Lessons in Longevity: How Matt Mullenweg Scaled Automattic to $500M+  ## Metadata - Author: [[The SaaS Revolution Show]] - Full Title: Lessons in Longevity: How Matt Mullenweg Scaled Automattic to $500M+ - Category: #podcasts - URL: https://share.snipd.com/episode/cd5fbfdc-a71b-4353-8f4c-7c3640eeb843 ## Document Notes ## Highlights - **Matt's Jazz and Web Beginnings** - Matt Mullenweg started building websites by bartering with local jazz musicians for lessons. - He still plays saxophone occasionally and co-owns a jazz club in San Francisco. Transcript: Matt Mullenweg 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 called HSPVA, where there was no sports, but we did three hours of our art area every day, which for me ended up being jazz saxophone. Great school. Like Beyonce went there, Barbara Glasper, all sorts of amazing musicians and artists and actors. 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? Cause lessons are pretty expensive. So, uh, yeah, that was how I got started with everything. My old username was Saxmat, like saxophone. So 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. In any city I go to, I always try to find good live music, a lot of jazz, but also I enjoy all live music. ([Time 0:05:03](https://share.snipd.com/snip/1c422487-a637-4c4b-8816-da09dace989e)) - **AI Enhances WordPress Usability** - AI can simplify WordPress by making complex functions more accessible through an AI site builder. - Users can interact with the AI editor to customize sites without coding knowledge. Transcript: Alex Theuma Automattic? Matt Mullenweg It's really exciting because I would say one of the biggest barriers to people adopting WordPress is it's, you know, 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. But, 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 in WordPress called the Gutenberg editor. And so it's using those blocks and building very cool sites. ([Time 0:10:18](https://share.snipd.com/snip/38397146-de46-42f8-94dd-5d8256200390)) - **Use Customer Support for Growth** - Start with high-touch customer support to gather quick, direct feedback when building products. - Use this to create loyal fans and harness the power of word-of-mouth for growth. Transcript: Alex Theuma About this and apply. Matt Mullenweg 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 are 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 10. And 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. It's 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, 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 got to go through like five little processes to hook up your whatsapp and your instagram and so it's actually Like a pretty uh 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's, it's, it really helps. So that word of mouth, I think is, 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. It'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 ([Time 0:12:57](https://share.snipd.com/snip/de57e3be-fb2f-4aed-8ea1-4fdd93830e29)) - **Know When to Retire Products** - Shutter products that don't gain users or economic viability quickly. - Maintain products in stable autopilot mode if feature-complete and profitable. Transcript: Alex Theuma 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. Matt Mullenweg 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 Tumblr is actually a great example. Huge number of daily active and weekly active and monthly active users. Like a good-sized city in the United States. But, however, it's a user base which doesn't like paying for things. It 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 in essentially maintenance mode, though. 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. ([Time 0:17:11](https://share.snipd.com/snip/200517c3-330d-400e-921d-8a23667849fb)) - **CEO Time Balancing Act** - A CEO's role evolves from coding to primarily focusing on people, product, and emergent issues. - Balanced time among hiring, product development, and unique CEO tasks maintains effectiveness. Transcript: Matt Mullenweg It's probably actually kind of similar. The biggest change for me was just, 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. So I try to, 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 spend about a third of my time on products. So I've been in a lot of product meetings, architecture meetings. Yeah, working with business leads. Sometimes it's working more on the business side. Sometimes it's on the design side. Sometimes it's on the server for more products. Sometimes it's engineering. I 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 there's a lot of small things. So I do enjoy that variety of moving between scale products where the biggest thing might be like 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. Might be sort of like the weird emergencies that you know make the way to the it's gone through a couple layers so by the time it gets to you it's pretty unique um so that's uh yeah 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 ([Time 0:19:04](https://share.snipd.com/snip/9cb3d8f3-8d66-4c6b-b79a-25bf7c8260f7)) - **AI Revitalizes Founders and Products** - Advancements in AI energize long-time founders by enabling faster coding and new product possibilities. - AI can improve plugin security across the massive WordPress ecosystem. Transcript: Alex Theuma Passion there so you're showing up and you're being your best self like every day and you're the you know the best ceo for the business yeah well one cool thing was that the first eight Matt Mullenweg Or nine years i actually uh 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. So, 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 happen 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. Very, 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. ([Time 0:21:46](https://share.snipd.com/snip/3b8fce26-5800-4329-8ceb-f812ef676428)) - **Mitigate CEO Isolation With Peers** - CEOs should create a peer network for sharing challenges and support. - Isolation is common but can be mitigated through regular communication with fellow leaders. Transcript: Matt Mullenweg It can be a little bit isolating, you know, certainly within your company. There is sort of, 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. I, you know, part 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 just talk about what you're going through because they've probably been through something similar. ([Time 0:28:32](https://share.snipd.com/snip/0b95aad1-313b-4cd3-b482-49b08a55d8e0)) - **Learn Constantly Through Content** - Embrace continuous learning through newsletters and podcasts to improve product knowledge. - Use available high-quality educational content to enhance skills beyond traditional universities. Transcript: Alex Theuma 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? Matt Mullenweg Give you two all-time favorites um from and this one's a little more traditional from a business point of view but not entirely it's uh by nassim taleb called anti-fragile and to me this Has been really interesting because i you know i i want wordpress and automatic to be very very long-term companies you know 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 stock market, but actually can become stronger in those periods Is an incredible challenge. That's what anti-fragility is. And I pair that with the book Sid Hartha by Herman Hesse, which is one of my favorites of all time. Maybe a little bit more on that, this shall pass like the philosophical side but i i think that's just as important to study because when you're building something you need to have a why And you need to understand how it fits in and you need to understand people and you need to be able to motivate people and inspire people and you need to be able to motivate and inspire yourself As well so something like i said hartha I think is a book everyone should read. ([Time 0:29:29](https://share.snipd.com/snip/650dcaa9-7d73-4cd5-9633-24fada2a49c9)) - **Blog to Build Audience and Thinking** - Start blogging and building an audience to improve thinking and community engagement. - Publishing regularly forms a foundation for growth and networking. Transcript: Alex Theuma And then that built an audience and then I started doing events. And so, you know, WordPress has played a part of our journey for sure, or a big part. That's amazing. Matt Mullenweg And yeah, that's, I would say, a great ending advice to everyone is blog. Blog, build an audience. Blog more, publish. Like you'll be amazed both how it improves your thinking, but also when you start to build a community. I think that's when it's really special. ([Time 0:33:50](https://share.snipd.com/snip/f3c993b1-c0ac-4685-a327-5838088662d3))