Episode 26: Jack Dorsey and Matt Mullenweg on Remote Collaboration, Finding Serendipity, and the Art of Deliberate Work

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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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How to Produce a Remote Podcast

As the world continues to work from home, podcasts are serving as a helpful diversion to listen to when we’re washing dishes or walking the dog. 

They’re fairly easy to produce from home, too. 

Many of the conversations we’ve featured on the Distributed podcast have taken place over Zoom, with each of us calling in from our respective home cities. In the spirit of transparency, we thought we’d share some of our best practices and must-have equipment:

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Distributed FAQ: How to Transition to Remote Work

In Distributed FAQ, Matt Mullenweg addresses some of the most common issues companies, executives, and individuals face as they consider transitioning to a distributed model.


Q. With the rapid rise of distributed work, what are your top pieces of advice for someone going through the transition from a traditional work environment to a remote one?

A: There are many things individuals can do to make the switch successful, but here are five pointers to get you started.

  • Make a list of all the things you like and don’t like about previous work experiences and use it to design — and implement — micro-habits to increase your health and happiness. Remote work comes with the autonomy to build your own bespoke work environment.
  • Writing ability is crucial, and distributed work only amplifies its importance. Assume positive intent when using written communication.
  • Look at the outcomes you’re producing, not the time you spend at your laptop. It can be powerful to self-track and document what you’re working on. At Automattic, we encourage self-analytics — taking agency over the assessment of one’s own outcomes.
  • It’s important to structure your day. A little more schedule actually helps, whether it’s to keep a normal grooming routine in the morning or to set a firm time at which you turn off everything. Set a time to stop as well as to start, and find a dedicated workspace. Implement systems that help you maintain focus (e.g. the Pomodoro Technique for time management).
  • Implement self-care and opportunities to interact socially.

For more insights on how to design your own distributed work environment, listen to Matt’s conversation with Lydia X. Z. Brown, or browse our gear and tools recommendations.

Episode 18: Jason Fried on Treating Workers Like Adults

Read more about Jason Fried in “Working Smaller, Slower, and Smarter.”

For our first episode of the year, host Matt Mullenweg talks to Jason Fried, the CEO of Basecamp. Jason runs a semi-distributed company that’s been making project management software for 20 years. He’s accumulated a wealth of wisdom about how trusting employees and treating them with respect can yield long-term success. 

The full episode transcript is below.

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