A Different Kind of Leader

business, lessons learned, technology, Wall Street Journal 2 Minutes

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 Dorsey.

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

Published by Jim Borden

A 60-something guy trying to figure out the world, and his place in it. Happily married for 40-plus years, three wonderful sons. Accounting teacher, fitness enthusiast, blogger, reader.

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36 thoughts on “A Different Kind of Leader”

  4. I can understand why people would question a double CEO role. You could only do it, in my opinion, if you had a good COO who you were prepared to rely on. Judging from this man’s attributes, he is a believer. Personally, I have no faith in other people and find it very difficult to rely on others so I could never do this.

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  5. I can’t fathom how anyone can be CEO of two large companies at the same time. The most incredible part is that leaving work to attend yoga class was a factor in being fired as Twitter CEO in 2008. His board must have changed since he plans on spending 3 – 6 months in Africa.

    I wonder which African culture(s) he plans to study since the continent has probably hundreds of distinct cultures (each African country has multiple cultures, languages, and dialects) and getting a good understanding of a single culture could take longer than 3 – 6 months for a normal person.

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  7. I am surprised anyone questions his ability to lead two companies. Both are very successful within their markets and have generated record profits for their investors. Where exactly is this guy failing because he is CEO of both? Like most CEOs, I am sure he relies on the executive team he has selected to see to the daily operations, allowing him to manage to the exceptions and be the compass for the future. Just because someone can do something we cannot, does not mean they are doing something wrong. I like this guy and his approach. I hope he starts a third company with great success!

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    1. I agree; the companies seem to be doing fine, but maybe some investors are greedy and want even higher returns. If he starts and runs a third company, I’ve really got to pick up my game… 🙂

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  11. He sounds a very interesting man. I think your Twitter stock could start rising in value from next Wednesday, when one of its most prominent users begins a whingefest to outdo all his previous ones…

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      3. And if he doesn’t, four years from now you’ll be thinking how restrained Trump’s first four years were compared with his second: a future I for one hope never happens!

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  12. I’m sure there’s a lot going on in that head of his. I only just recently became aware of him, after the kerfuffle over blocking the New York Post’s posts. He looks like a street bum, to me. And nose rings gross me out, I don’t care who’s wearing them. But I sure as hell can’t argue with his success.

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  14. I love Jack and how he manages Twitter with the current state of affairs, making sure all of the information users revive are accurate. It is also good note he is good friends with Jay Z and Beyoncé .

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