Growing as a Leader: Matt Mullenweg on the Starting Greatness Podcast with Mike Maples Jr.

I'd run a meeting and it would just go all afternoon with no agenda, no deliverables. I can't be this terrible manager. Like, I need to start reading some books, finding some mentors. I need to like start being better at my job because I'm, I'm just kind of scraping by still.

That's the voice of Matt Mullenweg, founder and CEO of Automattic, which owns WordPress and many other properties that are the foundation of today's web. WordPress alone is now used by more than 60 million websites and more than a third of the top 10 million websites. This is Mike Maples Jr. of Floodgate, and it's go time with Matt Mullenweg. Welcome to Starring Greatness, a podcast dedicated to ambitious founders who want to go from nothing to awesome super fast. When you're a startup founder, you have to channel your inner James Bond, your MacGyver, your Wonder Woman. I'm gonna help you win by curating the lessons of the super performers, but before they were successful. So without further ado, ignition sequence start. Let's get started. When Matt and I connected, we were in the midst of the COVID-19 pandemic. On the one hand, I wanted our conversation to touch upon Matt's distributed management model because I thought it might help other entrepreneurs navigating this new paradigm for the first time. Matt's been a pioneer of this for many years. And by the way, he has an entire podcast devoted to this topic called Distributed, which I highly encourage you to check out. But as Matt and I chatted, it became clear to me that this episode was about something even more timeless and broadly applicable. You see, Matt has truly stood the test of time as a CEO, but this success story almost came to a screeching halt because of Matt's early struggles as a leader. This is no knock on him. As one of the most honest leaders I know, and as you'll hear in a minute, Matt has no reservations about sharing his early shortcomings or even his concerns about how to avoid mistakes in the present time. This is one of his many strengths, and because of his learn-it-all mentality, Matt's been able to capitalize on some breaks and valuable connections early on in his career to set him up for greatness. And I think you'll see from the interview that Matt Mullenweg is just a gem of a human being. Let's talk to him.

Matt Mullenweg, welcome to the podcast.

It is a pleasure to be here. Thanks for having me.

Oh gosh, you kidding? Uh, delighted to have you on the show. So you're a very young guy still, but that doesn't mean you haven't been at this for a while. How did you even get interested in computers and the internet in the first place? How old were you and how did you get exposed to technology?

Yeah, for me, a lot of it came from my dad. Like many sons in Texas, Houston, I know you're from Texas too. I just did everything my dad did. So when he mowed the lawn, I'd walk behind him with a little toy lawnmower. I played saxophone, started playing saxophone 'cause he played saxophone in high school. And his job, his day job was programming. He worked for oil companies pretty much my whole life. And he had gotten from University of Houston, kind of early computer science degree when they started offering it in the '70s. And that was his whole career. So there were always computers around the house and he was very much a tinkerer. So he was fixing our cars, building furniture, fixing up boats, like whatever he would kind of get, he would always kind of hack on it. And so I feel like seeing that, I sort of applied that a lot to hardware and software. Initially making some computers for myself, for gaming or friends or local musicians or things. And then later getting into the craft of writing software. So that was just the path I decided to go down. The sort of big things were I visited San Francisco. So that was like Mecca to me.

How did you go from Houston to San Francisco? How did that transpire?

Totally random, complete coincidence. In Houston, I organized a user group kind of at a local nonprofit. We have interest user groups and I organized the one around PalmPilots. So every month I'd organize a program, invite speakers, kind of lead this PalmPilot user group, which is, let me tell you, I was very popular. But it was really fun and actually really good to get in front of a group of adults and do this thing every month. This designer named Jeffrey Zeldman made a set of icons for the Palm Pilot that would change all the default icons with like these cool '50s, you know, kind of Art Deco looking icons. So I became a fan of Jeffrey Zeldman. That's also how I— he started learning HTML and CSS standards. That's how I got into that. He posted on his blog that he was going to be in Austin, Texas for this thing called SXSW. South by Southwest, which was going through, the interactive portion of South by Southwest had shrunk, kind of after the bubble of the late '90s, 2000s, it was probably only like 400 or 500 people, so really, really small, and I was like, Zeltman's gonna be in Texas, no way, so I wrote what was actually a hot check to get a student ticket to South by Southwest for a couple hundred bucks. My sister lived in Austin, so I just crashed at her place, I had a gas card from my parents, so I was like, "Hey, can I use this gas card to go to Austin and go to this conference?" They were like, "Yeah, okay." At the conference, it was so small that I ended up sort of meeting my idols, Jeffrey Zeldman. There was a fellow named Tomasz Czajlik who was developing one of the major web browsers at the time, Eric Meyer, who was a big advocate of teaching people how to code. So I just got to meet all the biggest bloggers. I mean, Ev was there. I met Ev and Jason Schellen and all the blogger folks. So it was kind of the whole internet at that time, the independent internet came together. And again, it was just, it felt like a couple hundred people. So you kind of met everyone.

So this is still early in Web 2.0. I remember going to the O'Reilly Emerging Tech Conference in Oakland.

Yeah. Was that the one that Bezos came to?

Yeah. I remember he was sitting a few seats down. Just, he's there sitting in the audience, just like a normal person with his MacBook Pro Pro Laptop.

Totally. I was at that one. Yeah. And I got a picture with Jeff Bezos and it's funny, like, it's like a really young dorky me and a really young dorky Jeff Bezos before he got swole. Yeah. So Tom Tekcelik later invited me to come out to San Francisco to crash on his couch. And I was like, cool. I was like, okay. So, you know, saved up some money, flew out. And that week I was in San Francisco, both through Tom Tek, met a lot of really cool people here, but I really felt like I found my tribe. Like in Houston, there was like a dozen of us who were into like 802.11b and open source and the Linux group and the PalmPilot group and everything like that, but it was kind of the same people in all the groups. We'd all go to each other's stuff. And in San Francisco, I felt like this was all the people we were following online. And I visited Yahoo, I visited Google, I visited all the companies I could, and one of them was CNET. I blogged that I was going to go out, and a fellow at CNET named Mike Tatum reached out and said, "Hey, you're gonna be in San Francisco. Why don't you come out and meet us?" What I didn't realize was all these companies were interviewing me essentially. I think at Google, they wanted to make a Blogger appliance. They had a Google Search appliance. It would literally be a box that you'd buy that looked cool. It was in Google colors and you'd stick it in your data center and that would be like your internal Google. They wanted to do that for Blogger, for internal blogging. Very prescient actually, but the way they had written Blogger wouldn't work for that, so they wanted to see if WordPress could run on this box that they sold to people. It was kind of funny, it reminds me of Silicon Valley where the guy comes in, he's like, "We're going to make this box." It was kind of what you did at the time. So I talked to them about that. Basically, when I returned back to Houston, I started getting some job offers from these companies. And WordPress was still pretty early and was generating $0, so it wasn't like there was any— I was still just making money from computers and building websites. So the most interesting ended up being CNET, and the reason was they were a media company. Not a technology company. So if you go to work for Google, still today, if you work for any software company, you kind of sign off all the intellectual property to that company.

Yeah.

For good reasons. They need to— if they sell the company or IPO, they need to know that they own all the IP for what they do. But CNET didn't care about that because they're a media company. And so they said— they essentially did a carve-out for me where they said anything you do that's open source, you can retain the copyright and all the intellectual property rights. So to me, especially growing up steeped in jazz culture, there's so many stories about these musicians who sold their masters. They sold the rights to their original recordings.

Without even realizing it.

Without even realizing it. Kind of had been taken advantage of. And so honestly, it wouldn't have mattered. I could have gone to Google and kept doing WordPress. But in my head, there was this concept of you have to own your masters. So that was the thing I optimized for. It ended up being a great decision because WordPress is a CMS, content management system. Content management systems were kind of invented at CNET because they were the first large-scale publisher. So Vignette and all the early ones, Vignette had actually spun out of there.

So then, okay, so then is WordPress a business yet or is it still, it's still kind of a hobby with a group of people?

It was, it would get some donations, but I mean, we're talking about hundreds of dollars. I was basically funding it out of my CNET paycheck. And credit cards that were running up. It wasn't really clear it was going to be a business yet, but when I moved out, I did start to hear from some venture capitalists who said, "Hey, you should go do this as a thing." One of the earliest users of WordPress and one of my best friends today is Om Malik, who was a journalist. He was kind of hyperconnected and as a journalist knew everyone. The very first WordPress meetup we did at Chat Café, which is an Indian place on 3rd Street, there's maybe 8 people. Anon was one of them. One of the early times we met, he really kind of connected me to both our initial investors, Phil Black, Tony Conrad, including some people who I ended up not taking money from that I should have, like Jeff Clavier, Marc Andreessen. But he introduced me, and he also introduced me to Tony Schneider, who is the gentleman who recruited to be the CEO of Automattic. So it was really, really special. Tony had just sold his company called Oddpost to Yahoo, which was the big exit. If you sold to Yahoo, that was like, you made it. And Om did a cover story for Business 2.0 on the sale. And he said to Tony, you're not gonna last at this big company. There's this kid out of Houston, who's making this cool thing. You should meet him. I think you'd get along. And that was kind of the matchmaking that led us to meet.

And so, but it sounds like it still wasn't a company yet.

So all the places were saying you should raise money or these VCs trying to put in. But honestly, like, I had just talked my parents into letting me move out from Houston. And, you know, part of the pitch was, oh, it's a public company. They have healthcare, like they have a building. You know, my mom drove out with me so she could like, check it out, make sure I wasn't getting scammed or joining a cult or something. So she kind of warmed them up to it. I wasn't yet ready to say, "Hey, all that healthcare, all that everything is all going away." My idea was kind of that WordPress was working well, but to use it you had to be a developer. You had to set up a database and upload all these files and things like that. So if we could make it where you could click just a few buttons, kind of like Blogger, and get a blog going, we had a cool interface and flexibility that would be really compelling. So I pitched this to CNET and said, hey, you know, all these other internet giants have a blogging system. Literally, they all did. The big four at that time, AOL, Yahoo, Google, Microsoft, all blogging systems. You should have one too. But blogging kind of was becoming a bad word. So the ones that were kind of going mainstream were more political blogs. And they were known for what I think we describe now as an early version of like a cancel culture. So there was like one story I remember, I'm going to mess it up because I don't remember exactly, but there was like a politician, a congressperson of some sort who said something he thought was private at like an event down in Louisiana. It was recorded. Someone, you know, had like a little recorder and that became like a huge big thing on the blog, Drudge Report, the kind of sites at the time blew it up and he ended up resigning. And that seemed to people what it was going to be. It was like a bunch of people fighting on the internet and like CNET just didn't want to touch that. And also the other thing going on was CNET was like kind of like a mainstream publisher for tech news. So they had News.com, GameSpot, they had these like big tech publications with hundreds of employees and developers and editorial staffs and everything. They looked a lot like newspapers and they were starting to be disrupted by blogs as well. So Mike Arrington was starting TechCrunch, you know, Nick Denton had Engadget and all the Gizmodo blogs and things like that, or I think Jason Calacanis had Engadget. So whatever it was, people were starting these blogs that were creating content for 1/100th the cost with 1/100th the staff of these big publications that CNET was running, and they were pretty good and they were getting popular and in fact getting quite competitive to CNET's publications. So internally, there was almost this anti-blog thing where they were like, we don't want, we don't want anyone to be able to publish. You know, we're about trusted content that gets edited and fact-checked. They were right, it was amateurs. It just turned out those amateurs could get really good and they actually knew a lot. And one of the amazing things about Arrington was he was a lawyer. So he was great at reading stuff and could write really quickly on any number of topics. So he would get the post out hours before, you know, they could boot up their old CMS. That was another thing I'd seen at the most awkward meeting I'd ever been in. I think it was the editor-in-chief or something, you know, had this— it was one of the big conference rooms, 12, 15 people, and it was the team and the leads of the people building the in-house CMS. And he said, all right, you know, they projected the screen and they said, okay, I've got a post ready to go, you know, here it is, here's the text. He emailed the document, said, now post this to the website, like the live website, and let's see how long it takes. Long story short, the process took about 15, 20 minutes for them to load it into the system, set all the fields, and then the publishing time was probably 5 or 10 minutes. He says, "Matt," and I'm literally, I look like I'm 12 years old on the corner with my laptop. And he's like, "Okay, post it to WordPress." So plug in the laptop and copy and paste and you post it. It's live seconds later. And the daggers, the lasers, these guys were looking at me, they were just like, "This punk kid, what the—" I felt like 1 foot tall, it was definitely awkward. But to CNET's credit, they had started to use WordPress a lot of places and they were really seeing that the speed of publishing, the agility of the content management system was holding them back, so they wanted to make their thing just as fast.

Didn't you pitch CNET to invest in WordPress and you would have stayed there, but instead you started the company because they turned the pitch down?

I pitched it to build it there. CNET had all these cool domains like online.com, com.com. They just had every cool domain in the world because they got them early. I was like, "Hey, why don't we do like an online.com or like a web.com or something and just allow anyone to make a subdomain, publish, have a website?" They just didn't want the user-generated content. They were really about editorially driven stuff. I also felt a lot of loyalty because they had moved me out. They gave me this great salary. They gave me a few thousand dollars to move my stuff and everything. But I wanted to do this thing. I was pretty committed. But they say, "Hey, well, will you finish up these projects you're on?" So I was like, "Yeah." So I ended up staying another 3 or 4 months to finish out those projects. But they were like, "You can go do this thing." In fact, Shelby, who is the CEO, and CNET itself each put in, when we later raised a round, put in $25K each, which they sold for over $1 million 2 years later. They should have held on to it. It would be even more now. But part of it as well for me is I was again conscious, like, I don't want CNET to come back later and say, like, "Hey, we own this thing you did." I actually ended up being the 3rd or 4th employee at Automattic. Started the company and just started paying the other guys out of my paycheck, and we started working together. They kind of got that, started working on what would become WordPress.com, and I finished up my work at CNET. It ended up being a project that saved them over $5 million a year, so I was really proud of that. They could replace some software they were using with something with WordPress, so they saved a ton of money. I felt like I kind of paid my dues and could then start this company. So that was, it was very kind of informal. The first 3 employees were other engineers who I'd already been working with on the open source thing, and then I joined myself. We were all taking de minimis salaries, probably, I think me almost nothing, maybe like $40,000 or $50,000 a year, like much less than we'd work at any other jobs we could get. But that was kind of like the bootstrap. We were like, okay, let's build this thing together. If we do it right, maybe we can like be full-time contributing to open source, which was really our dream.

And when did Tony join as a CEO then?

I think I met him, I don't remember the exact timeline, but he ended up joining probably 6 or 8 months later. When I got introduced to Tony, it was like meeting a business soulmate. He was very kind. He's from Switzerland, came over, ended up going to college at Stanford, did startups, eventually became the CEO of this company that sold to Yahoo, but had kind of an engineering background, so he really understood the tech side. Had this Swiss-German mentality, always on time, really like no drama, like just kind of wants to figure out the best thing, and also believed and believes now in open source. Like just got it from the very beginning. So, this guy's always on time. I ended up being like 45 minutes late to our first meeting 'cause I just moved to San Francisco. I didn't realize how far things were. And so I thought, oh, this is just like 2 miles away, I'll walk to it. And ended up like not realizing there were hills and other things. So I ended up getting there really late, but he waited. And what was supposed to be probably an hour we were together, we both ended up staying until basically nighttime in this patio, outdoor restaurant thing, to the point where I hadn't brought a jacket and I was like just shivering because I was so cold. But we were just connecting when we were talking so well, it was like, Neither of us wanted the conversation to end, so we ended up speaking like 6 or 7 hours. He was the reason I decided to raise money, actually, because I was just planning to bootstrap, and we had some early revenue. We were making $10,000, $20,000 a month. I started to really build the revenue of the company, more than enough to support us, but I knew that if I raised money, they'd want to bring in adult supervision, because that was the Eric Schmidt at Google, you know, that's kind of the thing you did then, and I was like, well, I don't know if I want that. But then I was like, well, I can pick the adult. This guy, I'd be lucky to work with him. You know, I can, I learned so much every time I talk from him. And so it wasn't that I was hiring CEO. I was just like, I really want to work with this guy in whatever capacity we can, probably the rest of my life. And it was really like meeting a business soulmate. So I was able to convince Tony to join. And then we've raised our first round, which is about $1 million.

Was there anything about, you know, he was your business soulmate, but was there anything premeditated on either one of your parts about knowing the traits you were looking for in a business partner, or is it just an accident of fate that you just happened to run into each other at the behest of Om and it just worked out?

You know, it was matchmaking. It's kind of a blind setup. Neither of us had met each other before, but Om was like, "Y'all, y'all get along. You should really get together." And once we got together, it became clear. You know, I wanted him to be CEO because I believe in clear lines of reporting. So I was going to report to him, but he did a really fantastic job knowing that I loved running things and leading things, like making a lot of space for me to essentially be like an understudy in a lot of ways. So learn from his experience. He took a lot of things off my plate that I didn't like, but later grew to love. But like at the time, I wasn't into HR, legal stuff or other things, and made space to really collaborate, you know, let me lead the product, but like let's collaborate on it. So bringing his experience to bear and his kind of common sense approach to things. So true partnership in a lot of ways. I've learned a ton. Like I could have never been the CEO, become CEO of Automattic or be the CEO I am today if I hadn't studied essentially under Tony for 8 years.

Did you ever have any struggles as Was that automatic in the early years or was it one of these things where you were just happy to be getting a paycheck so that you could keep working on this thing and it just started to get a life of its own and it just one thing led to another?

You know, especially Fortuna, we made every mistake in the book. So, we had no credit at the time because I had gotten like a Best Buy card in high school, forgot to pay it. So, as a sole founder, the company credit became my credit. 600 credit rating or something. And so we couldn't get any credit even after we raised money, had $1 million in the bank and the limit on our credit card was like $5,000. So the servers were just costing more than that. And so there was like crises or like, how do we pay the credit card bill for all of our servers and things? How do we wire money to people? How do we, you know, there was issue where we didn't have the wordpress.com domain. There's a whole drama around getting that domain. People suing us. There was just all of the above that we were going through. And, you know, in some ways tumultuous, in some ways we didn't make a lot of mistakes that I saw by other companies years down the road. So, for example, we brought in a CFO really early, part-time, a great woman named Ann Dorman, was part-time CFO. And, you know, Tony took over the books for me and kind of did it for a little while, but then he found this person who could come in and really kind of kept all that clean. She also did HR, so like, and kind of gave us the documents and everything. So we were pretty good about following HR best practices from early on and how we hired, how we did compensation. And compensation is never perfect. You know, at any snapshot in time, there's going to be things which are not perfect within it, but I want it always on the arc towards fairness. Any decision in the company, You know, if someone wants to talk about it, we're totally open to it and we can explain it and we can talk about it and strive to be as fair as possible. Because ultimately, that's really what you want people to feel. We're, you know, we're still a growing company. We're not gonna— we're not as profitable as like a Nintendo or an Apple or something like that. So it's not the highest salaries in the world, but we want people to feel like they're contributing to something and they're getting fairly compensated for their contributions to it.

And was there a palpable time when you felt like you kind of transitioned from this 0 to 1, what were some of the things that kind of where you had to have a new kind of fun as you got bigger?

We had a lot of friction around the like 15 to 20 people range. Yeah. Because I had no idea what I was doing. So I'd run a meeting and it would just go all afternoon with no agenda, no deliverables. And I was working with people who were generally much more experienced. And so I remember once at our first offsite, we were up at Stinson Beach and we were all in one house because it's pretty small. And this fellow who had joined from Cisco actually just got up and walked out. Just so fed up with us. He literally just stood up, walked out of the house and walked down the beach. He was just so pissed off. So those things were rough. And also because we were such, you know, better or worse, you become really close personal friends with everyone because you're kind of in the trenches. So, you know, when you fight, it feels like you're fighting with your partner or with your significant other. So we also had an offer to buy the company. Someone tried to buy the company pretty early on. So when we were around that size, like 20-ish people. And one of the, it's kind of silly to say in hindsight, but one of the things that made me seriously consider it was that I was like, "Well, we're all fighting with each other. Like maybe this is not fun. This is not something I want to do. Maybe this is kind of just where it gets to." Because it was just so heart-wrenching to disappoint these people who you really respect and care about and to be at odds with them. That was definitely a pivot point, deciding not to sell.

How did you get your act together? What were the things that helped you transition into being more effective? I mean, I suppose Tony helped quite a bit.

Yeah, but he would give me a lot of rope too.

Yeah, but now you run the place and it's pretty big. So clearly you've made some progress in your ability to manage things.

Yeah, probably some of it was I didn't listen to Tony enough. I was pretty headstrong. I remember, distinctly. So one of the big things was the offer to buy us was kind of like $200 million, which was just ridiculous because we were not making that much money. It would have netted me, you know, 9 figures, and we would have joined a new thing that we'd have pretty significant equity going forward in this new thing. And so that was, you know, definitely a serious consideration. 'cause I'm 23. Someone's like, you can be a centimillionaire. And there also was a culture back then, a little bit more of exiting early.

Oh, I remember well. I remember even the Flickr folks, right? They exited for, I think, $25 million. And it was one of the defining early companies of Web 2.0.

Yeah. Yeah. So you kind of like rinse and repeat, you know, sell it, stay a year or two, then do it again. Actually, I think when I started Automattic, I felt like a good outcome would have been if I could have sold it to Yahoo in a few years. Yeah. Owen was even like, you should get this Mike Moritz guy, have him invest because he's on the board of Yahoo, so he'll help the deal in a couple of years. He'll make it happen. He'll make it happen. But I also realized that while there was challenges, I was like, well, what would I do if I had $100 million? I was like, well, I kind of want to do exactly what I'm doing. I want to write software. I want to travel the world and meet WordPress users. And I want to, you know, build something with a team because that's like the funnest thing. Like you build something that has an impact. And will I— will the chance that gets messed up be larger or smaller if we join this larger thing? And there's also a time when lots of things will get shut down by the big companies. Yep. Yeah, or neglected. So I was like, well, I think we should make a go at it. And the— our investors as well were also making a pretty compelling alternative where they said, you know, take that as a valuation. We'll put in another, I think it was $25 or $30 million. You know, some of it can go in the company, but also take some as secondary. So instead of making, you know, this million, make a few million And then you can just focus on this. You don't have to worry about paying your rent or something like that. Just like really work, build for the long term. And I give them a ton of credit because this was not common at the time, secondary sales. Now they're pretty standard, but at the time, especially for a young kid, this was probably something that was not something you see a ton. But I don't know if it was Phil Black or John Callahan or maybe someone, one of the True Folks was like, If you're saying no to this, what are you saying yes to? And that just etched in my mind, like, well, what am I saying yes to? And so I was like, well, let's say yes to create the web operating system, to make the thing that could be 85% or 95% of the web. And what do we need to change to do that? Well, we need some more capital. So we raised the money. And how do I need to work on myself? I can't be this terrible manager. Like, I need to start reading some books. I need to start, like, I need to start finding some mentors. I need to like start really being better at my job because I'm, I'm just kind of scraping by still. Maybe what I was doing in college, I just doing the minimum to get by. So I need to really up my game. And that was a big wake-up call.

And was there any, in terms of your transition from sort of minimum viable sort of leader with making a lot of mistakes to now running an organization with a huge number of employees. What's the latest count? It's like 1,300, yeah, 1,300 people distributed throughout the world, multiple product lines, 38% of internet sites. Like, was there a single book you read or a bit of advice or a course you took, or just was there— was there— was it— were there a couple of things that were just defining moments in your improvement?

For me, I learned from books probably the best. So I consider like these authors my mentors, you know, even though I might never ever meet them. So things that I came across, I had already read a little bit of Plato, but I started to read some of the Stoics, Epictetus. My friend Tim's book, I know you're friends with him too, The 4-Hour Workweek. Seth Godin books, I don't remember which particular one, but they're all good. Guy Kawasaki did a book called The Art of the Start. Started to read some of the business classics like Good to Great, Robert Cialdini's Influence. I think there's Jeffrey Gitomer, Little Red Book on Selling. I just read books on sales, kind of anything that we're trying to figure out. I just go to Amazon, order 5 or 6 books on it and just read them all. I felt like we weren't doing our pricing right, so I just got 6 books on pricing, went through them all. I think the one that worked out well was Pricing on Purpose. But I also read the GE book on pricing, the super corporate stuff. Zen Habits, it was a blogger that led into a book. So all these, and I still try to read as many books as I can per year now because I still have so much to learn. Black Swan by Nassim Taleb, I feel like was kind of around that time. Hugely influential, not just because it was amazing book on its own, right, that really changed how I thought about things, but it was a portal to so much other literature. Like he would have dropped so many allusions and references to other books that it was almost like I stumbled into like this magical Aladdin library or something full of treasure and just everything I took off the shelf would blow my mind. You can find gold everywhere, even like the really cheesy, corny stuff, like a book of quotations. Those can be really powerful. And I do believe in like extracting something from all of them. So a lot of what Automattic was, was also just an experiment. Like, I read a book like Drive by Dan Pink. He says mastery, autonomy, purpose are more important than anything else for people being happy. It's like, okay, if that's the framework, let's try it out. How do we give people more of those 3 things and see how it goes? And, you know, one of the things I'm very proud of is like Automattic's retention rate is off the charts. We've never regretted, regretted a retention that the big acquisitions would do will throw it off sometimes, but most years it's like 4%, 5%, which for tech companies is really, really low. I think it's because we really invest in these things that help people feel fulfilled in their work.

But another thing I seem to notice about you, Matt, is that you seem to have this trait that a lot of the long-term successful founders that I've seen have, which is you're more of a learn-it-all than a know-it-all. And so I've seen some founders get attached to the idea of being right or being the smartest person there or feeling sort of an imposter syndrome if they don't know. Whereas it feels to me like the folks that can go much farther than you'd ever imagine are the people who are just learning all the time. And they, you know, they always realize there's more to know and there's always more to learn. And it's like, there's no, Nothing wrong with not knowing all the answers. There's just more joy in being able to learn it all than in trying to keep the illusion that anybody could be a know-it-all.

I wish I was more of that in my 20s. If you were to zoom back, you might see a bit more arrogance or strong-headedness back then. But definitely in my 30s now, that's been probably the title of the decade. Is this so much more? You just get knocked on your butt a few times. It's very humbling and you really start to realize all the things you don't know versus when you're young and think you know it all and really don't.

And there's gonna be a lot of founders listening to this. What would you like founders to know? I mean, we're in this pretty wild time where we have a pandemic, we've got all types of political unrest and social strife. International friction and Fortune 500 spending trillions of dollars just to buy back their own stock. What would you like entrepreneurs to know? What would you like to see from them? What do you think they could learn from your experience? Or if you were in their shoes now, how would you think about the future?

I mean, the two big things I advocate for are distributed and open source. Distributed is a little easy now, but if you're building a company, if you can create opportunity all over the world through a distributed structure, that's really powerful. And then open source, I believe if you want to accelerate humanity, if you get jazzed by the idea of going to Mars or all this other stuff like thinking of the Earth as like a big connected thing, open source is the best way to accelerate humanity because software is now the software of our culture, of our evolution. We're evolving now in the information space, not the not the physical biological space, although maybe someday, and open source is the best way to do that. So that's first I'd say if you're considering anything like, you know, you only get a few chances to have a swing at it, and life is relatively short. Your younger years, you do have a ton of energy and like natural resources you can put to bear on problems, so just work on the thing that really, really, really matters, and I believe open source and big problems can be that. You know, in Perl, there's this funny saying that there's more than one way to do it. I would get really discouraged early on because I didn't have the background, the college education, the whatever it was of all the other entrepreneurs that I was seeing, all the role models I was looking at, knowing that there's more than one way to do it. You know what? There's never going to be someone with exactly my path or exactly Mark Zuckerberg's path or someone else again. It was a point in time, and that's cool. Because the thing that replaces Facebook, hopefully that doesn't replace WordPress, but maybe someday, you know, would be created by someone who does it from a completely different point of view and completely different frame and a completely different way of doing it.

If you could think about how to improve the internet in the next decade, how do we get back to a world where it feels like it's a bottoms-up phenomenon? Rather than a few really big companies that own all the data and seem to be aggregating and amassing more power all the time. Cooperation.

I really appreciate the idealism that existed then. It's very much open web, very much connecting things, something that John Battelle and Tim O'Reilly really advocated for. This Web 2.0 was going to be about how everything was open and connected. And I try to bring that idealism today. You know, 2020, the world is like a little a little rough sometimes. We have, you know, the internet's turning into the splinternet. We're having like firewalls, balkanization, and I think there is still so much potential in that vision of an open, connected, independent web that really I try to make it my business and life mission to bring that back. You know, the deep psychosis of a lot of these companies that survived a dark period or went through something really tough, including like an Apple, is that they end up with this permanent underdog mentality, where it's like them against the world. And, you know, Apple is now a $2 trillion company, wildly profitable, has more in cash than the GDPs of most countries, but they'll still not let you change, you know, they'll still lock you into iMessage and not let you change your default web browser engine and things like this that, you know, probably are good for them competitively, But it feels a little bit like, hey, can you open it up a bit? One of the things I liked about that time was the companies were all building businesses, but they would try to interoperate with each other. I would love if just particularly the big tech companies just look around the room and say, okay, we won. We've captured so much of the economic growth of the past decade. We have unassailable cash positions and things like that. Patriots. You know, we can be Microsoft. We can go through a dark decade and still come out the other end with hundreds of billions of dollars and the ability to reinvent ourselves. So let's go consumer first. Let's go user first and say, what do our users really want?

You know, I've seen this happen time and again. You, you start a company and it becomes a platform and it grows really fast. The rising tide lifts all boats. But then you start to fight your own ecosystem because the pressure to grow is so great. That you end up not being able to grow without extracting value from the ecosystem at ever accelerating rates. And before you know it, the world around you would rather find a new platform. They'd rather find a new way to run their business.

And there's so many examples of this. I mean, you have Shopify now starting to go to war with their own ecosystem and like take— I think it's rent-seeking behavior. And where they're just capturing value, not adding value as much. And if this, you know, I know this is for early entrepreneurs going from zero to one. There's one thing I would, I would ask everyone to remember is like, when you make it, like, try to make it for some other people too.

Cool. All right, Matt. I really appreciate your taking the time. I think that this is gonna, I think people are gonna be excited.

Thanks for listening to the Starting Greatness Podcast. If you've enjoyed this episode or you're new to the show, I hope you listen to our past interviews with legendary founders like Reid Hoffman, Mark Andreessen, the Instagram founders, and Keith Rabois. I'd love to have you subscribe wherever you get your podcasts so you don't miss an episode. And if you like the show, I'd be grateful if you leave us a review on Apple Podcasts. You can also follow me on Twitter @m2jr and subscribe to our newsletter for exclusive content and events at greatness.substack.com. Until we catch up again, I hope you'll never let go of your inner power to do great things in whatever matters to you. Thank you for listening.