Down a tiny alleyway, barely wide enough to fit the procession of delivery vans, BMW SUVs, and Audis that creep through its protected and shadowed asphalt, we were lighting cigarettes, drinking the house Shiraz, and sipping black coffee. It was early — 3:00 pm — and we had the entire afternoon to drink and to talk and to be, and there was nobody to nudge us for the time or glance at their watch.
We were at a café called York Lane, a wine bar in the evenings and a haven for the Startup tragics and government staff and tech “visionaries” desperate for their last round of funding.
The crypto startup had been running on fumes for months. They’d been desperately short on cash, after a failed ICO, and they were broken and broke and bewildered. We drank together because drinking was the last thing we could think of to do. I had given all I could, edited pitch decks and written strategies and tried to help.
We were all hanging ourselves, running out of rope and hoping against hope that we could manufacture a gubernatorial pardon. We were all fucked and we could see it in each other’s eyes and smell it in our shared desperation and taste it in the increasingly cheaper rounds we bought as the minutes ticked by and our runway ate itself.
The product had been there, the team had believed, and the stars had not aligned. The bloggers had told us to avoid having a plan B, to believe in ourselves, to stay on our laptops when the bourgeoisie had retired to the bar and the understanding was that somehow it would all work out. We were lied to, and we lied to each other, convinced that the bleeding hands that clutched the life rope could hold on in the midst of the tempest and the raging storm.
The crypto startup’s ride was over. It was over for the dreamers and for the believers who held equity in a breath of nothing and a sparkle of pixie dust too abstract to reliably evaluate. The startup dream was over because we had failed. We had failed in the same class as Steve Baxter’s social skills, we had failed in the same class as 90% of the social networks from the early 2000’s, we had failed like Pets.com.
We had failed like so many startups, so many founders, so many dreamers of the scalable dream. We had failed and we had marked it with the cocktail of substances, Slack messages, admissions of fault and upbeat tweets that accompany every startup blow out.
The conversation ranged, from who we’d fucked to who we’d screwed, to who we wished we’d never known, never betrayed or never been unlucky enough to desire. The conversation covered vague responsibilities for our predicament, badly worded copy, unfinished tech priorities and unrealised milestons. One by one, we smoked and we talked, and we shared, and we opened up in a way that we had wanted to for weeks, and had hid.
I’ve had the same drinks, in the same way, a few times before. I’ve had a few drinks as my own team, my own investments, my own pet causes and game changing ideas drove themselves into the dirt and ate mud where profits ought to have been. This was failure. Failure in its most pure form, failure to make it, failure to live it, and failure to find a way through.
To walk away from failure is to live in the world of Startups. Failure is considered a badge of honour and a necessary evil and a right of passage — in the abstract. Failure is admired in hindsight when captured through the rose-tinted lens of a wrap-up blog post.
But failure in its moment, at its zenith, in the midst of its pain and violent host rejection, feels nothing like the wisdom they share on LinkedIn or the fragile narratives encased in hardcover Startup self-help volumes. Failure in its moment is devastating. It’s ruinous. It takes who you are and it strips away the defences and it vomits you out, naked, cold and soiled, wretched vermin who once owned All Birds shoes and branded startup hoodies.
When the CEO came to me and told me that the crypto game was over for him, and for the team, and for those of us — such as myself — who had bet our time and our capital on his ability to deliver, I hugged him. I held him for a moment. And I bought him a round.
Because the failure was an old friend to me, the sense of loss my comrade, the bitter doubt and pain my peers. I knew his hurt and I knew his self flaeggelation.
The reality is that anyone who has ever chased the elusive and ephemeral dream of Startup success has felt failure and felt it keenly and felt it late, when the lights have gone out and the bottle is empty and there’s nobody with whom to share your ticking clock and accruing regret. Failure is our darkest hour and the enemy we battle, with weapons and with hands and with feet and with every particle of the compromised and bloodied self respect and idealism that we once mistook for a sense of purpose.
When the party broke up, it was three of us, in the corner of the bar, and the nervous laughter and braggadocio was gone, and the tab was gone and we were deprived of the ego that let us stand and avoid our own reality.
The CEO was silent. The COO was silent. I filled that empty space with vapidities and platitudes and I told them that persistence was the key to success. It was swampland and they knew it and I knew it. The silence grew, until it encompassed me and it filled the cracks and it filled the shadows and the bar staff could sense it and the patrons with their booze and nachos could no longer walk past us without feeling an acute blow to their emotional energy.
We had come close to touching the sun, without realising that the goal itself was beyond us. We had tasted the specific failure that can only come from throwing anguish and caution to the wind.
We gave it a shot, didn’t we?
We had a fair go.
We would have regretted it, if we hadn’t tried.
But the comfort of knowing that we had given what we could and driven what we could was not enough to keep us warm. It was one more loss in a night of blind gambling, one more shattered break up in a couple where neither party can face their agony or place their blame or accept their part.
I lifted my glass and drained it. I knew failure, I had known failure, I would know it again. We walked out, and the alley was dark, and the cold was biting and we promised each other that our next ventures were a market fit, were an undiscovered jackpot. We promised each other the world and walked away.
The failure had visited us and one day it would visit us again. Walking down the alley towards the station, no quote from a dead billionaire or a celebrity could have cut through my defeat.
Like so many startups, we had reached our final act, our last scene, and the curtain had gone down. We would all wake up the next day, wake up and find a reason to push that rock up that hill. The failure would not be permanent, it would not mark us forever, it would be a lesson.
The next idea might come, the new new thing, and with it would come healing and a second chance, a third chance, a fourth and a fifth. And so failure beats against us and wears down the jagged rocks and we are eroded, but along the way, we are smoothed and sculpted and shaped.
[This post appeared first on Medium and has been reproduced with permission.]