The Remote Show

Show Notes:

Many of you know Matt Mullenweg, but what you may not know is that Wordpress (the open source blogging platform that he co-founded in 2003) now powers over 40% of the internet. You read that correctly -- 40% of the entire internet.  

After briefly reviewing the arc of Matt’s entrepreneurial journey, we discuss how remote work evolved with Wordpress, as well as his brief stint with a designated office space. Wordpress is one of the largest and most successful remote companies in the world, so digging into the beginnings of Wordpress and scaling was a particularly unique insight. 

One thing Matt keyed in on was the importance of a balanced work, and top down encouragement to lead healthy and balanced lifestyles. For example -- giving back and supporting your community is something Automatticians are encouraged to do. 

We also discuss at some length open source vs proprietary software, what this means for the future of the internet and freedom of speech and expression in an internet dominated society. That could likely have been its own podcast all together. Hopefully it will be!

This discussion was particularly interesting because of Matt’s success and notoriety as influence on the internet, but we were also was struck by how kind and thoughtful Matt was. The team at Automattic are aiming to democratize the internet, and they practice what they preach! 

Matt’s advice to Entrepreneurs: “you have to be very comfortable being misunderstood for a long time. And that long time could sometimes be a decade.”

To look for openings at Automattic, see the positions on We Work Remotely, or go to they page for all of the live positions: https://automattic.com/work-with-us/

Thanks so much for listening!


Matt Hollingsworth (00:02):

Hello everyone. My name is Matt Hollingsworth and welcome to another episode of The Remote Show, where we discuss everything to do with remote work with the people who know it best. Thanks so much for listening. The Remote Show is brought to you by We Work Remotely, the largest community of remote workers in the world. With over 220,000 unique users per month, We Work Remotely is the most effective way to hire.

Matt Hollingsworth (00:21):

My guest on today's show is Matt Mullenweg. I'm sure many of you know Matt. He is the CEO of Automatic and a co-founder of WordPress, which he began in 2003 as a simple open-source blogging platform. And in 2021, it now powers over 40% of the internet. Automatic is also the company behind other well-known brands, such as Tumblr, WooCommerce, and Jetpack. The Automatic team have been remote for many years and are considered just some, including myself, to be one of the shining examples of a successful large remote team. They are hiring. Go to WeWorkremotely.com and search under the top companies tab. You will find lots of their Automatic jobs. We recommend also you go to the Automatic/work-with-us to find more.

Matt Hollingsworth (01:04):

So, Matt, thanks so much for joining me on the podcast. We really appreciate your time. I'll start this off where I start every podcast off, which is what is the thing that you're most proud of that you've accomplished over the past 12 months?

Matt Mullenweg (01:17):

It's hard to answer that without including all the pandemic stuff. So I'm really proud of things safe and keeping folks around me safe. And I'm really proud of how the company Automatic and the WordPress community came together to keep having an impact in the world during this tough time. And part of that, it was a very, very small impact, but it was helpful, was coming on things like this and sharing some of what we've learned about distributed work as the entire world started doing it.

Matt Hollingsworth (01:47):

Yeah. And we can't thank you enough for joining us. And we'll get right into this as well about the remote work piece because you've been a longstanding remote team. I know that things kicked off ... Has it been 10 years since you started WordPress?

Matt Mullenweg (02:01):

17 now. Coming up on 18. So it's about to graduate.

Matt Hollingsworth (02:05):

Wow. Okay. So when you started, was the intent to work remotely right off the bat, or was that something that just came naturally to you? What was the intention behind the remote distributed team when you first started?
Matt Mullenweg (02:19):

It really came naturally in a few ways. First, I was in Houston, Texas. So there weren't a lot of people. The tribe there of folks who are passionate about the same things that I was passionate in was fairly small. I was part of the Linux users group and the wifi users group and the [inaudible 00:02:35] users group. But ultimately folks passionate about the web, it was a smaller community doing it in Houston, Texas. So naturally, I was connecting with folks online.

Matt Mullenweg (02:44):

The second and actually far more important was although in some ways we were early, in other ways, open source has been working in a remote and distributed fashion for decades before WordPress started. So this idea that whether it was BBSs or IRC or probably things even before that, that folks could work together on software, that's been possible for a long time, probably since before I was born. At a point in time, broadband was becoming more ubiquitous. The tools were getting better and better with subversion. So everything was getting easier to work and collaborate without having to be in the same room with someone else.

Matt Hollingsworth (03:24):

Right. Because I'm sure what was happening around you at that point was when you were starting companies, the typical route I'm sure was get an office, go to San Francisco, start the process of having a team and then growing that team from there. Did that cross your mind as something that you wanted to do? Was the office set up something that you tried and then went back to the remote setup or was that something that you'd never really needed and therefore never tried?

Matt Mullenweg (03:50):

Well, the nice thing was I was doing WordPress for a few years before starting the company. And WordPress was, and continues to be today, a volunteer effort with people from around the world. So it was also my most significant work experience. I'd had jobs doing tech and IT and all sorts of stuff around Houston, but WordPress was the most meaningful work I had done, and that had happened in a fully distributed fashion.

Matt Mullenweg (04:17):

So a few years later, I moved out to San Francisco to take a job actually at a CNET. And then it was a year after that, that I ended up starting Automatic. The first people I wanted to work with were the people I was already working with. So to me, the exciting part about starting the company was I'd be able to pay people who were doing WordPress in their spare time. I would be able to pay them to do it as their day gig full-time, myself included. My measure for success was if myself and a few others could pay our bills and still work on open source and WordPress as much as we wanted. So we wouldn't have to split our time between something that paid the bills and then this thing we were actually passionate about.

Matt Mullenweg (04:57):

I was in San Francisco. So the job had moved me to San Francisco and I didn't really have a strong opinion whether we would need an office someday. I kind of assumed that if this became a real company or we scaled past 20 or 30 people, we might need to move people to the same place or being in the same office, mostly because that's what everyone, including people far, far smarter than me like a Marc Andreessen were telling me that that was the only way to do it.

Matt Mullenweg (05:23):

We just sort of kept that in mind as a possibility. But we said, "Hey, as long as this is working well, the advantages," which I'm sure listeners here are very familiar with, were being able to work with great people all over the world, have a 24/7 development cycle, bringing different perspectives. All the things that working in a distributed fashion allow for you seemed pretty good. So as long as those were working and we were competitive in the marketplace, like the market was telling us that we were creating the best products, let's just continue it.

Matt Mullenweg (05:52):

And it turns out that has now gone to 1300 people, so far beyond what I think anyone would have predicted. But also to be fair, far beyond what I would have predicted. So it wasn't that I had a magic Oracle. I was just like, "Hey, let's keep doing this thing until it breaks." And it just didn't break for a really long time.

Matt Hollingsworth (06:08):

Yeah, that's so interesting. I think it must've been hard, and maybe you can correct me here if I'm wrong, but having grown up for as long as you have in this space and been leading a company for as long as you have that does things in a different way when it comes to remote work, because again, you were a first adopter of this and you said you just sort of went along and it just kept working and so you didn't change it. But there must have been some pushback or people telling you you're crazy as you were growing your company to where it is today when remote work wasn't as popular and it wasn't as well adopted. What was the most common thing that you heard about how you were doing things incorrectly early on?

Matt Mullenweg (06:44):

Yeah, it was common and it is an unfalsifiable hypothesis. So it might have been correct is that although we were successful, we would have been more successful if we had all been in an office because that's how Google, Facebook, Microsoft, Oracle. Go back as far as you want to computer history, there are far more examples in the past of the ultra successful companies that did take an office centric approach. And they go global. They'd have hundreds of offices, but they started with that headquarters and still kept that headquarters.

Matt Mullenweg (07:16):

I do meet entrepreneurs now that I see in a similar place to where I was, particularly in my twenties. The thing I always tell them was you have to be very comfortable being misunderstood for a long time. And that long time could sometimes be a decade. If you're able to both survive and stick with it in that time, the rewards can be enormous, but you don't know beforehand, or you don't know often during whether you are just stubborn and wrong or ahead of your time. And I don't know if there's any way to really tell between. You just have to look internally, question yourself all the time and say, "Do I believe this if I really break this down to the first principles?" And sort of look at this as an objective third party, or as an alien might look at this. "Is this working? Does it make sense?" If the answer is yes, then stay with it. But that's probably the hardest thing to know whether you're wrong and stubborn or right and misunderstood.

Matt Hollingsworth (08:20):

Right. And was there a time when you realized that you were right and stubborn? Was there a turning point or a threshold where you realize, "You know what, this is really what I think it is"?

Matt Mullenweg (08:29):

For folks listening who might imagine that there's some day when I realized that we were right, it still hasn't happened. So if you're ever unsure of yourself, don't worry. No matter how successful someone is, if they're truly honest with themselves, have those moments of being unsure. I think it's a sign of self-awareness and having a growth mindset.

Matt Mullenweg (08:52):

The things that have given me certainty are also the most meaningless and emptiest, which tends to be external validation from the market either in terms of investors, evaluation or something like that. The more meaningful things are the longterm trends of free market share adoption. So the sort of percentage of the web, which WordPress powers, which is now about 39%, which is more than 10 times the number two in the market, is I feel a fairly objective and good signal that we've done some things right in how we're building the software.

Matt Hollingsworth (09:28):

So you mentioned there's this fundamental belief that you have about not only that there's the objective metrics about how much of the internet WordPress powers. Has the mission itself changed? And this is a two-part question. How has it changed since you first started and has it changed particularly over the past 12 months in any meaningful way?

Matt Mullenweg (09:49):

Early on it changed a lot because initially the ambitions were somewhat like, "Hey, let's make some blogging software."

Matt Hollingsworth (09:57):


Matt Mullenweg (09:58):

I don't remember exactly what had happened, but fairly early on and before really I saw anyone else do it, we adopted the word democratize and has been very key to our principles of what open source does when it does something best. We want to democratize publishing. That gets tossed around so much now. People want to democratize ice cream. But I think if you really interrogate the word and see what freedom with a capital F means in that context, it can be a very good filter for choosing what you're investing your time in as a company and as an individual. Are you making the world more free or less free with your work?

Matt Mullenweg (10:38):

Where it changed for Automatic and for me personally as well was in 2015, we acquired a company called Blue Commerce. So we added two words to it. So democratize publishing and commerce, because it seemed clear that as more and more of the economy moved online, the means of production and the tools there being locked up in proprietary platforms, even if they're very good and I love them like Amazon, ultimately would decrease the freedom of the internet. So we felt like we needed to be part of creating a free commercial infrastructure and operating system much like we created a free and open publishing operating system.

Matt Mullenweg (11:20):

So that has been the only change kind of in the past. I would say that we were nothing for maybe the first year or two, then became democratized publishing, and then 10 years later became democratized publishing and commerce. And nothing has changed in the past 12 months. Maybe a little bit what we talked about earlier, where we felt an opportunity and a responsibility to share what we've learned about distributed work and put some of our tools out there like P2, which is a key communication infrastructure for us. We began to invest more time in making it available for people outside of the company to use. But it's not really part of our mission as much as we see it as an altruism of our work.

Matt Hollingsworth (12:02):

Yeah. And we'll of course link-
PART 1 OF 4 ENDS [00:12:04]

Matt Mullenweg (12:03):

... altruism of our work.

Matt Hollingsworth (12:03):

Yeah. And we'll, of course, link to those things in our show notes for those listening as well. So I'm curious when you say increase the freedom of the internet, and that seems to be the guiding principle. If we were just to distill it down to the mission of the company, would that be fair to say that that would be the guiding star here?
Matt Mullenweg (12:21):

It is. Yeah. But we talk about it in terms of democratization.

Matt Hollingsworth (12:23):

Right. Is there anything that is happening right now on the internet that is also doing the same thing and has a similar mindset that Automattic as a company, isn't a part of? Is there anything that you can point to that you think they're doing a great job of continuing our mission or is alongside our mission with increasing the freedom of the internet?

Matt Mullenweg (12:43):

So much, actually. I would say any place where open source is transforming the world. So a little bit older, but still highly relevant example is Wikipedia, which is doing it for information. When you see it happening with the standardization of browser engines. So the Google team has done an incredible job, both with Android and with the Chrome engine, chromium and allowing the world to work together on certain of these things versus compete.
Matt Mullenweg (13:10):

And then it definitely in the past year, there's been a lot of attention on cryptocurrency and distributed finance and Bitcoin, the best of which, including Bitcoin and Ethereum are open source and are I think a big part of what's going to transform the monetary and commercial side of the world over the coming decades.

Matt Hollingsworth (13:29):

Yeah. It's fascinating. I'm curious, and this is going to be a difficult question to answer because it's kind of counterintuitive, but what is the best argument that you've heard that is against this freedom of the internet mission that you have at Automattic at WordPress? Is there something specific that you've heard that you feel like is a good argument for pushing back on the way that you've democratized the internet?

Matt Mullenweg (13:52):

Sure. I don't think it applies in the democratization sense, but for freedom, sometimes people's minds go to sort of unfeathered actions by individuals. So you could easily imagine chaos or people causing harm to each other or things like that under the ages of freedom.

Matt Mullenweg (14:11):

In democracies though freedom is always in the context of society as well, in the context of a social contract. There's funny ways to put this, like your freedom to swing your arm stops when my face is there. There's the idea of freedom of speech, but if you yell fire in a crowded theater in a way that causes harm, that's obviously not protected. So democracy and why I prefer that from just saying freedom, although you could add this to freedom as well, is it's also a set of responsibilities and a social contract that everyone who is part of that society enters into with everyone else who's part of it.

Matt Mullenweg (14:52):

And we have a mechanism generally for folks who violate that social contract, for example, by harming others. They essentially get removed from that society and that's the concept of justice or the criminal justice system. That is obviously very fraught with issues because it is a exercise of power, but I don't remember if it was Yuval Harari or Sam Harris that talks about the monopolization of violence by the states, right, by an entity which we enter into a social contract with, and that has a non-capricious and arbitrary way of applying rules is maybe the best innovation of humanities since we stopped using the restroom where we eat. It is that meaningful to our ability to advance the civilization.

Matt Mullenweg (15:40):

And there's versions of this that happened on the internet. Sometimes we create a free and unfettered space and the impact of bad actors in that space can crowd out the good parts. And then we need to figure out a fair and just way to have an equality of opportunity and participation while still sort of having the accountability of the responsibility for those who are participating in that space.

Matt Mullenweg (16:05):

That was a poor version of what folks like Hobbes, and Locke and Yuval Harari, and Sam Harris and others have articulated very, very well. So if it's an area that interests anyone I encourage those to dive into the classics because what seems like a new issue in 2021, like, "Ah, how does Facebook regulate speech?" There are versions of throughout history, whether it's the East India Company, or monarchies, or the Catholic Church or other institutions throughout history that have become ultra scaled relative to the population and how these issues were navigated then, both in good and bad ways.

Matt Hollingsworth (16:44):

Yeah. It's such an interesting topic. And obviously top of mind for a lot of people considering what has been going on over the past year or so, and I'm sure there's more to it than we have time for this podcast, maybe a conversation for a different time and probably at least for an interviewer that is smarter than me, but it's a good call out for people that are interested to go back and look at history when it comes to our current environment.

Matt Hollingsworth (17:07):

And I think people are realizing the extent to which the different parts of the web are part of their lives. I agree with you that there's lessons from history, but I think that nowadays there's so much a part of us that is online and therefore the online platforms know so much about us, that it becomes even more of an important conversation.

Matt Mullenweg (17:27):

One way to think about it is that I think it's over half of all new relationships, couples, and later marriages start online-

Matt Hollingsworth (17:36):


Matt Mullenweg (17:36):

... with apps, websites and so that means literally our evolution is now being influenced by these algorithms and the technology.

Matt Hollingsworth (17:45):

Wow. So I think maybe I know the answer to this question, but how do we do we open source everything when it comes to our relationship with, is that the goal to make this all open source?

Matt Mullenweg (17:56):

To take it historical again, every society ends up recreating a few things like a means of abstraction for trade, which is like a currency, a way of disseminating information, which is publishing really, a way of storing information, which could be a library or papyrus scrolls, and today's really the internet and things like the Wikipedia.

Matt Mullenweg (18:16):

So for these core fundamentals, I think society deserves in this modern era to have them have an open source alternative, even if it's not the dominant one. So, and CMS's WordPress has been winning in terms of market share, but even if it wasn't, if just our presence, we're making the proprietary alternatives be more open than they would otherwise, that would be a success.

Matt Mullenweg (18:58):

And I think you can look to the dynamics between a iOS and Android that, many markets iOS is still dominant, but the existence of Android forces their most successful company in the world of our market cap, Apple to be more open than they would otherwise. So it can serve as a check and balance on the unfeathered commercial interests of a corporation in a way that a monopoly or duopoly or a plutocracy, which is often what forms in a purely commercial sense does not. That's why you need an open alternative. In societies and countries, the existence of the United States as a flawed, but aspirational, open society pushes other countries to do better.

Matt Hollingsworth (19:25):

Yeah, I'm guessing that the DuckDuckGos of the world, for example, would be, is that a similar kind of comparison with Google in your mind?

Matt Mullenweg (19:34):

It should be, but I think the scale is two or three orders of magnitude too small to put any real pressure.

Matt Hollingsworth (19:41):


Matt Mullenweg (19:42):

I think what actually happened is we thought things like DuckDuckGo, general purpose search engines would challenge Google and what's actually happened is the specialized ones have. So the fact that so many commercial intent searches now happen first on an Amazon than a Google. That's what's actually created more of a challenge, but as we've seen it doesn't actually truly create an alternative because Amazon has started to adopt a similar advertising model and all the bad incentives that are inherent in that to Google that sometimes perhaps business models are too attractive to stay away from. And the reverse auction word ads type model is really one of the best business models that has been created in the past, really in the past century. So it's almost like Gollum's ring, right? It might be too tempting.

Matt Hollingsworth (20:31):

Yeah. Fair enough. So this is a call out for anybody else that's out there that needs to, where the goal is to create a open source, a true open source counterweight to Google. So, listeners feel free to go do that and keep us updated on your progress and we'll preach it.

Matt Hollingsworth (20:48):

So we've gone a bit off topic here, and that's my fault. I'm just so interested to hear your thoughts on these sort of things. So let's get back into the remote work specific piece of this puzzle where you have so much to add here. How has Automattic as a company done things a little differently? And in what ways do you think the Automattic way of doing things is different from most other remote work distributed teams? And I guess another way of asking that question is what has surprised you that more companies haven't adopted that you have been doing so successfully for so long?

Matt Mullenweg (21:23):

Hmm. I do expect that other companies will adopt the things that have made us successful. It's just a matter of time. I have a post and of course people can check out called Distributed Five Levels of Autonomy. And it kind of goes into what I have seen as the common phases of organizations, including Automattic in their history as they move from being kind of synchronous and in one place to asynchronous and in many places.

Matt Mullenweg (21:48):

The asynchronicity I would say is one of our super powers. We are truly fully distributed. I think we're in close to 90 countries now, almost every time zone in the world and we have invested a lot of time and cultural effort in making sure that people, regardless of where they are, can be fully effective, that they can have an impact on the product and the company. They can stay connected to users that they can progress in the organization.

Matt Mullenweg (22:16):

There's not a time zone ceiling to how far you can get in the executive ranks based on where you are. And that is, it's taken a lot of work. And it's been kind of funny. The past year was strange for me in several ways. One, I had set as a personal goal to make more organizations remote and distributed because I thought it would make the world a better place if people didn't have to commute and things like that.

Matt Mullenweg (22:41):

And then kind of woke up one day and it happened. Right? So, I expected it was going to be a 10 to 20 year goal. And it ended up being a three-month one, which was very strange. And then this other thing which was what was a very unique differentiator of Automattic and the marketplace for hiring talent began to be something that at least if, from a checkbox point of view, almost every technology company was doing or committing to do for sometimes a long period of time, like Twitter or Square.

Matt Mullenweg (23:12):

So that got me actually very, very worried at the beginning because I thought, "Ah, how are we going to be able to hire, the world-class best in the world talent like we have been?" And it turns out that sometimes we would miss people on the first go round, but as companies were adopting distributed, many were bringing along the dysfunctions or pathologies of their previous ways of working. And they were either bringing them online or making them worse online.

Matt Mullenweg (23:39):

And so where we might lose an amazing engineer to Google on that first pass, sometimes they would be back six or 12 months later say, "Hey, that was a hot mess. I want to be at an organization that doesn't just say they're distributed, but actually really does it well." And so I think culture can be a long-term differentiator, but we do need to get better at describing why it is a different-
PART 2 OF 4 ENDS [00:24:04]

Matt Mullenweg (24:03):

But we do need to get better at describing why it is a differentiator for us when others appear to be doing the same things.

Matt Hollingsworth (24:07):

Right. Yeah. And so to go a little deeper on a point that you made there, how do you address people's opinions and or practices that they may have come to Automatic with? Do you have a system for saying, “Hey, pretty much scrap everything you've done so far and like, let's start from the ground up with how to work remotely”? Is that something you've thought about when it comes to onboarding?

Matt Mullenweg (24:29):

Automatic has a creed and the very first line for over a sentence in that creed is, I will never stop learning. You can't learn with a closed mind, just like you can't hold anything with a closed fist. And so if there's one thing that's allowed us to adapt, it is keeping that open mind. That's including keeping an open mind that someone joining might have some wisdom or way of working that's more effective than what we've been doing, even if we've been doing it for a very, very long time. So that humility and keeping that learning and growth mindset in everything we do is I would say the only thing that is key to keeping us competitive in the long-term.

Matt Mullenweg (25:10):

Some practices that helped this include sometimes just trying the opposite. Look at the thing that you feel like is your most sacred cow, the thing that you're most attached to in your culture and set up a team or a time period where they're just going to do the opposite. It actually hasn't happened recently and it obviously can't happen now, but I've opened it up to teams in the past to say, “Hey, if you want to open a building and move everyone there, or only hire people that are going to go into that every day, like maybe a design studio or something. Like why don't we try that and see what we learn from it?”

Matt Mullenweg (25:42):

So even the things that you hold most dear to your culture, it is perhaps worth trying the opposite. The only thing I would make an exception to that rule is the learning aspect. Kind of like you should be tolerant to everything except intolerance. I think you should be open-minded to everything except close-mindedness.

Matt Hollingsworth (26:01):

And what has allowed you to do that and be so experimental? Because I've heard from other companies that maybe don't have ... Or there's a lot of risk involved with trying things as open and experimentally as you have. Is there anything that you think restricts companies from doing the kinds of things that allow for that open-mindedness that you obviously have cultivated in your company? Is that something that you find is sort of like a function of venture capitalists not wanting companies, their portfolio companies to be doing these sort of things? What do you think is the hold back for companies like this?

Matt Mullenweg (26:33):

Yeah. I mean, luckily, you don't have to invent anything. In the 17th century, humanity discover the scientific method, right? A way to have a hypothesis, observe, measure, and experiments, and then iterate on those hypothesis. So I think that every company should be testing a number of hypothesis all the time. We put so much into A/B testing, multi-variant testing or doing other sorts of research with our customers and our product, but we so rarely do that with the way that we're working. And so if you were just to take the approach that you do to your product development and design and everything else and put a mirror to the organization, I think that would be healthy. And what's great about it is that you will find what works uniquely for you and your market and your people and your employees and everything.

Matt Mullenweg (27:24):

One of the reasons I've always been hesitant and didn't really, prior to 2020, share as much about how Automatic work is because I also have a deep humility that what's worked for us won't necessarily work for anyone else because you might be in a different market or have different employees or just be a different leader. So what I really want is every leader, every company, every organization, every non-profit to experiment their way into learning what works the best for them. And of course there will be some commonality and some best practices that emerge that may be apply 95% of the time, but there's always going to be an exception to every rule.

Matt Hollingsworth (27:59):

Right. I'm curious about the way that you think that ... And this is again, a little bit more open-ended, but when it comes to remote work and you mentioned before that you woke up one day and everybody was working remotely, which is obviously most people's experience as sort of a hectic and anxious ridden one when it comes to remote work over the past little while. So do you think that there is a negative aspect how abruptly this shift happened and maybe it has affected people's opinion about remote work in a negative way? Is that something you've thought about?

Matt Mullenweg (28:32):

I mean, undoubtedly, but I'm sure people listening here know that lockdown or pandemic, remote work is not the same as normal remote work. I would say a big key and something that we often have to encourage people for whom Automatic is their first job is encourage them to build a really rich social network outside of the job. Have people that you can go to lunch with, have organizations you're a part of, have things you contribute to in your local community to stay really connected. Because if you're just at a computer all day and not connected to the nature, the people, the needs around you, it can be very easy to get into a negative loop or a state of depression and disconnection. But when you're in an office, you get some of that for free, right? Because you're forced to be someplace for seven or eight hours a day, or you're going to end up having lunch with folks around you. So we can take that for granted.

Matt Mullenweg (29:25):

The beauty is when you're doing it in a distributed fashion, you get to design that from scratch. So you don't just have to have lunch with the folks who happen to work with you. You could say like, “Well, who in my community do I want to connect with, do I want to learn from, do I want to contribute to?” Maybe you do lunch like a big brother, big sister style, where you take someone in a school in your neighborhood that needs extra help and you can be a mentor to them, going to lunch once a month or once a week or something. So there's so many different opportunities to connect that might be trickier if you were forced to be in an office all day.

Matt Mullenweg (29:59):

But that I would say is something that I think I've been very impressed with how even the most conservative state organizations have learned those lessons really, really quickly, right? Because you can only have so many in a days, in a row exhausted from being on Zoom for 10 hours a day before you hit a wall and you say like, “Something has to change here.” That happened for a lot of people in April, May, June. And I've been actually really pleasantly surprised by how fast organizations have adopted. Including banks, places you wouldn't think are that hip or cool.

Matt Hollingsworth (30:34):

Yeah, I know, it's been interesting and actually quite encouraging as well. I hold the opinion as well that what we've been forced into has led to a lot of positive changes with more conservative organizations. And I think that is a positive, but I'm holding your view of putting the mirror on that idea. I'm curious if there's anything else that you can point to that's sort of a, maybe a negative about the way that remote work has been forced on us. Is this a something that you think has knock on effects for cities in general? Like what is your opinion on how the sort of second-order effects of what remote work is going to force us all to do and what that ends up looking like for society?

Matt Mullenweg (31:16):

Two things come to mind. First, was the importance of meet-ups to Automatic's culture. So we would invest a huge amount of time, typically three or four weeks to have someone's ear and a large amount of money, like over $10 billion a year to get people together. Usually, three or four times per year, depending on what team you're on and once a year, the whole company. So that is obviously something that was very key to building trust and connection that we've had to try to recreate virtually. And I'm also really looking forward to getting back to when it's safe to do so, because I really love the people I work with. And those times when you are able to be physically together are so, so, so rewarding. And some of my most cherished memories of my adult life. I started when I was 19. So really like a lot of my adulthood has been working with people from a distance and then coming together periodically. And it makes that time together that much sweeter.

Matt Mullenweg (32:11):

In terms of the downsides of how we've been forced into this experiment, I think at the beginning I called it the remote work experiment no one asked for, has been that it's not available in all jobs and all roles, very obviously. I call these level zero roles, and it could be being a surgeon. It could also be delivering goods or manufacturing or other things that require physical co-presence for the work to happen. And I'm very glad that in the U.S. and in many other places, we are prioritizing those roles to get vaccination first. I think it's great if folks like me who can work from home have to wait a month or two longer to make room for those folks who are forced to be in physical proximity in the time of COVID, at risk to do their job and to both make a living and serve society. So that's where I worry the most. We are at a height of inequity as well. And typically, when societies become this unequal, it's not healthy for social cohesion, it's not long-term sustainable. So probably the best thinker and writer and advocate of this is a fellow named Nick Hanaue‪r. He has a podcast called Pitchfork Economics, and he very famously wrote an essay five or six years ago called The Pitchforks Are Coming. And it's like, “My fellow plutocrats ... ” Nick was one of the ... Maybe the first investor in Amazon. So he's a billionaire many times over.

Matt Mullenweg (33:38):

He says, “My fellow plutocrats, if we keep doing what we're doing, pitchforks are going to come for us.” And he has been a tireless advocate for raising the minimum wage and has helped be part of that happening in many cities, including Seattle, around America, of raising the minimum wage to $15. That is not a full solution, but I think things like that are a good step towards creating a society that shares its growth and its success as widely as possible. And that's a society, by the way, we all want to live in, right? You can look at countries around the world that are even more unequal than the United States, and they're not places you want to be.

Matt Hollingsworth (34:16):

Yeah. We'll link to that as well. I haven't actually listened to that podcast, but it sounds very interesting. And again, quite relevant for what's been happening. This is sort of a relevant question from what we've been talking about, but I'm curious if there's anything that you held dearly, and it could be an opinion or a thought about work or just in general, that you held prior to the 12 months ago that you've changed your mind on over the past year.

Matt Mullenweg (34:44):

Two things. One is around education. We assume that training and learning and development would have to happen in person. So even Automatic would fly people around the world in the world and stick them in a classroom for three or four days to do this. We've obviously have to shift to do that in a remote fashion and the opportunities that opens up, including creating things more ongoing. So instead of packing in 30 hours of work in three or four days in person, if you spread that 30 hours to be three hours a week for 10 weeks, you can actually get a much deeper level of engagement and learning than you would if you try to crunch it all together in a workshop.

Matt Mullenweg (35:22):

It's also is humbling to see friends with children who are doing remote learning and the challenges that it creates. For adults in the professional workplace and technology companies, a place like Automatic, I think it opens up a lot of opportunity.

Matt Mullenweg (35:37):

The second is around hiring. I think that our hiring process is very, very thorough. It involves a trial process, a project, interviews, et cetera, which is fantastic because it does do a great job at allowing people who might not have the resume or background or sort of traditional markers of success to show their ability and be hired at Automatic. You also know that everyone that you work with has gone through this process.
PART 3 OF 4 ENDS [00:36:04]

Matt Mullenweg (36:03):

Okay. You also know that everyone that you work with has gone through this process. So, the number one reason to stay at a job is great colleagues. Even people who leave [Automatic 00:36:09], that is the number one thing they remark on is the quality of their colleagues. So it, I think is the number one thing we do for making it a great place to work. But as other companies, and this happened a little bit pre pandemic, but there's so many other great distributed companies to like GitLab or Basecamp, or I'm sure your company that as, our process taking 45 or 60 days, we would lose people to these other good companies who could do the same thing in 30 days. So we began to really have to question our assumptions about what in our process was long because it needed to be long, and what was long because we just haven't optimized it? So if we're able to get to the same answer of knowing someone's ability to thrive in the job in a shorter amount of time, we should absolutely do that, because it's better for both us and them, and also keeps us more competitive in the very, very competitive hiring market.

Matt Mullenweg (37:03):

Now we need to hire right now, 350, 400 people in the next 12 months, and a that's definitely a higher scale than we've ever done before. We've also been raising the bar in quality of how we're hiring, and who we're hiring. So doing those things simultaneously, both making the quality higher, and the quantity increasing by a significant percentage is a really fun challenge. And I'm very, very proud and impressed by my colleagues who are tackling it.

Matt Hollingsworth (37:32):

Yeah, that seems to be the number one time consuming and sort of iterative process that I've heard from companies is, how to optimize the onboarding experience to make sure that you are displaying your company culture and values to the person who wants to work for you, and also for you to make sure that that's the right person for the job and right fit for your culture. It seems like that's one of those ongoing, unanswered questions that are very specific to the company, and yet so important as well. So is there anything that you would point to about your process that you think is maybe the most important, or is there something you think you would tell a smaller company to make sure that you do to make sure that you are optimizing that process? Is there one or two things that you think people miss?

Matt Mullenweg (38:17):

There's two things; one at the top of the funnel and one at the bottom of the funnel. At the top of the funnel, we really have the widest possible aperture. That's how we ended up with people in 90 countries. And we really try to downplay where you went to school or other things, and look for markers, engagements, and possibility. At the bottom of the funnel, meaning that folks who make it through the first few rounds of things, we do what we call a trial project. And this is actually paid, it's 25 bucks an hour, it's a contract project. And it's something that looks just like the work. So if you're going for a Happiness Engineer role, which is our customer support, you're actually answering real customers. If you're an engineer you're working on real code, if you're a designer, you're designing real things. That's part of why we pay for this trial, regardless of whether we hire the person or not, because it is meant to be real work. And I believe that people should be compensated for that real work.

Matt Mullenweg (39:09):

We try to make this as short as possible. Yeah, that's my other thing where we're trying to make this quicker, but it is incredible the folks who might interview really, really well, but ultimately not be a good fit for the way we work. And the trial is two way as well, so it does allow people to really, really see how Automatic operates from the inside. Not just what I say on interviews or what the website says or anything like that, but you're actually working alongside people who will be your colleagues if you're hired, and it's not artificial, it's not a whiteboard coding session, or they're more interview thing, which I find to be not well correlated to success in the organization. So that's really the hard and easy part about it is you try to create something that mimics the work as much as possible, and then hire the people who do a good job at it.

Matt Hollingsworth (39:58):

Yeah. And I'm sure that people listening, Automatic is always one of those companies that we hear from job seekers as the ones that seem to get a lot more applications than other companies, so I think that you've created something that people want to be a part of, which I think is, is a really exciting and really cool. And I'm so happy to be having been able to talk to you today, Matt. I won't take up too much more of your time. I do have a couple of closing questions for you.

Matt Mullenweg (40:22):

Can I say one thing before then?

Matt Hollingsworth (40:24):

Sure. Please.

Matt Mullenweg (40:25):

Sure. The downside of our success so far is the number one reason that people don't apply to Automatic is because of imposter syndrome. So there are literally hundreds of thousands of people out there who could be fantastic colleagues and be very, very successful and happy at Automatic, but don't apply because they think they couldn't or they would make it. So I would encourage people to apply, even if you think you're vastly under-qualified. In fact, if you think you're under-qualified, it probably means that you are closer to being qualified than someone who is overly confident that they could get hired.

Matt Hollingsworth (41:00):

Right. Yeah, no, it's a great call out. And I think that speaks to not just Automatic, I think it's a good idea generally. Like, what's the downside of applying if you want to be a part of the company? I think it's something that more people should be doing. And hopefully this is some encouragement, right from the CEO that this was something that, if you're feeling an imposter syndrome, you probably are well enough qualified to apply for the job, so please do that. And we're fortunate enough to have a few Automatic jobs on our site [inaudible 00:41:30], so we'll link to those as well, and we encourage you to not only check our site, but also go to the Automatic and we'll link to your hiring page as well, Matt, to make sure that that's very crystal clear for those people who want to be a part of Automatic.

Matt Hollingsworth (41:43):

Anything else that you wanted to add onto that? Anything, reason why, I mean, outside of the fact that we have learned a lot about you in the business, anything unique about Automatic that you think is a value prop for anybody listening that to go and apply?

Matt Mullenweg (41:58):

Yeah, I think it's good to ask yourself, of the productive years you have in front of you, how many of them could you devote to moving society forward? And I believe if your talent is in creating and supporting software, a big part of that is doing it in an open source fashion. So Automatic is not the only, but one of the companies where pretty much everything we do is open source. So you can know that those precious, productive years that you have are kind of moving the needle on society forward in a way that working on proprietary software, which I believe to be an evolutionary dead end would not.

Matt Hollingsworth (42:36):

Yeah, that's great. Thank you, Matt, again, for your time. I have two questions before we wrap up. One is just that my curiosity, I went and did a bit of a deep dive on a couple of other interviews you've had, and I'm curious if you still have the, I believe it was a 1998, but it could be wrong, Chevy Lumina, do you still have that?

Matt Mullenweg (42:56):

Yeah, I do. That's the car I drive around in San Francisco.

Matt Hollingsworth (42:59):

That is amazing. One of my favorite things about you that I've heard upon other interviews so big fan of the Chevy Lumina choice for driving around San Francisco.

Matt Mullenweg (43:10):

Thank you.

Matt Hollingsworth (43:12):

And one more thing before we go here, what is the single thing that you're most excited about when it comes to the internet moving forward?

Matt Mullenweg (43:21):

The acceleration of open source impacting society. And we've mentioned a few areas earlier, like information with Wikipedia, finance and currency with cryptocurrencies and Bitcoin. Just seeing that play out in dozens and dozens of areas makes me very, very optimistic. It's been a difficult kind of 18 months to be optimistic, but progress is not always in a straight line. And sometimes these things which set us back, particularly in terms of software freedom or adoption proprietary or open versus closed platforms, sometimes the more successful closed platform is, that's necessary to create the reaction of the open platform and response.

Matt Hollingsworth (44:04):

Yeah, no, I think that's a great place to end things, and I think it represents an optimistic note where we all are really looking for right now. So great place to end it. Matt, thank you so much for your time. Again, really appreciate it. We'll link to everything that was mentioned here, and I think this could end up being a second podcast. I have so many more things to ask you, but we'll hold off for now. Thanks again, Matt. And we'll talk soon.

Matt Mullenweg (44:27):

And thank you for promoting this. I believe that every remote job you can get someone does benefit the world. So keep fighting it, keep promoting it, and I'll keep pointing people to the site as well.

Matt Hollingsworth (44:36):

Awesome. Thank you so much, Matt. We appreciate it.

Matt Hollingsworth (44:40):

Thanks so much again for listening to the show, be sure to check out weworkremotely.com for the latest remote jobs, and if you're looking to hire a remote worker, We Work Remotely is the fastest and easiest way to do so. As always, if you have someone we should talk to, any advice you have, or if you'd like to advertise on the podcast, please each out to us at [email protected]. That's [email protected]. Thanks so much again for listening, and we'll talk to you next time.

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