Last month I wrote about the “Wacky Genius of Herb Kelleher“, the founder and former CEO of Southwest Airlines, and I thought it would be hard to find another CEO who is not your typical chief executive.
Well, today’s Wall Street Journal had a profile of an individual who just might fit the bill.
Jack is the co-founder and CEO of Twitter (@jack), and the founder and CEO of Square, a financial payments company. That’s right, he is the CEO of two multi-billion dollar firms.
Many people have criticized Dorsey for trying to be CEO of two tech firms, saying it makes it difficult to devote the time needed to each firm to make it successful.
Current and former employees say he often acts at a glacial pace. Twitter took almost two years to increase the 140-character limit on tweets after Mr. Dorsey began asking about it in 2015.
However, Dorsey, who is famously hands-off in how he runs these companies, claims that it is not a function of time, it’s a function of prioritization. In an investor conference earlier this year, Mr. Dorsey defended his workload. “I have enough flexibility in my schedule to focus on the important things and I have a good sense of what is critical on both companies,” he said.
And to give you an idea of who Jack Dorsey is, here are a few of my favorite parts of the story:
- The enigmatic Mr. Dorsey has worn a nose ring, completed a 10-day silent retreat in Myanmar in 2018 and has said he takes multiple ice baths a day. He has an intense curiosity about people and social issues across the political spectrum, which even his critics say is genuine. Among the many people he has developed relationships with are Scott Adams, the creator of the Dilbert cartoon and a prominent conservative voice on Twitter, and DeRay McKesson, a civil-rights activist and leader of Black Lives Matter.
- A billionaire several times over, Mr. Dorsey sports a large tattoo of the S-shaped integral symbol used in mathematics on his left arm and typically wears black T-shirts and hoodies. He was fired as Twitter CEO in 2008 in part for leaving work early to go to yoga classes.
- He often walks five miles across San Francisco from his home in the mansion-studded Sea Cliff neighborhood to his office downtown. Fascinated by the minimalist style deployed by the late Apple Inc. founder Steve Jobs, he owns only a handful of pieces of furniture.
- Mr. Dorsey invited Mr. Mckesson (the Black Lives Matter leader) to join his family’s Christmas Day tradition of meeting at a coffee shop in St. Louis.
- Jack went to Africa in November 2019 to study how people used the Internet. After his visit, he stated that he planned to spend 3-6 months this year in Africa to immerse himself in the culture. The pandemic has put that trip on the back burner.
- Dorsey notes that his mom is a Democrat and his dad is a Republican, and he falls somewhere in between; both his parents are users of Twitter.
So as you can see, not your typical CEO, and that’s what I like about him.
I think Herb Kelleher would like him.
And I don’t think he is going to suffer from the Nobel Prize disease, despite the success he has had…
P.S. Full disclosure. I own a small number of shares of Twitter stock; in fact, it is the only company in which I directly own shares…
*image from TED Blog