Lessons of Greatness: Be a Learn-it-All, not a Know-it-All
Matt Mullenweg of Wordpress: How he built an Operating System for the Web
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Now, it’s go time with Matt Mullenweg.
Introducing Matt Mullenweg
Matt Mullenweg is the founder and CEO of Automattic, which owns WordPress and many other properties that are the foundation of today's web. WordPress alone is now used by more than 60 million websites and more than a third of the top 10 million websites.
When Matt and I connected, we were in the midst of the COVID-19 pandemic. On the one hand, I wanted our conversation to touch upon Matt's distributed management model, because I thought it might help other entrepreneurs navigating this new paradigm for the first time. Matt's been a pioneer of this for many years (btw, he has an entire podcast devoted to this topic called Distributed, which I highly encourage you to check out).
But as Matt and I chatted, it became clear to me that this episode was about something even more timeless and broadly applicable. You see, Matt has truly stood the test of time as a CEO, but this success story almost came to a screeching halt because of Matt's early struggles as a leader.
This is no knock on him - as one of the most honest leaders I know, Matt has no reservations about sharing his early shortcomings or even his concerns about how to avoid mistakes in the present time. This is one of his many strengths. Because of his learn-it-all mentality, Matt's been able to capitalize on some breaks and valuable connections early on in his career to set him up for greatness. And I think you'll see from the interview that Matt Mullenweg is just a gem of a human being.
Follow Matt @photomatt on Twitter.
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🌟 Highlights from the Episode
Golden Line
“I'd run a meeting and it would just go all afternoon with no agenda, no deliverables. I can't be this terrible manager. I need to start reading some books, finding some mentors. I need to start being better at my job, because I'm just scraping by still.” —Matt Mullenweg
Inspiration from my Dad
A lot of [my interests in computers and the internet] came from my dad. Like many sons in Texas, I just did everything my dad did. When he mowed the lawn, I'd walk behind him with a little toy lawnmower. I started playing saxophone because he played saxophone in high school. And [my dad’s] day job was programming. There were always computers around the house and he was very much a tinkerer, so he was fixing our cars, building furniture, fixing up boats. Whatever he would get, he would always hack on it.
I applied that a lot to hardware and software. Initially making some computers for myself, for gaming or friends or local musicians or things. And then later, getting into the craft of writing software, so that was just the other path I decided to go down.
Moving from Houston to San Francisco
[My move from Houston to San Francisco was] totally random. Complete coincidence. In Houston, I organized a user group at a local nonprofit. Every month I'd organize a program, invite speakers, lead a Palm Pilot user group which, let me tell you, it was very popular. But it was really fun, and actually really good to get in front of a group of adults and do this thing every month.
This designer named Jeffery Zeldman made a set of icons for the Palm Pilot that would change all the default icons with these cool '50s Art Deco looking icons, so I became a fan of Jeffrey Zeldman. That's also how he started learning HTML and CSS standards. He posted on his blog that he was going to be in Austin, Texas for this thing called SXSW, South by Southwest, which was going through the interactive portion of South by Southwest had shrunk after the bubble of the late '90s, 2000s. It was probably only four or 500 people, so really, really small.
And I was like, "Zeldman's going to be in Texas, no way." I wrote what was actually a hot cheque to get a student ticket to South by Southwest for a couple hundred bucks. My sister lived in Austin, so I just crashed at her place. I had a gas card from my parents. So I was like, "Hey, can I use this gas card to go to Austin and go to this conference?" They're like, "Yeah, okay."
At the conference, it was so small that I ended up meeting my idols and all the biggest bloggers. Along with Jeffrey Zeldman, there was a fellow named Chelik who was developing one of the major web browsers at the time, and Eric Meyer who was a big advocate of teaching people how to code. I met Ev, Jason Shellen, and all the Blogger folks, so it was the whole internet at that time, the independent internet came together.
I really felt like I found my tribe.
Google, CNET, and Job Offers
And in San Francisco, I felt like this was all the people we were following online. I visited Yahoo and I visited Google. I visited all the companies I could, and one of them was CNET. I blogged that I was going to go out and a fellow at CNET, Mike Tatum, reached out and said, "Hey, you're going to be in San Francisco, why don't you come out and meet us."
What I didn't realize was all these companies were interviewing me essentially. I think at Google they wanted to make a Blogger appliance, because they had a Google Search Appliance. It would literally be a box that you'd buy that looked cool, it was in Google colors, and you'd stick it in your data center and that would be your internal Google. They wanted to do that for Blogger, for internal blogging.
Very pressuring actually. But the way they had written Blogger wouldn't work for that, so they wanted to see if WordPress could run on this box that they sold to people. It was funny, it reminds me of Silicon Valley where the guy comes in and he's like, "We're going to make this box." It was what you did at the time. So I talked to them about that.
When I returned back to Houston, I started getting some job offers from these companies. And WordPress was still pretty early and was generating zero dollars, so I was still just making money from computers and building my websites.
The most interesting ended up being CNET and the reason was they were a media company, not a technology company. Essentially they said, "Anything you do that's open source, you can retain the copyright and all the intellectual property rights."
In my head, there was this concept of, You have to own your masters. So, that was the thing I optimized for, it ended up being a great decision because WordPress is a CMS, Content Management System. Content Management Systems were invented at CNET because they were the first large scale publisher.
“I felt like 1 foot tall”
At CNET, [I experienced] the most awkward meeting I'd ever been in. I think I was the editor in chief or something. This is one of the big conference rooms, 12, 15 people.
It was a team and the leads of the people building the in-house CNET, CMS. And I said, "All right." They projected the screen and I said, "Okay, I've got a post ready to go. Here it is, here's the text." He emailed the document and said, “Now post this to the website -- on the live website -- and let's see how long it takes. Long story short, the process took about 15, 20 minutes for them to load it into the system and set all the fields. And then the publishing time was probably 5-10 minutes. He says, "Matt," and I literally look like I'm 12 years old on the corner with my laptop. And he goes, "Okay, post it to WordPress." So plug in the laptop and copy and paste and post it, it's live seconds later.
And the daggers, the lasers, these guys were looking at me, they were just like this punk kid, what the... I felt like one foot tall, it was definitely awkward. But to see it was great, they had started to use WordPress a lot. And they were seeing that the speed of publishing, the agility of the Content Management System was holding them back. They want to make their thing just as fast.
Beginnings of Automattic and Tony Schneider
[With Tony], it was matchmaking. It's a blind set up. Neither of us had met each other before, but a mutual was like, "Y'all get along. You should really get together." Then once we got together, it became clear. I wanted him to be CEO because I believe in clear lines of reporting, that I was going to report it to him. But he did a really fantastic job knowing that I loved running things and leading things, making a lot of space for me to essentially be an understudy in a lot of ways. So I'd learn from his experience, he took a lot of things off my plate that I didn't like (but later grew to love) and made space to really collaborate.
Bringing his experience to bear and his common sense approach to things, it was a true partnership in a lot of ways. Learned a ton, I could have never become CEO of Automattic or be CEO where I am today, if I hadn't studied essentially under Tony for eight years.
Struggles in the Journey
We had no credit at the time because I had gotten a best buy card in high school, forgot to pay it, so as a sole founder, the company credit became my 600 credit rating or something. And so we couldn't get any credit even after we raised money at a million dollars in the bank and the limit on our credit card was like $5,000. The servers were costing more than that. And there was crises like, how do we pay the credit card bill for all of our servers and things? How do we wire money to people? How do we... There was issue where we didn't have the wordpress.com domain. There's a whole drama around getting that domain. People suing us. They were trying to catch us, all the above that we were going through.
In some ways tumultuous, in some ways we didn't make a lot of mistakes that I see solved by other companies, years down the road. For example, we brought in a CFO really early, part time, a great woman named Ann Dorman, who was part-time CFO. And Tony took over the books for me and did it for a little while. And he found this person who could come in and really kept all that clean. She also did HR and gave us the documents and everything, so we were pretty good about following HR best practices from early on and how we hired, how we did compensation (and compensation is never perfect).
In any snapshot in time, there's going to be things which are not perfect within it, but I want to always [be on] the arc towards fairness. Any decision in the company, if someone wants to talk about it, we're totally open to it and we can explain it and we can talk about it and strive to be as fair as possible because ultimately that's really what you want people to feel.
We want people to feel like they're contributing to something and they're getting fairly compensated for their contributions to it.
Transitioning from 0 to 1
Yeah, we had a lot of friction around the 15-20 people range because I had no idea what I was doing. So I run a meeting and it would just go all afternoon with no agenda, no deliverables. And I was working with people who were generally much for our space. And so I remember once at our first offsite, we were up at the Stinson Beach and we're all in one house, it was pretty small. And this fellow who joined from Cisco just got up and walked out, just fed up with us. He literally just stood up, walked out of the house to walk down the beach. He was so pissed off. Those things were rough and, for better than worse, you become really close personal friends with everyone because you're in the trenches. So when you fight, it feels like here you're fighting with your partner, with your significant other.
So we got an offer to buy the company pretty early on. When we were around that size, like 20 ish people, one of the things that [we] seriously considered was, well, we're all fighting with each other. Maybe this is not fun. This is not something I want to do. Maybe this is just where it gets to, because it was just so heart wrenching to disappoint these people who you really respect and care about and to be at odds with them. That was definitely a pivot point, deciding not to sell.
Aside: Now, the latest employee count of Matt’s organization is 1400.
Reading
I felt like we weren't doing our pricing right, so I just got six books on pricing and went through them all. I think the one that worked well was the Pricing on Purpose. But I also read the GE book on pricing, the super corporate stuff. I still try to read as many books as I can per year now because I still have so much to learn. Black Swan by Nassim Taleb felt like it was around that time, hugely influential, not just because it was an amazing book on its own that really changed how I thought about things, but it was a portal to so much of the literature. He would have dropped so many illusions and references to other books that it was almost like I stumbled into this magical alladin library or something full of treasure.
And just everything I took off the shelf would blow my mind. You can find gold everywhere, even like the really cheesy, corny stuff, like a book of quotations. Those can be really powerful and I do believe in extracting something from all of them. So a lot of what Automattic was, was also just an experiment.
I read a book, Drive by Dan Pink. He says, mastery, autonomy, purpose are more important than anything else for people being happy. I was like, okay, that's a framework. Let's try it out. How do we give people more of those three things and see how it goes? And one of the things I'm very proud of is: Automattic's retention rate is off the charts. I think it's because we really invest in these things that help people feel fulfilled in their work.
Learn-it-All, not a Know-it-All
I wish I was more of [a learn-it-all] in my 20s. If you were to zoom back and you might see a bit more arrogance or a strong headedness back then, but definitely in my 30s now, like that's been probably the title of the decade. You just get knocked on your butt a few times. It gets very humbling and you really start to realize all the things you don't know versus when you're young and thinking no at all, I really don't.
Advice for Founders
Only two big things I advocate for distributed and open source. The issue is a little easy now, but if you're building a company, if you can create opportunity all over the world through a distributed structure, that's really powerful. And then open source, I believe if you want to accelerate humanity, if you get jazzed by the idea of going to Mars or all this other stuff like thinking of the Earth as a big connected thing, open source is the best way to accelerate humanity because software is now the software of our culture, of our evolution. We're evolving now in the information space, not the physical biological space, although maybe someday open sources is the best way to do that.
And life is relatively short, your younger years you do have a ton of energy and natural resources you can put to bear on problems. So just work on the thing that really, really, really matters. And I believe open source and big problems can be that.
In Pearl, there's this funny saying that there's more than one way to do it, I would get really discouraged early on because I didn't have the background, the college education, the whatever it was of all the other entrepreneurs that I was seeing, all the role models I was looking at, knowing that there's more than one way to do it, but yeah, there's never going to be someone with exactly my path or exactly Mark Zuckerberg's path. And that's cool because the thing that replaces Facebook's, hopefully that doesn't replace WordPress, but maybe someday it would be created by someone who does it from a completely different point of view and completely different frame and a completely different way of doing it.
Thoughts on Improving the Internet in the Next Decade
Cooperation. I really appreciate the idealism that existed then is very much an open web, very much connecting things, something that John Battelle and Tim O'Reilly really advocated for this Web 2.0 was going to be about how everything was open and connected. And I try to bring that idealism today. It's 2020, the world is a little rough sometimes, we have the internet turning into the splinter now. We're having firewalls, balkanization and I think there's still so much potential in that vision of an open connected, independent web but really I try to make it my business and life mission to bring that back. The deep psychosis of a lot of these companies that survived a dark period, or went through something really tough, including Apple, is that they end up with this permanent underdog mentality or it's like them against the world.
And Apple is now a $2 trillion company, wildly profitable. Has more in cash than the GDPs of most countries. But they'll still not let you change, it'll still lock you into iMessage and not likely to change here to things that probably are good for them competitively. But it feels a little bit like, hey, can you open it up a bit? And one of the things I liked about that time was the companies were all building businesses, but they would try to inter-operate with each other. I would love it if, particularly the big tech companies, will just look around the room and say, okay, we won. We've captured so much of the economic growth of the past decade. We have unassailable cash positions. And no matter how bad it gets, we can be Microsoft and go through a dark decade and still come out the other end with hundreds of billions of dollars and the ability to reinvent ourselves. So let's go consumer first, let's go user first and say, what do our users really want?
For early entrepreneurs going from zero to one, there's one thing I would ask everyone to remember which is: when you make it, try to make it for some other people too.
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If you found this episode insightful, you might enjoy my interview with Bob Metcalfe who started 3Com and later learned a great deal from Bill Krause, the CEO he decided to bring on board.
Questions / Comments / Have a favorite quote or moment from the episode? Send us an email at greatness@floodgate.com
Always a great podcast, with tons of golden nuggets. Love the writes of the episode, it helps grab a few of those ideas I want to explore more after listening. Thanks for the greatness.