Endure or Quit? That is the Question

Tim Leatherman – the creator of the Leatherman multitool – endured for 7 long years before making his first $175 sale of a single Leatherman tool. In a comparable 7-year time span, Travis Kalanick started and quit two startups before starting his 3rd called Uber.


Uber would not have existed if Kalanick had endured with his first startup for as long as Leatherman did. The Leatherman multitool wouldn't exist If Leatherman quit as quickly as Kalanick did.


One had to quit fast to succeed, the other had to endure long to succeed.


To endure or quit? It is the hardest, and perhaps the last question, of your startup journey.


Mind Bending Question


I faced this question multiple times in my startup journey. It felt like this.



The hard thing is that you don’t see the inflection point until you reach it. Is it a month or two years away?


The harder thing is that for most startups, the inflection point doesn’t exist at all. Is it going to stay flat like this forever?


You want to win badly, you don’t want to give up prematurely, and you don’t want to spend 10 years on something that’s not working.


And then the smartest people in the world disagree about the answer.


Two Conflicting Answers


There are two conflicting schools of thought when it comes to the endure/quit decision:

The last 3 words of Graham’s article – “Don't give up” – sum it up. Bad stuff is coming, surviving is enough to make you rich, just don’t give up.


Never giving up optimizes the chance that your particular startup will succeed, but is that optimal for your career? Is that optimal for your happiness? What if you’re unhappy working on your startup? Does Graham have investor bias?


Derek Sivers says, “If you’re not saying “HELL YEAH!” about something, say no.”


Sivers's advice is to follow our gut. Our gut is smarter than our frontal cortex, it has much more evolutionary experience. But it has a problem too: startups are so hard that at some point you will viscerally want to quit.


Is it Graham or Sivers who got it right?


My Answer


As a fan of Graham and Sivers I must agree with both. Both are correct about different things.


You should never quit your startup because it is hard, because you’re having a hard moment, or because things look grim. Why not? Because every successful startup in history went through terrible difficulty, facing hardship implies nothing about success or failure. This is the lesson Graham teaches us.


But, you should only be working on your startup because it’s a HELL YEAH. You like what you’re doing, feel challenged and fulfilled, and believe it is worth the best years of your life. It makes you a happier person. If it’s not, go find your HELL YEAH somewhere else. That’s the lesson Sivers teaches us.


And there’s your answer:


Endure when it’s hard. Quit if you’re not saying “HELL YEAH!”