My startup failed, and this is what it feels like…

My startup failed, and this is what it feels like…

We had users and traction, then we fell off a cliff

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.

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