In Which Jack Dorsey Reads Us Some Poetry And Lists And Plays Us A Jazz Tune

Jack Dorsey seems to be at the tech world’s center of attention, thanks to a series of articles and an upcoming book about the early days of Twitter, and whether or not he screwed over friends and coworkers in the early going. But the co-founder of Square and Twitter (a company which also just happens to be in a quiet period while it prepares for IPO) sidestepped any unnecessary or awkward questions that might have come his way at Y Combinator’s Startup School today.

Instead of doing an interview or relaying anecdotes of his early founder days (like Evernote’s Phil Libin, Optimizely’s Dan Siroker, or Airbnb’s Nate Blecharczyk), Dorsey took the occasion to dispense wisdom by reading from a couple of his favorite books, as well as his own daily “Do” and “Don’t” list.

First up: quotations from The Art Spirit, by Painter Robert Henri. In this section of the program, Dorsey noted the similarities between Henri’s descriptions of creating art and what it’s like to be a startup founder. In a nutshell, founders (like artists) need to find their own way to create products that they’re passionate about. That is, what matters is not so much the ideas themselves but the execution of those ideas.

He followed that up with an extensive list of lists found in Bill Walsh’s The Score Takes Care of Itself. The legendary 49ers head coach wrote that book as a leadership manual, and former Square COO Keith Rabois gave it to Dorsey. Most of the advice listed involved how to be a leader (“be yourself,” “be committed to excellence,” “be positive”) and how to manage others (“exhibit patience,” “become best buddies with some employees”), giving founders a guide into how to navigate the difficult waters of managing teams (something that Dorsey reportedly wasn’t so effective at during his Twitter days).

But the most fascinating bit might be Dorsey’s own use of lists. He told the crowd that he creates notes for each person he meets, building detailed lists of important things that come from meetings with them, or that he’d like to relay to get things done. He also has a “Do” and “Don’t” list that he takes a look at daily.

That Do list is as follows:

  • Stay present
  • Be vulnerable
  • Drink only lemon water and red wine
  • Six sets of 20 squats and push-ups every day
  • Run for 3 miles
  • Meditate on this list
  • Stand up straight
  • Spend 10 minutes with a heavy bag
  • Say hello to everyone
  • Get 7 hours of sleep

And the “Don’ts”:

  • Don’t avoid eye contact
  • Don’t be late
  • Don’t set expectations that you can’t meet
  • Don’t eat sugar
  • Don’t drink hard liquor or beer during the weekday

At the end of the presentation, he played a jazz tune for the audience that I didn’t recognize. It was inspiring.