About this episode

My guest this week is Matt Mullenweg, co-founder of WordPress and CEO of Automattic. In this episode, you are going to hear from the creator of the platform that powers over one-third of the entire internet. Yes, you read that correctly! Wordpress powers one out of every three websites that is accessible online.

There are many unique elements to Matt's story and we cover many of them within this episode. Two main topics that we unpack is the broader discussion around open-sourced software and the economy behind it, as well as his thoughts on the distributed workforce. Both of which, Matt is (without argument) the defacto expert on.

As brands all over the world are scrambling to adjust to a remote workforce, Matt has built his business on this model from day one. As of today, Automattic has a distributed workforce of around 1,300 employees. We discuss why he built it this way, how he has done so successfully, and what other people need to consider if they want to move in this direction.

There is a tremendous amount of value in this episode and I cannot wait for you to hear Matt Mullenweg’s startup story.

In this episode, you'll hear:

  • How he grew up in Houston in a household that was on the lower end of the middle class, watching his hard-working parents constantly pushing themselves to do more and picking up any extra work they could find.
  • From a young age he always had an entrepreneurial flair, starting his first company as a window cleaner, then went onto build computers at high school.
  • How he originally wanted to be a Jazz musician coming out of high school, but through competing in a high school challenge called ‘Federal Reserve Challenge’ Matt found his love for microeconomics. With competing he was able to travel to Washington DC and experience his first taste of the intellectual business world.
  • How the first 25 years of his life was very modelled after his dad, until he broke away and started to create his own path.
  • Matt shares his love of Rap music, due to it being the most popular among the Jazz students growing up and he would trade CD’s on and get excited by it.
  • His views on the Qwerty keyboard layout and how thinks it more functional to use the Dvorak keyboard instead.
  • Matt explains how he come up with Wordpress and the problem he was solving.
  • He unpacks the back end of open-source platforms and how to monetize them.
  • Why he created his other company Automattic
  • Matt’s advice on remote working
  • The importance of communication and always communicating with intention and honesty.
  • How Matt defines success, working alongside people who he love and respects doing the best work of their

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Matt’s podcast - Distributed: https://distributed.blog
Matt’s interview with Jack Dorsey - https://distributed.blog/podcast/

Matt’s about page: https://ma.tt/about/

Nonviolent communication Book: https://amzn.to/3kB1gIN
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Episode transcript

Matt Mullenweg: Howdy, this is Matt Mullenweg. I'm the cofounder of WordPress and the CEO of Automattic, and this is an update on MY startup story.

  • Every wildfire began with a spark. Every superhero has an origin story. And every single startup has a moment that they point to as their beginning. And every founder has a purpose that drove them in the midst of all obstacles. THAT is The Startup Story. *

[00:29]

James McKinney: Hello everyone and welcome to another episode of The Startup Story, and what an episode it is. For the next 60 minutes we get to hear from Matt Mullenweg, the cofounder of WordPress and CEO of Automattic. Now, you might be thinking, "Oh, the founder of WordPress. That's pretty cool," and you're right. It's incredibly cool. But let me hype it up just a bit more for you because this might be the best 60 minutes of your week. Regardless of your technical knowledge, you are probably aware of WordPress and that it's a CMS platform that can help you establish a website online. But did you know that WordPress powers over 30% of the global internet? Let me repeat and rephrase that for you. 1 out of every 3 websites on the internet are built using WordPress. How insane of a statistic is that?

And I love crazy statistics, the kind that almost seem too crazy to believe, right? I mean a third of the internet, how about these statistics for you. There are over 2.4 billion robocalls made every month, or how about the fact that the average person will fill 23 two-liter bottles per month with the amount of saliva they produce in a month. I know, that's kind of gross but it's a crazy statistic. And last one, how about this right for those who use Instagram, Cristiano Ronaldo is kind of a very popular soccer player right? Well the amount of energy used every time Cristiano Ronaldo posts to his Instagram and gets distributed to his 260 million followers is the same amount of energy that is necessary to power 10 American homes per year. That's crazy, right? Those are remarkable statistics.

But let's go back to the very first one. Our guest today created a platform that powers 1 out of 3 websites on the internet. And did I mention that it's free? Now, I'm going to let that hang there for just a moment. Like I said, this episode is an incredible one because like all episodes, we discuss his journey to WordPress and Automattic. We even cover the inefficiencies of the globally recognized QWERTY keyboard. Yes, Matt has opinions and thoughts and data round why the QWERTY keyboard is inefficient, and we even discuss his love of rap music. Yeah, one more thing, we even talk about why he built a product that powers 30% of the entire global internet and not charge for it. But like all great stories, we don't just jump to the final chapter. No, we need to start at the very beginning.

[02:58]

Matt Mullenweg: Very early days growing up, my father you know worked at the same job for 25 or 26 years. So but I definitely saw from him an incredible work ethic. He would be up very, very early in the morning. Even though he was a computer engineer he put on a suit and tie, carried his briefcase to work every day. And he'd often go in on weekends, and he'd take me. It was actually some of my favorites because he'd often take me to the office and I got to play on just a spare computer while he was there, in this giant cubicle farm of Brown & Root, Halliburton, or whatever it was at that time. They had really fast internet, like a T1 connection.

And for my mom she did have an entrepreneurial knack where she would bake bread and sell it to hunters, or do some different things just to earn a few extra bucks. We were definitely on the lower end of middle class, never needed for anything. But they would always try to do whatever extra work they could find. Whether that was consulting on the side for my dad or would often take the assignments for overseas kind of, what's it called, overseas rotations. Six months a year because then he'd get an extra per diem and things like that. As a youth, I thought all you needed to start a business was a business card. I don't know if you remember those perforated sheets you could buy.

[04:30]

James McKinney: Yes.

[04:31]

Matt Mullenweg: And we had a printer I was obsessed with, so I would design these business cars and print them, and they had the little perforated sides. And I would just have a different business per sheet of business cards. I never really went more than eight, but just from a young age I liked the idea of that. I had a window cleaning company. Obviously later in high school I built computers and websites, but just kind of whatever hustle was available to make a few extra bucks.

[05:01]

James McKinney: What did you think you wanted, coming to the end of high school though, what did you think you wanted to do? What was your vision for your future at that time?

[05:09]

Matt Mullenweg: I wanted to be a musician.

[05:11]

James McKinney: Really?

[05:12]

Matt Mullenweg: Yeah, so I studied jazz saxophone from a fairly young age. There's incredible jazz in Houston, so really, really great musicians, teachers. Actually on my about page on my website, ma.tt/about I added a thank you to all the most influential teachers and 80 or 85% of them were music teacher.

[05:35]

James McKinney: Wow.

[05:36]

Matt Mullenweg: Just jazz musicians in town who were educators as well as incredible artists. So that was really what I thought I was going to do. Later in high school I got pretty into economics as well, macroeconomics, because there was an academic competition called the Federal Reserve Challenge or the Fed Challenge. It was run by Federal Reserve bank and it was for high schoolers, and Houston was actually the most competitive region in the whole country. So if you won Houston you had a good shot at winning the whole country. And so first year we got totally creamed by a private school, and then second year we were able to really work hard and won the city, won the region, and got to the final round of nationals. So that was very influential for me as well because it got me to travel to Washington DC where I would return the following summer, where I started blogging for the first time. I met folks like Alan Greenspan, Ben Bernanke, Susan Pies, a lot of very influential economists. I met Milton Friedman through a related thing. So really kind of exposed me to a very rich intellectual and business world, and thinking about things in terms of incentives and systems design, which is really what economics is.

It was also I'm proud to say the first academic competition my school ever won. I went to an arts high school. It's called the High School for the Performing and Visual Arts, so primarily focused on the art areas whether that's drama or vocal, or jazz, or classical or dance or something. Wasn't known for its academics, but the folks who were on that team with me, it was a team sport of five people, all went on to have really fantastic careers. So it's a kind of fun little microcosm within that school.

[07:23]

James McKinney: That's really cool. So but being that you had a leaning towards music, obviously that is an experience that probably set an imprint within your thinking as to what your future was. But being that your dad was a computer engineer. Again I don't know what year this was, but my assumption is that a college degree was part of his journey, especially around that era it was probably required, less so now. You know I assume you thought well I need to go to college. Is that a safe assumption or am I off base on that?

[07:58]

Matt Mullenweg: To be honest you could look at most of what I did in my first 25 years of life of very modeled on my dad. I played saxophone because he played saxophone. He did go to University of Houston. They didn't offer comp sci at the time, so he was doing a mathematics degree but they introduced the degree while he was there and it was what all his electives were in. so he graduated with a computer science degree. I later went to University of Houston as well. Yeah, it was very much following in that path. I ended up trying the computer science classes and I didn't really enjoy them. I had already started programming and learning things on the internet at that time. They were using more of like proprietary Microsoft technologies and I was pretty into Open Source already. I was going a different path, but I really enjoyed the political science courses I took, and I was planning for that to be my major.

[08:53]

James McKinney: You know let's put a date stamp on this season. So what years were you at University of Houston?

[08:59]

Matt Mullenweg: 2002 to 2004.

[09:03]

James McKinney: 2002 to 2004. Can you give us, you said you were already in open source a bit, can you give us a framework and reminder of what the open source landscape looked like in those years?

[09:13]

Matt Mullenweg: I'll also give you a fun fact is Lil' Wayne was at University of Houston at the same time I was there, although we did not cross paths.

[09:23]

James McKinney: You love rap, though, right? I've heard a few different interviews, you're a big rap fan.

[09:27]

Matt Mullenweg: I am I think because it was kind of the popular music that all my friends in the jazz department listened to, so it was what we were all trading CDs on and really excited by. So when I was at that very impressionable age it was the music me and all my friends would obsess over, besides jazz. So you asked what was the state of open source at that time. In some ways it seemed incredibly mature and of course looking back now we know it was the earliest days. It was kind of before Wikipedia had really taken off and lots of other things. So open source started in late, or when I think of modern open source, kind of late 80s, you know Richard Stallman, GPL, et cetera. Of course there's roots going back much further than that. Linux was very popular. I was part of a Linux users group in Houston.

[10:21]

James McKinney: That's the 90s correct? Like Linux was that mid to late 90s maybe?

[10:25]

Matt Mullenweg: Yeah. Redhead had IPOd, Netscape had IPOd. There was the whole internet boom and subsequent crash, the dotcom crash. I think Mozilla might have gone open source, kind of out of the ashes of Netscape. So open source I would say was known in the geek communities but had not yet created a ton of user facing successes. The early ones that were probably around that time, although I don't know my exact dates, would have been when Mozilla turned into Firefox and sort of became the preeminent, most influential browser. The file sharing acts of the time, so Gnutella or BitTorrent I believe were around in open source.

[11:12]

James McKinney: Okay, I remember.

[11:13]

Matt Mullenweg: And of course Linux on the desktop and growing on the server as well, or maybe even dominant on the server already.

[11:21]

James McKinney: Now when you are in this scene, you're not really interested in what's taking place in your college classrooms. It's more enterprise level computer science than what you're doing in the open source world. What was the process that you went through in order to make the decision you know what, I'm done with this, I want to move onto something else? What was that like and then also too what was the conversation at home like?

[11:48]

Matt Mullenweg: Yeah. I felt a lot of guilt at the time for not being as engaged with school as I felt like I should have been. I had stayed in Houston versus going to other colleges kind of for family health reasons, trying to stay close to home. But compared to my father, who I think he might have already been married and had my sister at that point, and he was working a day job at the Ford factory moving boxes, like doing things that even today I don't think I would be able to do, and going to school, and paying for it all himself. I was able to get a full scholarship to University of Houston, and so I kind of had this free ride a little bit. But my passion was definitely on the internet, so I would spend all my time on IRC and forums and chat rooms, and building websites and reading code. Kind of soaking up as much as I could about internet culture.

Part of that was it's kind of a funny path but I'll try to shorten the story. I was very into Palm Pilot devices. While still in high school I had saved up money to get a Handspring Visor which was kind of the first alternative Palm Pilot.

[13:10]

James McKinney: I love that. I have listeners who have no idea what these devices are, but I absolutely know all of them.

[13:15]

Matt Mullenweg: It would later influence WordPress actually because the Handspring Visor was basically a Palm Pilot, a PDA, personal device assistant or something I think it stood for.

[13:26]

James McKinney: I think it's personal assistant, I just can't get what the D is. Digital assistant maybe?

[13:29]

Matt Mullenweg: Digital assistant, yeah. But it had a little slot where you could plug in add-ons where it could turn into an MP3 player, add a camera, or add a modem actually-

[13:38]

James McKinney: Oh wow.

[13:39]

Matt Mullenweg: … which was pretty innovative at the time. So I started a user group for this. So they had a user group, they were called Palm User Groups, or PUGs. There were ones in every city, but Houston didn't have one at the time so I started the Houston Palm User group, or HPUG. There was a local kind of computer nonprofit called HALPC, Houston Area League of PC Users, which went back to the 80s and had a space, so we'd host the meetings there every month. And you know 30, 50, 80 people would come and we'd have some sort of topic of that month. We'd often invite speakers, like Palm Pilot software developers would fly down to Houston and speak and we'd do giveaways.

[14:20]

James McKinney: Oh wow, okay.

[14:21]

Matt Mullenweg: Kind of had a little bit of a format there. And yeah, started running this. The cool thing to do, which is funny because it's still cool on iPhones now, was to change out all y our icons on your Palm Pilot. They actually allowed you to change the default ones with something cooler. There was a designer named Jeffery Zeldman who made this icon set that was kind of inspired by the sort of Hollywood in the 40s and 50s, kind of had that art deco-

[14:51]

James McKinney: That's really cool, yeah.

[14:52]

Matt Mullenweg: … Hollywood vibe. And of course that was an era I already had a predilection to from my interest in jazz, and just thought this was pretty cool. On Zeldman website, Zeldman.com, which is by the way still running, he's still blogging, he was sort of going through his journey as a designer and a designer that was learning how to code for the web and code in something that was called web standards. So before you used to have to build your website multiple times, like once for Internet Explorer, a version for Netscape, and often you'd go to a website and it would tell you which browser you were, you'd have to click on a button, and the idea was web standard would create… you could code it once and it would work for every browser and have better markup, and be more accessible, and things. So Zeldman became my idol.

[15;41]

James McKinney: That's awesome.

[15;42]

Matt Mullenweg: It's like I followed everything he did. He had this way of writing… he's an amazing writer actually. He could write about grass growing and it would seem like the coolest thing. He was really my portal into this world. Actually I work with him today. He's a colleague at Automattic.

[15:55]

James McKinney: That's really cool.

[15:56]

Matt Mullenweg: It's kind of a funny lead into the story. So I saw that he was going to be speaking at something called SXSW, which stood for South by Southwest, which was a conference in Austin. I was so excited that Zeldman was going to be in Texas I had to figure out how to go to this. At the time, the interactive part of SXSW was only a couple hundred people. It was pretty small, much smaller than the music or film. I think now it's reversed with interactive as big or bigger. I was able to get a student ticket for a reduced price. I did write a hot check to buy that ticket, when you could use checks… I didn't have quite enough money in my bank account but I think I was able to, I don't think it bounced. Then I had a gas card from my parents that they let me use sometimes so I used that for the road trip. And my sister already lived in a suburb of Austin so I stayed there with my sister. I figured out a way to basically do this whole trip on probably less than $200. While there it was like the entire internet - every blog I followed, everyone I looked up to - was in this relatively small conference.

[17:05]

James McKinney: That's awesome.

[17:06]

Matt Mullenweg: SXSW was then, and I think still kind of maintains this, of being incredibly accessible. Like the speakers don't like go out a secret door and get whisked away. They just kind of walk down the hallway, and so being able to hang out with all the people that I really looked up to, or had the chance to meet them, was very exciting.

One dinner, there was a dinner at a Mexican restaurant, where they had this super long, long table. And I got there a little bit late and I sat down, and all the seats next to me were empty and I felt like, "Oh no, no one likes me. Do I smell? What is going on here?" I was actually pretty insecure at the time as well. But then what happened was four people sat down around me. So Zeldman, who I hadn't met yet, and his wife. A browser very influential engineer named [Tontac Chelleck 17:59] , and another influential blogger/web developer named Eric Meier who was kind of the father of teaching people CSS. So these, all the people who I was hoping to meet and hadn't for the whole conference literally sat down next to me. And we had a great conversation, debate, et cetera that led to some collaboration on some sort of mark up based rich data things I collaborated on with Tontac and Eric. And then Tontac also invited me out to San Francisco, so that summer in between classes when I was done with my classes, I visited him and crashed on his couch in San Francisco.

[18:39]

James McKinney: That's really cool.

[18:40]

Matt Mullenweg: SXSW was like going to a festival where all your favorite musicians were playing, going to San Francisco was like Mecca. Every street, every restaurant, every coffee shop was just filled with people who were passionate about building the web, and I felt like I had really found my tribe. Not to mention San Francisco is just a cool city objectively.

While I was there I visited a lot of companies as well, so I visited yahoo, Google, CNET, et cetera and after I returned home that week, I started to get job offers from them. I didn't realize it but they had kind of been interviewing me while I was there. WordPress had started a bit, so it was in the very early days, probably like tens of thousands of sites running it. Those job offers, it was sort of a really interesting point because it was jobs and salaries that I would hope to make if I finished school for another few years, and opportunities that were just beyond what I could imagine. It turned out I found out later when I decided to accept one of the jobs and told my father about it, the salary was actually more than he was making at the oil company even though he'd been there for 25 something years, which later led him on an entrepreneurial journey which is kind of funny. He left the company shortly thereafter, I think tripled his salary, and again doing the exact same work co founded a company with a few of his former colleagues that he was at until he passed. That was also really, really exciting that he was like, "Oh."

[20:15]

James McKinney: That is really cool.

[20:16]

Matt Mullenweg: I actually use it as a story for why we are so aggressive about keeping salaries at Automattic competitive with the market, because you want to reward the people who are most loyal to you. In my father's story, when I told him this opportunity, it was bittersweet for him. He was so proud of my as a son, but he was also like, "Oh, I've been a fool for giving my loyalty to this company, working weekends, travelling around the world, putting so much into it," when his market rate had obviously grown a lot beyond what they were offering him. So I always use that story to say this is why we need to be competitive because you never want anyone to wake up at Automattic and say, "Hey, the company wasn't paying me what I was worth for a long period of time." That was a rambling answer but-

[21:00]

James McKinney: No, that's incredible.

[21:01]

Matt Mullenweg: … that's part of how I went to San Francisco, how I got the job offer. CNET because they were a media company allowed me to retain my intellectual property rights, which I knew a lot of stories about owning your masters from musicians who were exploited so it was very important for me to retain the IP, and like a Google or Yahoo would never do that, or other software companies. But CNET offered that and so that was the job I accepted, and I moved out I think in October of 2004 to San Francisco.

[21:29]

James McKinney: So you were an employee of CNET while building WordPress and having ten thousand users or so?

[21:33]

Matt Mullenweg: Yeah, probably tens of thousands of users, but WordPress had some early traction but was small. And it's why they hired me, you know, because technology companies even at that time, and Google, all the others said, "This kid doesn't have the right school or background but obviously he can code." So I really appreciated that kind of meritocracy, or opportunity that was given to me even though I didn't have the same background as many of my colleagues or other folks at those companies.

[22:08]

James McKinney: When you started coding WordPress I assume you started to solve a problem that you had with whatever it is you were doing for yourself at that time. What was the problem that wasn't out there already that you had to solve?


[22:23]

James McKinney: All right, before we continue on with Matt's story I just want to ask you, The Startup Story listener, you, how valuable would it be to have direct access to some of my past guests to learn exactly how they executed certain strategies to grow their business? Well, that is the experience and the knowledge sharing that is delivered to you each quarter when you become a Grindology member. Grindology is an entrepreneurial subscription box that ships every quarter full of resources to help fuel your Grind and your hustle. Now what's included in your Grindology shipment? Well, each shipment delivers two bags of uniquely crafted coffee specifically roasted for you, the founder, the hustler, the entrepreneur, the maker and creator. We all drink coffee, we love coffee so each box is going to include two custom roasts for you.

Each shipment also includes an exclusive mug that speaks to the unique nature that is you, the entrepreneur. But arguably the most important part of that box is that every single shipment will include a copy of the Grindology tactical manual, and within that manual every single issue of Grindology is chock full of real tactics from real business builders, not journalists. Within the pages of the Grindology tactical manual we will be delivering to you tactics and strategies you can integrate into your business immediately. How great would it be to receive real marketing funnel strategies from those who are doing it? Wouldn't it be helpful to your business if a successful founder laid out specific user acquisition strategies that they use to grow their business? Well those are the types of tactics that will be found in each issue of Grindology. Like I said, real tactics from real business builders.

Everything about Grindology is about helping to fuel your grind and that is why our friends at Design Pickle have partnered with our first shipment by hooking up one lucky subscriber with a full year of unlimited graphic design resources. You can visit Grindology.com to learn more. Like I said earlier, we ship our first box this month and it'll be an exclusive shipment so make sure to secure your box today at Grindology.com. We'll include a link to Grindology.com within our show notes for easy access. Now let's get back to our episode.


[24:17]

James McKinney: What was the problem that wasn't out there already that you had to solve for? Now again, I recognize within the internet space, the early 2000s are relatively early to where we are today which is crazy to think it's only 18 years ago, but there's still a lot that has taken place in that span of time. But for you, why did you develop WordPress? What problem were you solving?

[24:39]

Matt Mullenweg: In my high school and middle school years I had become radicalized towards two world views. The first was the inferiority of the QWERTY keyboard layout.

[24:50]

James McKinney: Really?

[24:51]

Matt Mullenweg: QWERTY was designed I guess so the typewriter arms wouldn't run into each other, and there are more efficient layouts that have been created since, and we probably would all be using a different one if World War II hadn't happened. They were going to switch all the typewriters, but they didn't want to slow down during the war. So I switched to a keyboard called Dvorak. There's another one called Colemak which is really good. But so I switched to that. And also Open source. It just seemed so obvious to me that if the future wasn't going to be digital we needed a bill of rights and freedom for our digital world, and that all software would be open source eventually. Eventually might take me to decades, but the sort of market forces, the things I'd learned in my economics studies made it so clear that the flywheel effect of when open source starts working, gets more users, then gets more developers, then gets more users, then gets more developers… would eventually become unstoppable if the community was healthy.

I was blogging. I really loved blogging. I love writing, I love sharing. There was no… the blogging software that was my favorite was not open source, so the most popular was one called Movable Type. My favorite was a really well designed one called TextPattern, and if TextPattern had been open source I never would have created WordPress.

[26:10]

James McKinney: Oh wow.

[26:11]

Matt Mullenweg: But it wasn't, it was under proprietary license. So I was looking for an open source alternative, came across one called B2 and then became active in that community, helping people in the forums, contributing code, just kind of like volunteering and helping out wherever I could. Even though my skills were relatively limited at the time, I would kind of learn on the job and use it as a way to learn more. So that was the impetus. I just wanted software for me and my friends could blog with that allowed us to have our own domain, be open source, and be in control of our digital destiny.

[26:44]

James McKinney: So it was definitely principles based versus financial based. This wasn't something you thought you were going to, or maybe it was something you thought you were going to grow that was really going to shape your future going forward from a financial perspective. This was more of a community and principle decision.

[27:01]

Matt Mullenweg: There was no even hope of financial reward from it, that's why I took the job. My assumption was that I'd have a day gig. Almost every musician that was my friend had some sort of day gig, teaching or playing weddings or something like that, and then they had the thing they were passionate about that they do at night, like music that they really cared about. I kind of assumed that my day gig would be coding because I got pretty good at that point. And then my passion product would be WordPress.

[27:32]

James McKinney: That is remarkable. In most cases this is where I ask the founder to say can you tell us a little bit about what the brand is so that they know who it is. WordPress is not one of those ones that I need you to unpack for my listeners, but can you unpack a little bit about the economy behind open source. Because I think when most people hear open source what they think of from a business perspective is this altruistic community where the only monetization is in the third party apps and the plugins, and everything else that gets attached to the open source core. Can you unpack the back end of open source as to where people see the opportunities to monetize?

[28:19]

Matt Mullenweg: You know there's as many businesses and business models in open source as there are in proprietary software, so it is really the way I like to talk about it is specific to WordPress. WordPress is under a license called the GPL. The GPL gives you four freedoms: the freedom to use the software for any purpose, the freedom to see how the software works, the freedom to modify the software, and the freedom to redistribute those modifications. Built into those freedoms is even though you can download WordPress for free, if you wanted to resell it to someone that's allowed in those four freedoms. It's the freedom to use it for any purpose and redistribute it. So built in there is like I said it's like a bill of rights for end users that provide you the ability to do pretty much whatever you want with it, as long as you redistribute those modifications under the same license. So when you redistribute WordPress you can't make it less free, and you can't hold basically the developers liable, so you couldn't sue WordPress developers if it breaks. You kind of get it as is. So instead of copyrights which usually protects intellectual property, often license like the GPL is called copy left, which is a little joke saying basically kind of forces you to make things really open if you build anything on top of WordPress, or on GPL software.

The business model we started with was zero, there was no business model. The early monetization of WordPress was where people would essentially provide you a hosting account. So whether that was GoDaddy or Bluehost or TextDrive, the early ones, the WordPress part would be free but they'd charge you the $10 a month to get a domain and have a server on the cloud essentially that would allow people to access your website. Later what Automattic developed and helped pioneer was essentially premium add-ons. So there would still be a GPL, so the code would be free, but you would essentially pay for a license to access important updates, and that could be a service like Akismet which was our anti spam servers. So when someone would submit a comment it would check that comment with the centralized server that would say is this spam, yes or no. or premium designs or themes that could have value because they were scarce. So that plus hosting is kind of where Automattic's business models ended up developing. This is also probably where I should say that WordPress is still this open source, nonprofit thing and a few years later in 2005 I started a company called Automattic, which was essentially created to commercialize… create commercial things on top of WordPress so that we could pay ourselves salaries to continue working on it.

[31:09]

James McKinney: That's remarkable. Now you're at CNET though in the early days of WordPress. So how long were you there for and what started taking place that you said now it's time for me to leave and build something, leaving WordPress free and to build something alongside the platform that I've built? I just want all my listeners to understand this is a data point that I heard, and you can correct me Matt if it's wrong, but it blew my mind away because I've heard a lot of data points that are super impressive but this one just blew my mind is that a third of the internet is powered by WordPress. That is amazing to me. One, it's amazing to me because I don't think I ever tried to think through the breadth of the internet, like how broad this is. And then to think that whatever that number is, however big it is that a singular platform can power a third of it. That is remarkable to me. Absolutely remarkable. But obviously that's a data point for 2021. That wasn't a data point for 2005 or earlier. So what took place that got you think it's time for me to leave CNET and move into, or establish Automattic, or whatever version 1.0 was?

[32:30]

Matt Mullenweg: Hm, WordPress just really took off that year and also being in San Francisco I was exposed to a lot of startups and investors, and folks who were sort of beating down the door saying why don't you raise money and make this a company. I was at CNET for about a year. I was very appreciative to them hiring me out of college and moving me across the country. So I wanted to do some projects there and finish up some projects. I think I told them I was going to leave about eight months in but I stayed like another three or four months to finish everything up. They ended up also investing in the company Automattic to start. What was it that changed? I think that WordPress just really took off. It turned out that we had, we were moving really quickly, iterating really fast with our users. We were sort of quickly replicating all the features of the competitors and starting to create new ones that were beyond that. WordPress was attracting more and more developers so that was going to help that fly, and the propriety alternatives in the market were often changing their licensing or pricing, or there were things that created little windows of opportunity for people to say I want to work with software where that can't be done. If you use proprietary software they could release a new version that updates the license and you're stuck with that. But with the rights, the freedoms and rights given to you by the GPL can never be taken away. They're yours for life. So anyone who uses WordPress just has as many rights to it as I do, which is a really powerful concept. People started to appreciate that. There were some influential essays and Switchrs at the time.

So really my focus was just on making the software as great as possible. CNET was also a user of the software so they really contributed a lot to high scale. I would debug all the highest traffic sites at CNET and work out all the bottlenecks. But really what I wanted to do and I guess the final reason why I left was I pitched this to them and they said no, because I wanted to create a site where anyone could go and start a WordPress site instantly. So at the time to use WordPress you had to download the code, upload it to a server, manually configure a database kind of like do lots of manual stuff to use it and update it. I wanted to make it just a few clicks, kind of like a blogger or LiveJournal that the more self serve things of the time. CNET had the most amazing domains you could imagine. They had like computer.com and online.com and com.com, and literally everything, news.com, download.com. that was kind of their thing was having all the good domains. So I kind of pitched them and was like, "Hey, why don't you just give me one of these like online.com, and then we'll make it so anyone could start a sub domain like matt.online.com, and that could be their website? We'll make it a really easy WordPress." I just couldn't convince them. I think they thought blogging was going a different direction, but they were very supportive of me to leave and do this as my own company, so that's what I ended up doing.

[35:48]

James McKinney: When you think… so as you tell that story right there I immediately start thinking through all the easy website solutions that are out there now, that all have a monthly fee to it or an annual fee, whatever the case may be. If anyone were to go to crunchbase they could probably see how much money is being invested into online CMS solutions out there. But when you tell that story about a sub domain, whatever.online.com and you want to make it super easy for them, that to me is the very first iteration of these modern day CMS solutions out there. But I wasn't in the scene in 2005. Was there anything like that, that was so easy for someone to get a website established back then?

[36:38]

Matt Mullenweg: Totally, yeah.

[36:39]

James McKinney: There was? Okay. I mean wait, there was like EarthLink or Earth web-

[36:46]

Matt Mullenweg: There was Geocities.

[36:47]

James McKinney: Geocities, thank you, that's right.

[36:48]

Matt Mullenweg: Yeah, sold to Yahoo for $3 billion.

[36:49]

James McKinney: Yes, that's right.

[36:50]

Matt Mullenweg: In the nineties. There were FrontPage and Dreamweaver, two like very visually focused website builders. I think there was one called HotDog as well that would kind of let you drag and drop, kind of like the equivalent of a web flow today. You could create very exact designs but usually the code was terrible, and it was hard to manage really big sites. For blogging, every internet giant actually had a blogging service. So Google had Blogger. Microsoft had something called Spaces. Yahoo had 360, and AOL had Journals, so those were the four dominant internet companies at the time and each one had a blogging service. But I just didn't like how any of them worked. They kind of looked like social networks of today where they force you to have a very generic site. You couldn't really express your creativity or customize it very much. So I kind of wanted that ease of blogging that people had already done, like Blogger, but with the sort of customizability, the hack ability that allowed you to kind of make it your own. I still to this day am very bored by websites that look the same, and I really love it when people are able to express their creativity a bit more deeply which is why I'm so excited about our new Guttenberg feature.

[38:02]

James McKinney: yeah, I love it. So you leave CNET. You're pitching for or raising money for Automattic to build. So can we walk through a little bit of your capital journey? Again, 2005 was the Wild West in venture capital. It was you could have literally brought in a napkin and they would have, with an idea on it, and they probably would have invested in anything at the time. It was absolutely crazy. But for you what exactly were you pitching to investors in 2005 for that initial round? And what was the company… how has the company grown over the last 10 or 15 years?

[38:46]

Matt Mullenweg: Yeah. It was interesting because on the ground in San Francisco it felt a little bit like a winter in startups and investing because there was still so much shellshock from the internet crash, so valuations were incredibly low. To put in perspective we actually bootstrapped to start, and we got it to probably $40-50,000 monthly revenue through kind of early versions of wordpress.com and Akismet and things we were doing. That which today would probably raise money in the $20-100 million range, we raised money at $4.4 million valuation.

[39;29]

James McKinney: Oh wow.

[39:30]

Matt Mullenweg: And that was Automattic. I was very, very fortunate in that one of the early users of WordPress was a journalist named Om Malik who ran a site called GigaOM. He was a journalist for Forbes and Business 2.0 and things like that. I just I didn't know who he was but he was one of the people asking for support, and I used to do all the support. So he appreciated the help I had given him. He was a promoter of WordPress. And then when I moved back to San Francisco became friends, and connected me to some of the same people I work with today on board, as investors, and things like that.

[40:05]

James McKinney: Oh wow.

[40:06]

Matt Mullenweg: Yeah, he had been covering the internet through the ups and downs, and so I think had a good nose. He covered Interon for example, and so I think had a good nose for high integrity people. So the folks who he connected me with like Tony Schneider, Tony Conrad, and Philip Black. I still am very close to all of them 17 years later, 16 years later. And Phil and Tony are actually still on the board, and Tony Schneider was the CEO of the company for the first 8 years, and then later an employee at the company for another 8 years after that. Very, very long career with the people that Om happened to introduce me to. And Om is now one of my best friends too, so I feel like I just won the lottery with the folks I was connected to because at the time, it was kind of a "four of the founder CEO thing" was popular, so it was more the period of adult supervision. The Google cofounders, Larry and Sergey brought in Eric as the adult supervision, so with every investor potential they were wanting to bring in adult supervision, and I didn't like that idea.

I was very opposed to it actually so that's why I didn't raise money for a few months. Then when I met Tony Schneider I was like wow, this isn't adult supervision, this is someone I'm going to learn from every single day, and really will make the company so much better. So once I got the chance to choose my own adult it seemed… I made the deal for him to join as CEO and the raised a round. He had to wrap up his gig at Yahoo because his company had been bought by Yahoo, but he joined sometime within that first six months or eight months. I don't remember exactly. But luckily I had been CEO for a short enough time that I hadn't messed it up too much yet, around like not paying taxes or doing payroll wrong or something like that. He got in and was able to clean it all up, because he had been CEO of a few companies before.

[42:02]

James McKinney: You know one of the things to me that makes your organization and your leadership so remarkable is right now especially, or coming off of the events of 2020 with regards to the pandemic, the shutdown, the distributed workforce, everyone is being remote, you have 1,300 employees that are fully remote across the globe. A majority being in the US and I assume probably Canada. But you literally have employees all over. Was that the model from day one or did you go the typical startup route with everyone being in a building, together, working on everyone has that picture of Bezos with a door on top of an A frame type thing? Was that the original from day one or were you fully distributed immediately? What was the model and how did it change?

[42:56]

Matt Mullenweg: We were fully distributed from the beginning and the reason is that's how open source worked already. So there were sites like the equivalent of the GitHub was SourceForge, where people collaborate online. Pretty much every open source project was people from all over the world as volunteers working together, just united by that shared passion. So the lead developers and the folks I was working most closely with on WordPress were in Ireland and Vermont and Washington and Texas, just spread all over the globe. So I thought why not continue working with them? Because we're working great together, we've done all this amazing stuff, let's keep it rolling.

Now we did get kind of a desk early on, so for the first I think 10 or 11 years of Automattic's history we either had a desk in someone's office or later had our own office, or even our own building in San Francisco. And we always had a good chunk of the company, like 10-20 % was in the Bay Area. But then even the folks who were in the Bay Area no longer wanted to commute or go to the office. We got so good at working online. There's really not that much reason except for purely social to go to the office, so it became more like a one day a week thing. We ended up shutting it down entirely when it came up for renewal because prices had gone up so much that it was like maybe we can justify $10-20K a month for this at the scale of our business, but if that were going to go up to $100-150K there's just better things we could spend the money on so let's shut down the office and just go to nothing. And it was fine.

[44:40]

James McKinney: Now was that a tough sell from a model when you were pitching investors? Or was Tony on board with that when he came on, I'm using air quotes here "as the adult" if you will? Because it wasn't common. Yes, there were people that co working was hot, or it was starting. I shouldn't say hot, it was starting. But it was not nearly as common as it is now, especially with the events of 2020. Was it a tough sell?

[45:09]

Matt Mullenweg: Early on we were always co working and that was pretty normal, like investors were used to it. And in fact the building we were in, Pier 38, was our investor True Ventures, GigaOM was there. Burbn which later turned into Instagram was upstairs. Zynga got it start right around there. Like so it was just everything was kind of like a desk or two over from each other, so that was pretty normal. The end of the office story is that we later re-got an office. So after several years of not having one, we were doing a fundraising procedure and while at the early stage when you're raising $3 million as a few people no one cared that we didn't have an office. I was trying to raise hundreds of millions of dollars for a hundreds of persons company, in coffee shops essentially. It was super awkward because I'd be like at some coffee shop, The Creamery or something in San Francisco. One, people were listening in to the pitch, but then other investors or bankers would like interrupt the meeting and come over. I was like ugh, I can't. I knew we needed to do a big round. I just couldn't do it in coffee shops.

So we started using our lawyers office, investors office, but that was just awkward. So what we ended up doing was returning to one of our older spaces so it was a small office. It was only a few thousand square feet in the Mission that after we had left it we passed it to sort of a cousin company that was shared an investor with us. As they had outgrown it, we had kind of gotten small enough that we wanted to move back into that space. And so we basically just got it just for meetings, board meetings and investor pitches. Still had this kind of secret no one in their normal office San Francisco. And also we did an acquisition in New York when we bought Tumblr, and they did have an office. So we technically have two offices. Usually what happens is when we bought a company they had an office, like when we bought WooCommerce they have an office in Cape Town and they keep it for a few years and then like within the first five years being part of Automattic they're just like eh, I don't think we need this anymore.

[47:27]

James McKinney: I love it. Let's talk about this remote working a bit, because it is incredibly relevant for business today. If we had been talking six months ago I'm sure people just at that point were clamoring trying to figure out how does this make sense, how do we move forward on this. The tools and resources we have now were very different than what you had in 2005 when you started for online collaboration. Some better, some maybe you look back and wish those solutions were still around. Maybe there were some that were better back in the day. I think immediately people think Slack. Well of course Slack, but Slack wasn't a thing in 2005 and so that wasn't a solution there. So what I'd like to do is for the next few minutes if you could kind of talk about remote working in the early days and the lessons you learned with the limited resources that were there, or maybe there were resources that we weren't aware of, and how it's changed. And how you have gotten to a place now where it's really kind of for as best as possible perfected. You have again 1,300 people globally. It's the only model you've had since day one, a couple offices popping up here and there through acquisitions. But really if I was to have somebody be the expert of managing a team or growing an organization under the fully remote model I'd have to come to you. And so I'd like to afford my listeners this chance to hear what are the things you learned getting to the point you are today, and what are the things that we should be looking at now when it comes to a fully remote work team.

[49:09]

Matt Mullenweg: I'll start by saying this is a deep topic that I dive into very deeply on my blog and podcast, at distributed.blog. I'll give you the basics here but if you want to go deeper check out some of the interviews there. The latest was actually with Jack Dorsey talking about the transition at Square and Twitter through distributed, and I also have lots of pages of resources like the best equipment to buy, the best software to use, et cetera.

Early days when Automattic started it was very similar to what we do today, except it was like worse versions of it, the version 1 or 2. So Slack a lot of people don't know this was actually modeled on IRC. So the way that the channels work with the hashtag and things like that, it was all based on IRC. We used IRC, which stood for Internet Relay Chat, and think of it like a lo-fi text only version of Slack but with a lot of the same great features. Instead of GitHub for code collaboration and issue tracking there was a Git. There were earlier versions called SubVersion or CVS that were kind of source control sharing, and there was an open source site called SourceForge that you could kind of collaborate online and that's what most open source projects used at the time. So we had kind of our equivalent of GitHub.

For voice communication, we used that very rarely but Skype was already there. AIM and ICQ were pretty popular chat platforms so we'd use that a lot or Skype. We didn't do any video. Like both bandwidth, cameras and the tools, were just not worth it. In fact Automattic basically didn't do any video meetings until Zoom started, and Zoom was the first thing. Even after, we never really used Google Hangouts or anything, they just weren't that good. Once Zoom took off we were actually very, very early adopters of Slack, Zoom, a lot of the tools that have become very popular which is why we now invest in them. A lot of the things we early adopt I think are going to become bigger.

Where we're at now is kind of operating system of the company is Slack for real time chat. We use either Zoom of Google Hangouts for videos and meetings. We love Google docs and all the kind of G Suite tools. They're really fantastic. We don't use email at all. Instead of email we have an internal blogging system called P2, so the letter P as in pool, and the number 2. If you go to wordpress.com/p2 you can set a private one up for your company. It's a really cool, think of it almost like an internal Twitter or Facebook for your company where people can share what's going on common on it, and it gives you a very rich history and decision tree for all the things that are happening within your company. When someone new joins they can just read the old blog posts instead of trying to catch up with old emails or Wikis or things like that.

That's kind of what we run the whole company on. P2 is probably our secret sauce. We consider Slack ephemeral and you don't need to even use it as part of your job. It's just there for convenience. If something is important we always put it on P2. Trying to think what else. When we could in pre pandemic times we would do meet ups. So we would bring together teams a few times a year. So we'd fly everyone from wherever they were in the world, get an Airbnb or something, and for small teams were typically under... most teams Automattic are under 10 people, they would just all stay in the same house and work and eat together, and cook together and everything for a week. That would really build the trust so when they returned to their distributed work they would kind of have that know what someone's laugh was like or their sense of humor, or their tone of choice which allows you to read the text that they're writing in a kinder way really. Then once a year we would bring the whole company together, what we called the Grand Meet up. That was a little bit more like a conference because it got to be 800 or 1,000 people. But we kind of would take over a hotel, do talks, bring in speakers, have lots of different tracks people could choose. Do a hackathon or do customer support, or take classes or teach a class. That was always really fun. Automattic definitely over indexes for hiring people who aren't just supremely talented but really nice. It's really one of the number one things people say after they work here, even people who resign, comment on how friendly the colleagues are. That's so when we get together it's really great. It's almost like a family reunion even if maybe someone would get on your nerves if you had to sit next to them every day of the year. If you're only going to see them a week or two a year you could totally put up with pretty much anything and you really appreciate that time a lot more.

[54:08]

James McKinney: What were some things when you spoke to Jack Dorsey when Twitter announced they were going to go fully distributed, again you're the expert. Whether he came to you or not looking for advice before the decision, no idea, somewhat irrelevant, but what would you say to someone who is now looking at this idea like do we stay fully distributed or do we come back to the workspace once things start opening up? How would you, what things would you tell someone to be heavily considerate of when it comes to working fully remote?

[54:42]

Matt Mullenweg: Yeah. The number one thing that pandemic allowed us all to learn was I think so many people assumed that creating innovative, high volume, high scale products or whatever it was that they thought they were doing could only be done with people in an office. Once that became impossible we kind of figured it out. Automattic had done that a long time ago, but maybe they thought if you're going to do blogging software it's fine, but if you need to make an iPhone you need to be in the same room or something like that. And we kind of figured out whether that was true or not. Maybe for some things like doing industrial design for the iPhone you do need to have the prototypes and special machines. Maybe building iOS you don't need to be in the same room.

The other things I a lot of people got the taste of the autonomy and flexibility that working from home, working from anywhere or working in a more asynchronous fashion opens up in their lives. Once you have a taste of that freedom it's hard to return to your previous state, much like any type of freedom, much like democracy. So I think that the companies - Microsoft, Twitter, Square, Facebook has a version of this - that have said they are going to support people working from anywhere indefinitely are going to be more competitive. The talent market in technology is incredibly competitive so if you've had the taste of working from home you enjoy it. And Apple is telling you that you need to go back to an office, and you're now seeing your commute times come back, all the things, the trade off of the small house you had to live in to avoid the commute… I think they're going to lose talent to companies that are doing both distributed work and then companies that are good at it.

I have this framework that I encourage people to Google. It's called The Five Levels of Distributed Autonomy and that talks about essentially how you get good at distributed work. It's a useful framework. A lot of companies, even the big ones who are doing it by force are doing distributed work kind of poorly. They're still forcing people to be in too many meetings, and people are getting Zoom fatigue. They're not doing the best work. If you do it right people are actually able to be more creative, more productive, more innovative than they ever would have been in an office. It sounds impossible but we probably thought a lot of things we've done in the past year were impossible.

[57:01]

James McKinney: Yeah, no kidding. No kidding. You know when you mentioned the losing talent to the brands that are going to be fully distributed, you know do you find that was a competitive advantage for Automattic from the early days when most people, most brands were not fully distributed, that you were able to get such great talent because of that model?

[57:22]

Matt Mullenweg: 100% and now it's probably 85%. It is a reality that Automattic is a smaller company and much less profitable than a Google or an Amazon or an Apple, so at some level we couldn't necessarily pay someone the exact same salary or as much as an Apple or Google could. So I think that's true of every startup, or every smaller company. You end up having to differentiate on your culture, your mission, your product, your principles. And then hopefully make the company successful enough that you can kind of get to that level without having to make too large of a tradeoff. Maybe they're trading off some percent, but it's not double or triple. That's part of why we try to grow our business because I have fantastic, world class colleagues and I want them to be as compensated as highly as possible.

[58:16]

James McKinney: Oh, I love it. Absolutely love it. If we were to have a "where are they now" episode in let's say five years from now with yourself and Automattic, where would Automattic be?

[58:28]

Matt Mullenweg: Yeah I hope within five years we're able to reach a majority of the websites in the world powered by open source. I think we have an ability maybe in a longer timeframe like 10 year time frame to get to a super majority, sort of like Android with handset where 80-85% of all handsets in the world, smart phones, are powered by Android. I think we can do the same thing with websites and WordPress. Ecommerce is a very nascent area for us but last year we had over $20 billion of goods and services sold through WooCommerce which is incredible. By the way that number was more than doubling. I think that should be huge. The idea of creating an economic operating system and enabler, much like we have for publishing with WordPress, doing that for WooCommerce is incredibly exciting. And if we do it correctly the opportunity is actually larger than all of other Automattic's products combined.

[59:23]

James McKinney: Wow.

[59:24]

Matt Mullenweg: I'm very, very excited about that and it's also an area where I've been learning so much. Ecommerce, I've been a blogger forever but I don't have a store online necessarily where I sell things myself. So learning about shipping and taxes and inventory, and point of sale and all this, it's pretty exciting. It's a fun new area. That's the other thing I think would be pretty large and dominant for Automattic.

Finally I would hope to say we've stayed true to our creed, stayed true to our principles of being open source. Always be learning and try new things, and hopefully in that time frame will have found another WooCommerce. So much like Woo was an addon to our business. I don't know what that next area of investment could be for Automattic. Maybe it's a learning management system or LMS for people doing online education. Maybe it's something with video. Maybe it's something with memberships. I don't know, but there's lots of interesting areas worth exploring and hopefully in that five years one of them will be as equally exciting to me as WordPress and WooCommerce and we can talk about it.

[60:33]

James McKinney: I love that. Absolutely love it. We've been talking a lot about the exciting things in your entrepreneurial journey, but sometimes it's the more challenging things and the more painful moments of the journey that also create the greatest lessons and the greats growth within us internally. When you look back at your journey, what is maybe one or two lessons that you experienced from a misstep that grew you tremendously as a leader, as a human, as an entrepreneur? Whatever category it may be, but that misstep just accelerated your growth in a certain category and what was that?

[61;11]

Matt Mullenweg: So many to choose from. You can imagine as a 20 something year old kid with a lot of early success I often had a mistaken confidence in my abilities to lead teams. When I think back to some of my biggest mistakes they're often around communication. Where I feel like I've grown the most as a leader particularly in the last 10 years is investing in communication. Example of mistakes, not being fully transparent internally with the company. Not communicating to someone when they're not doing a good job and then developing like a kind of two way resentment on where you're unhappy they're not doing well, they're unhappy because you're treating them differently. And partnerships, trying to over optimize for one side versus trying to look for the win-win. These are all sort of versions of communication. I think what's helped me most there was meditation, which helps with self-awareness, mindfulness.

Books like "Nonviolent Communication" which is just a way to talk about how you're feeling, your boundaries, and to communicate that very clearly to someone else in a way that isn't threatening or isn't putting them in a defensive pose. And just kind of learning that honesty and transparency is always the right answer. It's so much easier. Telling someone the thing that you think will hurt their feelings or they don't want to hear, but is the truth, is still hard to this day because I like people. I don't want to tell them something they don't want to hear, but it is always better and they always appreciate it when you're able to be very direct and straight forward. If you do that for many, many years you then develop the reputation that's always what you're going to do, and people will do the same with you. And they'll begin to know that whatever you're telling them, whether it's something they want to hear or don't want to hear, they k now it's the truth. That is just one of these investments that every single person listening to this can invest in it in their personal life and their business life or professional life. You can lose it in an instant, but it also has compound interest so the longer you do it, the more it becomes part of your identity which means the easier it is for you to continue doing it and the more that people know it's part of what you do and so they want to work with you. Or be in a relationship with you.

[63:40]

James McKinney: Oh my goodness.

[63:41]

Matt Mullenweg: It works for personal relationships as well.

[63:43]

James McKinney: Yeah. Oh, absolutely love that. You know one of the interviews that I've heard with you is I want to say it was probably five years ago. It was with Tim Ferriss and in that he kind of razzes you a little bit about not cursing, and I love it. One of the things you said is something I've been saying for so long, because I too am not a curser. And the thing I've said all the time is a curse word is an easy substitution for a diminished vocabulary. You said something much more eloquent as to your response, but along the same lines and very similar. For as big as the English language is there are so many great words to use where we might user a curse word. And as you were talking about this communication and I'm very curious on that book "Nonviolent Communication", that was the name of the title right?

[64:42]

Matt Mullenweg: Mm-hmm. It's actually not a good title. It sounds kind of, I don't know what it sounds like but they mean nonviolent in the Gandhi or the Martin Luther King sense, nonviolent resistance.

[64:52]

James McKinney: Yeah. So I'm very fascinated in reading that, but what I heard as you were speaking about that was to communicate with intention. I think a lot of times we use words so flippantly. Any words so flippantly and sometimes our emotions get ahead of our intent and our thinking, and that's when the communication gets raw and hurtful. So I love that through your lessons you learned that intent in your communication. I think you're right, there's so many levels that communication, being a great communicator will be valuable for personal, your leadership, obviously within the entrepreneurial space whether you're selling as your management of team, across the board. So that was so powerful. I'm going to find a link to that book and include it in the show notes. In fact, if there's other books that you recommend along this category I would love to receive those from you and I'll include those in the show notes as well.

[65:48]

Matt Mullenweg: Yeah the other thing I'd recommend is one of the apps like Waking Up for Calm around mindfulness, because it doesn't matter if you know how to communicate well if in the heat of the moment you don't do it. By the way I'm human. I get made, I get jealous, I get angry, I get frustrated, I get all the full range of human emotions and guess what the Dalai Lama does too, every human does. What we know about neuroscience is that you can't control those reactions happening. There's little monkeys in our brain that are always going to say this thing or that thing, and all the voices that are critical of yourself or others, or whatever it is. But what you can develop is almost like the background process, the identity, the thing that is observing all those voices, and kind of catch it before it goes from your brain to your mouth, and just gives you that almost millisecond to say, "What does that mean? Is this true? How do I want to respond to this? What does my higher self think about this? What are my principles?" and this can all happen in split seconds.

What I think mindfulness training does is it just increases that sort of split second. It gives you just a little more buffer to decide what to do. And maybe children being the opposite or pets, they have nothing between the reaction and the action. We're too young to understand really the theory of mind or affect on others, or other things like that. It's just pure id, that pure reaction. As we grow up we develop a little bit of a buffer. Sometimes I think of it like a background process. There's actually a pretty good book called I think it's "Search Within Yourself" from a Google engineer that talks about it all in computer terms. Like you need the background process that's running, observing all the other processes and can jump in to interrupt one of them before it outputs an output. It just increases that. All the years I've been doing this maybe my buffer went from like 25 milliseconds to 35 milliseconds, but that extra is enough to keep me out of a lot of trouble, and having actions that don't reflect my kind of principles or higher aspirations.

[67:55]

James McKinney: You mentioned the calm and being a very popular meditation. I've watched the success of that app grow over gosh I don't know how many years now. It's been a few though. As I've watched that I started seeing more and more about morning routines, and people having a disciplined morning routine. I'm a Marine Corps Vet so as a veteran I'm a big fan of Jocko Willink and hearing about his morning routines. That tends to be my leaning when it come sot morning routines is the much more SmashMouth, in your face, discipline type messaging. But for you, what is your morning routine? How do you get the day started in order to achieve greater success throughout the day? What's your morning routine look like?

[68:45]

Matt Mullenweg: You know maybe this is helpful for people listening to this who might admire like the Jocko and Tim Ferriss' of the world but aren't able to do it, is my mornings are very inconsistent. I find that sleep is super important for the functioning of my day. When I can get things in the morning like a little bit of reading, a little bit of meditation… I generally do intermittent fasting so usually I just have one meal a day at dinner, and then once a month or once a quarter I'll do a longer fast. I've done as long as seven days actually.

[69:21]

James McKinney: Oh wow.

[69:22]

Matt Mullenweg: So those types of things I find very useful for developing my self control, discipline, kind of quieting internal voices and things. But I must admit particularly the past like seven or eight months, which have been a very fruitful and successful period in my career and products, it has every day has been different. I've been extremely inconsistent. Now I don't love that. So for example something I'm about to do the blog posts that's all the books I read in 2020, and it is the shortest list of pretty much any year I've been posting this. One of the casualties of not having some of that structure was not making the time in my day for reading, which is to be honest like my favorite thing in the world. My perfect vacation is like hammock and some books.

[70:13]

James McKinney: I love it.

[70:14]

Matt Mullenweg: And I really get so much value and I feel like so much of the best things in my life have come from things I've learned from books. Most of my mentors are authors, through their books, not through their personal relationships to me or anything. That was a year I just didn't get a lot of it. I am looking to structure a bit more time for that, to build it. Because particularly what I found with a few things. One, I took back over running WordPress.com directly, so I've been sort of having that extra direct reports and everything for about a year, year and a half. And then just the company getting really big, passing 1,000 in the Tumblr acquisition, things like that. It kind of soaked up all my spare time, time I used to watch movies or books, or see friends. Then the pandemic, you also have a bit more extra time. So I went kind of like in a hardcore workaholic mode, which was productive but I don't think it's something I could sustain for years. And I hope to work on WordPress and Automattic the rest of my life so I really want to find modes of work which are sustainable and productive and creative over long periods of time.

But last year with the crisis and everything was a little bit more of a wartime CEO mode where it was really about execution more than it was about the kind of necessarily super long-term, big, more marathon part of it. It was a little bit of a sprint, which is okay. I've definitely had months or years of my career where it's that, and I think that's also something I just want to put out there for folks. A certain mode of working might be appropriate for a different point in what's going on in your life or career. Don't beat yourself up if you're not doing the three hour at 4 a.m. wake up and two hours of work out and things like that. Keeping that in mind is something that you might want to try and see what works and what doesn't, and that might be appropriate for certain times. But here might be other times when you need to bring different tools to bare. Think of all these things as a means to an end, not sort of something that is… we don't want to, what's the phrase, mistake the map for the territory, right? Look at the reasons why Jocko does that. Look at what he gets from it and don't just copy exactly what he does, look at what he gets and say what are other ways I can get that, and then ask yourself am I getting that or not, and let me try some things including exactly what Jocko does perhaps to try it.

[72:50]

James McKinney: Absolutely love that. Obviously love it. So when we think of as you're talking I'm loving your perspective on so many things, but I want to honor our time. Unfortunately I do have to bring this episode to a close and I always want to honor my listener's time with the final three questions that I know they look forward to each time. But before we get to those I just want to ask one larger question to get your perspective, because you had said I want to work on Automattic and WordPress for the rest of my life. I think a lot of people probably were thinking okay, if he saw investment capital there's probably some type of exit that Automattic has in the future, and they're probably thinking that's what success looks like. Or maybe my listener is thinking well he's got 1,300 people remote, that's what success is. How do you look at success? What is that for you?

[73:39]

Matt Mullenweg: For me personally it's definitely working alongside people who I love and respect, doing the best work of their careers, on something that has an impact in the world.

[73:56]

James McKinney: I love it.

[73:58]

Matt Mullenweg: If you can get those three things, I think that's a recipe for happiness.

[74:03]

James McKinney: You know, because I know you're intentional with words, you had said that they're doing the best work of their careers. Was that intentional? Is it about, do you view that as serving?

[74:14]

Matt Mullenweg: Yeah. Implied in that was the best work of my career as well, so hopefully I'm doing the best work in my career. But we're all kind of operating at… it feels good to be operating at that high level, and be in the flow state, or be achieving things we haven't achieved before. Much like it might feel good if you were a surfer to like nail the perfect wave or maybe move on to bigger waves, but not necessarily. You could maybe just do the same wave in a better way. As a musician, there's the same 12 notes on the keyboard everyone has, but it's about how you approach them, how you play them, how do you learn them. One of my favorite things to take it back to music is jazz musicians could play the same song their whole career and never get bored of it. I think it's one of those things where the boredom is a sign of you, not a sign of the thing you're doing.

[75:06]

James McKinney: I love that. Absolutely love it. You know now to bring to our final three questions, because I do, I truly want to honor your time and you've been so gracious with giving me these 90 minutes. But that first question I want to lead off with is similar to the success story, but it's about entrepreneurship as a whole. I think the headlines and the media have painted a picture of entrepreneurship that is not real. It sides toward the success stories, this persona of if you don't have funding within two years you're never going to make it. The idea that all success stories leave in an exit. And I think there's a lot of people that struggle with that persona because it's not their story. But at the same time I think it's also created this idea that anybody can be an entrepreneur, so I want to as you do you think anybody can be an entrepreneur or is it something you're born with?

[76:08]

Matt Mullenweg: I think anyone can, yeah. I don't know if everyone should, all right? I do think we've romanticized it a little bit to say that's the only valuable role. It's not, you know, and I would say that l of my job is not being an entrepreneur. It's doing some very basic or mundane things in service to my colleagues or other sort of stuff. I do think that it's good that folks like yourself and others do raise the story of people that have different paths to their success, or whatever they define as success. That's so powerful. Even hearing people's different definitions of success I think is also really helpful to know that there's not one canonical one that we all have to aspire to. But it could be different for different people. I imagine if I had kids that would suddenly change my definition of success because they would become part of it. Right now that's just all focused towards my work. All of that kind of like energy that might go towards raising a family, but if I have a family I hope that becomes something that is just as important or more important. Yeah, it's okay to be different and there's so many paths to it. It's also, again this is a downside of the media but it is getting a little bit better, is just knowing that every success story that you hear had many moments in their journey where they almost failed. Or if a coin had flipped the other way would have failed. So there's a survivor bias for the big successes you hear of. Just keep that in mind. Also that's the inspiration to always keep trying. I do believe that regardless of the work there is a way to make it a craft, and that was something that I really appreciate my parents for instilling in me. They were very open with me being whatever I wanted to be, whether that was a computer engineer or a musician, or a janitor, or whatever. They were just like whatever you do, do your best at it. Not even be the best in the world, but just do your very best.

P78:27]

James McKinney: I love it, I love it.

[78:28]

Matt Mullenweg: That has led me in some cases to be the upper echelons of the world for being CMS, but also very clarifying where I thought I'm doing my very best at music and I'm never going to be a Joshua Redman or a John Coltrane, or these guys that I look up to, the musicians I really admire. Maybe I should try something else.

[78:53]

James McKinney: Oh my goodness, so good. You shared a little bit about your appreciate for your parents and I think one of the things that also gets overlooked in the entrepreneurial journey are the many people that contributed to where we are today. And so one of the things that I really if I had to trim the episode to 20 minutes this is the singular question that would never be cut, and that is when you look back along your entrepreneurial journey who are the many people that you are so grateful for, for their contribution to where you are today?

[79:22]

Matt Mullenweg: It's almost innumerable. I would say that in the direct sense it is the teachers that I thank on my About page, that are kind of pre 18. 19, so post WordPress it is the folks like Om Malik, Tony Schneider, Phil Black, Tony Conrad, my early colleagues some of whom I still work with today like Donna and the people I work alongside that really make me a better human every day.

Then there's so many authors, some of whom I've met and some of whom I will probably never meet because they passed away like Peter Drucker, Keven Kelly, Nassim Taleb, Tim Ferriss, Shane Parrish. There's so many out there, many of whom have podcasts and things today, that through their work I've learned so much from. That's beautiful. All of them are flawed human beings, and we might not actually get along if we were friends, but they've created some work and something that has a real value, and that has expanded the way I thought. For me, one of those porter books was Black Swan by Nassim Taleb.

[80:33]

James McKinney: Really?

[80:35]

Matt Mullenweg: I don't remember… because it had so many references and allusions that it was almost like I discovered a whole new world of literature and research, and thinking that I'd just never been exposed to before. That one book led me to dozens and dozens of others. I remember Phil Black gave me a copy of Predictably Irrational by Dan Ariely which is about behavioral economics, and all the sudden it took something that I knew a lot about which was macroeconomics and microeconomics, and brought in the human side of it where humans were not perfect, idealized economic actors but they could in fact have a biases and predilections, and behave in predictably irrational ways. Wow, that was so powerful. That's so powerful for designing any business but particularly a software driven one. That's why for me reading is something that I hold in such high esteem before the exposure through these books, you get something that someone invested often years of their life into producing, that will only take you hours to consume. So that kind of ratio of how much work they put into it to how long it takes you to get the value from it is, that's the best ratio of anything in the world. It's better than movies, better than podcasts, better than anything.

Podcasts are also really darn good though, and sometimes now I listen to a podcast instead of reading an author's book. If they are a great writer there's something in that book that you'll never be able to get any other way.

[82:02]

James McKinney: Oh, I love that. Thank you so much for sharing all of that. As much as I would love to give my 85,000 listeners access to you to have coffee or a virtual coffee chat, it would be unreasonable. And so one of the things that I do like to afford my listeners is the chance to what I call a mentoring minutes. It allows you to speak directly to them with some… with a parting words of some type. Maybe for you, the person of my listener who is the struggling entrepreneur because 2020 just ravaged them and they're not sure if they can continue on, or maybe it's the wantrepreneur who has a 9 to 5 and a book full of dreams and ideas, but some narrative that they can't move forward on. Maybe it's because of financial responsibilities, maybe it's because they think they're too old because the narrative of entrepreneurship is it's a young person's game. Whatever that may be, whoever it is, what would you like to say to that singular listener?

[82:58]

Matt Mullenweg: If I were to pull out two that I think are really key. First whatever you choose to do, do your very best at it. Make it a craft. And part of that is you have to always be learning. That's the first sentence in the Automattic creed. If you Google "Automattic creed" you can read the rest of it, but if you keep that learning mindset through everything you do, you can make any job, any task no matter how mundane it is a craft and a vocation, and something you can learn from every time you do it. That is I believe one of the paths to contentment, satisfaction, and for some happiness regardless of what you're doing.

[83:45]

James McKinney: Once you've had a few moments to process all the value that Matt Mullenweg brought us in this week's episode, please hit me up on LinkedIn, Facebook, or Instagram and share with me your thoughts on this episode. And lastly if you've been around The Startup Story for any length of time, then you know how much emphasis I put on the idea that entrepreneurs support other entrepreneurs. And Matt's request, you might be asking, it's for you to demand open source software whenever possible. If open source is a new idea for you then join him in these many conversations that he has around open source by following him on all the social media platforms under the handle of PhotoMatt. He can be found on Twitter, Instagram, Tumblr, and even Clubhouse under the handle of PhotoMatt.

Another great resource that he is passionate about is his blog, and that's at distributed.blog. This is his blog that hosts conversations around the distributed workforce model, as well as a collection of his top tools and resources. Again, you can visit distributed.blog. And lastly, as if Matt didn't have enough things to work on, he hosts a podcast called Distributed. You can find the Distributed podcast on all major podcast platforms as well as on his blog at distributed.blog. in fact, he had an amazing interview with Jack Dorsey, the cofounder and CEO of Twitter and Square about transitioning to a fully distributed workforce. It's an incredible conversation and we'll include a link in our show notes for this episode for easy access for you. I say it in every episode because I believe it with my very being, entrepreneurs support other entrepreneurs so let's show up for Matt Mullenweg in a huge way as a show of appreciation for all the value he delivered to us today. And now for my personal ask.

The Startup Story community has been so incredible about sharing our podcast with others, but we have more stories to tell and more people to reach. We too are a startup and word of mouth is everything, so please follow us on Facebook and Instagram @TheStartupStory or on Twitter @StartupStory_. If you're on LinkedIn, please search for The Startup Story and follow our company page. LinkedIn is a really powerful way to raise awareness of the show. But the most impactful way you can help us grow our audience is to leave a review on Apple Podcast. Or if you listen to the show via Spotify, then please simply share the podcast directly from your Spotify app or wherever you listen to the show.

These simple actions can make a huge impact in getting these amazing founder stories out to the masses. And please make sure to tag or mention The Startup Story when you do share so that we can connect with you and say thank you directly. I'm so incredibly appreciative of the fact that you listen to the show each and every week, and I look forward to sharing these amazing stories with you every Tuesday with hopes of encouraging and inspiring you to start your story.

If you like this podcast and are thinking of creating your own, consider talking to my producer Danny Ozment. He helps thought leaders, influencers, executives, and authors create, launch, and produce podcasts that grow their business and make a real impact in this world. You can contact him today at emeraldcitypro.com/startupstory.

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March 02 2021
Matt Mullenweg, co-founder of WordPress and CEO of Automattic

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