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.


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 starting our companies, we followed the giants who came before us, especially in Silicon Valley and most notably Google. There’s so many practices that we borrowed from Google to start both Twitter and Square, culturally, process wise, tools. Obviously we are entirely on a stack created by them for their own work and now is benefiting others. 

But one of the things I wish we would have questioned earlier is do we all need to be in one city, do we all need to be in an office, is that really required to make our work and to make our work valuable and to continue the urgency? I think open source is seen as inherently distributed but also I think slow, yet deliberate. And I think that deliberateness is undervalued and the focus on slow is overvalued. 

And I think you can go into the patterns and still have all the benefits of having something that is more distributed, that is more global that could be fast and could maybe not be as deliberate so that we’re working mistakes much faster than we’re learning from at scale. When we were starting these companies, we just drafted off a bunch of assumptions that this was how you build a company, rather than questioning some of the fundamentals.

And I’m really happy now in that most of the entrepreneurs that I meet today are starting out questioning all that and starting out with an intention of not having an office, being fully distributed. And that’s meeting the expectations that I experience when I go to recruiting conferences of kids who are coming out of  university and asking, as a first question, do I have to move to San Francisco? Can I work from home? Whereas like five years ago, that was not the first question but now predominantly it is. And I think that signal is interesting, especially as we have to consider bringing new people into the work force. 

MATT:  Yeah and it’s an interesting thought experiment to imagine if you had been able to start these from St. Louis and the impact that would have had on the local community.

JACK:  A hundred percent. And now we have 1,000 people in St. Louis for Square and we want to hire even more there and get back to my hometown but I wish we were able to do that on day one. But we’ve learned more importantly why it’s important now and how to unwind some other things. And coronavirus certainly accelerated a bunch of our plans to the positive I think, generally.

MATT:  Were there any other practices that you had copy and pasted from Google that you would look back at now as being particularly valuable or, like distributed work, you wish you had not brought over? 

JACK:  Yeah, tens of.. [laughter] I’m trying to think of the right ranking in terms of impact here. But I think because we were in San Francisco, because we were in Silicon Valley, we let ourselves be in that bubble of ‘this is how you build a company here.’ And it certainly removed ideas that would have benefitted us internally.

But also, like, even in other cities like Seattle and Amazon has this practice that we take on right now, which is phenomenal for distributed work, which is writing a document before a meeting and adding comments to the document in the meeting and then having a discussion based on those comments. And what that does is a few things – one, for people who tend to be a little bit more reserved or quiet or shy, they have no problem writing their feedback in a document so you see a lot more feedback and a lot more ideas. 

Second, it records interest in where the meeting should go and it’s not just within the meeting, it goes beyond that. So when the notes are shared or when that document is shared, the whole history is preserved. And third, I think it gets people out of a presentation mode and into a discussion and debate mode much, much faster. 

And we kind of just ignored the Amazon culture, what that meant, because we’re so in the bubble of what Google created. So I think it’s more of a wish that we were able to break out of the bubble a bit more and see things in a different way. And there were so many incentives to stay in that bubble, like the VCs that we took money from were in Silicon Valley and they had success indicators like Google and would suggest similar things.  So it was hard to see outside of that isolation of concentrated ideas around what success meant and what it looked like.

MATT:   How about OKRs?

JACK:  Yeah, yeah we use OKRs, there you go, that’s one example.

MATT:  Do you like them?

JACK:  I have mixed feelings. I think they are good in terms of allowing us to articulate why we’re doing something and what we expect to see out of it but it just feels like there has to be a better method of that that I certainly haven’t discovered. The main benefit is there is a greater understanding of what they are, so there’s less ramp up time for most people coming into our company because they are part of the industry. What are your feelings?

MATT:  We have some teams that use them but we don’t do them company wide. I don’t know if I love the structure. And I think where I chafe at it a little bit is in that the metrics might need to change more frequently than I have typically seen OKR update processes go. 

JACK:  Yes.

MATT:  So it doesn’t always survive that contact with the problem. And so where I see it or where I feel like it was a negative for teams that have tried it have been when they stick to it for too long. But at the same time, it’s also a negative if your teams are always changing their priorities. So we have some teams that have.. I think there’s one called Gist that I liked a little bit better. It was like goals.. gosh, I don’t remember what it stands for but I resonated with that one a little more.

How about meetings? Even today I feel like my friends at Google are in meetings all day long. And they were distributed, they’re in offices all over the world, but lots of these meetings are usually on video. What’s your thoughts on meetings? How were they early and how are you doing them now?

JACK:  I know a lot of people in our organization and certainly around the world are definitely fatigued by the camera. I mean, look at us doing this podcast, we’re doing it on Zoom right now but the camera is off and I know that’s to save bandwidth but.. There is a fatigue that develops in just being on camera every single hour of the day and I think it’s real.

And I think it points to a general issue with meetings, that a lot of our work is optimized around synchronous points of collaboration instead of asynchronous. And I think if we don’t focus more on the asynchronous problems and how to solve for asynchronous work we’re missing a bunch of opportunities. And that is one of the things I appreciate so much about the open source community.

And most recently, in just studying how Bitcoin has developed, which is.. a lot of what I got excited about in Linux development is now in Bitcoin development – it is global, it is complicated, it is impactful, it is asynchronous, it is slow and it is deliberate. I think there’s just so many lessons there that I think can be applied. But I think generally the meeting forces.. meetings force a way of working. I would rather have answers around how to do similar..  how to perform similar sorts of use cases but in an asynchronous way. 

I think meetings are great for when a debate really needs to happen and certainly text mediums are not. But I think it’s kind of enumerating the list of like what is the job of a meeting, why are we having this in-person meeting? What do we expect out of it? Just to borrow Clay Christianson’s Jobs To Be Done framework, like, why (do we hire in?) in-person meeting? And what are the hiring criteria and what are the firing criteria? 

I don’t think we have done enough of that work. We are certainly doing it at both companies right now just to further unlock our work so that we can be more asynchronous, which frees us up to hire more people in different time zones, which I think is the important goal and making sure that if someone happens to be happy in a particular area that they can stay there because they feel really creative there and they can still have as much impact as someone who might happen to be in San Francisco.

I don’t know, it goes.. it just asks the broader question, whenever I have to have a meeting, of is this necessary to be synchronous right now? And what is the asynchronous equivalent and why didn’t we do that?

MATT:  And even people living in time zones, we find a lot that people like to work in different times regardless of where they live. Some folks really like starting super early in the morning, some folks might want to break up their day to pick up their kids or do different things. And even if an office culture said they were cool with that, it could feel against the social mores of an office to leave for two hours from two to four PM or something. 

Have you seen my post on the five levels of distributed autonomy? 

JACK:  I did.

MATT:  Oh cool.

JACK:  I think, Matt, I mean, you’re one of the teachers in this space because you have been doing it for so long and have had so many experiences and incredible experiments with it. So I definitely am a student of your work in this space.

MATT:  Well we have messed it up for 15 years so if we can share the things that we have learned from those mistakes I hope it helps other people accelerate. I had heard that you, a few years ago, started doing where a day of the week you worked from home. Can you tell me a little bit about the context of that?

JACK:  Yeah, about two years ago I started doing a day a week. And then a year ago, before this Covid year, I was doing two days a week. So every Tuesday and Thursday I would work from home. And the reason I structured it that way is Monday at both companies we have our direction setting meetings, so we review everything that’s going on at the companies – and they are four hour meetings – and the goal is to get as much of that out in the beginning of the week so we don’t have to be dependent upon meetings during the rest of the wee, we can focus the majority of our work on the work and not scheduling this time together and however that manifests. 

And then we would have Wednesday  – 

MATT:  Are these big meetings? How big are the Monday ones?

JACK:  It depends. It’s with my direct team and then we bring in folks from their direct teams and beyond to review some work or have a discussion or a debate. But it is generally meant to like.. let’s get everything on the table that is important for this week, let’s tie it as much as we can to previous weeks or previous months or previous years if the context merits that, and then well have a 30 minute check-in on Wednesday and Friday.

So we always know we have a lot of time together on Monday and we have a consistent and predictable check in point on Wednesday and Friday. And I found that that really creates an ability for us to not have to feel like we have to schedule the together randomly. We know that something might be able to wait until Wednesday or until Friday. So it sets a higher bar on when we do meet or when we don’t.

And that structure works pretty well. And I was finding on Tuesdays and Thursdays that I was more or less free to work on more strategic stuff and really spend some time thinking and having broader conversations, not meetings, but actually conversations around ideas. And I didn’t need to be in an office to do that. And I felt very focused at home because there was no other noise or people walking by every now and then and snacks and all these distractions within the office that come to occur were gone. And I really got more focused and I felt even more creative and even more productive. And then Covid happened and it became every day. [laughter] 

MATT:  Would you encourage your executives to also work from home on those days or the whole company?

JACK:  I believe in showing and not telling. So I certainly talked about the fact that I worked from home and the reason I did is because I felt more creative and more focused. And if you’re on a role that enables that you should consider it, maybe. I didn’t ever say that word, I would just assume that people would. And if you’re in a role that doesn’t enable that maybe we should figure out how to enable it for people as well. 

And that is not a reality for everyone, like the folks in our data center have to go into the data center every day . But for a lot of our folks there is something there that may be worth exploring. And again, Covid really forced the issue immediately. And it was one thing when school was still open and something completely different when schools closed and your whole family was suddenly in the same room as you every hour of every day.

MATT:  Yeah, we’ve seen definitely a bifurcation of people’s experience in Covid. I think you mentioned that you consider yourself an introvert, is that true?

JACK:  Yes, meaning that I get my energy from being alone. That’s where I draw my energy, it’s not from groups of people that energize me, it’s from being alone, being in nature, having some space to think and be present.

MATT:  And you’re running companies with I think 4,000 – 5,000 people each, right?

JACK:  Yes, I think we are up to about 6,000 at each company.

MATT:  What was the experience, again, pre-Covid, of walking through the office?

JACK:  In terms of being an introvert and walking through the office?

MATT:  Yes, would you feel that people’s eyes were on you? If you’re in an elevator with someone, are they nervous?

JACK:  Yes, I do also appreciate the fact that I am going to.. I want to have a mindset that every experience I have or every person I meet is going to be a teacher if I decide to let  them be. And when I’m in the office and I’m walking around, there’s all these moments of serendipity, all these people that I don’t encounter on a daily basis, all of them have something to teach me. So I do try to at least go out of my way to say hi or ask questions and also if there is any opportunity to take the edge of a bit when we are having a stressful week, that I think is also important and great. 

So yes, when I was walking around the office.. as much as I can to learn as much as I can. And that worked. And that is one thing I have missed. Because you can’t just.. You don’t have serendipity on all these video calls that we’re doing. Every now and then you do but it’s very rare. I think that is what has been lacking. And they haven’t found a replacement for, in distributed work, I would love any insight  you have on it, but the randomness and what the randomness creates can be quite powerful. And I haven’t found a good way of creating that digitally and virtually.

MATT:  I ask partially personally because I tend towards getting my energy alone or in smaller groups. But usually one week a year we’d bring the whole company together and that week was both my favorite week, cause I love my colleagues, I love spending time with them, but also my most exhausting. 

JACK:  Yes.

MATT:  And I really felt that.. I don’t know if maybe I became more introverted since I’ve been working from home for so long but I kind of felt just.. a little self-conscious. Normally I’m able to walk around quite anonymously and just that presence or I would find that people would get a little nervous. And I have heard this from other leaders in the company as well – as you might  move up in the org chart at our company, your day feels very flat and egalitarian but then sometimes how people act, especially if they haven’t interacted with you directly before, can change based on your perceived position.

We have found some serendipity with these donut chats, which is a Slack-bot that randomly pairs people. Have you tried that?

JACK:  No.

MATT:  Oh, it’s literally just a Slack-bot.

JACK:  That’s a great idea.

MATT:  There’s different channels that I’m part of and it will randomly pair two people in there and the bot kind of pings you both to schedule it, checks in if you’ve scheduled it, it just has some nice, built in.. I think it even has a thing where it will find a free spot on both your calendars. 

And I’m part of a few of these, one for leaders in the company where we do talk more about professional stuff, our work contacts but random pairings, and then one that’s randomly paired with anyone in the company who joins the channel and that tends to be more personal where I try to.. I do my best to not talk about work and just try to learn about them as a person, which used to happen a little more organically in those in-between, liminal spaces, like waiting in line for coffee or at the bar after or something like that. 

And the other thing is just when there’s lots of internal spaces for other stuff. We have a lot of what we call water cooler channels, like Slack channels about Magic the Gathering or gaming or P2s about it and people self-organize among us and stuff like that and those can be nice, particularly some of these remote games, which can really connect people for people that like them.

JACK:  Yes, those are great points, good idea with the donut chat. I’ll look into that.

MATT:  Gitlab also is a fascinating company to follow if you don’t already.

JACK:  Yeah I definitely do.

MATT: And they have been sharing some fun things they’ve been trying. I’m curious to see this. You mentioned being on video all day being tiring, which yes, we started saying hi on video and then we turned it off to relax a little bit. I’m also curious.. I love the concept.. it is so much more intimate now that we’re all in each other’s homes all the time, right? 

JACK:  Yes.

MATT:  I found that people would start at Automattic.. or when we actually had a team, the Tumblr Team, which was in an office and then had to go home unexpectedly and wasn’t really set up for work from home, particularly in Manhattan where they might have roommates or a small place. And at the beginning, folks would often have a virtual background probably because they didn’t feel like they had a very professional background. But over time, when they could rearrange their desk in the room or often sometimes move, we’ve had a lot of people that have moved, they designed their background to be part of their personality, almost like you might decorate  your locker in high school or something.

JACK: Oh that’s cool.

MATT:  The virtual backgrounds I see that too but I don’t know why we can’t do that for the foreground, some equivalent of Apple’s Memoji or Bitmoji or something, which would then remove the pressure that people feel to appear a certain way.

JACK: Hmm. Yes, you can do that on group FaceTime, which we have used as a team pretty effectively.

MATT:  Ah.

JACK:  Which makes it a little bit more fun too.

MATT:  I like that. It is a feedback I get from some colleagues that they worry about their appearance. When we do an on-demand thing, it’s almost never a video because it feels so rude to unexpectedly video someone, they might not feel like their room is set up or something. But audio is usually pretty clean. 

JACK:  I will say one benefit and one moment of serendipity that video does enable is that when people come to an office you only see what they choose to share and to bring up and make manifest. So you hear about their kids, you hear about their pets and their life outside of work. But to your point, when you’re inside their home and the camera is on, you see their kids and you see their pets and you see more dimensions of your coworkers, which I think creates a lot more empathy for who they are and what they go through on a regular basis. 

So that has been one positive element of being on the video is that I know my colleagues in a very different way that I don’t think would happen in an office environment because it’s just so challenging to bring the kids in or the pets in or whatnot. And we certainly have events around that but they are more staged and synchronized. And this, a kid just randomly appears on the call, everyone’s kind of disarmed and taken aback in the right way. And that has been very positive. 

MATT:  It’s really beautiful how quickly that shifted from people being mortified, usually the person who it happened to, to seeing the reaction and it being such a positive reinforcement of that humanity.

JACK:  Yes, exactly. It’s like the BBC News anchor who has their child storm in and he’s absolutely mortified.

MATT:  You’d mentioned some moments of serendipity even in this.. everyone on video. when did they pop up?

JACK:  Maybe as we start using these technologies more we get less wrapped around the axel around the precision of their use and we allow for me messiness. When we all went back to work from home because of Covid, I think there was a lot of angling of the cameras and backgrounds and making sure everything was just right but now people just don’t care. Just.. you’re gonna se the bottom of my chin and that’s what it is for a while because I’m tired of holding this phone in front of me and I don’t have my laptop working. I think that’s when all this emerges. 

And I think that’s true of how we use the documents to organize our meetings and our debates. Running a board meeting in this environment has been interesting and different, especially for our board members, which tend to be a little bit older, more traditional. Having them read a doc and comment in a Google Doc about what they are curious about has done such amazing things for helping us steer the conversation and make it so much more productive than if we were in person. 

And we have boards that are (comprised of?) people all around the world and when you have someone flying from London or Nigeria to come to San Francisco, it puts a lot of weight on the value of that meeting and how much time you inherently spend. Like, you’re just incentivized to spend more time because wow, this person came from all the way all around the world to spend time with us. 

MATT:  A high transaction cost, yeah.

JACK:  Yes, you can have greater impact if you focus the time more. And I think the in-person meetings hid that. And I would say our board meetings now at both companies are just so much more effective, so much more impactful. And I don’t want to go back. I mean, I do think we should meet at least once a year, again, just to build that empathy up and to have dinner with one another and drink together and just get to know each other in a different way and be present, but the conversations we’re having right now are just not the same as they were in these forced, in person meetings.

MATT:  And you feel like it has gotten deeper, more relevant to the topic or more helpful to the company?

JACK:  Yes. Because even with our board members, I mean, they are at home, they’re thinking from home, they are comfortable because they have full control over their whole environment so they’re not worried about not having the right tea or coffee or the lunch was terrible. They are fully in control of everything. And I do think that gets us a better mindset from meeting start.

And then  because we are so aware  of the time we are spending together and we are focused on making it effective and impactful, we put a lot of work into these documents so that we can really have a productive conversation. And we give these documents to our board members a week ahead of time and they have plenty of time to read and put questions in and as they are putting questions in, we get live notifications so we can see how they’re thinking in real time. And yes, it’s just been great. Whereas we couldn’t do that in the past. 

MATT:  It sounds like you’re rehiring your board meetings. 

JACK:  A hundred percent. Yes. Like, why do we hire the board, why do we have these meetings and how might we make them solve the problems we are identifying in a better way.

MATT:  And do you still have slides or is it all prose?

JACK:  It’s mainly prose. I mean it is mainly a written Google doc. We do have demos every now and then. There are things that just need to be on slides just because of the flow. But generally it’s a lot of paragraphs. And when you look at it in the meeting, there’s highlights on certain pieces and discussion around it and we zoom in on that. And  we also get a sense of like was this document robust enough based on the question that was asked here. So it’s just a lot of really good signal in terms of how to make our meetings better and better every quarter. 

MATT: I remember I was at actually a Gitlab board meeting and there was a bajillion slides at the time but it was like hey, go through them beforehand and then we’ll talk about the questions. And I think I heard that but I didn’t entirely hear that and I was amazed and it sort of taught everyone the lesson that they did not go through any of the slides, they only would jump to the ones that people had put questions in the document about. So it was actually jumping around a lot. So if you hadn’t already studied them, you were a little bit lost. And it was maybe rough the very first time but  now I do, I block out on my calendar three, four, five hours before every one of their meetings to make sure I go really deep on all the documents. It taught the lesson.

JACK:  That was one of the greatest lessons that we learned from Amazon is having these documents be read not beforehand but in the meeting, silently, and commenting on them silently for the first 15 minutes of the meeting before we get into discussion. The greatest thing it does is everyone is on the same page. 

MATT:  Literally.

JACK:  Yes and there’s no excuses in terms of I didn’t have time to do the pre-read or whatnot, it’s all right there and everyone has the same information at the same time. There is a lot of value in that that I think we benefit from. 

MATT:  Do you think you (are at a place?) where people do it beforehand?

JACK:  Yes, there’s certain information in certain meetings that probably need more consideration than the start of a meeting allows and the board meeting is one of those. We haven’t – although we may have tried it once. Actually, we have gone through a few sections of the board meeting where we encourage board members to read at the start of the section and we are then on the same page and that is often when it’s fairly nuanced in terms of like, we all need to be.. we don’t want to waste time here so we all want to have the same understanding at once. So generally we need to balance that with how efficient we are with  the discussion itself.

MATT:   One thing I love about pre-reads or asynchronous versus in-meeting reads is you don’t just get people’s reactions, you get after they have walked around the block with it, taken a shower, slept on it, had time to really develop their thoughts over time.

JACK:  Yes, it’s a great point. There’s definitely positives and negatives. But I do think the more asynchronous work we have to do, obviously it doesn’t allow for that. We need to optimize for more of that.

MATT:  Yes. You’d mentioned those four hours, which is five percent of a normal work week at least in this e-team meeting both at Square and at Twitter. Why are you rehiring those every week it sounds like? What is done in those that can’t be done asynchronously?

JACK:  Yes, that is exactly what I’m trying to figure out right now is like do we need to restructure that even more. I think right now I’m just trying to observe what is the criteria for spending so much time together at the beginning of the week. And I think the biggest value we get is that we feel like we have this incredible touchpoint of shared understanding on very complicated topics that we all experienced at the same time live. And I think there is value to that because it makes the conversation so tangible. But I don’t know if it’s necessary. I think it’s additive but I don’t know if it’s critical. So we are going to experiment more with why we hire that meeting and why it has to be synchronous and what we lose if we shift it. That’s probably a start of next year thing.

MATT:  Do you do anything at these meetings to have social ice breakers in the beginning?

JACK:  It kind of naturally happens. We get on the call and someone brings something up that feels a little bit random and we give space for that because it does enable people to see different dynamics and different dimensions of each other so we definitely give space for that. And there is a lot of laughing at the beginning of the meeting usually, which also sets a tone that we can have laughter in the rest of the meeting too if we find an opportunity for it because it de-stresses so much. 

MATT:  Reed Hoffman has a really good anecdote on that in his new book “No Rules Rules” where I guess it was.. And Automatic was guilty of this as well. We made the meetings like ultra work-focused I think because I had been burned by bad meetings, we mad them way too focused and there was no space for that more social side. 

And he talks about it in the context of expanding internationally. As they had more Brazilians come into the company, they saw this as very impersonal. Or during their interview day they left them alone at lunch instead of taking the guy to lunch. And how they started to incorporate what he terms as Brazilian but I actually think of it as just a personality type, like, more of that warmth and personal side at the beginning of things. And now it’s their new policy that they do this at all their meetings. So I found that interesting.

JACK: Wow, wow.

MATT:  I think you’d enjoy that book too if you check it out. Netflix has some interesting heterodox ways of working.

JACK:  I’ll definitely look at it. I’ve been trying to avoid books that have anything to do with our industry or society or technology at all recently. So the last book I read was this book entitled “Surf” by Gerry Lopez who is a legendary big wave surfer and wow it was refreshing. It was just so beautifully written and its distracting in all the right ways.

MATT:  Do you surf?

JACK:  I try. I’m not great at it. I’m really good at paddle boarding, which is much easier for everyone but I would like to become better at it because it’s so pure. I used to wind surf a bit and I love sailing but just the purity of understanding a wave such that you can be in the same flow with and be in the same power of it is a pretty incredible adrenaline rush and a reminder of what flow feels like, literally.

MATT:  The ocean is so humbling.

JACK: And that, and that. Just how powerful it is.

MATT:  I think I’m in the same space. I’ve been learning more – particularly this year I’ve been able to make it out a bit more. Yeah, my dad was actually a surfer but he had long stopped that by the time I was  born and so after he passed  few years ago, I began to do a lesson on his birthday as a way of remembering him.  Just this year I was able to get a few days in a row and get a few times. It was so nice to be disconnected. I have also felt that with diving, if you’ve ever done scuba diving.

JACK:  Yeah.

MATT:  Because it’s so connected to the breath.

JACK:  I really want to do free diving because it freaks me out. It feels so scary and that’s exactly why I want to do it because I just learn so much when I put myself in uncomfortable situations. 

MATT: Speaking of uncomfortable situations and scary things, you had talked about going from I guess two days working from home to actually working from Africa and India where you’re going to do two or..? 

JACK:  Yes.

MATT:  What was the plan there before everything in the world happened?

JACK:  This year before Covid really emerged, I spent November of last year in Africa going between Nigeria, Ghana, Ethiopia, I mainly focused my time there. And the reason why.. I had never been to the continent, I had never been to those countries and never really immersed myself in the culture and the people, and I wanted to do that personally but I also see Africa as an incredible opportunity from a entrepreneurial standpoint and also from our businesses, both Twitter and Square.

So I wanted to go and in November I met with entrepreneurs, I met with schools, high schools, and colleges, and that was it. I didn’t talk with anyone in the media or the government and that was the intention. And the goal was to learn enough that I could go back and send four or five months there and my goal in that four or five months was number one, to understand the countries more because it will impact our business and our opportunities in the future. 

And in that dimension, also how to work from halfway around the world, from our headquarters in San Francisco, how do we figure out a structure where we can truly force ourselves to be asynchronous because the time zones demand it. And if I could do that, then we could probably scale it to a bigger majority of the company. And then the second goal was to hire and to have partnerships with local companies there for both companies. 

And then the third was to help entrepreneurs that I met in whatever way that I could. And I was all set to spend four or five months and then Covid happened and changed everything. So, it is still my intention. Maybe it’s next year, although it doesn’t seem tingly probable. Maybe the year after that. But I definitely tend to spend a significant amount of time there to really understand it and to build and to support in any way that I can the phenomenal entrepreneurs that I found there. And there’s just so many solving extremely tangible problems in very creative ways.

MATT:  I love that. The altruistic side is also really good and laudable. But I think even just purely for your business it would be huge.

JACK: Yes.

MATT:  Were you planning to continue all these standing meetings, the Monday, Wednesday, Fridays while you were there?

JACK:  No, we were going to figure something out with that. But I wanted to use that time zone change as a forcing function because obviously it would not work, I would not be able to sleep in a healthy way if that were the case so we would have to  change a lot. And that was the intention is if we can run the company without missing a beat in such a distributed, asynchronous way it really opens up the door for a lot and especially our ability to hire anywhere as we. 

MATT:  Yeah, I found I can get by.. I did one month where I was actually taking some writing classes in Paris and I just kept my normal schedule. So I’d work.. it would be like 2PM to 10PM. So I guess you could still do your.. if your meeting is in the morning, you could still do it.. Oh, but you must have two because you’ve got the Twitter and a Square one.

JACK:  Yes.

MATT:  So that full eight hours…

JACK:  Spread it between two days but.. 

MATT:  But when I’m in Asia or even Hawaii, that gets so much harder because it’s the middle of the night when you try to keep the time of those meetings. And it’s one of the biggest I think fair criticisms Automattic gets is that a lot of our meetings are optimized for morning west coast, early evening Europe to cover the most people and we don’t do time zones or things as friendly, like town halls as friendly to Asia-Pacific time zones. and our executive team, even though we have the ability to hire people almost anywhere – we’re in 77 countries and we try to be very open there  – the folks who are at the very top of the company tend to be more North American based. 

JACK:  Yeah, last year we did this thing called a (tweet?) tour where I visited every single one of our offices around the world and I just took a whole year to do it and we spread it out throughout the year and I was able to.. It was a Twitter initiated effort but I would also visit the Square offices around the world. We don’t have as many as Twitter but there are still some.

And the first thing you notice, the first thing I noticed, I should say, was how much of the company runs on the San Francisco clock and just how immediately unfair that feels and how much friction there is and  how much friction that creates. You can assume that that’s the case and when you’re in San Francisco, you don’t think about it as like, oh, we really need to change it. But when you’re actually on the other side of it, it just puts such a weight on the need ultimately to change that. For serving a global audience, which is our intention, and we’re  building a company that is in service to one time zone, it just feels so out of synch and so ridiculous.

And again, pointing back to open source, it’s a solved problem and I just don’t think we’ve gone deep enough in really understanding how to take all those benefits that we receive from open source and how it is structured and add a little bit more prioritization and urgency around it. Because I think again that is a thing that people tend to put open source down for is the slowness of the development cycle. And  I don’t think we need to rest there. I think there is a lot of goodness there that can also be done in an urgent, quick way. It’s just a function of how deliberate it is or not.

MATT:  That’s funny, I actually don’t think of the speed as much, I think because our release cycle for WordPress is a lot faster than most of our competitors. But I think a lot about that most successful open source projects are more developer facing or more back end and there’s only a handful, Chromium, some of the file sharing tools, WordPress, that are more consumer facing. 

Something I’d be curious your thoughts on.. how they evolve over time, or if you have some now, are engineers working asynchronously versus designers, product managers, all the other people who make great consumer facing products working that way?

JACK:  That feels like a great unlock. And just in my own personal experience.. Let’s take Bitcoin, Square funded this thing we call Square Crypto, which is an independent organization of five developers, and the intention was to have one or two designers as well whose goal was just to do whatever it took, whatever they thought was important to help Bitcoin be better every single day. 

So they had nothing to do with Square’s goals, they don’t have a manager at Square, they don’t take direction from anything that Square is doing, we can’t tell them what to work on or what not to work on. They are completely independent but they’re working on something that ultimately will benefit our company just.. it’s unpredictable as.. at this point how that manifests. 

And we found developers right away but one of the big problems with Bitcoin I believe right now is that there’s a lot of design problems that have not been solved. (Key entrant?) is a great example of this. I think it pushes more incentive towards these custodial wallets and.. which is more or less against the ideals of Bitcoin and having this concept of self-sovereignty and being completely independent of a custodial, like a corporation like Square. 

But there’s a lot of design problems. And we were searching and searching and searching for designers who did their work in an open source model and ultimately didn’t find any and struggled with it a bit and ultimately decided that we would kick off a project to fund a bunch of designers and a community, to build a community up first, so that people would have a foundation with which to share best practices around designing in an open source way and designing for open source and designing for consumers in that open source model. 

And it’s early but it  manifests as like a Slack channel  and a group of designers showing off work and commenting and critiquing on it. But I think there is ultimately something there. And if we do figure that out, I think it will point to expanding those ideas to other disinclines as well. And that is our intention. But I think the problem.. the immediate problem that I think will bear a lot of fruit for us is solving his open source designer problem. 

MATT:  Two things there. One, we have something in WordPress called Five for the Future, which is the idea that whatever you are benefitting from in the WordPress ecosystem, if you could take five percent and put it back into core, kind of like  you had those engineers just working on core Bitcoin and things, that will avoid the tragedy of the commons. For some people, maybe that’s two hours a week as a freelancer or for some, like at Automattic, now it’s 60-65 people essentially working on the dot org side of things.

Often companies will come to me and say okay, who should we hire? And their first inclination is to find someone already  contributing to WordPress and hire them. And I was like, okay, well that will get you the points but it won’t actually add anything to WordPress, that’s just changing where someone’s paycheck is coming from. So I really started to encourage them to hire folks who we don’t already have a representation inside of WordPress and more other roles. So, product managers, project managers, designers, researchers. And it has been kind of fun. 

And actually, this has been another place I’ve been inspired by Gitlab, who actually streams their product review meetings. Actually, Steven Wolfram does that too. Check out his  Distributed interview, it’s kind of funny because he’s been doing this for like 30 years. Yeah, we just started doing user tests and then posting the videos on our P2. We would of course have to get extra permission for that. 

Yeah,  just radically opening that has had a pretty good impact so far and also changed the people contributing. We actually just had WordPress 5.6,  named for Nina Simone, was the very first in our project and maybe in [00:54:20.17] open source, all women release squad. So 36,37 women led that entire release from start to finish.

JACK:  Wow. You said it was named Nina Simone?

MATT: Oh yeah, we name every WordPress release in honor of a jazz musician.

JACK:  Oh, that’s excellent, Nina is one of  my favorites. That is an excellent choice. It  must be an incredible release.

MATT:  A lot of people focus on that you’re the CEO of two companies. And my bugaboo there is they don’t ask Tim Cook how he runs a  hardware business and a services business. If you look at any of these larger entities, they typically do some very different things, you just have a structure where you can have independent shareholders in each. How much do you try to run them in the same way or share best practices or even cadence of how things work or hire between the two?

JACK:  So to answer that question, I would go back to what to what I believe my job is. And I think I have three jobs, I think there are three reasons why the company hires me every day in my role. And the number one is to create a healthy team dynamic. That’s the interconnection between the members of the team. It’s the ‘how we work together’ it’s the purpose that aligns us, it’s the values or the principles that guide our work to serve that purpose better. 

I am not as concerned with the individual nodes or individual people on this big graph of the company. I’m more concerned with what connects them and how they connect and making sure that we have something that is healthy. And to me, that means it’s positively reinforcing, always. So any contrast in the team is a positive reinforcement that increases our creativity, (why not??) So that’s job number one is building and actively building that dynamic and there are multiple tools I use to do that. 

And job number two is to insure that decisions are being made. I see a signal and if I have to make a decision that ultimately there is something I can, I’ll say debug in the organization, and I think it’s more important that I insure that the organization is making decisions and not just that they are making decisions but they are making decisions in context of our purpose, in context of our customers who are serving, in context of the technology trends that are emergent, in context of societal or cultural trends that are emergent and they are showing that context as they make these decisions.

Because what that ultimately does is it removes single points of failure. And it builds a framework and a system that can expand and that can outlive myself or anyone that is currently in the company. So I pay a lot of attention to those frameworks of decision making and I’m constantly looking for opportunities to help them.

And then third is I believe my third job is to raise the bar on what we thought was possible. As we get older as individuals and as companies, as we grow, we tend to take things for granted, we tend to stop asking questions around various aspects of who we are and what we are, what we’ve built, we tend to take less risk because we are more precious about what we have built up and what we have and we don’t want to lose it. 

We are less likely as individuals in our late twenties, thirties or forties to jump on  skateboard as we were when we were a teenager or four years old. And in that risk taking, in that appetite for risk, there is learning and if you remove that, we remove some potential for that learning. So I think injecting some risk every now and then, injecting uncomfortable situations or questions with the goal of raising the bar is important.

So I say all that because I perform those three jobs at both companies in the same way. But the outcomes are different at both companies. And the outcomes are different because they inherently are working on different canvases, we have different people, we have different problems that we are trying to solve and raising the bar on one problem is very different from raising.. in terms of how it manifests, raising the bar in another problem. 

For instance, at Square, one of the things I believed fully was that we must understand.. the biggest societal and technology trend that is affecting us as a financial company are crypto currencies and namely Bitcoin. We need to do everything we can to learn about it. And the only way I know how to learn about it is to build it. We’re going to build it into our Cash App. And that was very scary because Bitcoin is seen as kind of an unknown thing and seen as a scary thing by a lot of people, and we were a public company. There have been no other public companies that talk to the SEC about Bitcoin so we had to do that for the first time.

And all those firsts that we had to do to secure all this Bitcoin to introduce it to our customers in way that they are not going to be financially unhealthy with it, which was a big concern for people, to do all that for the first time really upped our game and really reminded us of what we’re capable of and what is newly possible. 

So applying those three jobs to two very different companies.. sometimes I see parallels. Like they are both very supportive companies, they have amazing cultures, they’re both working in spaces that I think are inherently foundationally conversational and I see commerce and transactions as conversational as conversations are, [laughs] as social aspects are. 

There is a lot in the culture of Twitter that the product was trying to do in bringing more transparency to the world that the company became. We became very transparent internally. And I took that when I started Square because we were going into an industry that was very obtuse and it actually profited from the fact that there was very little transparency. And we also wanted to bring more transparency to the financial industry so we had to be a transparent culture, a transparent company, because we needed to know what it felt like every single day.

So it’s just really sticking to my understanding of what my job is and applying it in the exact same way and knowing that these principles will lead to the right outcomes for each company because it’s putting the focus in the work and its focusing the work around who we are serving ultimately. And that is how I designed them and what I want to make sure I’m holding myself accountable to.

MATT:  How do you choose when to do the same best practice at both? I felt like around the same time, although it might have been a week or two apart, you announced that at each company people could work from home forever versus allowing one side to do one.. one company to do it and not the other company?

JACK:  Yeah, that becomes tricky. Just given my particular situation, I think there’s some ideas that are just good for companies. And if I have weight in two incredible populations that we can change the outcome at the same time for, I’m going to take the opportunity. So our reaction to Covid and encouraging people to go home in early March and then you never really have to come back was a discussion that we had at both companies and a push at both companies and something that was accepted equally at both companies. It wasn’t difficult. 

There are other things, like let’s say Square’s investment of $50 million Bitcoin, that makes absolute sense for Square because we are building for this financial future and you could also argue, as other companies have, that we should put some of our balance sheet, Twitter should put some of its balance sheet, into Bitcoin as well. But the connection is not as apparent and ultimately you’re becoming more of a currency trader rather than what the intention is. And that investment that Square made is only one part of what we have done I believe to the benefit of the broader Bitcoin community, including opening up our patents and creating a non-profit to enable other companies to join in and help defend the open source nature of Bitcoin and crypto currency against patent trolls to the five developers that we hired to work on Bitcoin. 

I think there are certain ideas that may benefit both companies but are much more important for one and I’m not going to force it. I think it has to be adopted if it was meant to be adopted. But there’s some that I do want to force because I just think we need.. it’s a step to move forward.

MATT: And you open sourced that treasury management stuff, right? I’m sort of remembering a document that came out..?

JACK:  Yes, we did. Yeah. 

MATT:  Is that with the intention that other companies.. obviously with the intention that the companies adopt it, so with the intention that the relevant folks at Twitter might see that and start to explore it as well with it out [01:04:51.06] to be top down?

JACK:  Just to make.. that wasn’t necessarily the intention for Twitter. We didn’t have Twitter in mind, I didn’t come up with the idea to open source the process behind it, it was actually our CFO and her team. I love that because it gets more of what felt sacred in the past in terms of a company and how it did things as proprietary. Now, we’re going to open this up and we’re going to share all of our learnings and if it’s useful to inform a decision that you have questions around or are considering, great. And we’re putting an artifact out there that hopefully will be built upon in the same way that you would with open source software.

And I think our companies have taken so much from open source and from that culture specifically. It’s anything that we can do to give back to it in a meaningful way we should take. And when we set up Square Crypto, this nonprofit, external group of Bitcoin developers, Steve, who runs it, decided that he was gonna write everything down and he wanted to share that playbook with other companies who are considering the same in the hopes that they would do the same. 

And now we have seen more and more crypto focused companies start funding developers and engineers just to work not on what they’re doing but on Bitcoin and ideas in the crypto space. So I think it has worked. And if we can contribute more to those ideas of like just being open and sharing, not just our code but our practices so that others can follow and make it better, that’s important to me because that will come back to us. If they make it better, it comes back to us.

MATT:  Kudos to that. I hope you do a lot, lot more of it.

JACK:  Yes.

MATT:  Do employees ever drive something across the company, so whether that’s large things like hey there’s this HR policy at one but not another or trivial things like Twitter employees being like oh the Square office looks so cool, why can’t our office look cooler?

JACK:  They do a little bit. I think they tend to be smaller but there’s a lot of conversation between folks at both companies in terms of best practices. And I think a lot more coordination, especially around Covid, because we.. because the companies are so close in terms of ultimate leadership there is a desire just to  make sure that we are sharing as much information as possible so that we can both get on the same page as quickly as we can.

MATT:  How much coordination – I mean, you have the benefit of building hem both –  how much is the head of HR or [01:07:42.05] or folks talking to their counterparts at the other company?

JACK:  Between these two companies specifically?

MATT:  Yeah, just sharing?

JACK:  I don’t know actually. I don’t know. We do have one time a year where both my leadership teams and myself get together from both companies, which is always fun and  usually involves roasting me in some way. And I love when they do get together because I just see so many similarities in the people. I love who I work with and really I’m so grateful and so appreciative  that I’m at a point in my  life where I can say that I fundamentally love the people I work with and I learn from them. And when I see them see each other through that lens as well it just makes me so, so happy. So I imagine that’s happening elsewhere in the company as well, I’m just not really all that aware of it. 

MATT:  It sounds like you really want people to experiment within the companies as well. You framed it as learning even as you get older. Are there any temporary autonomous zones or some equivalent within the companies where you allow people to do something really different?

JACK:  I love the concept of a temporary autonomous zone, I used to read (Hackerbay?) as well. I think we have had some of those. Some of them have been more top down enforced. Like Cash App came out of exactly that where we had a very small kernel of an idea and we tapped three people just to.. and shielded them from the rest of the company.. and it ended up being a great idea and it ended up requiring a shield for four years because the rest of the company effectively wanted to kill Cash App. 

Our company was started to serve the needs of underdogs, small businesses, this is not that. We had some people who had experience with PayPal and they said that has been won. There is no value in peer to peer so let’s stop doing this thing. It costs too much right now so let’s stop doing this thing. And I think a big part of my job became just defending Cash App’s existence (as it grew?) and people. And ultimately it worked out because we believed in it so much. And there are other things that we protected for a little bit and then didn’t and they died.

MATT:  Anything that long, that you protected for four years?

JACK:  Not that long, not that long. We had a number of things in Square. This product called Card Case, which was a phenomenal experience and really cool which kept it around. But I don’t have any regrets because we have a better path with Cash App against the same sort of experience. So  Cash App was definitely the greatest test of my patience and my ability to defend. 

Because every time you do something like this – and you know this – you lose credibility. Every day I was defending Cash App, for a lot of the company I was losing credibility. And it’s taking a lot of that credibility out of the bank constantly and eventually you earn it back. And I feel like if I’m not losing credibility to someone in the company I’m probably not doing something interesting because I think it is a constant cost benefit analysis of like I am going to lose credibility for this move and that is okay because of X, Y and Z. And we have had many experiences in both companies around that.

MATT:  I think about that a lot because I feel like it is a responsibility. As a cofounder or  CEO, you get some extra of that credibility in the bank that you can spend down on things. But I think a lot about how to allow others who aren’t a cofounder or have that sacred place in the founding of the company to be able to make those same bets. Because I’m not going to have all the good ideas.

JACK:  Yes, exactly.

MATT:  So, how to set up that structure. We’re basically out of time. I feel like we covered a lot. I did want to end on one quick thing. I know mindfulness is important to you. How has that influenced the organization structures or how do you encourage mindfulness throughout the organizations that you have weight in?

JACK:  I don’t know if it’s affected the structure as much as it has our reaction to what’s ahead of us and what we are presently experiencing. Because the greatest tool I learned in meditation is observing my reaction to something and ideally observing it to the point where I can make a different decision and not just blindly react but decide to go in a direction based on this thing that is in front of me. 

I think for me it’s just made me a lot more observant around what we inherently react to, what natural, organic incentives are in a company, where those incentives ultimately lead. And you know this is a big one with Wall Street, obviously, it incentivizes a very different thing if you don’t pay attention versus the intention when you start the company. There is an inherent incentive in the stock price and it being a thermometer every single day for how people might feel about their work with us or their value or our value as a company. 

And being able to show that that is an output, it’s a very emotional one usually especially on a day by day basis and it’s affected by so many variables outside of our control. And it’s a reminder of what do we control? Well, the only thing we truly control is  how we’re spending our time, what we’re spending our time on, and what we do with this minute in front of us. And if we let the minute dictate what we do versus what we intend to do with a  minute, we get to very, very different outcomes. 

So I guess the meditation practice and mindfulness has really just taught me so much about observation, understanding, self-awareness, organizational self-awareness, and then most importantly recognizing  reaction and deciding to accept it or go a different way, if that makes sense?

MATT:  Yes, that’s beautiful. I think that is a good place to end. I really appreciate – I want to be respectful of your time – I really appreciate  your time. You are @jack on Twitter, is that the best place to follow you?

JACK:  That’s the best, yes. Thank you so much, Matt, for the time. I always love having a conversation with you and I’d love to do it more, it doesn’t have to be on a podcast. But I love that too.

MATT:  I appreciate that. You’ve been listening to the Distributed podcast. Thank you so much, Jack, thanks for tuning in. See you next time. 


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