in, you know, a well-paid job in the Sydney CBD at a bank, doing IT stuff.

And he quit his job, came and joined me, and just as his wife… like, he knew this at the time that his wife had gotten pregnant. And then, you know, he knew that, like, he was gonna have to move to the other side of the world. But he’s not moving to the other side of the world with his wife and his, like, three-month-old daughter. Stuck it out with me there, stuck it out through the tough times. And even at the very end when, like, I was assuming he’d have to, like, go get a job because of what was happening with the funding and he was like, “No. We can get through this.” And he stayed until, like, the very end fighting. And he has, like, character. He has staying power. He has loyalty. And I would take consistency and character and, like, work ethic over skill any day. But he’s also very, very skilled, which is great, too.

I’ve worked with someone before who was technically very brilliant, but not consistent. And so I look for, like, consistency and, like, just someone who’s quite emotionally mature. And also, like, you can tell this upfront when you’re negotiating stuff with people who are too demanding. Like, I’ve worked with before people who… like, those co-founders who left, like, I should have seen the warning signs. But just very much a sense of entitlement and when I’m, like, negotiating things. And when they haven’t proven themselves, like, huge… Oh. I can’t deal with egos as well. So they have to…

For me, another lesson I learned was the guy that left, main guy, like, he had an ego the size of Jupiter. And I was the one like, you know, the face of the company. Like, it was my job, you know, to do all this stuff. And I just don’t think he could deal with it, especially the fact that I was a 20-year-old chick at the time, and he was, like, a 34-year-old dude. I mean he even said something kind of to that effect, but I think he was really emasculated. But the problem is he had a huge ego.

And one thing that kinda Paul Graham said to me when it all fell through, he said, “If you have a founding team, you’ve gotta have the Steve Jobs and the Steve Wozniak. You can’t have two Steve Jobs because they’ll butt heads on everything.” And that’s what me and this other guy was doing. Whereas Marcin was kind of, like, my Steve Wozniak.

Nathan: He’s sensible. Yeah.

Nikki: Very sensible, and, like, just good character and backbone, and, like, would put his head down and get the work done. And he didn’t expect, like, fame, glory, and all those. Like, he just wanted to get his hands dirty and kind of be in on the ride. Whereas, these other guys wanted all the appearances of success, but they weren’t willing to put in the work. It was like they thought, like, Y Combinator was very glamorous, and then after that, it was like, “Oh. Well, now it’s just hard work.” So it was, like, just hard work without the glamor. And I was like, “What do you expect? It’s a startup. What do you think you’re getting into?” like, I think people just think that, “Oh. It’s glamorous, and you know, it’s gonna be easy,” because that’s the way the media portrays it. It’s all survivors bias, and I was like, “No. It’s just freaking hard work.”

Yeah. So I think those were, like, a few of the qualities that… And some of them, I think you can’t immediately tell. They might look fine when you first meet them, but you need to work with them. You need to work with them for a while, especially seeing them under pressure. Like, that’s when people’s true colors kind of come out. And that’s why I think, like, I’d much rather start something with people I know or people I trust and have worked with before than, you know, strangers because you just don’t know what they’re, like, under pressure. So I got lucky with Marcin, definitely.

Nathan: I’m really curious. When you had to get these co-founders on board to get into YC, what did your gut tell you?

Nikki: I’m trying to remember. I mean pretty much I was so pumped. Like, I applied to YC with a guy I’d been working with for about 9-10 months. And literally, he told me a week before I found out that I got an interview that he had to drop out of the company because he was literally in the hospital, like, very serious illeness. And I got this email. I got an interview with YC, and I rang up my adviser, and I was like, “I’m so fucked. I don’t have co-founders.” And he was like, “Don’t worry. We’ll sort something out.

And I think it was just…then it was like this sense of excitement. Like, this was my way out of Australia, and to get some funding, and to, like, go and, you know…it was like my dream was to kind of do that. And this was my chance. And so I think that was a really bad position to be finding new people and also the time because it was pretty much, like, you’re willing to come over here and join, and you have good skills and objectively look quite good. You know, cool. Let’s do it. And it was very much a shotgun wedding, which is not what I’d recommend, but at the same time, if I hadn’t have done that, I reckon 99dresses would have probably failed in Australia. So I needed to get to the U.S.

And so even though it was like, you know, two steps forward, one step back with that because they left, it still got me a foothold over this. I don’t regret it, but I wouldn’t do it. I wouldn’t advise someone to do that.

Nathan: Okay. This is really interesting insight because it sounds, like, there’s so much you’ve learned. There’s no doubt in my mind the next thing you do, you know, you will be successful with it.

Nikki: I hope so. We’ll get there.

Nathan: I’m curious. What advice would you give to aspiring entrepreneurs that are on the fence? They wanna start a business, but they don’t know where to start.

Nikki: I don’t know. Like, stop thinking about it, and just do it. Like, I know it’s not great advice, but I see a lot of people, like, who do that. They’re, like, thinking about it, and they’re thinking about it, and then they never actually do it. It’s kind of, like, it’s not even worth thinking about, really, unless you’re gonna do something about it. But I’d say do a little research into the market you wanna go into, and I would say talk to customers. It’s the best way of figuring out if you’re actually… like, make sure you’re solving a problem. And that’s the best part, I think, is if you can scratch your own itch, and then there’s a big market of people who also have the same, you know, itch. And then just talk to a lot of these people.

Like for instance, I was chatting with my mom, and she’s like, “Oh, I have this problem with,” you know, the way she does, like, her accounts payable. And I was just chatting with her, and I, like, mocked up, you know, a way to solve her problems. She’s like, “Oh my gosh. That would, like, really solve my problem.” And I’m like, “Whoa. You know, if you wanna go and talk to some other local business owners who have the same problem,” you know, she’s got plenty of friends around our town who run business, who…and just see how they do their accounts payable. You might find that they’re also having the same problem, and then, you know, maybe there’s, like, a business there.

And so I think that’s kind of, like, probably often overlooked because people are just like, “I have this brilliant idea.” And then they wanna like… Oh. The other thing is don’t…I always see people doing this where they wanna do everything all at once. So for instance, they’re like, “Oh, we’re gonna have the website, and then we’re gonna have, like, the mobile app and everything.” And they don’t realize…especially because they’re not technical, they don’t realize, like, how much work and time not only to build it, but to maintain it and keep iterating.

For instance, like, a lot of people I see, like, I’ve spoken to who were, like, just starting, they’re like, “Oh, we’re doing this for the app. And oh, we wanna do the app, too. ” And it’s like, “Why don’t you just pick one platform and try it on there?” because otherwise if you get it wrong, you’re gonna have to change it on multiple platforms, or if you build some, like, big thing and then release it and it doesn’t work, you’re not gonna know what feature isn’t working because there’s too much crap in there.

So I think generally, like, I see a lot of people who wanna start businesses, and they think that…from a product design point of view, like, they wanna put everything in there. And they’re thinking big, which is great, but you’ve gotta start really, really small and really close to your customer. I think they’re kind of, like, the main things but mainly, like, just do it. Do something. Like, do some research. Talk to some customers. You might find, after talking to customers, that it doesn’t sound like, you know, other people have that problem. You know, it could invalidate a lot of things. And I think just starting small with a prototype iterating from there is great.

That’s another reason why marketplaces look quite difficult because it’s really hard to validate stuff in that respect because the value kind of comes from the community rather than the product or technology. And then just do it. Do something and stop talking about it, I think. So, yeah, that’s just me. For me, personally, like, I just get restless if I have an idea that kind of keeps nagging me.

And I think, also, realizing that what you build your first time around is probably not gonna be right. So I know there’s a lot of people, like, they put so much effort into their first version, and they think it’s…like, they spend time debating with the co-founders – I’ve seen this before so many times, and I’ve done it myself – the most trivial things. And once you’ve been doing it for a few years,  like, “What that title says there does not, like…it’s so trivial, like, or how that’s done.” Like, all these trivial things, because my attitude to stuff now is, like, a product…you know, like, managing a product is, “We can always change it later. Like, if it’s not right, we can change it later. Just get something shipped. Go and get it out the door instead of debating, like, miniature details,” I think. So, yeah.

Nathan: Yeah, that’s a great point. So, from what I’m hearing, you’re a big fan of the Lean Startup methodology.

Nikki: Yeah, definitely, I think Lean Startup’s great. I think it’s easier to apply to businesses where you can kinda get value without needing a lot of other people. Like, that kind of methodology is more difficult to apply, I think, to network-based businesses, because you can build great, minimum, viable product, but you’re not gonna be able to validate it unless you have a big community there, right? So, whereas, if you’re doing software as a service, like, that’s perfect. Like, you go and talk to customers. You put it in front of them and iterate.

But I find always, like, talking to customers is great. but I didn’t do that enough. And when I kind of resent it ourselves around talking to people who actually used our product, and what they loved about it, and how they view it, and how it can change our messaging around that, and what features, and what bits and piece they don’t like, what actually solved their problem, like, our product was just so much better.

Nathan: You know, this is great advice. There’s a lot of good stuff here. We have to work towards wrapping things up, but I’m curious. You mentioned around, and in your post, and it felt so true where you said that the media glamorizes the startup world and, like, you know, becoming an entrepreneur. And people don’t realize that it’s hard work, and you’ve gotta make a lot of sacrifices, and there’s a lot of things you have to give up. I’m curious. What’s your take on that?

Nikki: I mean it’s totally the case. I think there’s two issues here. One is the media, which is they’ll print a success story, and then they make it look, like, an overnight success when in actual fact, if you talk to most success stories, it took them four years, you know, two to four years to kind of get off the ground, and then it looks, like, an overnight success. And I think the other issue is all these stories are all told with survivors bias. So, if you think about it, the media prints stories, right? The success stories. And because they’re success stories, the company’s still a going concern. They have a reputation to uphold. So they’re not gonna bare all their dirty laundry, you know, to the public, because they still have a brand name to protect.

So, therefore, even if you do get a story of, like, what happens, or what happened in Facebook, like, it’s still not gonna be really authentic. Like, it’s always gonna have a PR spin to it, because if you’re running a company, you’ve gotta care about what the public knows, right? So that means that even the stories that you do read about startups, the successful ones, they’re probably not entirely true. Like, they probably got a lot of PR spin, and they’re gonna gloss over all the details about how freaking hard it was, and all of the, like, backstabbing, and the drama, and the investments falling through, and all that kind of stuff, because they wanna look successful.

And then you’ve got the other side of the education which is, what, like, 90% or more of people, like, their startups fail. And because they’re not successful, like, they don’t have a brand name to protect, so they can actually talk about what actually happens in businesses, but they don’t because failure is embarrassing, and it’s kind of…you know, you feel guilty, and ashamed, and all these, like, emotions. And the media just wants to talk about, like, the success stories. And I think it’s dangerous as well just because I was always of the belief that if I kept going and I kept persevering, you know, because that’s what my identity is as an entrepreneur. It’s, like, I will persevere, because, like, I’m an entrepreneur. This is what I do, and I read all these stories about, like, all the companies that persevere and are eventually successful. But what they don’t realize, the stories that aren’t told, the people who persevered and tried just as hard, and they’re not successful.

So I think just, like, from a realism point of view and also from a point of view of, like, knowing when it is time to throw in the towel and not, like, give up, but just, like, from purely a point of view of like, are there more productive ways that I could be spending my time. Because, like, I said, if you’re working… You might be persevering and persevering and, like, you know, doing what the media kind of portrays, it’s, like, the entrepreneurial thing, and, like, overcoming all these obstacles. You know, doing it for a product that’s never gonna be big because you’re in the wrong market, and you’ve realized that but you’re too stubborn to give it up. And I think maybe I’ve kind of had that a little it. Like, I was not gonna give up on my dream, I guess.

But after reflecting now, I think that… Actually a really good thing for me to do was for me to stop just because, from what I know about the business now, I think I was persevering all to the fact that, like, “If I keep persevering, I’m gonna be successful. Like, I’ve just gotta keep overcoming these obstacles,” when in actual fact, like, I could probably spend my time, and the lessons I’ve learned on a more productive business, and a better market, and actually be successful, if that makes sense. Does that make sense? I don’t know.

Nathan: Yeah, 100%. That’s really, really spot on. And it’s so true. And I know what you mean. Like, you don’t want to say that your business is going bad. Especially when the press wanna talk to you, right, it doesn’t make sense. It’s, like, counterintuitive to say, “Yeah, we’re going really badly. We’re struggling really bad,” because you want it to seem, like, it’s going great.

Nikki: I think also it’s…and it’s not necessarily, like, the media’s fault. As an entrepreneur, you kind of have to fake it till you make it. Like, you can’t let on to potential clients, or customers, or potential employees. Like, you don’t wanna make it look like…you don’t wanna be that transparent necessarily because, like, otherwise, they’re not gonna believe in you. It’s kind of, like, these self-fulfilling prophecies. You might be doing badly, but if you’re transparent about doing badly, like, you’re not gonna get the right employees, you’re not gonna get investors, you’re not gonna get customers, and so you’re gonna do really badly.

Whereas, like, if you were doing badly and then you kind of fake this, like, “Oh, but we’re doing really well,” like, suddenly, oh, the investors are interested, the employees are interested, the customers are interested. If you can get the customers, you’re gonna get the investors. And it’s kind of, like, you kind of have to fake it till you make it. Like, it’s not necessarily I think a question of… The companies that were still going out, like, need to be more transparent about what’s happening, because you can’t really do that especially… Like, Silicon Valley’s built on…

Oh, I guess it’s the whole hype thing and kind of, like, giving off the sense of, “Oh, we’re doing it.” And it is. And if you can raise money, like, on that, then that’s great. And I think it’s just really hard to actually be super transparent when you actually have a company. Like, I can do it now because I don’t have a brand name to protect, 99dresses is over. So I can be quite transparent about it, but I wouldn’t go saying all this stuff out in public when we’re still, you know, going…

Nathan: Yeah, it wouldn’t make sense. So, yeah, that’s why I think, yeah, your post that you wrote on Medium was so heartfelt because a lot of people felt that.

Nikki: Yeah. Like, just the number of stories… Like, people have reached out. That’s the thing. It’s, like, when you’re going through failure, you think it’s just you and everyone else is killing it and having, you know… Like, I remember after we decided to shut down, and the next day, or two days later, or something, I went out with a friend in New York to… She runs this thing called Dreamers // Doers. So it’s, like, a group of women who do stuff in startups, and we get together and do brunch every weekend. And my friend was like, “Oh, do you wanna come?” And I was kind of feeling like, “Oh, I should make an effort.” But, like, I just decided to shut down my company, and she knew. And so she was like, “Are you up for it?” And I thought I was fine. But then everyone was kinda standing around a circle, and they’re, like, kind of going, “Oh, your biggest win this week and your biggest, like, challenge or whatever.”

Nathan: Oh, wow.

Nikki: And, like, I just started crying and walked away. I just could not deal with it. It was really emotional, I think, because it felt to me like, I was… like, everyone’s, “Oh,” like, their wins and, “Oh, I signed up a new client. I did this. I got this new contract.” And I know that that’s not necessarily like… I’m sure they’ve got a million problems as well, but on the outside…like just being in that situation, I was like, “No. I can’t deal with this.” And I just, like, walked away and left. Because when you do go through failure, it feels like you’re the only one, when in actual fact, like, after I wrote that blog post, I got so many emails from people who were all like, “Yup. Happened to me, and I just kind of, you know, faded into oblivion, like, licked my own wounds and didn’t talk about it.” And that’s what’s happening all over the place. So it’s kind of comforting, I guess.

Nathan: Yeah. It is extremely comforting. And yeah, it’s a little bit like, at me is actually something that one of my mentors taught me was that you always think about yourself as…you know, you compare yourself to others, and you think, “Oh, you know, it’s only me that has this problems and challenges.” But at the end of the day, every single person, like every single human being has problems and challenges. And it’s just like every single startup or every single business.

Nikki: Yup. That’s so true.

Nathan: But you just don’t see that because it’s shameful to communicate that stuff, and it’s embarrassing, and it’s making yourself vulnerable. Yeah, I know. You know, I just wanted to say thank you so much…

Nikki: Oh, no worries.

Nathan: …for taking the time to speak with me.