Lessons in longevity: How Matt Mullenweg scaled Automattic to $500M+ (and what's next)

0:00And I like to think of things you can do when you're small that are very difficult when you're large or when your competitors are large. and that really really really high touch people building the product doing the frontline customer support you can't do forever at some point it becomes too much but the longer you can do it the better and it pairs with like really tight product quality feedback because you really do need to be completely friction free welcome to the sas revolution show the podcast by sas.com here we interview sas founders from around the world who've been there and done that as they share the ins and outs of how they built their businesses, their operations, their path for securing investment, and more.

0:40Our mission with the podcast is to help you, the founder, learn how to scale your SaaS, maintain your well-being, and navigate the complexities of this ever-changing industry. I'm your host, Alex Thiemann, and together, we'll explore the good, the bad, and the ugly in the journey to SaaS success. All right, welcome back to the SaaS Revolution Show. I am your host, Alex Thiemann, CEO, founder of SaaStock, also general partner of BackFuture Ventures these days and delighted to be joined for the first time in the podcast. We've been going for 10 years and I'm really excited to have this conversation with Matt Mullenweg, who's CEO and founder of Automatic.

1:18How are you doing, Matt? I'm doing fantastic. Thanks for having me on today. Yeah, great. Great to have you in the podcast. And are you dialing in from Texas, specifically Houston? Is that where you're based? Oh, I am based in Houston, Texas. Yes. Although today I'm in Montana. Today you're in Montana. Okay. Very nice. I've been watching with my partner, Yellowstone, where we're a little bit behind the curve, but I think I'm on season four now. So like we've been cracking onto that. So are you on vacation there in, I almost said Yellowstone, in Montana? And is it anything like the series? Doing some work from here and seeing some friends.

1:57so awesome awesome uh good stuff well thanks for coming on the show matt we always ask our guests to kind of like kick off who they are so i'm not going to buck the trend uh so i'd love to know know who is matt mullenweg sure yeah i say matt mullenweg born and raised in houston texas which is still my home base today but um when i was 19 i co-founded a software called wordpress open source publishing software and then when i was 20 i moved to san francisco take a job I dropped out of college to take the job and then a year after that founded the company Automatic, which I'm the CEO of today. And Automatic, the idea was creating SaaS services around open source.

2:37So we did a SaaS version of WordPress, WordPress.com. We have sort of a small business version called Pressable for agencies and things. Enterprise version called VIP, run some of the largest WordPress sites in the world. And we also run Tumblr, just sort of like as a thing we acquired a few years ago. Our mission is to democratize publishing, commerce, and messaging. And so cover the publishing. In commerce, we've got an open source Shopify called WooCommerce, which is an extension for WordPress. But, you know, it's ginormous. Over 30 billion of goods and services are sold every year through WooCommerce.

3:12And finally, in messaging, I'm very excited there because we've got a brand new thing called Beeper. Beeper.com. It's in beta right now when you hear this. Basically what it does is it takes all of your messaging apps, all of your messaging DM platforms, whether that's LinkedIn DMs, Telegram, Signal, basically everything, and brings it all to one app. So you can sort of manage everything across everything. So if you ever remember, this used to work like 15 years ago. There was programs like ADM and stuff like that, but they all broke. So Beeper's got this really amazing technology that's kind of reverse engineered all different networks.

3:51and also just the regulatory environment is good for this. So it brings them all together and it's a great experience. Outside of, I can imagine, although you've been building software, scaling a business for a large part of your life, outside of that, I imagine that consumed the majority of your life, right? But outside of that, what do you like to do? How do you get away from maybe just the day-to-day of what you're doing? The two big things for me are jazz and photography. So my username on everything is Photomat, P-H-O-T-O-M-A-T-T. And that's because I actually have uploaded over 30 ,000 photos over the years and I do a lot of photography.

4:37Less carrying around the giant camera these days. You know, they say the best camera is the one you have on you. And the iPhone is pretty incredible. Actually, all the smartphones are pretty great. I've got a Pixel 9 as well. so that's probably what I do a lot of my photos on today but occasionally if I'm doing a special trip I'll bring the big rig out on the jazz front are you playing or are you just listening are you going to like you know jazz cafes or whatever jazz was my original thing so I was very lucky that the public schools in Houston had amazing music programs so I started playing saxophone in second grade I ended up going to a performing arts school I called HSPVA where there's no sports but we did you know three hours of our art area every day which for me ended up being jazz saxophone great school like Beyonce went there Robert Glasper like all sorts of amazing musicians and artists and actors and and um so how I got started building websites was I barter with local jazz musicians a you know I build them a website in exchange for like 10 lessons right because lessons are pretty expensive so uh yeah that was how I got started with everything um my old user name was Saxmat, like saxophone.

5:49So I switched to Photomat when it got hard to carry my saxophone. You know, I was traveling a lot for WordPress, like visiting communities all over the world. So yeah, that's how it all got started. So today I play a little bit still. And I'm also the co-owner of a jazz club in San Francisco called Keys Jazz Bistro, which has live music Wednesday to Saturday. And any city I go to, I always try to find good live music, a lot of jazz, but also I enjoy all live music. And then in Houston, all the people I grew up with are the jazz musicians. Would it be easier to own a jazz cafe in Houston or in Texas?

6:26Oh, it's funny because San Francisco actually has four or five great jazz clubs, jazz venues. Houston right now has no dedicated ones. although one's opening in a few months in july called docks so um yeah just a funny thing where the markets end up being a little different now the cool thing about houston is um there's great live music uh lots of restaurants so lots of restaurants so amazing musicians will play at like you know eddie v's you know or something like that on wednesdays is one of my favorite ones to go to it kind of like austin you know how there's just like this great live music culture everywhere so houston has that too what can we do to get you playing the saxophone and taking photos at sassock usa i don't know i don't want to drive away your at your conference attendees not as good as i used to be but um yeah no as you said there's a huge amounts of uh music and great music in austin uh so we would expect uh certainly the welcome parties maybe at the conference itself some uh i don't know some austin infused texas uh uh style uh music uh for sure so um uh watch watch out for that a big passion of mine is getting creators paid you know and that's something we do a lot with open source and you know wordpress and everything so um that was part of the idea behind the jazz club in san francisco was a place that would uh it's part of this fair wage thing so it pays pays very well for the uh for the jazz musicians and um yeah something in new york and houston in the future uh would definitely be interesting but i'm pretty busy so you know san francisco works because that you know there's a partner that that does everything i'm just kind of like uh i just uh you know get to show up and can you can you just share like paint a picture look i'm i'm gonna make an assumption that our listeners they've heard WordPress, they've heard of Automatic, they've heard of you.

8:23I think it's hard not to, but maybe just share any sort of like data in terms of how big the business is, you know, whether it's sort of a team size, revenue, or just anything that kind of gives that sort of color. And also you're bootstrapped or venture backed as well. Yeah. So Automatic is venture backed. I've raised a fair amount of money over the years. What have we publicly said? So we publicly announced that we're over half a billion in revenue and ARR and everything. So that was an exciting milestone to reach. Looking forward to a billion next. WordPress, you know, the open source runs over 40 % of all websites in the world.

9:04Do you see this as your life's work in terms of, well, I guess, you know, on that statement? And do you foresee that 20 years time, you're going to be the CEO of automatic and however that looks uh like uh then yeah assuming i still have my wits about me um yeah so i do consider wordpress my life's work and i consider actually automatic the culture the way we do things we're distributed from the starts you know we have this open source really good culture um one of the things i'm most proud about creating and and really excited about working about day to day. One exciting thing about the WordPress ecosystem is that we're a small percentage of it.

9:50The WordPress ecosystem is at least$10 billion per year. And so it's really a true platform where there's lots and lots of plugin companies and hosting companies and agencies and everything built on top of it that generate a huge amount. And that's not even counting the e-commerce stuff that I spoke about earlier. How are you thinking in the age of AI, How do you think about that with regards to WordPress and Automattic? It's really exciting because I would say one of the biggest barriers to people adopting WordPress is it's a power tool in a lot of ways. It's got a ton of functionality, which is we try to our goal is always to make simple things intuitive and complex things possible.

10:38But, you know, with software design, that's always, you know, a work in progress. we actually just today so probably it'll be out for a few days once this post on wordpress.com launched our AI site builder which we've been working on for a good while it was kind of easy to build something simple but what we wanted to do was also teach people how to use WordPress as the AI builds it and so we've got this incredible block editor on WordPress called the Gutenberg editor and so it's using those blocks and building very cool sites and it can do all the stuff You can just talk to it and say, change the colors, change the fonts, change the images, make more starter text, all these sorts of things.

11:18So it can take what sometimes people would have needed to hire a developer before or they would just struggle trying to do it themselves. I think it'll be a path that will be very intuitive for folks, especially if they're familiar with the chat bots and everything like ChatGPT. I think everybody is getting certainly very familiar with those these days. And I'm still having to remind myself not to go to or try not to go to Google to search things and try and go to one of the Gen.AI chatbots. Yeah, I've completely replaced Google with perplexity, basically. I really like perplexity. Very, very cool.

11:59Very cool. And Matt, you've built a business that's over half a billion dollars now. Now, and that, you know, it's taken time, but also it's a fantastic achievement. And I think none of our listeners, I would imagine, have done that. And they're probably quite far from doing that. But I would say generally our sweet spot is the early sage, you know, SaaS founder and their teams. But if you've got any key lessons into how you've done it that may be transferable to, you know, founders that are listening, I would love to hear these, right? So like how you've grown and scaled, you know, Automatic to be this huge success, but actually might be some lessons that, you know, people listening say, you know, okay, I'm a million ARR or 10 million, but this is super interesting.

12:56And I could perhaps like think about this and apply. Well, one thing that's fun inside Automatic is that we've got businesses at different stages. So some are very mature and scaled like WooCommerce or WordPress.com. So some of the lessons from when those are going from zero to one, probably less applicable. Things are actually, I would say, so much easier now. You've got things like strike billing and other things that make it a lot easier. So for our newer products, like we've got some apps, day one, a journaling app, Pocket Cast for podcasting, Beeper, which I mentioned earlier. Those are more going from that zero to one or one to ten.

13:31And it's so fascinating. I would say, you know, there's things that are very relevant for me right now. One, product quality is incredibly important. So easy to lose someone if they're running into bugs. Now, however, if you have a really nice feedback loop, make it very easy, especially when you're small, for people to contact you. And you want the founders, the developers doing that frontline support. Those bugs or when things are broken actually become an opportunity to create a lifelong fan, depending on how you respond to them. and don't underestimate the power of word of mouth. You know, it's easy to spend money on Facebook and all these other places, but nothing beats word of mouth in terms of, you know, one really passionate person could bring in dozens of their friends, you know.

14:18We see that with things like Beeper, like people get so into it and they just get everyone else on it. Beeper actually has a pretty, I'm not saying challenging, we make it as easy as possible, but you have to set up every single network with it. So if you have five things, you've got to go through like five little processes to hook up your WhatsApp and your Instagram. So it's actually like a pretty – it's a lot of investment. So when you have a friend who's like walking you through that or sort of like helping you with that, it really helps. So that word of mouth I think is really, really key because you're really also finding that product market fits and your customers are going to be the number one source of truth there.

14:57It's important to talk to people who aren't just current customers, because you are trying to build for maybe the hundreds of millions or the billions someday, and dog food as much as possible. Ideally, it's kind of easiest. Pretty much all of our products are things we can use ourselves, which is nice. And I think I might have to, if I were making like MRI software or something, or a defense startup. I don't know if I'd be as effective at that because I do get a lot out of just using it myself, doing customer support myself, going to work camps, hosting events, and just kind of that really close contact with customers.

15:37In terms of the word of mouth, actually funny, because this is the second podcast I've been recording today. I just finished with Rahul Vora from Superhuman. he also talked about word of mouth and the key for word of mouth in that growing the business and you know having this product that surprises and delights you know like really kind of focusing on the product side of things I guess from from your side what I'm hearing like obviously the product is really important but perhaps also at this early stage just that that customer service and how you perhaps handle the bug fixes, how you show up, how you communicate with the customer and delight them from that side as well.

16:20I like to think of things you can do when you're small that are very difficult when you're large or when your competitors are large. And that really, really, really high-touch sort of people building the product, doing the frontline customer support, you can't do forever. At some point, it becomes too much. but um yeah the longer you can do it the better um and it pairs with like really tight um product quality feedback because you really do need to be completely friction free and uh also like with with the business that you have you you have a platform and then you have multiple products that you're you know continuing to build onto that platform which helps you know grow the revenue And I'm sure some of them are a massive success or a success just in general.

17:08But perhaps not every single product works. And how do you know? How do you kind of just launching, testing, trying and say, okay, maybe this one is not working. At what point do you kind of make that decision to maybe shutter that and look at something else? Yeah, that can be a tough one. But it's probably easiest if it doesn't work and you don't get any users. Some of our failure modes, though, are things that have a ton of users but just don't monetize. Tumblr is actually a great example. A huge number of daily active and weekly active and monthly active users. Like a good-sized city in the United States.

17:52But, however, it's a user base which doesn't like paying for things. tends to be a little younger. It's been challenging to find things that they'll consistently subscribe to, to make it a really sustainable business. Because of course, with that much usage, it costs a fair amount to run. So that's the hardest. And honestly, I don't have a good answer there. Things that we retire or shut down are things you wouldn't have heard of because they didn't get any usage at all. I would say that's the easiest. We do have a number of things that are essentially maintenance mode though so and it might be something that we get to sort of a feature complete stage and it doesn't need necessarily a full-time team working on it anymore we can put it into a mode where it's stable it works well and it can kind of go on autopilot and those can actually be very profitable i'd love to know what does the day-to-day look like for you you know and of a ceo that's running a company that's generating over half a billion right what what does it look like for you and maybe how does that differ to like 10 years ago as well it's probably actually kind of similar the biggest change for me was just um i forget exactly when it was but going from like daily coding or coding mission critical things to more like, you know, what I do now, which is coding stuff for myself, or that's not like in the sort of mission critical line of path.

19:25So I try to, you know, what I would call an ideal week is I spend about a third of my time on people. That's hiring HR, which reports directly to me, performance management. So kind of the people side, which if you don't get that right, nothing else matters. And if you get it right, things can be very easy, you know, running a company or managing a team. And if you have the wrong people in there, it can be miserable, you know, and also demotivating for their colleagues. Second is I spent about a third of my time on products. So I've been in a lot of product meetings, architecture meetings. Yeah, using like working with business leads, sometimes it's working more on the business side, sometimes on the design side, sometimes on the server for more products, and sometimes it's engineering.

20:16I love all of those, and I've done a lot of each in my career. So it's nice to be able to work across all the things we do, which, like I said, there's some big ones, and then there's a lot of small things. So I do enjoy that variety of moving between scale products, where the biggest thing might be internationalization or something like that, and something brand new where you're still figuring out that a product market fit. The last third, I would say, is just stuff that bubbles up to the CEO. I'm not going to even call it emergencies all the time, but it might be things that only the CEO could do, like fundraising, dealing with the board, dealing with existing investors.

21:00It might be sort of like the weird emergencies that make their way to the... It's gone through a couple layers, so by the time it gets to you, it's pretty unique. And so that's probably the last third of my time is just that kind of like things that are popping up that week. And it's different every single week. And I guess sort of connected to that, like you sometimes hear or read that people say that after this 10-year mark of being a CEO, often CEOs get a little bit tired. They decide to sell their business or they replace themselves as CEOs. But not always, but sometimes. You've been going for longer than that.

21:37So I would love to kind of know maybe like what your, whether they're secrets, but like the tips to kind of like keeping the energy, you know, keeping the passion there. So you're showing up and you're being your best self like every day and you're the best CEO for the business. Yeah. Well, one cool thing was that the first eight or nine years, I actually did have a CEO, a gentleman named Tony Schneider, who's still on the board today, still very close to the company. and he actually filled in as CEO again. I took a sabbatical last year for three months. So he came back for, you know, like Michael Jordan returning back to basketball and was able to sort of run things for three months while I was out.

22:20So, yeah, but I am around that 10-year mark now. I think I'm coming up on 10 or 11 this year. For me, the business changes so much. and actually with a lot of AI stuff, I'm as energized and excited about the potential of things as I have been, I think, since we started. So it's, including, it's allowing me to code a lot more and do things that maybe used to, would have taken me eight hours or 10 hours, now it happened in like 20 or 30 minutes. It's kind of incredible. And also seeing the pockets where Automatic is adopting that, not just for our users, like the AI site builder, but really engineers or designers now creating full prototypes where they might have previously just done a mock-up.

23:05Very, very cool and very, very exciting. I think it's also going to be huge for WordPress as a platform because we've got one thing about WordPress we didn't mention was there's over 60 ,000 plugins and themes. So almost anything, just like there's an app for that, anything you can imagine, there's a plugin for it. A lot of them are free. Some of them are free with paid versions. Some of them are paid only. But, you know, there's a lot of variable quality code across all of this. As you can imagine, being, you know, 21 years old, the WordPress code base is very secure, very performant, very everything.

23:40It's had a lot of people, I mean, tens of thousands of people working on it at this point. But the plugins is where when you see a headline like 30 ,000 vulnerable WordPress sites, it's 30 ,000 because it's a plugin that 30 ,000 sites have installed. So I think AI is going to allow the finding and fixing of those bugs way better than anything that's ever happened. So I'm looking forward to that, improving the overall security, just of like the long tail of, you know, the tens of millions or hundreds of millions of WordPress sites out there. The, you know, I do, I'm a big believer in sort of the, you know, I'm a shareholder as well.

24:20So if I felt someone else could do a better job, I would love that. And I would say a big part of what I do actually is hiring executives to do something I used to do better than I could do it and do it full time versus just part of my time. So I think that's part of how I've scaled, something I think about a lot. it's also because of my role as a founder and the history and my ability to recruit and do things is you get like a little extra boost there versus someone who might have come in as a professional CEO or something like that and that said there are some great examples whether that's Satya or Tim Cook there's some really good examples of non-founder CEOs essentially becoming like founders I think it's Jeff Wiener at LinkedIn.

25:12So, I mean, there's a few out there. But there's also a lot of examples of founder-led companies far into it, you know, whether that's a Mark Zuckerberg or a Warren Buffett or even like a Rupert Murdoch or something like that. Like there's a lot of those examples as well. And that tends to be the archetype that I both study and aspire to. Awesome. Awesome. Awesome. Do you ever get anyone saying to you, Matt, you know, you're the CEO of the company. It's so huge now you should stop coding.

25:44No, I think, you know, in general, my colleagues appreciate, well, anyone, I think, you know, if you if you're able to understand the work a little bit better, it just allows you to have higher bandwidth conversations. so um i i i kind of like that and maybe the engineers in the company think i'm i'm better at design but then the designer's like nope he's better at co-selling if everyone thinks you're maybe like you know it's kind of like being a having a bit of a wide area and exposure and i read a ton and and uh listen to a lot of podcasts and other things to try to always be learning about different areas.

26:26Like for product, there's this amazing podcast by Lenny, Lee's newsletter. It has this great newsletter and podcast. And if you read that for a year or two, you're going to actually get like pretty decent at understanding product. And you've heard from some of the top product people in the world. So, I mean, that's one of the great things about the sort of medium blogging culture right now. The newsletters, the podcast, I include it all in that. These are different forms of blogging to me. You can get like the best education in the world better than anything at a university. Current, up to the hour almost, you know, with new podcasts like this one that are just coming out.

27:01And really, you're only limited by your ambition and your curiosity. Yep. No, 100%. 100%. We're going to move into the quickish fire round, sort of, Matt. So we'd love to know what's the best advice you've ever received? Ooh. It's actually the phrase, this too shall pass. And there's a beautiful story about it. I'm not going to do it justice, but that this too can, that will pass also applies to really positive things. So knowing that like, you know, it seems like you're on top of the world or, or you just like fundraised your company or whatever it is, that's like, you know, a huge thing like, well, that this too shall pass.

27:38And then, you know, whatever you consider your most challenging days. And that's definitely something true about, you know, founding or running anything is there's times that are, how did Elon Musk put it? Like chewing glass and staring into the abyss. It's actually amazing how many of the companies that we look at as like straight line successes, when you dive in, they've had like existential crises or huge things. So I always tell entrepreneurs, you know, I'm an investor in a number of companies. And, and so so I'll hear from them often when they're like, it's all going to heck, you know, everyone hates me, the employees, the investors, everything.

28:12I'm like, this too shall pass. And you would, you would be amazed that basically every entrepreneur that you look up to has experienced stats. 100%, 100 % and great advice there. What about in your opinion, like what is the hardest thing about being a CEO? It can be a little bit isolating, you know, certainly within your company. There is sort of a, especially as you scale, there's just sort of a distance that can be created just by virtue of your position. A funny thing, actually, in automatic is sometimes people ping me less because they think I'm really, really busy. And it's true, I am really, really busy, but I don't want them to communicate less to me.

28:56Part of something I really enjoy and good at is processing lots of incoming information. So that's hard. I would say a best thing to do is if you could find other CEOs or other people who have been CEO in the past or something like that, whatever role you're doing. It can be really, really helpful to have sort of a small cohort that you can speak to or vent to or just talk about what you're going through, because they've probably been through something similar. Awesome. I wholeheartedly agree as well. And you mentioned that you read a lot. Whether it's your favorite of all time, or perhaps in the last 12 months, what has been like your favorite book that's helped you from a business perspective?

29:38I'll give you two all-time favorites. And this one's a little more traditional from a business point of view, but not entirely. It's by Nassim Taleb called Anti-Fragile. And to me, this has been really interesting because I want WordPress and Automatic to be very, very long-term companies where we're measured in decades. And who knows, maybe with life extension even longer in the future. But there is, as you know, this huge turnover in S &P 500 and other things. And so building a company that isn't just resilient to things that might happen, like the current economic blowups in the stock market, but actually can become stronger in those periods is an incredible challenge.