Foreword
Over 90% of tech startups fail, but I never thought my baby, 99dresses, would be one of them.
If there is one thing that doing a startup has taught me, it’s that I am much more resilient than I could have ever imagined. Looking back, when I started 99dresses fresh out of high school I was very naive and had zero idea what I was doing. In fact, I didn’t even know what a startup was! I just knew I wanted to solve a problem I personally experienced: having a closet full of clothes but still nothing to wear.
Since then I’ve survived being stabbed in the back by cofounders, investment rounds falling through, massive technology fuckups that brought sales to a halt, visa problems, lack of money, lack of traction, lack of a team, hiring the wrong people, firing people I didn’t want to fire, lack of product-market fit, and everything else in between.
And yet I failed. I won many battles but I lost the war.
I take complete responsibility for this failure. Were other people involved in 99dresses? Of course. Was any of this their fault? Absolutely not.
The startup press glorify hardship. They glorify the Airbnbs who sold breakfast cereal to survive, and then turned their idea into a multi-billion dollar business. You rarely hear the raw stories of startups that persevered but ultimately failed — the emotional roller coaster of the founders, and why their startups didn’t work out.
As things were looking bleak at 99dresses I started seeking out these stories, desperately hoping for someone — anyone — to relate to. Failing is lonely and isolating. Every time I’d scroll through my Facebook feed all my startup friends were launching new products on Techcrunch, announcing their new fundraising rounds or acquisition, and posting photos of their happy teams. Ask any founder how they’re doing and you’ll hear something positive. Whether that’s the truth or not, that’s what we’re trained to say.
I found postmortems of startups outlining what didn’t work and why the company went under, but I was hard pressed to find anything that talked about the emotional side of failure — how it actually feels to invest many years of your life and your blood, sweat and tears, only for your startup to fall head first off a cliff. Maybe it’s because most founders are men, and men generally don’t like talking about their feelings. Maybe it’s because failure is embarrassing.
I don’t know why this is the case, but here is my contribution to the cause: my story. This is what failure feels like. I hope it helps.
***
Where it all began...
Many startup folk say that failure should be celebrated. “Fail fast, fail early, fail often!” they all chant, trying to put a positive spin on the most excruciating pain any founder could experience.
Let me tell you — failure fucking sucks. If I would have failed fast, early and often then I would have given up 99dresses years ago when, in 2011, I travelled to my parent’s place in the countryside of Australia, locked myself away in my room and cried for what seemed like an entire week. I had launched 99dresses in Australia 9 months earlier and received some great traction, but I was losing momentum due to technology problems that I didn’t understand and battling a whole host of other issues.
I felt like I was drowning in a black ocean, and I couldn’t see any light at the surface. I didn’t know which way to swim.
At the same time the Australian press would continue to approach me for interviews. The fact that I was a teenage girl working on a startup in a male dominated industry seemed to garner a lot of attention, and I’d take the interviews that came my way because that was my job. It was my job to be positive and paint a happy picture for the media, who seemed to talk about me as if I was some kind of entrepreneurial wunderkind because of my age and the fact that I had breasts.
This didn’t help my impostor syndrome — the constant feeling that everybody was always giving me way too much credit. I remember one reporter saying “you must be so proud of what you have achieved” and I was completely stumped by that statement because I’d never actually thought about it. Was I proud? What had I actually achieved? We had some traction, sure, but we also had many problems that needed solving. I was just waiting for the day when everyone would figure out that I’m not that extraordinary.
“But you’re taking a massive risk! That’s so brave!” they’d say. I never thought so. The biggest risk in my eyes was going to university, getting a stable job, and sliding into a comfortable life. There’s nothing wrong with that, but I knew it wasn’t me.
Plus, the worst that could happen if I failed was that I’d end up living with my parents. I think the really brave founders are the ones who will be out on the street if they fuck it up, and still do it anyway. It’s easy to take risks if you have nothing to lose.
My mother said “Nikki, are you sure that you really want to do this? It is so much pressure for a 19 year old to take on. No one will think less of you if you decide this isn’t what you want”. My parents are my number one supporters but my mum hated seeing me in so much pain, even if it was character building.
But despite the horrible sinking feeling in my stomach, and the fact that I had no money left, and the fact that I had no stable team, and massive product problems, and was feeling burnt out, and had no idea how to overcome any of the aforementioned obstacles, and felt completely alone in it all, I persevered.
I didn’t fail then. I couldn’t fail. This was my baby, and if it was going to fail it would be over my dead body.
I became numb to the pain, and despite waking up for weeks on end with no glimmer of hope and no desire to get out of bed, I still made myself sit at my desk and work.
Eventually, things took a turn for the better.
***
I stood in the hallway of the Computer History Museum in Mountain View, California. Founders darted about, occasionally stopping to chat as they moved in and out of the auditorium. The year was 2012. I was 20 years old.
It was Y Combinator's Demo Day. I'd just finished delivering my two-minute pitch to over six hundred investors. My mentor, Matt, happened to be in Canada that week. He'd flown to Silicon Valley to watch me pitch.
It was funny how I ended up in Silicon Valley, actually. Nine months earlier, I'd been crying on my bedroom floor over all the issues I was having with 99dresses. I'd started the business with so much momentum and growth, but I suddenly found myself drowning in problems. I ran the startup as a solo founder (with help from my mother) while also attending university part-time to maintain my scholarship, which paid for my living expenses. I'd barely attended class that semester.
A contact from Microsoft emailed me a week after I hit rock bottom. The company had nominated 99dresses for an innovation award and I'd need to fly to Melbourne for the finals. The last thing I wanted to do was attend an award ceremony while a fire raged in my business. It just seemed so wrong. But as luck would have it, Zac had to fly to Melbourne too. He and I embarked on a three-day adventure.
I was seated next to the managing director of Microsoft Australia at the awards ceremony. We talked for hours. She raved about 99dresses — about how it was such a great idea. I tried my best to sound excited as I clutched my trophy (I'd won my category), but inside my stomach was churning. My rational mind didn't want to be there. Yet somehow, I'd ended up in that room.
Slowly, as the night wore on and the wine slid down my throat, I began to feel more enthused about my situation. After giving my table-companion a detailed first-principles analysis of why the Australian postal system was the root cause of all my business problems, she suggested I move 99dresses to the US.
My mind was suddenly on fire.
The US. Fuck yeah! I'll just go to the US, I thought. Their postal system had APIs, and their population density made the cost of shipping individual items more suited to my business model.
The next night, while still in Melbourne, I caught the tail-end of a conference that my friend was running. The headline speaker was Matt — a tall, somewhat-intimidating man in his late thirties. Matt was the founder of a successful global online marketplace with many millions of users. I needed the help of someone like him.
Matt was mobbed by the audience as soon as he left the stage. Once the crowd had cleared, I walked up to him and introduced myself, chatted for a bit, then asked if he could give me feedback on some challenges I was having with my marketplace. He brushed me off. He was a busy man.
A few days later, I was walking around my local area in Sydney when I ran into Matt. I'd lived there for years and so had he — yet we'd never run into each other before. Trust me — I would've noticed. I'd watched Matt speak several times. He had a powerful presence that was difficult to ignore or forget.
A day later, I ran into Matt in the supermarket as we both approached the same shelf. Very strange.
Two days later, I was sitting at the bus stop when Matt strolled by.
"Seriously?! Are you stalking me?" he laughed.
"I swear to God, this is pure coincidence," I replied, hand on heart. "I'm just innocently waiting for my bus. But since we keep running into each other, we may as well go for a drink sometime. Or lunch. Or dinner. Or coffee. Or whatever is convenient for you."
"You're going to get crushed in the US," Matt said two nights later between bites of pizza. "You have no money, no local knowledge, no connections over there. Actually, you should apply for Y Combinator. At least that'd give you an on-ramp to the US market."
"What's Y Combinator?" I asked.
"It's the most prestigious startup accelerator in the world — the equivalent of Harvard; the crème de la crème. There are two batches every year. Thousands of startups apply for each batch and YC invests in a tiny fraction of them. During the program, you spend three months in Silicon Valley working with the YC partners. They bring in founders from the big billion-dollar tech companies to talk to the batch. The whole thing culminates in Demo Day where you pitch in front of hundreds of investors."
"Okay," I said. "I'm going to get into YC."
***
That was enough money to buy me a plane ticket and some accommodation to the US.
I met my friend and advisor, Matt, who took me under his wing and helped me more than I could ever have hoped. My developer was admitted to hospital with a very serious illness and dropped out of the company, but I replaced him with 2 co-founders. I got into Y Combinator and headed to Silicon Valley — startup Mecca for a starry-eyed young founder like I was — for 5 months. We rebuilt the 99dresses product and launched it in the US. We were getting traction. I signed a $1.2 million seed round with a group of investors on a valuation cap that I honestly thought was ridiculously high.
99dresses was back, baby!
And then, all of a sudden, we weren’t.
Another trip down the emotional rollercoaster
I had to fly back to Australia to get a working visa as soon as the funding paperwork was signed, and the next day my two “co-founders” decided to tell me they were leaving the company without even a hint of warning.
The $1.2 million hadn’t hit our account yet, but even if it had I would have felt uncomfortable accepting it with no team in place to execute my vision. I would have looked like a fraud and an idiot anyway — what kind of founder announces to her investors that she suddenly has no team the day after she takes their money? And furthermore, how could I not have seen this coming? I was completely blindsided.
I went over to Matt’s office, and he proceeded to pour vodka down my throat whilst telling me I was much better off without them. Like most of Matt’s lessons it was hard to see that then, but he was right.
The next day I rang up our lead investor who decided to pull out of the round. Then another investor fell off. Everything I worked so hard for was crumbling to pieces. If only I’d closed everyone individually, instead of agreeing to round up at least $1mil to get the lead on board. But then I realized that these “co-founders” would have left anyway, leaving me in this same position.
I was stuck back in Australia still with a big vision, but as a single, non-tech founder with no team, no product (I needed these co-founders to keep the product running), no US visa and just some money that I’d gotten from being a YC company.
I remember my sister taking me for a walk after it all happened. She sat me down in a park overlooking Sydney harbor at night time and made me listen to ‘Shake it out’ by Florence and the Machine. She told me I’d bounce back, that I’d overcome this like I always did. I wasn’t sure I believed her, but I knew I’d survived worse. This ended up becoming my motivational song that I would listen to when times were tough, because it reminded me that I could surmount huge obstacles if I wanted to.
I didn’t fail then. I just started again.
Starting over
There were 5 investors who invested in me, despite all of this. They believed in me when I was having trouble believing in myself, but I couldn’t show them that — that’s the cardinal sin of any entrepreneur. Always be confident. Always be smiling. Always stay positive. Sell, sell, sell!
I remember one investor sending me an email saying “Shit happens. Take the money and go sort it out.” Another told me to go make him some crack for women.
***
"I know!" Peter replied.
I was talking to a random guy I'd just met in a random bar in New York during a work trip for 99dresses. After feeling itchy to explore the city, I'd wandered down to West Village — one of my favorite areas — and entered a little bar that looked lively.
As someone who spent plenty of time alone in new places, I was used to saying hello to random people, hoping to strike up a conversation. On this particular occasion, I began speaking to two guys standing by the bar as I ordered myself a beer.
Turns out, they were both entrepreneurs too. One of them, Peter, was from Australia.
"What's your business?" Peter asked.
"99dresses," I replied. "We-"
"Oh my God!" He looked at me in shock. "I've met you before. You were speaking on a panel at that conference in Sydney last year. I think it was in Darling Harbour. We met for, like, three minutes."
"What!? Yeah, I never go to those conferences. I can't remember why I ended up at that one." I laughed to myself. "What a crazy coincidence!"
"I know!" Peter replied.
We spoke for a few hours together with his friend. After a while, they asked me what I was doing the following night. I had no plans, so they invited me to dinner with a small group of like-minded entrepreneurs.
"There's just one catch," Peter said. "We're going to rock up at Nick's airport hanger without a clue where we're going for dinner. We'll have one hour to plan the trip and take off. It should be fun."
And it was. We were in the air less than 24 hours later, soaring past the twinkling night lights of New York City. Nick flew the plane with four of us as passengers.
Dinner wasn't your typical small talk. We dived straight into big topics; deep topics. It was the kind of intellectual conversation that I'd always craved. If this was what New York had to offer, I vowed then and there to move to that city. I wanted more serendipity in my life.
***
put in a report for me. I hated doing it, but it was the only way to push things forward.
I finally got my visa and took the next flight I could get out of Australia with four suitcases — 2 full of clothes, 1 full of shoes and another with all my electronics and miscellaneous items. The contents of these suitcases just about summed up my life.
I’d achieved my dream of moving to NYC, and I was living in a shoebox. It was all I could afford on my startup salary.
***
I entered my shoebox apartment and walked straight into the alcove where I'd been living for the past year, devoid of any windows or natural sunlight. A few short strides later, I was in the living room — which was actually Zac's bedroom.
It was 2014. I was 23 years old.
Zac was sitting on the floor with a set of tools laid out beside him. As I approached, I noticed he was filling pale white powder into little baggies and stuffing them into the lining of his cello case.
"Zac!" I cried. "What in God's name are you doing?!"
Zac looked up from the floor, grinning from ear to ear. "I'm preparing for my European escapades!"
"By stuffing drugs into the lining of your cello case?"
"Drugs?" He looked around at all the powder that had spilled onto the floor and laughed. "No, Nikki. This is Soylent. You know — that meal replacement stuff I was telling you about. I hate hunting for food like a neanderthal every few hours because I think food is only useful for nutrition — unless it is delicious, like a cookie. So I thought I'd stock up on Soylent and take it to Europe with me. But my suitcase is full, and I wanted to take my cello-"
"Why are you taking your cello?"
Zac sighed. "Because I've always dreamed of sitting in parks playing classical music on my cello. It seems like such a great thing to do in life, y'know? Go to Europe and sit in parks, playing the cello."
I gave Zac a skeptical look. "You do realize you can barely play Twinkle Twinkle Little Star, right? You began playing the cello, like, three weeks ago and it has been agony listening to you when your teacher comes around."
"Hmm… This is true..."
"And I don't want to shatter the fantasy or anything, but do you really want to lug that thing around Europe with you? It's huge!"
"That's what she said."
"Not to you, though."
"How would you know?"
I sighed. "Because I like to think that penis size is inversely correlated to the size of one's ego. And your ego is the size of Jupiter. Which means..."
Zac scowled.
"Anyway," I continued, "I'm just gently suggesting that you rethink your Soylent transportation plan. The little baggies of pale powder stuffed into the lining of your cello case probably won't go down too well with customs."
Zac frowned and looked around at the hundreds of dollars worth of Soylent sitting in clear packets on the floor. He sighed. "I am now experiencing the buyer's remorse."
"What are your plans, anyway?" I asked. "I have to be out of here in a week. Oh! I haven't told you yet."
"Told me what?"
"I wasn't sure how I was going to afford a flight back to Australia. But a good samaritan just bought me a ticket to Sydney with his frequent flyer points. He read my failure story and it must have resonated. Isn't the world full of lovely people?"
Zac shook his head as his mouth curled into a smile. "Trust that to happen to you. Pandora, Bryce, and I are convinced you have some kind of weird, magical luck gene. The other day I was telling my mum about your luck. She told me it was bullshit. I defended you, saying, 'No, no! There is something to this!' After I hung up the phone, I stepped outside and found a crisp twenty-dollar note on the ground."
I giggled. "I'm flattered, Zachary. Really, I am. But let me put this in perspective for you. Your business is thriving and mine just tanked. I just lost everything I worked so hard for."
"Yeah. I guess that's a bit shit."
"Anyway," I continued, "what are your plans?"
"I just bought a one-way ticket to Lithuania to meet up with some people and attend a business thing. I think we might go to Italy afterward. I'll spend a few months in Europe, then head down to Colombia. Medellin is supposed to be paradise. They call it the City of Eternal Spring! I love spring!"
"Sounds like a dream," I crooned. "I don't know what's next for me. I think I want to be nomadic for a while. Like, I have this deep craving to do something useful with my life. I guess, something useful for humanity. But I also want to explore the world without feeling like I should be doing anything in particular. I've had so much responsibility and pressure for the past four years. I want to experience the polar opposite of that. I want to be free as a bird!"
"Do it!" Zac said. "I know you. You'll make it happen. And I'll meet you one day in Medellin! I think I might buy a place there."
"Deal," I said.
"Deal," Zac agreed.
We shook hands.
***
Closing down
With a few weeks of cash left, Marcin and I agreed to use our remaining time to shut down the app gracefully for the sake of ourselves and the community. I came into the office that day prepared to have a hard conversation with him, but we both looked at each other and knew it was over. There were some tears, and I was grateful to have a curtain of long dark hair to hide my bloodshot eyes behind as I walked through our co-working space. I felt physically sick all day, and my stomach wouldn’t let me keep any food down. I lost my appetite for the rest of the week.
My first instinct was to apologize — to Marcin, to my team, to my investors, to the loyal community we’d built. I felt shame, guilt, embarrassment — like a shepherd who’d led her sheep off a cliff when it was my responsibility to keep them safe. I logically knew that I shouldn’t feel these things, but emotions aren’t always logical.
In fact, I didn’t really know what I should be feeling. I’d been working on this company ever since I finished high school, so 99dresses was all I’d ever known. It was a huge part of my identity — I was “that 99dresses girl”. Who was I without this startup? I had no idea. Just an ordinary girl, I guess.
***
It was 2014 — just a few months after 99dresses failed. I was visiting my friends, Bryce and Pandora, in Sydney.
I walked past an old bookshelf in their hallway. Something caught my eye: The Holographic Universe.
That's odd, I thought. Isn't that the book I almost purchased on Amazon last week? Except I didn't have any money to pay for it. Maybe I can borrow their copy...
I picked the book off the shelf and continued walking down the hall, past Zac's old bedroom. Memories flooded my mind. We'd spent endless nights hanging out in that room, talking and pushing pixels on our laptops as we built our businesses. My venture had passed away, but his was still thriving. I wondered what he was up to in Europe.
"Nikki!" Bryce yelled as I entered the kitchen. He stretched out his arms, a burger flipper in one hand.
"It's so good to see you!" Pandora embraced me in a hug. "We've missed you!"
"How's country life treating you?" Bryce asked. "Is it all it's cracked up to be?"
"It's a nice change from New York," I sighed. "I feel like I can breathe and figure things out."
"What have you been up to?"
"Mainly teaching myself to code."
"Are you working on a project or-"
"Yeah. I've become obsessed with building games for some reason. I'm playing with different gaming engines and studying game mechanics. I'm not even a gamer! It's really weird. But, whatever. I'm just rolling with it."
I heard footsteps in the hallway. A bubbly Asian-American entered the kitchen.
"Oh! This is our new roommate, Jackie. She's in Zac's old room."
"Ah, the infamous Zac!" she giggled. "I've heard so much about him. He sounds like a character."
Bryce, Pandora, and I looked at each other and laughed. Understatement of the year.
"I'm Nikki, by the way."
Her mouth gaped open in shock before a wide grin spread across her face. "Oh my God! You're Nikki Durkin!"
Bryce and Pandora burst out laughing.
"What?!" I said. "What's so funny?"
"Well," Bryce replied, "Jackie always dreamed of moving to Australia so she packed up and did it. On one of her first nights as our housemate, she said, 'Guys! You have to read this viral story about failure and chasing your dreams. It was written by a 22-year-old. I found it so inspiring!' And then Pandora and I slyly enquired as to the author of said article, to which she said, 'Nikki Durkin.' We told Jackie that you're here every other night when you're in Sydney, so she'll probably be seeing a lot of you."
Jackie was acting a little star-struck. "I can't believe it's you!"
I laughed with them. Isn't it funny? That my words could inspire someone like that? That others could learn from my experience?
***
Moving on
So this is where the story comes to a close. My friends all ask me if I’m fine, and I honestly think that I am. It’s been a wild ride, but it’s time to move on.
A cruel consequence of my failure is losing the US visa I worked so hard to obtain. Once I stop being the CEO of 99dresses I technically have 10 days to sell all my possessions, pack my bags, say goodbye to my amazing team, my friends and the life I’ve been building here, and leave.
That being said, I’m excited to start a new chapter. As much as I love startups, it’s somewhat liberating to have no responsibilities to anyone but myself — no team, no investors, no customers to look after. Maybe now I can be a normal 22 year old for a while: indulge my wanderlust, make some bad decisions, try something new.
I’ll be taking some time out to recharge whilst living with my parents in a country town of 2,000 people where the internet is slow and there is no Seamless. I hope I survive. Honestly, I’ll probably get bored within a week and start working on a new idea. I already have a few.
When I started 99dresses I was going to go big or go home. It’s been a great adventure, but now I’m going home.
The year was 2015 — a good eight months after 99dresses went down. I was out for my daily jog around town, finishing up on Princess Street — the cute little road where I grew up. When I was in primary school, my brothers and I used to step off the afternoon bus, place our backpacks over our heads, cover our eyes, and run as fast as we could back home.