gastronomy + technology

The Trough Of Sorrow

 The Trough of Sorrow

Paul Graham once wrote of the time in a startup when the release fever breaks and the company enters into a difficult process of finding product-market fit as “the trough of sorrow”.


I am sitting perfectly upright in small bistro chair in Boston, staring into the face of an angel investor who returns my gaze with an equal blend of fear, greed and curiosity. I pitch the many virtues of my startup company to him in the rapid, Zuckerbergian monotone that founders everywhere have chosen as the cowboy drawl of the new tech frontier. I can see clearly these three emotions battle across his face, hands flinching distractedly to his iPhone each time it buzzes.

We’re 17 slides into a PowerPoint that I spent 32 hours making while our dessert glides across the restaurant in the hands of a busboy who makes less in a decade than I will receive from this man if our meeting goes well.  This investor is one of the stealthy 1% who walk among us, and despite being the founder of a tech company I make a similar salary to this busboy.

I’m wholly focused on selling him the team we’ve assembled to change the world when a wine glass slips out of the hand of another guest in the bistro and crashes to the floor in a spectacular burst of Rosé and glass shards, as if emphasizing the excellence of our executives.  He glances up at me from his phone when I mention the titans of industry our operations team worked for, and I see greed and curiosity slowly overwhelm the fear of losing money; from his facial expression I know I’m going to get him to write a check.

Dessert arrives and I pop the first victorious bite in my mouth and bite down hard, and to my horror a stray shard of wine glass breaks one of my molars neatly in two.

The sound is audible enough that he looks up at me in surprise, and I grunt in pain, my mouth full of blood, and hum a quick apology as I leap from the table and run to the bathroom. I spend an agonizing three minutes packing white bathroom tissue into my jaw and removing bits of teeth from my mouth, and then return, my head pounding in agony, to the table, intent on closing this deal with a cheek swelling and blood welling up into my mouth. This is the life of a startup founder.

This money I’m asking for is a seed extension, a bit of debt my startup needs to survive. For the past year, I’ve raised 6 figures of this kind of debt to keep our small company going, like a train conductor who sees there is no more track for the train to run on and so jumps from his driver’s seat to start madly laying track in front of the engine, manically trying to make time for the train to reach the next safe stretch of rail.

Most businesses reach these moments, however technology startups are unique in that the train is almost exclusively transporting people. Startups are a collection of (optimistically) brilliant people who come together to change the world, and so the money we need pays salaries, pays school fees and mortgages and car insurance and vacations and food. If I fail to find enough track to keep going, I fail my best friends and closest companions.

Most startups are founded by geeks, and most geeks are raised on fantasy and science fiction books. We revel in stories where heroes sacrifice everything to triumph over impossible circumstances. The startup journey is the hero's journey, we’re all Frodo and Ender, Paks and Miriamelle, each on our quest to change our world for the better. In this moment, bleeding and in agony, I know with perfect certainty that this angel investor is still winnable, when I should know that I need immediate medical attention.  He clearly sees my horrifying injury clearly and grabs the check, offering to drive me to the clinic right away. I see the opportunity slip away and I instead spend 15 long minutes getting blood on the seat of his Tesla while he drives me to Mass General.

The tooth is removed and a gap remains, a reminder of how close I was to success. I am forced to return to the office empty handed and gauze wrapped, delirious with painkillers.  Our shy developers look at me, expecting good news despite this awful appearance, hoping perhaps the injury was cycling back from the meeting with a check for a house-sized sum tucked in my pocket.

Each subsequent pitch, each new angel investor, I run my tongue gingerly through the gap in my teeth as I pitch them. I learn to smile with my teeth together, I learn to cope with my headaches, and I tell myself that I’ll have a Victory Tooth installed when the quest is complete.

The train barrels forward, I keep laying the track, and slowly sacrifice more and more. I no longer take days off. I no longer take vacations. I sell my car. I lay off staff. The train shrinks down, slowly, even as we accelerate; new growth, new customers, new deals.

I begin to sleep under my desk, I begin to not pay bills. I grin with closed teeth through another dozen pitches, even as my apartments heat shuts off and I sleep in the office. I begin to lose friends from the journey, who don’t understand that a night of drinking in Boston could mean one less day of survival for the business. I run my tongue along the taught skin where the tooth once was, and I pray for deliverance from the trough of sorrow.  

It all unwinds slowly, the team slowly drifting away to other opportunities, but I can’t leave. The sunken cost fallacy, all the sacrifice, it’s too much to give up. I see my eviction notice as an opportunity to sell appliances. Slowly the finances of the business seep into my credit card, then my girlfriend's credit card, and then one day there is simply no more money.  The train derails, but I am the only passenger left.

The quest fails, and I am left without a model for what comes next. Three years of my life, a thousand days of tireless effort, amount to nothing. I lose connection with anyone in the startup world, unable to face the reality of the failure.  I flail desperately from one moon shot to another, even moving to another state to take a job with a competitor, hoping beyond wild hope that I will convince them to purchase the rotting carcass of my own company. Even this falls through. Former employees sue. It’s truly over.

I head to the dentist one afternoon in late summer, having scraped together the money for a new tooth. I chuckle to myself, thinking back on the moment when I decided to not include myself in our employee benefit plan (heroes, after all, are never injured during quests). In the waiting room devoid of joy, I flip open a tired copy of the New Yorker and see a poem about walking in the Lake District, and I realize that I need clarity far more than I need dental care.

Tooth money buys a flight to London, a train ticket to St Bees in the north of England, and packs of instant coffee. I begin to walk, and my tech addiction, my sleepless zombified complexion, and my adderall-fueled jitters begin to fade slowly away.  I call old friends from pubs in tiny villages.

I walk from dawn to dusk, listening to podcasts, music, or the wind across hills, and finish the day eating simple meals in a tent next to sheep. I feel life slowly restarting in my body. I climb a high peak; looking out over the Lakes I cry silently.  All failed founders have thought of suicide in dark moments; my version was fantasizing about accidents that would claim my life and so save me from the defeat and failure and most of all the necessary explanations to everyone in my life. High on that cliff, looking out over an empty and beautiful landscape, I know with perfect certainty that I was not done with living yet; that I have vitality and purpose and passion ahead of me still.

I’m on a quest again, one that leads me 1300 km across England and Scotland, one that slowly walks the joy back into my life. I complete the walk.

Returning home I see the brutality of my first quest on the lives of those around me, and I’m thankful that I’m alive. My fog lifts, I see opportunities to change the world again, I begin to speak with conviction about the future. I begin to call friends in technology that I’ve avoided for months, years, and I nurture that restless creativity that led me to start a business in the first place.  I return to life grateful for the whole experience, and ready for what comes next.

PS- if you know a founder who might need a call, please pick up the phone.