How WordPress Became a Web Giant | Automattic Founder and CEO Matt Mullenweg

22 Sep 2025 · 1 h 10 min

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Podcast Episode Summary

Grit

How WordPress Became a Web Giant

Host: Joubin Mirzadegan Guest: Matt Mullenweg, co-founder of WordPress and CEO of Automattic Episode Description: Matt Mullenweg reflects on two decades of building WordPress, discusses challenges and strategies for success, and shares insights into Automattic's mission to democratize publishing and commerce.

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Key Takeaways

Evolution of WordPress

  • Origins: WordPress started as a simple domain with no clear monetization path and few users. Today, it powers over 43% of the world's websites, far surpassing its competitors.
  • Challenges: Mullenweg discusses the ups and downs of entrepreneurship, emphasizing that success is rarely linear. Companies can experience both significant media attention and periods of decline.

Automattic's Mission

  • Democratization of Publishing: Mullenweg's vision for Automattic focuses on making publishing and commerce accessible to everyone.
  • Work Environment: Employees are encouraged through policies such as paid sabbaticals and remote work, fostering a healthy work-life balance.

Leadership Insights

  • Handling Criticism: Mullenweg candidly discusses the cyclical nature of public perception, where founders can quickly shift from heroes to villains. He emphasizes resilience and learning from hard times as key to longevity in leadership.
  • Open Source Philosophy: Mullenweg believes deeply in the open-source model, which supports user agency and equality in publishing.

Legal Challenges

  • Ongoing Controversies: Mullenweg reveals current legal battles with WP Engine, reflecting on the stress and challenges of navigating corporate disputes and the impact these conflicts have on his work and mental health.

Personal Reflections

  • Work-Life Integration: Mullenweg advocates for integrating work with personal passions, noting that joy and productivity can coexist through meaningful engagement.
  • Creativity and Innovation: He finds inspiration in diverse activities outside work, such as travel and music, which help recharge his creativity.

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Discussion Highlights

  • The Entrepreneurial Journey:
  • The importance of resilience and learning from failures.
  • The necessity of navigating public perception and criticism as a long-term founder.
  • The Role of Open Source:
  • Mullenweg's belief in the power of open-source software to promote accessibility and innovation.
  • The impact of competition from proprietary technologies and the importance of maintaining an open ecosystem.
  • Personal Growth and Happiness:
  • The idea that fulfillment comes from contributing to something greater than oneself.
  • The significance of taking breaks and allowing time for personal reflection and rejuvenation.
  • Navigating Legal and Corporate Challenges:
  • The personal toll of legal disputes and the challenges they pose to creative and effective leadership.
  • Strategies for maintaining focus and productivity amidst external pressures.

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Conclusion Matt Mullenweg's journey with WordPress and Automattic exemplifies the resilience required in the tech industry. His insights into leadership, open-source philosophy, and the importance of personal well-being provide valuable lessons for aspiring entrepreneurs and seasoned leaders alike. The episode emphasizes that while challenges are inevitable, perseverance, learning, and a strong mission can lead to lasting success.

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Transcript

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0:00The entrepreneurial journey is not just up and to the right. Companies go from being on the cover of every single magazine to no one wants to touch them. But these struggles are where it defines you, ultimately. Because WordPress really was a domain I registered, a different source project, very few users, no clear path to monetization or being a business or anything. Today, 40 % of websites, I think it's 43 right now, are powered by WordPress, which is 10 times the number two in the market. Companies often start to exert too much control or things that can be user hostile as their interest or sort of embedded growth obligations.

0:30This can either be solved one through regulatory means or reversed by open source competitors. Typically, open source is at the key of that strategy. So between Akismet, the anti-spam and WordPress.com led us to launch the company automatic.

0:54Welcome to Grit. I'm Jubin, partner at Kleiner Perkins, a show where we go beyond the highlight reel and explore the personal and professional challenges of building history-making companies. Today, we're joined by Matt Mullenweg, co-creator and founder of WordPress and Automatic. As of mid-2025, WordPress powers approximately 43 % of all of the world's websites. Matt has been chipping away at this company for 20 years in the pantheon of long-lasting founders with Zuck, Sergey, and Larry at Google, and maybe a few more. He's a legend and somebody that I think we should celebrate rather than tear down, which if you look online, seems to be the status quo these days.

1:34Automatic just celebrated his 20th anniversary, and Matt is now looking ahead to the next two decades of what open source looks like, what the shape of his company looks like, and what's next. Enjoy. I had to do 20 hours or something in Chicago on Saturday. I'm just so busy that I had to go for a wedding and I just couldn't go more than like 6am leave and then leave 6am the next day basically. And you know, the next day, the inevitable like 30 minute delay turns into a three hour delay. And it's like those moments that tend to break my back and remind me why being on the road is so difficult. Does that not like, uh, that's part of what I love about travel is it's very humbling, right?

2:22Because we think we're in control, but we're really not. And travel really reminds you to make the best of every situation. So you have to, I, you know, I've got my, my backpack and if I've got my backpack and a cell phone signal or wifi, I'm good, golden, right? I can be productive. I can be entertained. I can be whatever I need to do just with that little pack. So I do a blog post every year called what's in my bag. Because I've definitely iterated on the things in my backpack to adapt for my nomadic lifestyle. What's in your bag? What's in my bag? Well, it starts with the MacBook, iPad, daylight computer, which is really nice for like sort of, have you seen that?

3:06No. Oh, daylight computer. It's cool. It's like an iPad mixed with a Kindle. So it's got the refresh rate of an iPad, but it's monochrome like a Kindle. It doesn't emit blue light at all. So it's an Android tablet. So it's like you can do pretty much everything on there. But yeah. So I try to have different devices, different adapters, different, you know, things to just be useful in every situation. A lockpicking set, a flipper zero. I've got, you know, I'm a hacker too. So I like have all sorts of things. Lockpicking set in case. In case you need to pick a lock. In case you get locked yourself out of something.

3:39Sure. Yeah. Have you ever had to pick a lock? Yeah. And WordPress now is like a very, you know, it's like a seven, eight billion dollar value. It's like you've been doing this for 20 years. Like, what, like, what's it stat? Like 40, 45 % or something of all? Yeah, so over 40 % of websites, I think it's 43 right now of websites are powered by WordPress, which is 10 times the number two in the market. And in 2005, I founded a company called Automatic, which is the, which has the valuation. So there's WordPress software and then there's Automatic, which is the for-profit side. Got it. So that that's the company I run day to day.

4:15That's my day gig. And as you like and you run a blog and and and I'm curious, like when you're like out and about, are you like too tech niche to be recognized when you're in some random airport somewhere? Or do you typically find yourself getting recognized? Typically not, but sometimes people will see the WordPress logo and that always sparks up a fun conversation because there's WordPress developers, users just all over the world. And I love to meet them. Oh, and they'll ask you like, oh, do you use WordPress or do you work for WordPress or something? Sure. Yeah. And I love those conversations because it's a great way to kind of get some unfiltered like user feedback or developer feedback or just something.

4:56And do you tell them you're the founder and CEO? Oh, at some point. Yeah. But not up front. Or they might recognize, but like, yeah, usually not fine. Of course not. Because you want to get like the best. Right, exactly. Otherwise, they'll change what they say to you. Totally, totally. 18 years? 20 years? So I have been doing WordPress since 2003 and automatic since 2005. And how old were you? 19? I was 19 when WordPress started. Yeah, I was in a college at the University of Houston studying political science and making most of my money at that time actually playing saxophone, just gigs around town.

5:30and in Houston, Texas. To get free lessons, I would trade websites for lessons with local musicians. And that's what led me to developing some of the software that is now WordPress. It was interesting to me. I actually didn't know this, but you were not the CEO. Were you not the CEO? You hired a CEO in the beginning? Yeah, actually. And one of our first meetings was right here in South Park. So when Automatic, the for-profit company started, this was a very, very different era of everything. It wasn't sort of the founder mode or founder-led era. It was more the Google era where like the founders of Google hired a CEO, Eric Schmidt.

6:16So, and I was also 20 years old. I had no idea how to run a company. And a journalist, actually, Om Malik, introduced me to this amazing entrepreneur named Tony Schneider, who had just sold a company called Oddpost to Yahoo. It was a big exit at the time on the cover of magazines and everything. And Om said to Tony, you're not going to last a Yahoo too long. You're going to want to do another startup. Meet this kid out of Houston, Matt. Om was an early WordPress user. and Tony and I met and our first meeting, which was supposed to be an hour, turned to like six hours. We just meshed on every single level.

6:52So I was like, ah, wow, this guy really gets it. He understands open source. He understands building like a different culture, why we're going to do things differently and where we're going to do things the same and has a ton of experience building companies before. So I was the original CEO, but I was probably six or eight months later, Tony joined the company. I got him to leave Yahoo and join. And he was CEO for the next nine years. And then, sorry, like maybe you've told this before, but why did you, why the structure of the, maybe you were ahead of your time on the nonprofit and for-profit dual structure relative to like what OpenAI and others have done.

7:27But why did you do the nonprofit WordPress and the for-profit parent company automatic? It wasn't even a nonprofit. It was just a no profit. It was a nothing. right because wordpress really uh just you know was a domain i registered and like you know project that started as an open source project had very few users no clear path to monetization or being a business or anything and so um like that's typically how many open source projects start so yeah i just registered myself and uh started bootstrapping things on wordpress.org with uh actually i had a co-founder mike little um and the united kingdom who sort of was the other main contributed to WordPress.

8:09We just started hacking on it. We wanted the software to work for ourselves. It started to get more adoption. And it was only a few years later that I felt like there could be a commercial opportunity around it. Basically taking what was kind of difficult to set up, like the software you had to download and install and set up a database and everything like that, making it kind of one click, essentially making it a SaaS service. And the other SaaS service we made was an anti-spam machine learning service called Akismet. So between Akismet, the anti-spam and WordPress.com, that's what led us to launch the company, Automatic.

8:44Fascinating. And now Automatic has a bunch of properties underneath it. Yeah. So it's really evolved over the years. It started really very modestly, again, just as a way to get me and a few other contributors to WordPress, a way to pay ourselves a salary. but the WordPress really struck a chord you know we had this unique philosophy of being very open web standards compliance having really radically open APIs for everything coming in and out of course being open source which is very very core to my beliefs and my philosophy and also how we built the company to also you know have open source at the center of everything we do and then just Just the whole web 2.0, social media, blogging, publishing, people basically knowing that they didn't have to go through intermediaries.

9:36Like they could publish themselves. They could use the same software, by the way, that CNN or New York Times does, which is WordPress. And they can publish and they can have an equal voice because everyone is just a click away from each other on the internet. Super cool. I was thinking like sitting down with you now, Like you're a very like nice, gentle human being. But it's funny, like when you go on the internet and look you up, obviously I've done all my homework. It's like, you know, the quote, like you either die a hero or live long enough to become a villain. I feel like that's what's happened to you.

10:16Like you've, you've spent so long at the helm of one of the early and most important technology companies that power so much of our technology that you've just lived long enough to like become the the villain online it's crazy the good news is it's cyclical so does it bother you oh no because it's not my first rodeo so it doesn't bother you of course it bothers me um because uh well i'll say yes and no so what i'll say is that um it's interesting because that sort of hero villain cycle or like you're at the top of the world or you can't do no right It is totally a cycle. And the longer you're an entrepreneur, the longer you're a CEO, you'll see that not just you will go through it, but every company goes through it.

11:02You know, companies go from being on the cover of every single magazine to no one wants to touch them. You can see this in stock prices, too. Like all the companies that are now like trillion dollar companies at some point have had like 70 to 90 percent drawdowns on their stock. you know, Facebook, Google, Amazon, like all these have had like incredible Apple being days from death. So the entrepreneurial journey is not just up and to the right. Although if you zoom out far enough, it does look that way. There's often, it's often filled with many battles, valleys, pitfalls, things you go through.

11:37And, and when you go through it, everyone's like, ah, this is the end. This is, you know, if I could tell you how many times people have said WordPress is dead over the years. I had a nickel for every time. But that's the time when you need to go back to, you know, what you believe in, your principles, your sort of core philosophies and your customers. And that's what gets you through it. How old were you the first time you've been dragged through it? Like you must've been young the first time you got dragged through the mud. It was actually before the company even started. Come on. Yeah. So a lot of people don't remember this, but it was, I guess, 2005.

12:15I had made a major, major, major screw up, which is this was kind of before people knew what web spam was or anything like that. And I was bootstrapping WordPress.org and just paying it out of my salary. I worked at a company down the street called CNET. and someone came to me and was like, hey, I'll give you two grand a month if you put these links on WordPress.org because I have all this great content I've been publishing. But people in other countries are stealing it and they're ranking higher than me in Google. So we need to associate with a domain. This all sounds very obvious now, but at the time I was like, oh, well, so sure.

12:51So it's like a little proxy on a subdirectory and actually invented a way to, because I was like, oh, these links are kind of ugly. Let me hide them with CSS. So Google will see them, but users won't. And this, honestly, it sounds so ridiculous now, but at the time this did not occur to me that this was spamming. And so, yeah, had these links and they were there for like four or five months and then someone discovered them. And at the time, Google, WordPress.org had a page rank of like eight or nine or one of the highest ranked sites on the internet. And, you know, it started to rise in prominence.

13:26and it was actually i had taken my first ever vacation in my life um with my uh college girlfriends basically so i dropped out moved to san francisco as she was i think in tennessee or baltimore at the time and we'd saved up you know bought a student ticket which was like a paper ticket and i'd gone to italy and um i i think we're in venice and uh again a long time ago so there weren't like cell phones. There wasn't common wifi. I had like a little, uh, one of those cards, which you could do long distance dialing. And I called my sister and I was like, Hey Charlene, this was probably like, by the way, 11 PM at night or something.

14:04And I was like, Hey Charlene, how are you doing? And she said, Oh, um, doing all right. Hey, I saw you in the news. Everything. All right. I was like, Oh yeah, yeah. It was probably this press article that was coming out, you know, something, something I assumed was, was positive. And she's like, uh, let me read it to you. And it was actually, I think, CNBC. And at that time, because someone had discovered this, a blogger had discovered this and blogged about these links. And it blew up on the internet. Everyone was talking about it. And it got covered by all the mainstream media as well. So CNBC, CNN, Slates, everything was covering this story.

14:40And Google actually banned WordPress.org. So we had been marked to zero. No. It had been like totally wiped out from all search results. And, um, and all this had gone on for like a whole cycle, like 12 or 14 hours when I just had no internet connection. And, uh, I was like, Oh, that sounds not good. So I start, um, my poor girlfriend at the time, like I was like, Oh, I gotta, I gotta get online. And, um, so I got up my little Mac book and the hotel had no wifi. I just started walking around the streets because at the time, Wi-Fi networks were often had no password. So you could have you ever heard of war driving?

15:24You could drive around and find open Wi-Fi networks. So I just started walking around the streets of Venice looking for an open Wi-Fi network. And just there was nothing like no place. All the Internet cafes were closed. Everything. The hotel had nothing. So finally, the hotel was like, well, the first water taxi is at 5 a.m. You know, we'll take a water taxi at the airport. they have Wi-Fi there. And so I kind of stayed up all night. I was like, oh gosh, it was like writing things down, trying to figure out what had happened. Took the first water taxi to the, I guess, Venice airport and got online and just like the whole internet had exploded.

15:58And it was one of these things where like there were people defending me, there were people attacking me. Everyone was saying WordPress was over, could never get funding, could never do anything. and I was like, ah, okay, I gotta fix this. And so, yeah. So that first ever vacation got short, cut short, but it was definitely a learning process. How long does that, like from that moment until it goes away, how long does that last? Oh, well, that's a good question. I mean - It's like the early versions of getting canceled, basically. Yeah, it was definitely a cancellation. Um, the, well, I think you have to respond, right?

16:43So you have to respond. Yeah, absolutely. And there's some people that don't think you have to respond. Well, it depends on the context. So I, in this case, I, I had made a legitimate mistake, so I had to correct it. Um, so, uh, there was that process. There was then the sort of subsequent coverage. I've always probably it erred on the side of being overly transparent and engaging with critics, engaging with even hostile press. I don't always think that's the best idea, so I don't know if I'll make that a recommendation, but just because WordPress being open source, my open source nature, try to be like a sort of lead with transparency and it's better and worse.

17:24I feel like that's better in the long run. And so, yeah, News Cycle was probably about a week, although it felt like to me at the end of the world. people asking you about it, you know, it was probably three to six months. It stayed on my Wikipedia page for probably four or five years. It's not on there now, but it was, uh, it's like a controversy section or something. And, um, You've added other things to that section now, I'm sure. I have it, but just like the sort of internet doesn't care anymore. It's not like notable. And I've done lots of other things since then. It's actually kind of what led me to create this first anti-spam technology is I had like this Catholic guilt.

18:03I had like this karmic debt. I was like, okay, uh, now I need to fix spam on the internet instead of like creating it. And, uh, the, um, and then, you know, you know, now what is it? 20 years later, people have never even heard of this hot nacho scandal. They're like, they, they look at me like, uh, uh, but like, it sounds like the most ridiculous overblown thing. And, uh, as you've gone through more of your, But these struggles are what define you ultimately. What do you mean? Well, you learn a lot more from the hard times than you do from when everything's going well. Don't you think that's easier to say than do?

18:38Meaning like, if you believe that, you still don't want to go through it. You don't go through hard times on purpose. And when you're going through the hard time, you're not thinking to yourself, wow, I'm so grateful I'm learning so much right now. See, that's not true because you do go through hard times on purpose, right? What is exercise? What is working really hard? These are things you do that are difficult. that you know are going to pay off in the long run. Now, the unexpected, the unintentional hard times when there's a mistake or just life happens to you, now, of course, you don't seek that out and you do everything you can to avoid it.

19:11However, you will often look back at those times as when you learned who your real friends are, who ran towards the fire versus who was just a fair weather friend. Those lessons get really deeply embedded in you and it can drive you to perhaps have new inspiration or create new things. So are you saying like, all right, you've gone through your fair share of hard times since then? Oh, sure. I've probably been canceled seven times since then. Yeah, you're like going through one probably right now. It's actually a little bit on the downside. You're saying you're post-cancellation right now. Well, let's not do cancel.

19:49The cancel is like a whole separate thing. More like a controversy. Getting dragged through the mud. Yeah, yeah. But I still look up articles and it doesn't, they're still heated. They still have strong opinions about you. Well, and some of this stuff echoes. So sometimes people, you know, it's kind of like that a lie travels around the world seven times where the truth has, you know, gets its pants on. Do you read the news about you? If it bleeds, it leads. And so people see controversial articles. And even if it's wrong, there's a correction issued. That correction usually does not get covered as much.

20:22Do I read news? I do. Yeah. Just because I like to be just fully informed of, of everything that's going on. And again, this sort of idea of, Oh, about my products, about my company, about the industry. I try to engage with the criticism as much as the, uh, good stuff, because, um, I think you should be able to, like, if you really believe in something, you should be able to actually argue both sides of it equally well to, uh, you should be able to argue the opposite side to really like advocate for something you believe in. It's not the same, but like, you know, I've given completely up on reading any articles about the podcast or any of the comments in YouTube.

20:59Half the people think I'm like some serial killer and the other half of the people really enjoy the show. And I'm like, what good is going to come from me reading about random people who have never met before throwing barbs at me online? You know, maybe this comes from open source as well. So this is kind of how open source works. Yeah. You look at old mailing lists of any like open source project or WordPress or the Linux kernel or anything. Like, gosh, people duke it out. It's very incendiary. They used to joke about, you know, you got to put on your asbestos underwear to survive the flame wars.

21:40So I do feel like maybe the modern version of that is you need to develop a sort of grounding and a little bit of a psychic armor to be able to engage with these things, but not become these things. That makes sense. So you're saying I'm soft. I'm not saying you're soft. It's fine. You could say it. I'm saying that that. Well, let's say you're soft. That's OK. Yeah. Everyone's soft. Yeah. You know. Yeah. Everyone has a soft side. We all need to have a soft side. That, you know, every sinner has, every saint has a past and every sinner has a future, right? We're all human. We're all fallible. Everyone makes mistakes.

22:26There was, what's the joke? There was one perfect man and they crucified him, right? Like there's no like, every story of humanity, of religion, of myth, like it's all, what's the hero's journey? It's about, you know, succeeding, failing, and then coming back. And the key is that coming back. And so I, you know, over the years also, and as, you know, as an angel and supporter of entrepreneurial friends, and also just seeing it within my company, this micro version of this, you know, this too shall pass. That's probably some of the most valuable words I've ever heard, which is knowing that Like no matter how bad it seems at the time, know that everyone you admire has also been through some really tough times when they also felt down like a failure, like nothing could go right.

23:17And you just got to get up the next day. Keep grinding, keep going at it. Keep doing what you believe in. And that will ultimately lead you to a better place. Of the seven or eight trials and tribulations, let's call it, that you've gone through. What was the one that hurt the most? Is it this one now? Oh, no. Gosh, what hurt the most? Well, I guess you could categorize them. The one we talked about at the beginning, Hot Nacho. That was one where I legitimately screwed up. So that sucks, right? And that's going to happen, by the way. No one is error-free or mistake-free. Ones that hurt the most, gosh, it's kind of one-way and two-way doors.

24:09So some mistakes, some decisions are reversible and some are not. So when there's a reversible decision, that definitely stings a little less when you're able to fix it. Some things, maybe you burn that bridge or that person's left the company, or sometimes people pass away or die. You have never a chance to repair things that's tough yeah so i would say um in that sort of four box you know things that if you weren't wrong and it's reversible easiest you were wrong it's reversible maybe less bad uh you weren't wrong but it's not reversible well it's bad or a little worse and then the worst is if you're wrong and it's irreversible when you go through these moments of suckiness, does it make you want to, honestly, does it make you want to dig your heels in more or just be like, all right, let's, let's go back to having a CEO that can go deal with this stuff for me?

25:08Oh, good question. Well, and one of the things I do for colleagues, you know, fellow developers in the WordPress community is I take the arrows sometimes. So in some ways I'm like, the poop umbrella, you know, shielding them from some of this, uh, online criticism or, you know, so again, you have to have a framework. So, uh, on one hand, you can't, don't be like so stubborn or blind to think you're never wrong. So you have to have some flexibility or pliability there to re-examine your priors and say, ah, maybe I was wrong about this, or maybe the environment's changed. I should do something different.

25:50And there's other cases where, well, you know, the arc of history will prove you rights. And we can see with many, many movements, especially social ones like civil rights and other things, they were deeply unpopular in their time. If you just polled people or done a survey, it would have not got a majority vote. But you could, or some people were able to look at the context, the principles of it, the philosophy, the sort of axioms and say, oh, no, this is actually the right thing to do, even though it's not the majority opinion. And I think also building great software, great products, you often have to do things that in the beginning do not seem obvious or perhaps even get a huge backlash.

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26:37Again, this is gonna sound like a very trivial example, but do you remember when the Facebook newsfeed launched? And the first thing people did was use the newsfeed to organize petitions that got millions and millions of people commenting and liking it. I don't remember that. The newsfeed was the worst thing and that they should get rid of it. So, obviously, they stuck by their guns. And that ended up being now an innovation that's at the center of every single social media platform in the world. But at the time it launched, it was deeply unpopular. So, that's why I love studying the history of technology.

27:15is it's remarkable how much pushback anything new can get and how many things we now see as like sort of fundamental to the human experience or just like they're like water. We don't even think about it anymore. That at the time people said it was the end of society or it was going to ruin the kids or like screw us up in some unrecoverable way. Do you feel like people are saying that about the new technology? like about these LLMs? Well, of course, yeah. It sure seems like it. And it is true that, you know, every wave of technology does have some downsides that we need to be aware of, that as a society, we need to develop antibodies towards to sort of be able to use in a way that actually is beneficial to us.

28:06You strike me as a real technologist's technologies. Like you really, like you geek out on this stuff. Is that fair to say? Well, technology is fundamentally about human progress. It's trial and error. It's learning new things. And it's funny, when we stop calling it technology, it's like when it becomes part of society. We don't think of reading glasses as technology anymore, or glass or windows. But at some point, those were brand new. Mirrors. So it's kind of fun to think about these things and say, oh, at one point, people saw a mirror and they were like, what is this? Is this evil? Are there demons on the other side?

28:41Is this portal to another universe? Hmm. You said you're on the downslope of the most recent controversy. Yeah. Are you on the downslope? Why do you say you're on the downslope? Do you want to define, do you want to give your perspective of what it is? I'll give like a one minute TLDR. Like one minute. Which is, we'll be brief also because it's a legal battle. You're still in it. I'm still in it. There's a company in the WordPress space called WP Engine that many people thought was an official WordPress project or associated with Automatic. principally because of the way they were using and misusing, we believe, the WordPress and WooCommerce trademarks, which in open source, you can use the code, you can do everything, but you still have to have trademark protection, right?

29:27Not unlike a Coca-Cola or any other large brand. And we try to resolve this behind the scenes for several years. In fact, the company had been like actually pretty much better behaved in the past. But at some point, I had started taking a turn for the worse. And it didn't resolve privately. So I gave a speech basically saying, okay, this company that a lot of people think is official or a good actor has actually been doing some things that I believe might not be best for the WordPress community. And they're saying they're contributing a lot, and they're actually not. And they're doing all these things.

30:04Their words and actions are not lining up. And this was pretty controversial. and this company is also backed by a huge private equity firm over a hundred billion dollars and um so they have a lot of resources to fight this yeah so this is definitely the time when um oh is it the biggest no because i've also been on the other side of like large multinationals or fighting for open source like sometimes you end up on the other side of facebook or something like that so it's not the first time there's been a large company on the other ends but definitely the sort of like characteristics of this particular thing because it's inside of WordPress, private equity owned.

30:43There's like, there's lots of nuance to it. That's a little bit inside baseball that make it a little complex. But the long and short is they ended up then suing me personally and WordPress.org and my company Automatic for like a bajillion dollars saying we're hacking antitrust 21 counts. They got the biggest, nastiest law firm, Quinn Emanuel, and started a really big PR campaign as well. Well, and this is, they know that they have more money than you. And so one strategy would be just to basically embroil you in legal fees. Absolutely. And make you spend time with lawyers instead of time building product.

31:28Yeah. And eventually that probably gets pretty tiring. And you know what? That strategy worked, especially the first few months. And it put me in a dark place. That was depressing. How dark? Ah. Define dark. Maybe you want to walk away from everything. You know, when you devote your whole life to like building open source, things that is designed. And by the way, hundreds, thousands of other companies built on top of WordPress in a way that has not caused any issues like this. So it's not about commercialization. It's not about making money. And then to essentially be like dragged through the mud, attacked, pilloried, all these sorts of things.

32:09Yeah, it does make you sort of question like, well, is this worth it? So I definitely went through that for a bit. So to my earlier question of when you go through these, do you want, do you dig in or does it just make you want to quit and give the reins to the CEO? What shifted for you after a few months? Well, I did take a little bit of a break. So there was, I think, two weeks at the end of the year or a week at the end of the year, sort of between Christmas and New Year's. We sort of like paused some things on WordPress.org. Automatic, which by the way, has contributed over the years, hundreds of millions of dollars in developer time and everything.

32:50So just pure open source. We paused that. So really kind of like took a pause to reassess things and just, you know, recollect myself. So I think that was necessary. At the end of it, you know, I couldn't stay away. I love open source so much. It's really my life mission. Like, I feel like I was put on this planet with a challenge and an opportunity to help technology, which shaped so much of our lives. be built in a way which gives us fundamentally more freedom, more agency. And that is open source. That is a mission of open source. And it's accoded into the very license. It's like a bill of rights or a constitution that's embedded in the way the software runs.

33:35These are inalienable rights. No one can take them away from you. And I do feel like that's my reason for being. It's what I hope to spend the rest of my life on. As long as I'm able to type at a keyboard, I'm going to keep doing that. And being away from it was actually worse than being part of it and being attacked for it. So we turned everything back on, dove back into WordPress.org, started contributing open source again, everything. And it's actually been hugely re-energizing and a great rest of the year because we were able to ship a lot of stuff, build a lot of stuff. I mean, it's one of the most exciting times to be a builder ever with the advent of AI and everything.

34:12So. Can I ask, what did you do during that week? Like, oh, I just spent time with family. It was Christmas and New Year's. You went to Houston. Oh, yeah, yeah. Yeah. You know, spent time with loved ones, unplugged, stopped reading the internet as much. It got particularly - Maybe a glass of wine. Stopped trying to engage with everyone. There is something, if there is something different this time, it is that, it is true that, you know, social media algorithms do reward engagements. and human beings are naturally more engaged by things that rile us up or make us angry than things that chill us out or calm us down or make us happy.

34:51So just inherent in the design of these systems is going to, like I said, people see the controversial article, they don't see the correction or they don't see people making up and making peace. So I'm very much in a making peace mode. You know, I said what needed to be said. I think we stood up to a bully and a bad actor in the space. You're still standing up to him, it sounds like. It is working its way through the court system, which by the way, will take years. Seriously? The court date's not until 2027. And in the meantime, you're just paying lawyers? I think both sides are probably spending millions of dollars a month.

35:27Yeah, so that's not great for anyone. But how horrible does that feel as like a business person? Well, I do really understand how the legal system can be weaponized, particularly by actors with more resources against actors with fewer resources. And, or how there's just a lot of asymmetries in our legal system, some of which were created with good intent, but some of which have been, I think, exploited in ways that make things, yeah, very tough. So my advice to entrepreneurs, I know that's your audience, is whenever possible, avoid legal. And that's what I've done the vast majority of my career.

36:10This is actually the first time I've gone through a case like this. How close were you to striking a deal in private with them before going scorched earth? I thought we were close for, you know, 10 months. Really? And so what I realized was that, again, words and actions were not lining up. What was the sticking point? What was your contention? And what were you mad about? You know, I don't know. So it doesn't make sense to me on the other end. It doesn't appear to be because rationally, this could have been resolved so easily for, by the way, less money than we probably spent on lawyers in the past couple of months.

36:49Do you regret going this route? I don't regret my actions. I regret what happens. Absolutely. And by the way, I still maintain hope that it could be resolved because I do think it is rational. This inter-nesting warfare inside of WordPress doesn't benefit anyone. Including their business or yours? Either business or the WordPress community at large. When, by the way, we have proprietary and open source competitors, which are getting better every day. So it's very important that I think we resolve this. And, you know, that is, I'm doing everything I can on my end, but it takes two to tango. How much brain space does this occupy for you?

37:30Today, 5%. yeah so but you know call it november of last year it was 120 it was taking over everything which sucked that's also what i think was a little of a bit of a downer for me is i love being in the technology i love being with designers with product people with users with customers doing support and uh yeah not not engaged in sort of this like legal back and forth

38:01brutal yeah but this is a podcast called grit so thanks for covering it everybody says they want to go be a founder and ceo and do all these things they don't think about these things well uh you'll learn it really quickly so um yeah there's definitely by the way i would not trade my job for anything else in the world. I feel so lucky that I get to be able to work with the people I do on the, you know, the mission of democratizing publishing commerce and messaging, like these things like deeply, like get me up in the morning. But couldn't you go back to doing what you did originally? Like go back to just doing product and have someone else take these bullets, be the poop umbrella, as you said?

38:44I could have retired when I was 24 or 25. Right. Yeah. Right. But that gets old pretty quickly. So it's actually one of the nice things about taking breaks is, for me at least, it reminds me how important working is to just sort of my general mood and happiness. Like I need to be productive. Like I get so much fulfillment from making tools, enabling others, like working for something bigger than just yourself in a way that I just don't get from self-improvement or exercise or anything else that just affects me. You think work is the mechanism that gives you all that juice? What do you think about it?

39:27I won't call it just work. I will say that contributing to something larger than yourself that benefits people other than yourself is just fundamental to the human condition, contentment and happiness. Yeah. I'm going to butcher the quotes, but it was Will Durant's with this amazing, it's posthumously published called Leaves of Grass, I believe, or Fallen Leaves. And he says something to the extent of like, let us not wish for possessions or consumption, but for like to produce. That's where happiness lies. That's where joy lies, is in creation, not in consumption. You think you lose your mind sitting on the beach?

40:10I think resets are really, really important. And actually at Automatic, we have a policy where every five years you get a benefit, which is a two to three month fully paid tobacco. And if you don't take it, the clock doesn't reset until you take it. So if you wait till seven years, you don't get it again until 12. So we try to encourage people to actually take it. And in some ways, this seems, it's a huge pain in the butt because like, oh gosh, really key important people are going to be gone for a couple months at a time. And, you know, once you're mature enough, that also means that like anywhere from 10 to 20 % of your company might be on leave at a given time, especially when you add in parental leave and other things.

40:49However, it creates, it's fantastic for the person because they 99 % of the time come back with a renewed sense of mission, purpose, and drive. And then for organization, it's also really key because it eliminates single points of failure. it makes the organization infinitely more resilient and adaptable. Right. Because people, leadership opportunities allows you to sort of figure out where your weak points are in an organization that might've been overly dependent on one person. If your company can't keep running when one person is out for three months, there's something wrong. Yeah. And one month doesn't do it.

41:25Two weeks vacation doesn't do it even. It's really after that sort of like first four or five weeks that you start to like, oh, you can't just put things off so people are back. I was, I tried to do a vacation. I'm not great at them, but I gave it a good college try. And one day I was going with my fiance and her family to the beach and the beach might as well be a death sentence for me. Like sitting on a beach chair and just staring out over the water. Sounds idyllic, but it's like my nightmare. It's just too many ants in my pants. And so, you know, I was like maybe a little nervous. Said, hey, you know, I'm going to bring my laptop.

42:00Like, what do you think? And my fiance just got so excited because she knew like, all right, now we're going to be able to be at the beach all day and he's going to be busy. And I loved it. I was sitting there. I get to pop up, look at the water, back on my work. Yeah. I loved it. I don't know if I could do that every day. So what I found in my life is I try to think not about like work-life balance, like they're opposite of each other, but more like integration. And how do you like manage your energy throughout the day that you're getting some things that give you some energy and some things that where you spend it?

42:38So, you know, I'm somewhat nomadic. I'm on the road 200 plus days a year, you know, because my company automatic is distributed with people in 90 countries and WordPress and WooCommerce communities are open source is vastly distributed. And so when I'm on the road, particularly, I try to find little things I can do each day that might reset me. And because a lot of our work is asynchronous or on different schedules, I might be able to find a time to like take a slightly longer lunch and check out a museum nearby. Or if I were on a beach, maybe I try to go surfing in the morning or something. Wake up a little extra early.

43:11So I find those things, those daily resets are actually really, really critical for longevity and momentum. And then these sort of longer breaks where you actually do unplug are just, I think, good for like sort of resetting your adrenal cortisol, stress levels, everything like that. and it can be tough to do. But like you, if I'm on like a shorter vacation, I find I'm a little less stressed if I check in, even if it's just 10 or 20 minutes every day, just to like, you know, just kind of make sure there's no fire. It allows me to relax a little bit more than if I was like forcing myself to not look at anything.

43:45But I have taken a lot of trips and done a lot of things that do force you to unplug a little bit more. So I've gone to Antarctica twice. That was pretty fun. I like doing long hikes. So I've done pilgrimage hikes. of, you know, I did, I think, 100 kilometers in Japan. I did the Camino Santiago in Europe. I did like 100 miles on horseback in Iceland. So I try to look for opportunities or trips where... You have to unplug. Just by nature of doing it. Physically, literally. Water sports are great. So diving or surfing, right? Because you can't be on your phone while you're diving. So at least for a few hours, it forces you to really unplug, which is nice.

44:23What other activities have you, when you travel the like daily resets that you do? What are the things that you found that you like are kind of the old faithful things that you can rely on? Ah, well, I mean, creating products is also fundamentally a creative act. So I'm always looking for how I can get sort of creatively inspired. And for me, that might be art. Could be street art, could be museum, could be anything, galleries, or live music. and my particular passion is jazz. I actually sponsor a jazz club here in San Francisco called Keys Jazz Bistro over in North Beach. Yeah. I love jazz. Actually, I love jazz clubs.

45:05Please check it out. Live music Wednesday through Sunday. Can I go with you? I'd love to, yeah. Let's go. Yeah. Well, I don't want to talk about competition now, but you've obviously been to Mr. Tipples. Oh, I love them. So Mr. Tipples is great. Black Cats, Dawn Club. Yeah. So San Francisco is actually blessed with like four or five really great jazz clubs. Keys is, think of it as a little like more like an old school jazz club, like a little grungier and it's a listening room. So it's really designed like smaller for the musicians. The sound is really fantastic, but for like people to like really listen while the musicians are playing.

45:39Or something like a dong club, I'll go and have drinks and talk to friends and like you can sort of dip in and out of music. That's so cool. So sorry, what's your involvement with Keys? I co-founded it. Yeah, yeah. I don't know. How long has it been going for? The proprietor, Simon Rowe. I think we're like maybe a year and a half, two years in now. Oh, it's new. Yeah, relatively new. Post-COVID. Yeah. And Simon, who's a musician in the Bay Area for decades and actually used to be in Houston. We got connected through. We shared a mutual jazz teacher that connected us. Really just saw a space for someplace that was like really focused on more local musicians, not touring acts.

46:17Fair wage. So it has sort of like a paid musicians as well. and was more of like a listening room. So I want to go. Please. And then tell Simon, you know, I sent you like he's amazing. The funny thing is, I was just thinking about going to a listening room. Like if we were to go together, it's not really a good place to go together with somebody because you're not really catching up with them. You kind of have to plan like this before the show starts. And then you got some time afterwards. And if you stay for two sets, you have like half hour in between the sets. But it's kind of like going to a movie with someone.

46:45You really want to plan some shoulder time. Yeah, like lunch before. to talk about it or like engage with it afterwards. Cause I mean, you can whisper a bit during the show, but you're not going to want to like have a full conversation. Okay. Those are good outlets. Yeah. So, you know, you got to feed your soul as well. You can't live in just business or work all the time. I mean, look, you've obviously, you've been, you started this company 20, sorry, 20 years ago? We're press, yeah, automatic in 2005. So 20 years now. 20 years. like you're probably one of the longest standing, serious tech founders, period, right?

47:27Like I can't think of that many that are. Well, there's tons of generations before me, obviously. That are still kicking? Like that are still running the company? Absolutely. Like when was Facebook founded? I think around 2004, 2005, so similar time. Obviously like Sergey's still active at Google. That's about empathy. That doesn't count though. Okay, that doesn't count though. There's tons of examples. So yeah, I've learned a lot from previous generations. We're talking about like - And I'm also learning a lot from the younger generations as well. We're talking about Google and Facebook here and you, you know, like we're like, there's not that, but like, there's a pretty small list.

48:02So you've obviously figured something out about longevity. Well, for me, what's, well, two things. One are the environment has changed so much. So running WordPress or WooCommerce or any of our products today is so fundamentally different from what it was even five years ago or 10 or 20 years ago. So it's almost a wholly different company. Challenges change, the environment changes, the technology stack changes even. You know, WordPress used to be the majority of our new code was PHP. Now the majority of our new code is JavaScript because it's all about the interface, the interactions. So that for me keeps it very exciting.

48:39And through, as you mentioned, through acquisitions, we have expanded our remit somewhat. So like I said, mission is to democratize publishing, commerce, and messaging. So obviously we're best known for WordPress, wordpress.com. In 2015, we actually expanded into commerce. We have an open source Shopify called WooCommerce. And now there's over$30 billion of GMV, things sold through it. So that's very, it's great to enable other entrepreneurs. So that's a very rewarding mission. And also infinitely more complex than content management. You know, when you get into commerce, You have taxes, shipping, fraud, payments, everything.

49:14It's like, it's a pretty fun area from an engineering point of view. And then most recently with a product called Beeper, we're going into messaging. So Beeper, do you have like different messaging networks like friends on Telegram or LinkedIn or Instagram? So Twitter DMs, what Beeper does is it brings today, I think 11 different networks, only in one application. So you get like a single inbox, a single way to manage them, single interface for all these different networks. That's cool. Very cool. And it does it in a way that is fully local and secure. So messages don't touch our servers. You know, it maintains full encryption for things like Signal and others that support it.

49:50So it's been pretty fun. So we just actually... Slack too? It supports Slack, Discord. Yeah. We're still missing a few, like some of the Asian networks, like Line or WeChat or something. But that's part of what we're rolling out. And it's been pretty exciting, actually, because fundamentally, like... I always think about democratizing technologies. Like how can we put superpowers in the hands of users, but control data ownership, sovereignty in the hands of everyday people? And this feels like an area which is ripe for that. And actually used to have it. There used to be a lot of interoperability between the messaging networks.

50:29Actually, the first version of iMessage was iChat, which supported, well, Yahoo, I think ICQ, and actually an open source standard called XMPP. And over the past few years, there's typically cycles where technology swings from being more proprietary to more open or open source. And the seeds of destruction of one are contained in the other. So when things get too proprietary, it can be very profitable. But then companies often start to exert too much control or things that can be user hostile as their perhaps interest or sort of embedded growth obligations. You mean like Apple taking a 30 % take rate on all apps?

51:10uh that's you could argue whether that should be 30 or 15 but i would say more it may be like it's apple not supporting usbc for a long time or not supporting other browser engines or not supporting defaults changing your default applications might be a little bit more to what i'm talking about where there's no real technical reason to do that but there are some perhaps profit motives or growth obligations. And this can either be solved, one, through regulatory means, which is slow and often is screwed up, right? Well, meaning regulations can often sometimes cause like, you know, the opposite of what they intended, or the process gets sort of subverted by lobbying and influence, or it's reversed by open source competitors.

51:57So consumers, customers just demanding a more open alternative. iOS and Android, a great, beautiful example of this. And typically open source is at the key of that strategy. We're actually seeing it play out in AI now with proprietary models versus the amazing open source models coming out of China and France. And then when things swing too far through the open, typically what happens is companies or other actors take the open thing, kind of close it down, make a lot of money, and then it's sort of the pendulum swings again. but it's a it tends to be like a 7 to 10 year cycle and right now I would say we're at the nadir probably around like 2019, 2020 of things being like the most closed down that they will be in this sort of cycle and it's been on a nice swing towards more open ever since then.

52:49Do you think you can still work as hard as you used to? That's a good question. So, energetically some things are different. You know, I'm not like a 20 year old. I think when, and what I encourage people to do when they are younger is like really cherish that like kind of boundless energy and the fact that you, I think you're, you're just a bit more resilient. Yeah, absolutely. What do you define as younger? Yeah. Teen years and twenties probably. It changes every decade and it's different for individuals. Like you as a teenager, but yes, yes, yes. It's different for different people. So definitely like the thing that you should lean on there and lean into is kind of like this ability to bounce back so quickly.

53:31Like you can have pizza and Red Bull and like stay up for a night or two nights or something and kind of bounce back from it pretty quickly. Hangovers don't last as long, whatever it is. Like you kind of like a bit more resilient. And there is an aging process. So at 41 now, I think I have to be a bit more deliberate about nutrition, exercise, all these sorts of different things, which, by the way, I probably should have been doing the whole time anyway. But I think it's fine to kind of like be a little faster and looser in younger years. But it is a tradeoff. And I think as you age, you have to work harder at these things.

54:07But I don't think it diminishes what you're able to accomplish. And in fact, in many industries, including jazz, like some of the most musicians that we look at the best of their best work in like the 30s or 40s, mathematicians, entrepreneurs, like there's, there are great examples at every age. So I would say like, although media in particular loves to glamorize or idolize youth. And that certainly happened to me when I was the wonder kid at 19 or 20. But I would always try to avoid those articles or avoid leaning into those headlines. Why? Because I was like, well, what's the one thing I'm certain is going to change?

54:43I'm going to get older. Right. So your brand can't be the kid. Right. Or being the youngest in the room because you won't be. And I remember the first time there was like, I think when True Ventures funded me, I was like the youngest entrepreneur they had funded. And it was like a year and a half later, there was someone younger. I was like, okay, I'm not the youngest anymore. Great, finally. I don't have to wear that hat anymore. And you can really focus on like what matters, which is like having impact in the world to your customers, to the business, to your colleagues. So you're saying you can't work as hard.

55:11It's just impossible. No, I think you can work differently. So work smarter, not harder. And you can still punch it sometimes. It's just that you'll pay a price on the other ends. Like right now in Silicon Valley, there's this very interesting renaissance happening around hard work in a way that I haven't seen in quite some time. It might be intermixed with like there's more young folks coming into the valley right now chasing kind of the AI gold rush like everyone's coming West, you know, than I think we've seen in a long time. Like we just graduated our KP fellows program, which is 35 of the most bright engineers in the country that come and do an internship with us and spend the summer with us.

55:52And all their friends are out here. And it's like it's something to behold. And and maybe it's even getting a little bit too far where, you know, all these, you know, 20 year old folks are cranking like nine, nine, six. Yeah. Sleeping in the office, all that. And I heard the Eric Schmidt from Google give an interview where he was like, you know, I think his number was 64 hours. After about 64 hours, like he's like, that feels like I'm pushing it about as hard as I can and getting every last drop. Yeah. Out. And then beyond that, it's just not very productive. Yeah. I've been pushing it pretty darn hard recently.

56:40And I think I can get probably like, I don't know, you just start adding up the math on these weeks. And you're like, all right, if I were to do 70 hours, you know, it's like, that's a lot of hours. Yeah. And then, you know, if you try and start pushing past that, it's like, well, you can keep doing it. But my view is you're about half as productive. Like you need maybe more hours in the day, but you're probably about half as productive. Yeah. And what are you sacrificing in those other hours as well? Are you sacrificing relationships, family or health? But yeah. Does that framing feel right to you, Eric?

57:18Roughly, yeah. You know, I hesitate. I think where this conversation goes awry is when it becomes prescriptive. so one humans are different i think different people even genetically might have a need for more or less sleep or trump doesn't like trump can do it with like three hours of sleep bless him right that's uh that's awesome and um there's also there might be hidden things so maybe someone from the outside appears like they're doing really well but like something's a disaster privately or that you can't see so keep that in mind um the other part of the conversation that I think is missing is that there are periods when it doesn't feel like hard work.

58:03It feels just like joyful or like you don't even notice the hours passing. So I think that that is something that can be embedded in some of these discussions is there's definitely probably in weeks I've worked 70 or 80 hours, right? A ton. But it didn't feel like it because it was in flow or it was with colleagues or working on something fun where that same number of hours on legal stuff, for example, would completely burn me out. Totally. I think there's seasons to this as well for individuals, like time of the year, et cetera, but also for industries. So that's another thing that I think is a nuance which is missing from this conversation or dialogue often, which is that there's moments of opportunity when, you know, the industry is ripe for disruption or new technologies are enabling some new channel or some new mechanism.

58:55or something that you can build that you couldn't before, where there's kind of like a window of opportunity. You got to catch it. And so those are times when you probably need to lean in a little bit. But I would say that if you're running at 120%, 100 % of the time, that's a recipe for disaster. And I've seen colleagues do it as well. I've actually, I've forced people. I'm like, you cannot come to work tomorrow. I'm like, literally like, I'm not firing you, but I'm saying like, you need to take two weeks off because you're getting toasty. You're getting like, you're a little shorter in meetings.

59:28You're not showing up as your best self. So take that time to rest and recharge. And so the thing that ultimately, I would say that the one thing I will say as advice for everyone is measure output, not input. So - Yeah, but input's a nice mental model. It's a proxy, but it's just a proxy. Yeah, but it's still an interesting proxy. Yeah. And by the way - When people say they work 90 hours, 100 hours a week, I just don't believe them. I will also say that in a year, there are probably 15 or 20 hours of my work that define the entire year. Oh, what do you mean? The crucial times, the key meeting, key partnership, the key decision.

1:00:12Those are not about working long. It's about having the context, the wisdom, that it's those key pivot points that I think are actually like really, really important. And also, if you get those right, you know, those key decisions, those key things, you know, it can cover up a lot of stuff not going well the rest of the year. So or for a business. So what's yeah, that's why I say it's all about measuring the output, not the input. I think this is also for managers as well. Like, I'm not going to go to my company and say, hey, you all have to work 100 hours a week now because things are changing a lot.

1:00:48That's not motivating. That's not, um, what I do want to do is, you know, frame the opportunity, frame the thing we're doing, make work fun. So that's, you know, if we do need to, and also not make it like the fire alarms always going off. So if I am asking people to come in extra or that we need to sprint for a bit, that it's meaningful because it's not, I'm not, you know, crying wolf all the time. I'm not saying like, you know, this is a constant thing. It's really appropriate and contextual to opportunity, the challenge or the problem. Right. Like, yes, if your website is down or you've lost data, like not a good time.

1:01:27And to, you know, say like every 5 p.m. I'm going to like my kid up from school. No, emergencies happen. Stuff happens. But that's maybe a good rule for yourself if you find, you know, for a certain family situation or something like that, you know, as your default. so it's uh i think that when you incorporate the you know the sort of energy you get from the work that not all things are creating equal the mission which you're working towards if you feel like you have agency um and uh the fact that it's it's uh it can be you can flex and it's not always a sprint it's a marathon life and business is a marathon so remember that you might have to go fast sometimes or maybe going up a hill sometimes, but that's not like, if it is 100 % of the time, you're probably doing something wrong in someplace else.

1:02:18And you need to like re-examine, like maybe what could I have done a month ago, six months ago, so we wouldn't be having this emergency right now or this feeling like we're always in crisis. And you can be addicted to being in crisis as well. That's a common failure mode I see sometimes in somewhat very successful entrepreneurs is like this great Jerry Colon, a quote. How am I complicit in creating the conditions that I say I don't want? So if you always need to come into a project to save it, why is that? Well, it's kind of like in relationships. Like if you're 10 last relationships, the other person was a jerk or, you know, it's wrong.

1:03:02Like, what are you doing choosing those people? Or what are you doing in the relationship to cause that? So I think that that sort of self-reflection, again, measuring output, not input, is really important. So how could you make it so you don't need to come in to save a project or save a deal? And perhaps, is there a need to be needed? Is there a need to like, that's maybe subconsciously, it's always subconscious, there's unconscious things anyone does, but subconsciously creating the conditions, hiring the wrong people, not giving them the agency, not giving them support, maybe not allowing them to fail sometimes, which is crucial for learning, as we talked about earlier.

1:03:38that's creating this need or this gap. One other thing I wanted to ask you about is I've heard you enter barbecue competitions and you're quite good. Is that true? Not anymore, but for, there were a few years where - How did you do it anymore? I'd go every year to the World Championship of Barbecue in Memphis. Did you win? I think one year we got third place in pork shoulder, which sounds silly, but it's actually a really big deal. I was very proud of that. And also just like, it was fun being on, the Mississippi River for a few days. And it's kind of like Burning Man with meat. Like each team would set up like a little booth camp and you make the food.

1:04:16You can go to other booths and like eat for free. Essentially all the competitors would all share things. You'd share some secrets, not tell others. It's just kind of a fun little like time to be, you know, on the river in Memphis. Do you still barbecue? Oh, I still love barbecue and I still might grill out with friends or something sometimes. Although I will say, first and foremost, I'm not like a great chef or cook myself, but I have lots of friends. What do you mean? You've entered barbecue competitions. You're probably pretty good. I sponsor the team. Ah, and then you go and eat more. I wasn't the one like over the grill, like a smoker.

1:04:51But, you know, you do putting together a team as an art and everything in and of itself. So it's funny. We were one of the pretty much the only tech sponsor. And it wasn't even my company. I was just doing it personally and putting the WordPress logo on it. But the other one I found was Microsoft. Again, this one truck that had actually run a bunch of years. They listed their sponsors this year. And like in the mid 90s, it was Microsoft. And I dug into it and it turns out it was Nathan Mervald, actually. So the CTO of Microsoft is actually someone I've studied a lot. He's also types Dvorak. He's the reason the Dvorak keyboard layout is built into operating systems.

1:05:30It's basically a keyboard layout where instead of ASDF, it's like A-O-E-U. It's like more efficient. And I've typed this since I was like 13 or 14. So he's a great photographer and also a great like culinary fan. And he was actually, he turned me on to, I told him I was going to this competition. He's like, I used to go to that. He'd sponsor his team. He learned from barbecue. And some of his colleagues were going to be there this year from Intellectual Ventures, the co-author of Modernist Cuisine, Chris Young, and like a few other people ended up hanging out with them that year and they became my lifelong friends.

1:06:06That's awesome. It's actually, it's kind of fun. And like I said, like I find that, well, two things. One, I'm still building a company. So I, one advantage of us being distributed and asynchronous is that I can actually work a lot when I'm at these things. And two, I find it like a great recharge. I guess how I'm doing this so long is I get ideas or I meet people or I get user feedback or like something like that from engaging outside of the normal bubble that I'm default in every day of my colleagues or people in tech. It's awesome. Well, I appreciate you doing this. Thanks. Yeah, really fun.

1:06:46Yeah, I really appreciate it. We'll have to get some jazz and barbecue sometime. That'd be amazing. That'd be absolutely amazing. What's your favorite place in the city? For barbecue? That's a great question. Um, I prefer my own. Is that, can I, can I answer that? Sure. Um, I prefer the act of barbecuing and I can eat as much meat as I want. It just gets a little bit cost prohibitive and I want to do that other places. Yeah. Um, I think four or five Oh five is probably the best barbecue in the city. They're pretty consistent. Do you think that's a good take? That's a good take. I'll tell you a cool hidden tip, which is a Memphis minis, which has been around a long time over in Haight-Ashbury.

1:07:23On Wednesdays, they do a pastrami special. And that sandwich is really good. Really? Yeah. But they just do it on Wednesdays. So check out the Wednesday. Anytime Wednesday. Well, they run out sometimes. So like go a little bit earlier, but. All right. Well, maybe we should do that. So that way we can actually hang out instead of, or do that before we go to jazz. Sure. I'd be happy to. Yeah. Good. How much are you in the city? How often? I visit here a lot. Obviously, this is the mecca of tech. And I have lots of friends here and I kind of spent my twenties here. So yeah, it's a deep roots in the city.

1:07:56I don't know, at least a few days a month. Cool. Awesome. Well, I appreciate this. Are you hiring? We are, actually. And one, we're hiring for just our normal remote everywhere in the world roles. And we do literally hire everywhere in the world. And we pay the same salary ranges regardless of location. So it's a fantastic opportunity. But two, I will plug that we are doing something different for the first time ever, which is we are actually spinning up an in-person AI team. Where? in New York City. We have this fantastic space in NoHo in New York City and that we kind of inherited from the Tumblr acquisition that, again, because AI is just changing so quickly.

1:08:38We're going to do an in-person experiment where we'll have a team where they're choosing to be in the office every day as default. And it'll be one of our several AI teams, but I'm curious to see what we'll learn there. And the other thing we're doing And also just to sort of upgrade the whole company is that'll then become a space where every single engineer in the company will rotate through once or twice a year. That's awesome. So they'll come through New York to spend some time with that team, do a hack week, learn the latest and greatest in the tools. And just also, again, with AI, literally every week there's new things launching, there's new things to try.

1:09:15So just that having that high bandwidth, synchronous communication, I think is a bit more efficient than trying to follow everything all the time. That's awesome. That's awesome. Good man. When you hear the word grit, what do you think of? Ooh, I think of two things. I think of grit and the gears, right? You know, something gunking up the gears. And I also think of that great book by, was it Angela Duckworth? Yeah, which I read a long time ago and really inspired me. She was the inspiration and namesake of the show. Really? That's awesome. Had her on the show, actually, which was amazing. I'll have to watch that episode.

1:09:50Yeah, it was cool. Anyway, thank you. I appreciate you. That's it for now. If you liked the episode, please leave us a review or go back into the archives where we've done more than 200 episodes with some fantastic folks. This podcast is a Kleiner Perkins production, and I'm Juven. Thanks for listening.

1:10:13you

From the publisher

What kind of founder builds a billion-dollar company around something anyone can use for free?

Matt Mullenweg, co-founder of WordPress and CEO of Automattic, joins Joubin Mirzadegan to reflect on two decades of building the platform that now powers over 43% of all websites through cycles of doubt, decline, and reinvention.

He also shares how Automattic aligns employees with its mission to democratize publishing and commerce through paid sabbaticals and remote work.

Guest: Matt Mullenweg, co-founder of WordPress and founder and CEO of Automattic

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