Jack Dorsey is unique. He’s a self-made billionaire. He sent the first tweet. He co-founded Twitter Inc. and has helped the business grow from no revenue a decade ago to more than US$3 billion last year. He later co-founded Square Inc., which is now worth more than Twitter, boosting his own net worth to US$5.5 billion. He serves as CEO of both publicly-traded companies. Instead of suits, he mostly wears black casual wear and sports a nose ring. He speed walks to work. He doesn’t have a computer at work or at home.

He’s also a profound thinker, when it comes to the subjects of management and leadership.

Dorsey is currently meeting with Twitter employees around the world, as part of a tour that will see him and other executives on his team visit 35 offices globally over the next year. I sat down with Dorsey in Toronto for a wide-ranging interview about the future of Twitter, his leadership approach, and what he really thinks about Tesla Inc. CEO Elon Musk.

Q: What’s the goal of this trip?

A: “We’ve never visited all of our offices so I’ll be visiting every Twitter office. Square has a few within these locations as well. And the goal is to see our people directly – see where they work and to understand what they’re struggling with. Our clock runs around San Francisco and I don’t fundamentally believe that is our future. I believe that work is changing. The location where you are won’t matter as much. I want to make sure we continue to be relevant for people who want to come work and serve our purpose of serving the public conversation. In the future, that might mean they’ll feel most creative in a city we’ve never heard of, or at home in a small town. We should be building our process and our work around that. I think this world of requiring folks to work and live in San Francisco is coming to a close.”

Q: You’re starting to spend time working from home as well. How much of what you’re saying has to do with tensions we’ve seen in cities like San Francisco where housing prices are a major issue?

A: “I think it has an effect. Twitter was one of the first technology companies of our era to say ‘No’ to Silicon Valley and say ‘Yes’ to San Francisco. And we did so because that’s where we wanted to live. We just appreciated city living, rather than living down in the suburbs. And the city has changed because of it, and it’s not just us bringing folks into the city. It’s also some pretty terrible policy by city government to not allow densification of the city as well, creating an element of scarcity which increases all the prices of all the housing in the era. Ultimately, we have people who want to work at Twitter but don’t want to live in San Francisco. Not because there’s anything wrong with San Francisco, but because they feel they are more creative where they currently are.”

Q: When you’re the CEO of two companies, you have to focus on what matters most. What is your number one priority at Twitter right now?

A: “Conversational health. Incentivizing more healthy contributions to the public conversation. We’ve seen abuse, we’ve seen harassment, we’ve seen people leave our platform because of it. We’ve seen voices being silenced because of what’s happening on the service. That is number one. We can’t build a platform of speech, a platform of conversation and a service that will remain relevant to people if people don’t feel safe to speak up in the first place. So for all those who believe in free expression and free speech, it’s critical that we’re not utilizing technologies like Twitter to shut down voices and to silence others. A lot of our policies and enforcement is aimed at addressing this problem. It’s never going to be fully solved because you have to constantly iterate. But we need to give people much better controls over their experience. We need to do more of the work for them. We need to take away the burden of reporting harassment or abuse. We need to utilize technology better to automatically identify where it’s happening, or where there is a high probability of it happening, so that people don’t have to see it when did they didn’t ask to get into the fray.”

Q: Mark Zuckerberg recently called for more regulation of the Internet. What’s your view?

A: “Generally, I think regulation is good thing. I think our role as a company should be that of an educator, helping regulators understand what’s happening with technology, the secular trends that we’re aware of, how our system works. And the job of regulators is to ensure protection of the individual and a level playing field. So as long as we’re doing that, that has good outcomes. I haven’t looked at all the specific feedback to [Mark Zuckerberg’s] post. But I generally think that there are things like GDPR that have been positive, not just for our platform but for the industry in general. And specifically, that adds a lot more clarity around privacy and how data is being used. Typically, our terms of service are hard to read and not necessarily the most customer-focused thing. So GDPR put a stake in the ground to at least bring out some elements that you have a lot more control over, and I think that’s a net positive. But there’s not going to be any one party that’s responsible for fixing this. I think putting too much of that weight on any one entity, whether it be a corporation, individual, a government … it’s not going to work. We have to think about it as a desire. Our purpose is to serve the public conversation. Our desire is to incentivize and increase healthy conversation. And for that, we can look much deeper. We can look at what we’re incentivizing, we can look at the very foundational nature of the service and making sure we’re not incentivizing behaviours that would take away from health. Today, there are areas where I think we are. So those are the questions we are asking and it will lead to some fundamental shifts in how the service works and how people experience it.”

Q: Twitter’s business has evolved from no revenue a decade ago to more than US$3 billion last year. As the business evolves, you and some others such as Facebook are moving away from sharing monthly active users as a metric.  How are you measuring success?

A: “We want to provide utility that’s valuable to people every day. Our purpose of serving the public conversation -- of answering the question ‘What’s happening?’ --  that’s a question that you ask every single day. We want to be measured internally by the value we bring to someone every day. We need to make sure that we’re not just utilizing that goal internally, but that externally, people hold us to that as well. So the move away from MAU (monthly active users) is better aligned with what we want to be and the value we want to provide. I don’t think it’s a general movement away from MAU, because there are services that are valuable on a monthly basis rather than daily basis. Any entrepreneur or leader of a service like ours looks deeply at what their goals are and how they’re thinking about driving their service or business, and make sure there’s no dissonance between what they say internally and what we saw externally.”

Q: When your team pitches an idea, you push them to show what the end product will look like and work backwards on how they will get there. That’s different than outlining where we are today and the roadmap to getting there. Why is that important to you?

A: “I like the power of storytelling. When we can tell a story about an experience it enables people to complete the story. It allows us to paint a picture of what ifs, which we can change and convert. The more visually we can speak about where we’re going, and how people will experience us, puts everything in perspective. It puts things in perspective of the customer, the person who we are actually serving. All businesses have one job: Solve problems. Understand someone’s struggle and solve the problem and ideally, in a unique, inventive way that separates us apart from others.”

Q: Does that mean you already have a vision for where Twitter will be in 10 years?

A: “I think visions are tough. It suggests you have perfect clarity around an end point. I would rather focus on getting a lot of conviction around what we believe, and then test a hypothesis towards it and work on a long time frame. It’s very rarely the case that you can do anything instrumental or important in a quarter or a year. Often times, these things take three to five years to click. If we get too short term in our thinking, we miss an opportunity to be truly creative and go a level deeper in terms of what we’re trying to build.

“I try to focus myself on what I believe is possible or feels impossible today, and then what’s blocking it from making it possible. And then the guide and vision stems from that. But if we get too concrete around a particular vision or direction, a new technology might come along that completely makes what we thought was right irrelevant. “

Q: Is it true that you only use a smartphone?

A: “I only own an iPhone. About five years ago, I got rid of my computer. I got rid of my iPad. And the reason why I like the iPhone as my single device is that I can turn off notifications and it only allows one app at a time, so I can really focus on what I’m doing and there’s no distraction whatsoever. I don’t do any engineering or programming anymore so my work allows for that. But even if I were, I love the freedom it provides. I love the focus it provides. I love that everything I need is always with me at any one point. And I love that I can put it away and just walk away too. So when I do need quiet time to think, to work through some of the challenges we’re facing, I know I can just leave it in one particular area and I’m going to be unbothered.”

Q: You often talk about your desire to build companies that will outlive you. Some of that thinking is based on your experience serving on Disney’s board. How do you build a company that will outlive you?

A: “By following some simple principles. The first one is that my job is not to make decisions. My job is to ensure decisions are being made. And that they’re being made in the context of who we’re serving, secular trends, new technologies that might impact us and competition. If I have to make a decision, I believe there is something wrong organizationally and it’s on me to fix it. And what that does is decentralize decision-making, so we don’t have dependency on one person, including myself.

“My job is also to make sure we’re raising the bar on what we thought was possible. Too often as we grow as individuals and with organizations, we start getting more precious about what we have and we stop taking as much risk because we fear losing it. So I serve a function of reminding ourselves that we should infuse more risk into our thinking and into our actions. That means realizing that what we thought was impossible is actually possible, but we just need to decide to do it. And ideally, we’re building a dynamic where we’re not competing with Facebook or Instagram or Snapchat. Instead, we’re competing with ourselves from six months ago, or from a year ago. And we’re seeing more urgency and more solutions to common problems. These are the things that give me confidence we’ll continue to be an organization that will be relevant to the world independent of me being there or the fact that I was a founder of the company. That should not be relevant at all. I want to set up a dynamic where the company has multiple founding moments and they come from people who are not me.”

Q: You’ve said that much of your success has come from going outside of your comfort zone. What are some of the things right now that have taken you out of your comfort zone?

A: “There are new ones every year. Certainly with Twitter, the dialogue we’re having right now on conversational health. And with Square, the work with cryptocurrencies. There are a number of new edgy frontiers.

“It just tests a lot of our thinking. The thing I want us (both companies to be) is just very open – open with our road maps, open with how we think about our challenges, open with our evolution. And that’s something that more broadly both companies are not comfortable with. It’s something new and something that we have some hesitancy around – all coming from a good place. But I believe we need to shift because we have to earn more trust. And we have to be more transparent in how we made decisions and how we’re solving these problems.

“Trust is in short supply these days. If we truly want to endure beyond my lifetime, we have to put trust as a premium. Otherwise we just become irrelevant and something that people just don’t want to use.”

Q: Speaking of going out of your comfort zone, you’re a fan of how Elon Musk uses Twitter. Many CEOs don’t use Twitter and wouldn’t feel comfortable using it the way Elon does. What do you like about Elon’s tweets?

A: “I appreciate Elon’s use because he tests the edges. I think that’s important to do. If we don’t figure out ways to support that, we don’t have inventions like Tesla or what SpaceX is doing. He is ignoring the data and ignoring a lot of what people said was possible and making it possible. I think it’s always important to test the boundaries of the frameworks that we put in front of ourselves.

“I think it is important that Elon shows himself so authentically on Twitter and is so playful with it because it inspires others to just think very differently about their work and what they’re doing.”

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