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

The entrepreneurial journey is not just up and to the right. Companies go from being on the COVID of every single magazine to no one wants to touch them. But these struggles are what define you ultimately. Because WordPress really was a domain I registered, open 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 2 in the market. Companies often start to exert too much control. Or things that could be user hostile as their interest or sort of embedded growth obligations. This 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 Automattic.

Welcome to Grit. I'm Juven, 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 Automattic. 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. Automattic just celebrated its 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 6:00 AM leave and then leave 6:00 AM the next day, basically. And the next day, the inevitable 30-minute delay turns into a 3-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? Because 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 Wi-Fi, I'm good, golden, right? I could 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, starts with the MacBook, iPad, Daylight computer, which is really nice for like sort of Have you seen that?

Nope.

By the way, 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. Doesn't emit blue light at all. So, uh, it's an Android tablet, so it's like, uh, you can do pretty much everything on there. But yeah, so try to have different devices, different adapters, different, you know, things to just be useful in every situation. A lockpicking set. 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.

Sure.

Yeah. Have you ever had to pick a lock?

Yeah.

And WordPress now is like a very, you know, it's like a $7, $8 billion value. It's, it's like you've been doing this for 20 years. Like what, like what's its stat? Like 40, 45% or something of all?

Yeah. So over 40% of websites, I think it's 43 right now, uh, of websites are powered by WordPress, which is 10 times the number 2 in the market. And in 2005, I founded a company called Automattic, which is the— which has the valuation. So there's WordPress software and then there's Automattic, which is the for-profit side.

Got it.

So that, that's the company I run day to day. That'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?

Uh, 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.

So, 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.

And, and do you tell them you're the founder and CEO?

Oh, at some point, yeah. But not upfront. Or they might recognize, but like, yeah, usually not upfront. 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 Automattic since 2005.

And how old were you, 19?

I was 19 when WordPress started. Yeah, I was in, uh, college at University of Houston. Studying political science and making most of my money at that time actually playing saxophone, just gigs around town. And, uh, in Houston, Texas, uh, was 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, uh, is now WordPress.

It was interesting to me, I actually didn't know this, but you did not, um, you were not the CEO Were you not the CEO of— you hired a CEO in the beginning?

Yeah, actually. And one of our first meetings was right here in South Park. Um, so when Automattic, the for-profit company, started, um, this was a very, very different era of everything. Yeah. It wasn't sort of the, the founder mode or founder-led era. Yeah. It was more the Google era where like the founders of Google hired a CEO, Eric Schmidt. Um, So, and I was also 20 years old, had no idea how to run a company. And a journalist, actually, Om Malik, uh, introduced me to this amazing entrepreneur named, uh, Tony Schneider, who had just sold a company called Oddpost to Yahoo. Um, it was a big exit at the time on the COVID of magazines and everything. And, uh, Om said to Tony, uh, you're not going to last at Yahoo too long. You're going to want to do another startup. Meet this kid out of Houston. Matt Mullenweg was an early WordPress user, and Tony and I met, and our first meeting, which was supposed to be an hour, turned to like 6 hours. We just meshed on every single level. So 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, where we're going to do things the same, and has a ton of experience building companies before. So, um, so I was the original CEO, but I, I was probably 6 or 8 months later, Tony joined, uh, the company. I got him to leave Yahoo and join, and he was CEO for the next 9 years.

And then, sorry, 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 what OpenAI and others have done, but why did you do the nonprofit WordPress and the for-profit parent company Automattic?

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, in the United Kingdom, who sort of was the other main contributor to WordPress. We 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 a 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, uh, 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, uh, led us to launch the company Automattic.

Fascinating. And now Automattic 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. Uh, but the, um, uh, 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.

Yeah.

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, um, uh, you know, have open source at the center of everything we do. Yeah. Um, and then just the whole Web 2.0 social media, blogging, publishing, you know, people basically, uh, knowing that they didn't have to go through intermediaries. Like, they could, they could publish themselves. They could use the same software. Yeah. By the way, that's CNN or the New York Times does. Yeah. Uh, 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, uh, Sitting down with you now, you're a very nice, gentle human being. But it's funny, when you go on the internet and look you up, obviously I've done all my homework. It's like, you know the quote, "You either die a hero or live long enough to become a villain." I feel like that's what's happened to you. 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 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 know, you're at the top of the world or you can't do no right. Um, it is totally a cycle. And the longer you're an entrepreneur, the longer you're CEO, you'll see that not just you will go through it, but every company goes through it.

Yep.

Um, you know, companies go from being on the COVID 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% drawdowns on their stock. You know, Facebook, Google, Amazon, like all these have had like incredible— Apple being days from death. So, um, 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. 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, if 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, like you must have 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, um, it was, I guess, 2005. Uh, I had made a major, major, major screw-up, which is, um, 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, um, someone came to me and was like, hey, I'll give you $2,000 a month if you, uh, put these, uh, links on wordpress.org because I have all this great, like, content I've been publishing, but people, you know, in other countries are stealing it and they're ranking higher than me in Google. So like, we need to associate with a domain. This all sounds very obvious now, but at the time I was like, oh, well, so sure. So set up a little proxy on a subdirectory and, um, actually invented, uh, a way to, 'cause I was like, all these links are kind of ugly. Let me hide 'em 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, uh, so yeah, had these links and they were there for like 4 or 5 months, and then someone discovered them. And at the time, Google, uh, WordPress.org had a PageRank of like 8 or 9, or the highest ranked sites on the internet. And, um, you know, it started, started to rise in prominence. And 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, uh, she was I think in Tennessee or Baltimore at the time. And, uh, 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 were in Venice and, uh, again, long time ago. So there weren't like cell phones, there wasn't common Wi-Fi. 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. And I was like, hey Charlene, how 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's 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, um, Slate, everything was covering this story. And 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 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 MacBook and the hotel had no Wi-Fi. So I just started walking around the streets because at the time Wi-Fi networks were often, um, had no password. So you could, uh, have you ever heard of war driving? Uh, no. 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 AM. Um, you know, we'll, you know, take a water taxi to 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, um, got online and just like the whole internet had exploded. And it was one of these things where like there were people defending me, there were people attacking me. Um, 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, um, it was definitely a learning—

how long, how long does that, like, uh, from that moment until it goes away, how long does that last?

Oh, well, that's a good question. Um, 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? So you have to respond. Yeah, 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 erred on the side of being overly transparent and engaging with critics, engaging with even hostile press. Um, 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, uh, sort of lead with transparency and, uh, it's better and worse. I feel like that's better in the long run. And, uh, so yeah, news cycle was probably about a, a week, although it felt like to me like the end of the world. Um, people asking you about it. You know, it was probably 3 to 6 months. Uh, it stayed on my Wikipedia page for probably 4 or 5 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. I had like this karmic debt. I was like, okay, Oh, 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? Meaning like, if you, if you, 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, 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. However, um, 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 the fair-weather friends. Um, 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.

And do they—

I've probably been canceled 7 times since then.

Yeah, you're like going through one probably right now.

Uh, it's actually a little bit on the downside.

You're saying you're post-cancellation right now?

Well, cancel— that's not canceled. The cancel is like a whole separate thing. More like a controversial—

getting dragged through the mud.

Yeah. Yeah.

Um, but I still look up articles and it doesn't, they're still, uh, heated.

Absolutely.

They still have strong opinions about you.

Well, and some of this stuff echoes. So sometimes people, you know, uh, it's kind of like that, uh, a lie travels around the world 7 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, if there's a correction issued, that correction usually does not get covered as much. Um, do I read news? I, I do, yeah, just because I, 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. So, uh, you should be able to argue the opposite side to really advocate for something you believe in.

It's not the same, but I've given completely up on reading any articles about the podcast or any of the comments in YouTube. Half 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 I've 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, it's, uh, very incendiary. They used to joke about, you know, you got to put on your asbestos underwear to survive the flame wars. So I do feel like Maybe the modern version of that is you, you need to develop a sort of grounding and a little bit of a psychic armor to, uh, be able to engage with these things but not become these things, if that makes sense.

So you're saying I'm soft?

I'm not saying you're soft.

It's fine, you could say it.

Um, I'm saying that, uh, that— well, let's say you're soft. That's okay. Yeah, everyone's soft. Yeah. You know? Yeah. Everyone has a soft side. We all need to have a soft side. Um, that's, uh, you know, every sinner has, uh, every saint has a past and every sinner has a future, right? We're all human. We're all fallible. Everyone makes mistakes. Um, there was, what's the joke? There was, there's one perfect man and they crucified him, right? Like there's, there's no, like, Every story of humanity, of religion, of myth, of 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, there's micro versions of this, um, you know, the 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 one, everyone you admire has also been through some really tough times when they also felt down, like a failure, like nothing could go right. And just got to get up the next day, keep grinding, keep going at it, keep, keep doing what you believe in. Um, and that will ultimately, you know, lead you to a better place.

Of the 7 or 8, um, trials and tribulations, let's call it, that you've gone through, what, what was the one that hurt the most? Is it this one now?

Oh no. Um, gosh, what hurt the most? Well, I guess you could categorize them. Um, the one we talked about at the beginning, Hot Nacho. That was one where I legitimately screwed up.

Yep.

So that sucks, right? That's going to happen, by the way. No one is error-free or mistake-free. Um, ones that hurt the most, gosh, uh, you know, it's kind of one-way and two-way doors. So some mistakes, some decisions are reversible and some are not. So when there's a reversible decision, um, 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 in that sort of 4-box, things that if you weren't wrong and it's reversible, easiest. You were wrong, it's reversible, maybe less bad. You weren't wrong, but it's non-reversible. A little less 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?

Oh, good question. Well, and one of the things. I do for colleagues, you know, fellow developers in the WordPress.org 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 reexamine your priors and say, ah, maybe I was wrong about this, or maybe the environment's changed and I should do something different. And, um, there's other cases where, well, you know, uh, the arc of history will prove you right. 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 had just polled people or done a survey, it would have not got a majority vote. But you could, um, 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, um, great products. You often have to do things that in the beginning do not seem obvious or perhaps even get a huge backlash. Again, this is going to sound like a very trivial example, but do you remember when the Facebook newsfeed launched? Mhm. And the first thing people did was use the newsfeed to organize petitions that got millions and millions of people commenting and liking it, saying the newsfeed was the worst thing and that they should get rid of it. So, uh, 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, is it's remarkable, um, how much pushback anything new can get. And how many things, um, we now see as like sort of fundamental to the human experience are just like, they're like water. We don't even think about it anymore. And that at the time people said was the end of society or was gonna ruin the kids or like, you know, screw us up, uh, in some unrecoverable way.

Do you feel like people are saying that about the new technology? Like, uh, about these LLMs?

Uh, well, of course. Yeah.

Sure seems like it.

And, 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, um, to sort of be able to use in a way that actually is beneficial to us.

You, you strike me as a real technologist's technologies. Like, you really, like, uh, 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 is like when it becomes part of society. Like we don't think of like 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, you know, people saw a mirror and they were like, what is this? This is evil. Are there demons on the other side? Like it's a portal to another universe.

You said you're on the downslope of the most recent, I don't know, controversy.

Yeah.

Are you on the downslope? Why do you say you're on the downslope? Do you wanna define, do you wanna give your perspective of what it is?

I'll give like a 1-minute TL;DR. Like 1 minute, which is, uh, we'll be brief also cuz this is a legal battle, but, uh, you're still in it. I'm still in it. There was a company, uh, in the WordPress space called WP Engine, um, that many people thought was an official WordPress project or associated with Automattic. Principally because of the way they were using and misusing, we believe, uh, the WordPress and WooCommerce trademarks, which in open source you can use the code, you can do everything, but like you still have to have trademark protection, right? Um, not unlike a Coca-Cola or anything, any other large brand. Um, 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 it started taking a turn for the worse and it didn't resolve privately. So I gave a speech basically saying like, hey, 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, their words and actions are not lining up., um, and this was pretty controversial. And this company is also backed by a huge private equity firm, over $100 billion. And, um, so they have a lot of resources to fight this. Yeah. So this is definitely the time when, um, how 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 end, but definitely the sort of like characteristics of this particular thing, because it's inside of WordPress, uh, private equity owned, there's like, there's lots of, uh, 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, uh, 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. 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? Define dark. Made me want to walk away from everything. When you devote your whole life to 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, um, and then to essentially be like dragged through the mud, attacked, pilloried, all these sorts of things, um, yeah, it does make you, uh, sort of question like, well, is this worth it? So So to my— 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 it, 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, um, there was, I think, 2 weeks at the end of the year or a week at the end of the year, sort of between Christmas and New Year's. Uh, we sort of like paused some things on wordpress.org. Automatic, which by the way contributes, has contributed over the years hundreds of millions of dollars in developer time and everything to 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, I couldn't stay away. I love open source so much. It is really my life mission. Um, like I feel like I was put on this planet with a challenge and an opportunity to help technology, which shapes 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 the mission of open source. And it's encoded into the very license. It's like a Bill of Rights or a Constitution that's embedded in the way the software runs. These are inalienable rights. No one can take them away from you. And, uh, I do feel like that's, 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, uh, being attacked for it. So, uh, we turned everything back on, dove back into WordPress.org, started contributing open source again, everything. And, um, And it's actually been hugely reenergizing and a great rest of the year cuz 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.

So can I ask, what did you do during that week?

Oh, I just spent time with family. It was Christmas and New Year's. You went to Houston? Oh yeah. Yeah. Yeah. Uh, you know, spent time with loved ones. Um, unplugged, stopped reading the internet as much.

It got particularly, maybe a glass of wine.

Uh, stopped trying to engage with everyone. Um, there is something, if there is something different this time, it is that, um, 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. So 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 in Yeah, so, uh, that's not great for anyone.

But how, like, how horrible does that feel as like a business person?

Well, I do really understand how the legal system can be weaponized, um, particularly by actors with more resources. Yeah, against actors with fewer resources. And, or how it— 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, um, in ways that make things, uh, yeah, very tough. So, uh, 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. This 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? Yeah. And so what I realized was that, um, again, words and actions were not lining up.

What was the sticking point? What was your contention and, and what were you mad about?

You know, I don't know. It doesn't, doesn't make sense to me on the other end. Um, 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 months. Do you regret going this route?

Um, I don't regret my actions.

I regret what happens. Absolutely. And, um, and by the way, I still maintain hope that it could be resolved because I do think it is rational. This internecine 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're— we have proprietary and open source competitors which are getting better every day. So it's very important, um, that I think we resolve this. And, you know, that is— I'm doing everything I can on my end, uh, but it takes two to tango. How much brain space does this occupy for you today? 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 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. Brutal. 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 umbrellas, you say?

I could have retired when I was 24 or 25, right? Yeah, right. But, um, that gets old pretty quickly. So it's actually one of the nice things about taking breaks is, uh, for me at least, it reminds me how important, um, working is to just sort of my general mood and happiness. Like, I need to be productive. Like, I, I get so much fulfillment from making tools, enabling others, like working for something bigger than just yourself, um, 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?

Um, what do you think about it? I won't call it just work. I will say that contributing to something larger than yourself. Yeah. That benefits people other than yourself is just fundamental to the human condition, contentment, and happiness. Yeah. Uh, I, I'm gonna butcher the quote. Um, but it was, uh, Will Durant with this amazing, it's posthumously published called, uh, Leaves of Grass, I believe. Um, or Fallen Leaves. And, uh, he says something to the extent of like, let us not wish for possessions or consumption. Uh, 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?

I think resets are really, really important. And actually at Automattic, we have a policy where every 5 years you get a benefit, which is a 2 to 3 month fully paid sabbatical. And if you don't take it, the clock doesn't reset until you take it. So if you wait till 7 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, ah gosh, really key important people are going to be gone for a couple months at a time. 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. However, it creates, um, 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, uh, eliminates single points of failure. It makes the organization infinitely more resilient and adaptable, right? Gives people leadership opportunities, allows you to sort of figure out where your weak points are in an organization that might have been overly dependent on one person. If your company can't keep running when one person is out for 3 months, there's something wrong. And one month doesn't do it. Two weeks vacation doesn't do it even. It's really after that sort of like first 4 or 5 weeks that you start to like, oh, you can't just put things off so people are back.

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 fiancée 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 I was maybe a little nervous, said, hey, I'm going to bring my laptop. What do you think? And my fiancée just got so excited because she knew, all right, now we're going to be able to be at the beach all day and he's going to be busy. Mm-hmm. 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, is I try to think not about like work-life balance, like that they're opposite of each other, but more like an integration. Mm-hmm. 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. So, um, you know, I, I'm somewhat nomadic. I'm on the road 200+ 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. Um, 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 run a beach, maybe I try to go surfing in the morning or something. I wake up a little extra early. So I find those things, those daily resets, are actually really, really critical for longevity and momentum. Um, and then these sort of longer breaks where you actually do unplug are just, uh, I think good for like sort of resetting your adrenal cortisol stress levels, everything like that. And it can be tough to do. Um, 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 fires. Allows me to relax a little bit more than if I was like forcing myself to not look at anything. Mm-hmm. But I, 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. Sick. That was pretty fun. Um, I like doing long hikes, so I've done pilgrimage hikes. Of, uh, you know, I did, I think, 100 kilometers in Japan. Uh, I did the Camino Santiago. Wow. Uh, Europe. I did like 100 miles on horseback in Iceland. So I try to look for opportunities or trips where you have to unplug. Yeah, just by nature of doing it physically, but 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.

What other activities have you, when you travel, the like daily resets that you do, what other things have 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. Uh, 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, I love jazz. Actually, I love jazz clubs. Please check it out.

Live music Wednesday through Sunday. So 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, Mr. I, I love them. So Mr. Tipples is great, Black Cats, uh, Don Club. Yeah, so San Francisco is actually blessed with like 4 or 5 really great jazz clubs. Keys is, is think of it as a little like more like an old-school jazz club, like a little, 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. Or something like a Don Club. I'll go and have drinks and talk to friends and you can sort of dip in and out of the music.

That's so cool. So sorry, what's your involvement with Keys?

You own it? I co-founded it. Yeah, yeah.

I didn't know that. How long has it been going for?

The proprietor, Simon Rowe. I think we're like maybe a year and a half, 2 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. Um, really just saw a space for someplace that was like really focused on more local musicians, not touring acts. Uh, fair wage, so it has sort of like a— pays musicians well and, uh, was more of like a listening room. So I want to go. Ah, please. And then tell Simon, you know, I sent you. Like, he's, 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, there's, there's before the show starts, and then you got some time afterwards. So you got like And if you stay for 2 sets, you have like half hour in between the sets. Yeah. Um, but it's kind of like going to a movie with someone. You really want to plan some shoulder time. Yeah. Like lunch before, talk about it or like engage with it afterwards. Cause, um, 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 I, you know, you got to feed your soul as well. Um, uh, you can't live in just business or work all the time.

I mean, look, you've obviously, you started this company 20 years ago.

WordPress. Yeah. Automattic in 2005. So 20 years now.

20 years. You're probably one of the longest standing serious tech founders, period. Right? 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. Yeah. Like when was Facebook founded?

I think around 2004, 2005. So similar time. Um, obviously like Sergey is still active at Google. That's right.

And is reengaged.

There's tons of examples. Um, so, uh, yeah, I, I've learned a lot from previous generations. We're talking about like, and I'm also learning a lot from the younger generation.

We're talking about Google and Facebook here and you. You know, like, we're like, there's not that— like, it's a pretty small list. So you've obviously figured something out about longevity.

Well, for me, what's, uh, well, two things. One, our— the environment has changed so much. So running WordPress or WooCommerce or anything, any of our products today, is so fundamentally different from what was even 5 years ago or 10 or 20 years ago. So it's almost a a totally 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, you know, because it's all about the interface, the interactions. So that for me keeps it very exciting. And through, as you mentioned, through acquisitions, we have expanded our remit somewhat. So, um, like I said, mission is to democratize publishing, commerce, and messaging. So obviously we're best known for WordPress, wordpress.com, Uh, in 2015, we actually expanded into commerce. We have an open source Shopify called WooCommerce that now does over $30 billion of GMV, things sold through it. So that's very— wow. It's, it's great to enable other entrepreneurs. So that's a very rewarding mission and also, uh, infinitely more complex than content management. You know, when you get into commerce, you have taxes, shipping, fraud, mm-hmm, payments, everything. It's like, yeah, it's a pretty fun area from an engineering point of view. And then most recently, uh, with a product called Beeper. We're going into messaging. So Beeper, um, do you have like different messaging networks, like friends on Telegram or LinkedIn or Instagram or so, Twitter DMs? What Beeper does is it brings today, I think, 11 different networks all 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, that maintains full encryption for things like Signal and others that support it. So, uh, it's been pretty fun. So we just actually— Slack too? It supports Slack, Discord. Yeah, we're still missing a few, like, um, some of like the Asian networks like Line or WeChat or something, but, uh, that's part of what we're rolling out. And it's been, uh, pretty exciting actually, because, you know, 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, you know, the hands of everyday people. And, uh, this feels like a, uh, an area which is right for that. And actually used to have it, you know, there used to be, uh, a lot of interoperability between the messaging networks. Uh, actually the first version of iMessage was iChat, which supported AOL, Yahoo, uh, I think ICQ and, and, uh, and, uh, actually open source standard called XMPP. Mm-hmm. 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 could 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?

Uh, 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 USB-C 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. Um, 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, uh, you know, the opposite of what they intended, um, or the process gets sort of subverted by lobbying and influence, or it's, uh, reversed by open-source competitors. So consumers, customers just demanding 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, um, and then when things swings too far to the open, typically what happens is, is companies or, or other actors, um, 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 were 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, uh, it's been on a nice swing towards more open ever since then.

Do you think you can still work as hard as you used to?

That's a good question. Um, 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? Um, yeah, uh, teen years and 20s probably.

Um, 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. Yeah, yeah. Definitely like the thing that you should lean on there and lean into is kind of like this ability to bounce back so quickly. Yeah. Like 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. Um, hangovers don't last as long, whatever it is. Like you kind of like, uh, 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 trade-off. And I think as you, as you age, like you have to work harder at these things. But I don't think it diminishes what you're able to accomplish. And in fact, in many industries, including jazz, like some of the, the most musicians that we look at the best did their best work in like their 30s or 40s. Mathematicians, entrepreneurs, like there's, there are great examples at every age. So I would say like, uh, although media in particular loves to glamorize or idolize youth, um, and that certainly happened to me when I was the, 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? I'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 a— 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 wasn't 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?

It'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, uh, you'll pay a price on the other ends.

Like, uh, 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. Yeah. 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, in the country that come and do an internship with us and spend the summer with us. And 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 all these 20-year-old folks are cranking like 996, sleeping in the office, all that. And I heard Eric Schmidt from Google give an interview where he was like, I think his number was 64 hours. He was like, after about 64 hours, He's like, that feels like I'm pushing it about as hard as I can and getting every last drop out. And then beyond that, it's just not very productive. I've been pushing it pretty darn hard recently, and 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, it's like That's a lot of hours. And then if you try and start pushing past that, it's like, well, you could keep doing it, but my view is you're about half as productive. 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? Which— yeah.

Does that framing feel right to you, Eric?

Um, roughly, yeah. Uh, 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, a need for more or less sleep, or Trump doesn't, like Trump can do it with like 3 hours of sleep. Bless him. Right. Yeah. 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. It 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 been weeks I've worked 70 or 80 hours, right? A ton. But, um, it didn't feel like it because it was in flow or was with colleagues or working on something fun where that same number of hours on legal stuff, for example, would completely burn me out, depress me. Um, I think there's seasons to this as well for individuals, uh, 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, the industry is ripe for disruption or new technologies are enabling some new channel or some new mechanism or 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 2 weeks off because you're getting toasty. You're getting like— you're, you're a little shorter in meetings. You're not, you'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.

Um, and by the way, uh, like 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, the key partnership, the key decision— those 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 honestly, 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. Um, 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. That'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, you know, if we do need to, and also not make it like the fire alarm's 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. And to, you know, say like every 5 PM I'm gonna like pick my kid up from school. No, emergencies happen, stuff happens. Um, 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 created 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, 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 you might be going up a hill sometimes, but, um, That's not like, if it is 100% of the time, you're probably doing something wrong in someplace else. Mm-hmm. And you need to like reexamine, like maybe what could I have done a month ago, 6 months ago, so we wouldn't be having this emergency right now, or this feeling like we're always in crisis. Mm-hmm. And you can be addicted to being in crisis as well. Um, that's a common failure mode I see sometimes in somewhat very successful entrepreneurs is like, uh, this great Jerry Colonna 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 your 10 last relationships, the other person was a jerk, or, you know, it's wrong, like, what are you doing choosing those people? Or what'd you do 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? Or, um, and perhaps like, 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. That'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 there were a few years where— Why don't 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, you know, the Mississippi River for a few days. And, and, uh, it's kind of like Burning Man with meat. Like each team would set up like a little like booth camp and, um, and you make the food. You can go to other booths and like eat for free. Essentially all the competitors would all share things. You'd, you'd share some secrets, not tell others. It's just kind of a fun little like, uh, time to be, uh, you you know, on the river in Memphis. Do you still barbecue? Oh, I'll still— I still love barbecue, and I still, um, might grill out with friends or something sometimes. Although I, I will say, first and foremost, I'm, I'm not like a great chef or cook myself, but I, I have lots of friends who are. What do you mean?

You entered barbecue competitions? You're probably pretty good.

I sponsor the team.

Ah, and then you go and eat.

I wasn't the one like over the grill, like, uh, or a smoker, um, but know, you do— putting together a team is 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. Uh, but the other one I found was, um, uh, Microsoft. Again, this one truck that had actually run a bunch of years, um, they listed their sponsors each year, and like in the mid-'90s it was, uh, it was Microsoft. And I dug into it and it turns out, uh, it was Nathan Myhrvold actually. So the CTO of Microsoft, who's actually someone I've studied a lot. He's also types Dvorak. He's the reason the Dvorak keyboard layout is built into, um, into operating systems. It's basically a, a keyboard layout where instead of ASDF, it's like AOEU. It's like more efficient. And I've typed this since I was, uh, like 13 or 14. So, um, he's a great photographer and, and also a great, like, uh, culinary fan.. And, um, and he was actually, uh, he turned me on to, I told him I was going to this competition. He's like, oh, I used to go to that. And he'd sponsor his team. He learned from barbecue. And some of his colleagues were going to be there this year from, um, uh, Intellectual Ventures, the co-author of, of, uh, Modernist Cuisine, uh, Chris Young and like a few other people end up hanging out with them that year and they became my lifelong friends. That's awesome. It's actually, it's, it's, it's kind of fun. And like I said, like, uh, I find that, um, well, two things. One, um, 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. You asked how I'm doing this so long, is, um, I get ideas or I meet people or I get user feedback or like something like that from engaging at outside of the normal bubble that I'm default in every day of my colleagues or people in tech. That's awesome.

Well, I appreciate you doing this. Thanks. Yeah, really fun. Yeah, I really appreciate it.

Well, 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. I prefer my own. Is that, can I answer that? Sure. I prefer the act of barbecuing and I can eat as much meat as I want. It just gets a little bit cost prohibitive when I want to do that other places. Yeah. Um, I think 4505 is probably the best barbecue in the city.

Yeah. They're pretty consistent.

Do you think that's a good take?

That's a good take. I'll tell you a, a cool hidden tip, which is, uh, Memphis Minis, which has been around a long time. Okay. Over in Haight-Ashbury on 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. Be happy to. Yeah. Good. How much are you in the city?

How often? Um, I visit here a lot. Obviously this is the mecca of tech. Um, and I have lots of friends here and I kind of spent my 20s here. So yeah, it's a deep roots in the city. Um, I don't know. Uh, at least a few days a month. Yeah. Cool. Awesome.

Well, I appreciate this. Um, 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. Uh-huh. We have this fantastic space in, uh, NoHo in New York City. And, um, that we kind of inherited from the Tumblr acquisition, uh, that, uh, again, cuz AI is just changing so quickly, we're going to do an in-person, uh, experiment where we'll have a team where they're choosing to be in the office every day as default. Um, and, uh, it'll be one of our several AI teams, but Um, I'm curious to see if, uh, what we'll learn there. And the other thing we're doing 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, through New York to spend some time with that team, do a hack week, learn the latest and greatest in the tools. And, and just also like, again, with AI, literally every week there's new things launching, there's new things to try. So just that, uh, having that high bandwidth synchronous, uh, communication I think is, uh, 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. Um, I think of two things. I think of grit in, in 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.

Yeah, it was cool. Anyway, thank you. I appreciate you. That's it for now. If you like 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.