This May Be the Most Honest and Emotional Account of Startup Failure You’ve Ever Read

July 7, 2014

10:30 am

With only a few weeks of money left, Nikki Durkin decided to shut down her fashion swapping startup 99dresses after four years of blood, sweat, and lots of tears.

“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 coworking 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,” she writes on Medium, in a post that got over 200,000 views in three days.


“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.” 

Before 99dresses failed, Durkin had started searching desperately for stories of other founders’ failures. “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,” she writes.

And while she found a bunch of post-mortems, none of the entrepreneurs seemed to talk about how it felt. “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,” she writes. 

So that’s what Durkin set out to write on Medium, and she hopes to collect similar stories from other founders and put them into a book. For her, 99dresses’s journey is the story of one obstacle after another, and how she persevered until she couldn’t persevere any longer. “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,” she writes. 

The story 

Nine months after launching in Australia, 99dresses was losing momentum and faced with big tech problems. “Let me tell you — failure fucking sucks,” Durkin writes. “I travelled to my parents’ place in the countryside of Australia, locked myself away in my room, and cried for what seemed like an entire week….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.”

For the first of many times, she decided to push forward. She writes, “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.”

At that point, 99dresses won a $10,000 business plan competition and Durkin moved to the US. She recruited two cofounders, got into Y Combinator, and was about to raise $1.2 million. 

But suddenly, her two cofounders walked out and so did her lead investors, leaving her with only $600,000. 

Betrayed by people she trusted, she finally put her faith in another cofounder, who helped her pivot 99dresses and launch an app in the US. Activity picked up as users were doing over $1,000 in trades every week, but the funding wouldn’t last. So she went out to raise a bridge round to tide them over until a Series A. 

“I’d be invited to cocktail parties full of VCs where I’d don my painful sky-high heels because I’d split tested heels vs. flats, and for some reason a 5’11 woman in 7 inch heels commands more talking time and attention from investors than one in the comfy flat booties I wear to work. Apparently height gives you presence. Once or twice I’d have an investor asking if I knew what an angel was, or if I also modelled because of my height, or some other unintentionally patronizing comment that I doubt any guy would be subjected to. I learned to take it all in my high-heeled stride,” she writes. 

But even her current investors weren’t on board, and no one was biting. It was time to shut down. 

“I didn’t tell many people about what was happening. You’re not supposed to talk about this shit. If someone asks how your startup is doing, you fire off some kind of positive phrase like a reflex. My friend gave me a hug and told me to go read The Hard Thing About Hard Things by Ben Horowitz. I bought the book and sat in a coffee shop that Saturday afternoon reading it through. I identified so much with the struggle — I’d been through it many times before whilst aboard this emotional rollercoaster.


“I realized something: I was fucking tired — physically and emotionally. I wasn’t sleeping properly. I hadn’t been on a proper holiday since our ‘schoolies’ beach celebration straight after I finished high school in 2009. The holidays I had tried to go on just ended up being long strategy sessions in my head to figure out my next move whilst lying beside a pool. All I could think about was this damn startup and it was completely consuming me.


“I had no bandwidth for anything else. When someone asked what hobbies I had outside of work, I’d laugh. I’d recently started having mini panic attacks whilst I was doing ordinary things, like taking a shower or doing my hair. I felt like a shitty friend. I couldn’t even contemplate having a relationship (I tried that before, but yet again this startup won out over him). I wasn’t sure how much longer I could do this.”

Read the full post on Medium. 

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Kira M. Newman is a Tech Cocktail writer interested in the harsh reality of entrepreneurship, work-life balance, and psychology. She is the founder of The Year of Happy and has been traveling around the world interviewing entrepreneurs in Asia, Europe, and North America since 2011. Follow her @kiramnewman or contact [email protected]

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