Let’s talk about failure.

Alexis Tryon
Aug 31, 2016 · 5 min read
An early, terrible Artsicle homepage.

The startup community loves to celebrate failure. We “fail fast”, pivot, learn and we move forward. Failure is just a step on the long path to success. Don’t be afraid — go fail!

But do we take time to talk about what failure actually looks like? How it works? What it feels like?

When it was time to shut down my failed startup, I scoured the internet to find stories of similar cases. I was looking for guidance, for reassurance, and for a reminder that I wasn’t alone. I found a black hole. Sure, there were plenty of stories about high profile company implosions and lots about changing market conditions that caused good ideas to go bad overnight. Even more about “acquisitions” that couldn’t possibly be paying out anyone. But good, old fashioned, “it just didn’t work out” failure? Nowhere to be seen.

I get it. Everyone loves a train wreck. A quiet shutdown isn’t very newsworthy, but it happens everyday. This is my story, told to the tune of the 5 stages of grief I’ve gone through. Get ready for some feels.

Step 1: Denial

Artsicle could have gone on a lot longer, maybe forever. We were ramen profitable, with a great small team and enough new customers to keep us alive. The core ideas to the model had worked — just not at any scale — and the B2B model we’d landed on was acutely uninteresting. I was less interested in going in to work each morning, feeling increasingly guilty for holding our team back from the rocket ship success opportunities I felt they deserved. Was this failure?

It’s been said that startups don’t die, they commit suicide. Artsicle wasn’t going to die on its own, but it certainly wasn’t flourishing. We were a press darling and everyone said we were killing it. They must be right. Everything is going to be fine. (Everything was not fine.)

Step 2: Anger

It’s not fair. It’s not even reasonable. How could the world possibly work this way? Hard work is rewarded. That’s a base assumption behind so much of what we do, and we worked harder than most anyone. We built something real!

Everywhere I looked I saw founders with mediocre companies selling to Yahoo for a few million before jetting off to travel the world. Their companies weren’t profitable. Hell, they weren’t even interesting. They were a bunch of second rate, idea stealing, visionless, lazy assed fucking fuckers. [Note: I was pretty damn angry. Friends who had exits during this time, I secretly hated you all and was likely a complete ass at least once.]

Step 3: Bargaining

Ok, if those fuckers can do it, then so can we. I built a giant spreadsheet of potential acquirers, fantasizing about why they’d want to buy us. We had a huge team of engineers! (We had 4.) We had a super sophisticated recommender system! (It had never been tested at scale.) We were nice people, damnit. (Ok, that one I stand by.)

I started getting intros and taking meetings. A few conversations were promising, with interviews for the team and early negotiations. We were going to pull this off!

As it turns out, those offers looked an awful lot like jobs — locking our team into market rate salaries, with no cash to distribute to our investors and a full shut down of the platform. The temptation to take a deal was almost overwhelming, to officially note “acquired” next to Artsicle’s name on TechCrunch or AngelList. At the end of the day, we walked away. We’d go get jobs of our own and find our own path to shut down.

Step 4: Depression

First, it was time to cry. And God did I cry. For weeks, I cried myself to sleep. I cried so hard I threw up. And I’m not a person who cries. I didn’t know this person.

I’ve never had children, but I felt like I’d lost a baby. The pain was physical, lodged firmly in my stomach. As I write this, I can feel the nausea coming back and am fighting the urge to stop writing, to go back to hiding. My company, my baby, was going to die. And there wasn’t a damn thing I could do about it.

I screened all my calls, lived on a diet of goldfish crackers, and quit going to the gym. I didn’t want to risk going outside, where someone might ask how the company was going. I showed up at the office everyday with my happy face plastered on. I was going through the motions, but mostly I was reading Twitter all morning and walking laps around Washington Square Park for hours every afternoon. I hid from everyone, sure they were ashamed of me. I was a total failure.

Step 5: Acceptance

There was no aha moment. No sudden great insight. It was just time to move forward and let Artsicle die. Slowly, I started to come back out of my hole.

I started reaching out to friends, family, and investors to tell them what was happening. No one was surprised — they’d known it was coming. I moved apartments, away from the pain I now associated with my studio that had been my cave of tears. I felt the cobwebs start to fall away. Then I took the first steps to dissolve the company, a process that would take nearly 18 months.

The road to acceptance has been slow. It started with a simple statement, repeated over and over: my company failed. Today, if you ask what happened, I’m comfortable saying that Artsicle failed. I no longer try to spin it as a successful business, claim a soft landing, or point to external factors that led us here. Sometimes I say “we built a great website, but it was a crappy business.” Most days, I can say that without crying.

Parts of Artsicle will live on. We’ve left a legacy I can be proud of, including an incredible group of individuals who started their career in tech with us. We created hundreds of new art collectors, helped countless artists grow their artistic practice and learned enough to fill books.

This month, I officially signed the paperwork to dissolve Artsicle Inc. I expected it to be a heartbreakingly painful moment, but in reality I felt a huge sigh of relief. We failed. And its going to be ok.


This version of the journey is all about feels. In the coming weeks, I’ll be writing more about the actual process we went through to wind down and what worked / didn’t work to get us here in the first place.

If you’re going through this, know you aren’t alone. Thousands have been here before you and will be here after you, even if they’re stories aren’t being printed. I may not be able to help, but I will be able to relate and am happy to talk.

Alexis Tryon

Written by

Doer, Maker & Enthusiastic Eater. Founder at Extra Yarn & Artsicle.

More From Medium

Also tagged Entrepreneurship

Also tagged Failure

Welcome to a place where words matter. On Medium, smart voices and original ideas take center stage - with no ads in sight. Watch
Follow all the topics you care about, and we’ll deliver the best stories for you to your homepage and inbox. Explore
Get unlimited access to the best stories on Medium — and support writers while you’re at it. Just $5/month. Upgrade