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Join us for the latest episode of Distributed, as Matt Mullenweg interviews Jack Dorsey, co-founder and CEO of Twitter and Square. They discuss how both companies have embraced remote collaboration, the underrated value of deliberate work, and how questioning preconceived models from the get-go can change everything.

This spring, Jack Dorsey told Twitter and Square employees they could work from home forever if they choose. But a year earlier –– before the global pandemic happened –– he had already started working from home two days a week. There wasn’t the noise or the distraction. It was a place and a time where he felt more freedom and creativity.

Now, he reflects on how his way of working has evolved alongside Twitter and Square over the past year. From leading thousands of employees as a self-described introvert, to why he planned (and still does) to work from Africa for an extended period (spoiler: largely, to support entrepreneurs on the continent), Matt and Jack share ideas for combining the deliberate, thoughtful pace of asynchronous work with the serendipity that occurs in the office.

“If we can run the company without missing a beat,” says Dorsey of planning to work in Africa, “it really opens the door for a lot, especially our ability to hire anywhere as well.”

Tune in to learn how meetings work at fully distributed Twitter and Square, what open source and the punk scene have in common, why bringing thoughtfulness into collaboration is more important than ever, and if Jack Dorsey ever wants to go back to the old board meetings. Plus a whole lot more.

The full episode transcript is below. Thanks to Sriram Krishnan for help preparing for this episode.

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MATT MULLENWEG: Howdy, everyone and welcome to the Distributed podcast. Today’s guest does not need much in the way of introduction. He is the co-founder and CEO of Twitter and also the Founder and CEO of Square. In addition to creating three iconic products, Twitter, Square and Cash App, he has been a philanthropist and a world traveler. And what we’re going to focus on today is he has recently issued an invitation to all Twitter and Square employees to work from home forever if they want. So everyone please welcome Jack Dorsey. Jack, thank you so much for being here.

JACK DORSEY: Thanks for having me and making the time.

MATT: Now I know that you like to live your life intentionally and I’m curious about the intentions that you have set currently for those three things we talked about, those three iconic products – Twitter, Square and Cash App.

JACK: For Twitter, our intention is to serve the public conversation. It is our purpose and we believe global public conversation is just so important in that it elevates and amplifies some of the common problems we are all facing as a global community. Never has it been more true and a better manifestation than what we’ve seen with Covid and how the world was focused on one thing at the same time, which was pretty incredible to think about. And I think we’ll have a lot more of those.

So, having a place for global public conversation that is valuable and is not just built around and encouraging more people to spend time with it but actually you can walk away from it and you learn something is ultimately the intention to learn from it, not be distracted by it.

With Square, we have two ecosystems. And I call them ecosystems because they are this suite of tools that I think positively reinforce one another. And one is focused on sellers and the other is focused on individuals. So the little white reader was our beginning and it was a very simple tool to empower people into the economy, which was the company’s broader purpose, economic empowerment.

And it has grown into a series of tools that not just help you take a credit card but actually understand your business or understand your customers and all of the goal of helping you grow if you make informed decisions about the data you have around you. So that business has done very well and we have helped sellers around the world, mainly offline sellers, physical sellers.

And then Cash App, its intention – and this is broader for Square as well – is we see more and more people who don’t have a need for a traditional bank and being able to go to the app store, download something that you can store your money in, that you get a Visa card to spend that money around, you can go to an ATM and get actual paper cash or you can do things you couldn’t do at a traditional bank branch, like buy bitcoin or buy stocks, or fractions of stocks – if you can’t afford one share of a company that you love, you can buy five dollar’s worth of it.

And all these things ultimately lead to empowering people into the economy in a way they didn’t have access to in the past. Like the stock thing is a great example. There’s a lot of people that love Disney, a lot of people can’t afford one share of Disney. But I can spend five bucks on it and I can see that five bucks grow over time. And if I don’t like the stock market, the crazy weirdness that is Bit Coin has had similar performance or greater performance.

So that’s the intention for both, one, empowering public conversation because we just believe it’s so important to understanding our common problems that we’re facing, which we think there’ll be a lot more. And then Square and Cash App have an economic empowerment, just simple tools to empower people into the economy around them, which is very conversational and has a lot of parallels between the two.

MATT: You mentioned the fractional thing. I’m surprised by how many people tell me they can’t afford to buy Bitcoin. I’m like, you don’t need to.

JACK: Exactly. Yeah.

MATT: You can get one Satoshi worth and…

JACK: Yeah, exactly.

MATT: Related, what’s your intention for coming on this podcast about distributed work?

JACK: Anytime I go on a podcast I get feedback and I always have an opportunity to learn from the feedback. So hopefully I’m gonna learn from the conversation with you because you’ve been doing this for quite some time. But also I imagine our conversation will result in some feedback that I see on Twitter or in my email inbox about how I’m thinking and how it might be better evolved in this direction or if I consider something new. So it’s really to learn.

MATT: Well I’m excited about it. Thank you so much for coming by. I know that distributed work is not a new practice for you. Can you talk a little bit about your history with it?

JACK: The only reason I’m in this space, in technology, is because I benefited so deeply from open source early on. I was a kid growing up in St. Louis, Missouri and was active in the BBS community and when the BBSs finally got access to the internet through Washington University, it just opened the door to so much.

And for me it demystified a lot of how computers and networks work because I could actually see the source code based on this extreme generosity by others to share their work and to, I think more importantly, be okay with failing in public and being open in public. And it resonated with me a lot because I was in the punk scene, which is very much a pick up a guitar, be horrible at it for a while and then eventually you get better and better as you play in front of people and you do that uncomfortable yet courageous thing to put yourself out there.

And I saw a lot of the same patterns with open source. And these people were not in any one location. They happened to be all around the world. I mean, obviously (Linus?) [00:06:33.15] started in Finland and had a community across the internet that was helping him build something of immense complexity that had incredible value and it was all visible. And not just the source code that made the operating system work but the way they worked together was visible. The way they disagreed was visible, the way they slowed each other down was visible.

So I guess I’ve been a student of these models for quite some time but they have been fairly limited in my direct experience to open source (rather than?) companies. And when we were start...