On Grind - from Investor to Creator to Founder

Sarah asks a provoking question that has been on my mind a lot as I transition from part time creator to founder:

Selected responses:

• ”Only one way. Evidence of grinding consistently in the past. Many instances.”
  • this is an obvious correct answer. problem is that to be early on someone, you have to pick an inflection where they go from not-grind to grind, though of course many pure-grind people exist.
• ”See how hard they grind in the open with zero incentive. COSS”
  • great, but to state the obvious, not everyone has the luxury of doing this
• ”do they workout and can you tell”
  • I like this one a lot, because it is the most personal, non showy, brutally accountable kind of grind, yet the most physically evident, and has implications on mental performance. It’s also the one I am weakest at.
• ”What do they do in their free time? Do they take it seriously and are they driven to be the best possible in it? Example: gamers. League of legends? What rank are you? Bronze? Yike. Diamond? Woah.”
  • great one. famously checks the TK Wii Tennis box. (if you don’t know this story, look it up, if you do, you are the right kind of startup obsessed lol)
• some more questions i havent thought deeply about yet

My problem with the phrasing of the question is treating “willing to grind” as a binary yes/no attribute. This is how it reduces down from the investment POV, but for the person living the grind, you can be willing to grind without knowing what kind of grind you are in for, and when it is actually wise to give up a grind.

Instead, I think about it as a continuous game. The person has to actively wake up every single day and choose to grind on the thing.

So with that in mind, one missing question that I would add is have you burned your boats?

• That is a specific form of a more general question I do ask in my founder interviews: ”of all the things you could be doing, why do you do what you do?”
• Some people have no choice - they dont have much in the way of credentials, they won’t be hired by traditional FAANG companies, they are stuck in obscure backwaters, the only way they will ever make their mark is by striking out on their own
• More common - I daresay the majority of founders I see - already have some form of professional accomplishment and could feasibly coast that way for the rest of their lives. They therefore have to be divinely dissatisfied with their success to actively opt in for lower pay, more discomfort, and much higher chance of failure.
• Doing it for money is a solid B+/A- motivation. Many people will say they do it for a mission or cause, but it’s tough to stick to it when the cause is intangible/not personal. Doing it for revenge/spite though is solid.
• But above all I think ”burning boats” is the ultimate commitment device - that you not only have chosen to do the thing you are proposing to do, but you have actively reduced your optionality in order to pursue it wholeheartedly.

I have done this to a small degree but will need to step it up over the next year.

Learning to Grind

I’ve been struggling with grinding myself. Most people who follow me know I can more or less adhere to the content grind; I’ve dropped things that didn’t spark joy, but most days and weeks I can come up with something interesting to say and be part of the conversation.

But founder grind, at least in the zero to one stage, is another matter. It is picking one valuable thing to ship in the market and then powering thru to deliver it. For better or worse I have had founder ADD and shipped developer, menubar, and (unlaunched) smol talk in quick succession to gradient descent my way towards smol ai. (and also launched AI Engineer Summit along the way) We will need to converge much faster over the next month to launch.

Creators constitutionally need to know a little about a lot of things. Founders need to know a lot about one thing. This is a fundamental horizontal-to-vertical “grind flip” that I am living through, and it is mostly a psychological barrier.

It is no surprise that the founders with the best grind in AI right now are getting appropriately recognized:

• https://twitter.com/jerryjliu0
• https://twitter.com/hwchase17
• https://twitter.com/mattshumer_
• https://twitter.com/mckaywrigley
• and ofc all of Vercel.

they ship often and consequentially. Many cannot do either, most cannot do both.