When one should go gently...

Startup death is a fact of startup life; most of us don’t need to hum Circle of Life to understand that it’s not all unicorns, roses and IPOs at the end. Indeed, the startup obituary has almost become its own literary genre, with lots of founders baring their souls about the individual circumstances of their company’s demise.

One of the more interesting ruminations we’ve come across is a terrific essay from Andrew Lee (@_andrewlee) which looks beyond the singularity of his startup’s demise to a broader view that compares medical end-of-life decisions to those faced by startup founders.

It’s a bold view. Since most startups fail to see a return on investment, figuring out what one wants the end to be like — should it come to that — is simply part and parcel of good leadership. Lee uses Atul Gwande’s excellent book Being Mortal as a general framework, and tries to shift the perspective to show that shutting down a company does not have to be exhausting all possible options until there is nothing left. In this context, Lee believes that “Failure is not having the agency to determine how the story ends.”

Lee cites some questions that are routine in medical end-of-life conversations, and recommends them for startup teams: What is your understanding of the situation and its potential outcomes? What are your fears and what are your hopes? What trade-offs you are willing to make and not willing to make? And once those are explored, it’s easier to focus on the final question: What is the course of action that best serves this understanding?

For Lee, too many startups unconsciously emulate one of the central flaws in medical care: preserving even the most paltry existence at all costs. His firm pursued a hail-mary acquisition against strong odds, one that meant the final days of his once tight-knit team were spent in a rollercoaster of uncertainty which made adversaries out of former friends and left pretty much everyone with a sour taste. In hindsight, Lee believes, it did not have to be that way. He ends his essay quoting Gwande:

“…you don’t want a general who fights to the point of total annihilation. You don’t want Custer. You want Robert E. Lee, someone who knows how to fight for territory that can be won and how to surrender it when it can’t, someone who understands that the damage is greatest if all you do is battle to the bitter end.”

There is a great pride in overcoming obstacles, in perseverance, in grit. But there can also be great harm — beyond the economic consequences and opportunity cost, the real and often unquantified destruction of professional and personal relationships. As the saying goes, every corpse on Everest was once a motivated person. There are times when the best decision might be to stop and turn around.