Nobody was quite expecting Jack Dorsey, the Twitter co-founder and now clean-cut tech superstar at the helm of payments company Square, to pull up a slide showcasing the novel "The Art Spirit" by the American painter Robert Henri. Then he began reading from the book off his phone, and it only got weirder from there.
In a self-described first, Dorsey decided to forgo mentioning Twitter's upcoming IPO, or any of the gossip surrounding the founding of the social network. Instead, he waxed philosophical on the things that inspire and motivate him every day, including a longstanding experiment of keeping track of all the things he likes to do and wants to prevent himself from doing daily -- a "do and don't" list that he says has trickled down from his personal life into the very management structure of Square.
It was an entertaining approach -- and clever PR tactic -- considering all the fuss of late about the origins of Twitter and just what role Dorsey played, portrayed first in an excerpt from New York Times journalist Nick Bilton's upcoming book and then in a New Yorker profile in its latest issue.
Surprisingly, it all seemed to work, at least from the crowd's perspective. Dorsey got plenty of laughs from the more than 1,700 up-and-coming entrepreneurs and startup founders. Now that Dorsey's persona has been carved to accentuate his appreciation of craft, design, and philosophy -- much in the same way Steve Jobs became a cornerstone figure at the intersection of art and technology -- it all fit into the tech luminary's self-image.
"In Silicon Valley especially, it's so easy to fall into the footsteps of others. You have to find your own path," Dorsey said, dropping in these lines of advice in between readings of Henri.
He also read passages from San Francisco 49ers coach Bill Walsh's book "The Score Takes Care of Itself," given to him by an early Square employee. "Be positive, one of the hardest things to do when you start building a company," he said after a passage from Walsh. "'Good luck is a product of good planning,'" he added, picking back up with his reading.
Dorsey also played the crowd some tunes from his iPhone to a slideshow of photos, one of the stranger moments that even Facebook CEO Mark Zuckerberg felt compelled to mention when he ended up taking the stage after Dorsey's departure. "I can't get away with that," Zuckerberg would say. "He can."
Dorsey ended the strange but surprisingly well-received lecture with a string of personal confessions related to his "do and don't" list, something he maintains on his phone an checks every day and night that "has been fundamental in establishing patterns for myself," he said.
"Be vulnerable, show people my mistakes and my fears because they can relate," he read. "Number three: Drink only lemon water and red wine." Don't drink hard liquor or beer on weekdays. Six sets of 20 squats and push ups every day. Meditate on this list."
He advised the crowd to do the same, even only for a week. It's something he says companies and students alike think is effective. "It's been fundamental in allowing us to move fast, continue to innovate, and keep pushing boundaries," he said of using the do and don't strategy at Square.
Eventually, Dorsey did bring it back with inspirational advice to the Y Combinator crowd.
Beyond stressing the importance of exploring the list-making strategy he swears by, Dorsey told the group of tech hopefuls that there would be failure, but that it was something to move on from and come back to later as an educational experience.
"You are the future," he said. "You are building things you want to see in the world."