Matt Mullenweg on OFF RCRD | TRANSCRIPT

This week, Cory speaks to entrepreneur, founder and CEO Matt Mullenweg, who is best known for have founded Automattic, which is behind brands WordPress.com, WooCommerce, Jetpack, Simplenote and more; reaching more than a billion people a month. In this weeks episode, Matt talks about how he got into technology, what his high school and college days were like, being young and in a position within a big company to leaving and risking it all to become a founder, what’s his trick to meet great people to work with or invest in and the great story of how he misplaced a half million check!


[00:00:55] Cory: Thank you Matt for joining me on the show today. I really appreciate you taking the time. I’d like to get started by asking you, how did you get started in technology? I know you started WordPress when you were 19-years-old. How did you get started in tech?

[00:01:07] Matt: The very first step — I know you’re from Houston too. So I grew up in Houston. First websites I made were actually for musicians. I studied at a performing arts high school and played saxophone. The very first websites, lessons were expensive. They were like 40–50 dollars an hour. I would exchange either building a computer, like a physical desk top computer, or building a website, in exchange for lessons for local musicians around town.

[00:01:31] Cory: I know you went to HSPVA in Houston. What were your teenage years like and what made you distinct as a teenager?

[00:01:37] Matt: I always had a big love for technology. I think because my dad was an engineer, tech guy for oil companies, nothing fancy but it’s like normal technology jobs but early on. I don’t know what else. My friends will probably say I definitely ran the computer club and the Palm Pilot Club and stuff like that. Going to art school, I also really enjoyed the more human side of things, the more liberal art side of things.

[00:02:03] Cory: You went to college for a little bit, is that right?

[00:02:06] Matt: Yes, just about two years.

[00:02:07] Cory: Two years. What made you leave school?

[00:02:09] Matt: I think two things. One, the college I went to, which was University of Houston, wasn’t like the strongest, especially in terms of on-campus culture. I don’t remember the exact number, but the vast majority of attendees there like 90% don’t actually live on the campus. It was mostly a commuter college. I didn’t live in the campus either, so there wasn’t a really strong social aspect keeping me there.

WordPress had already started at that point, so I was given an opportunity to move to San Francisco and work for a public company called CNET, now CVS Interactive. I was like, they’re going to pay me to move to the coolest city in the world, where there’s a lot of people who are passionate with what I’m passionate about. I took that opportunity. It was the summer after my sophomore year.

[00:02:47] Cory: How long were you at CNET?

[00:02:49] Matt: Just about a year actually. It was one of those things where they were starting to — WordPress had already started, they were trying to use it a bit. There was still a lot of push back against blogs actually. Early on in the days of blogging, particularly in major media organizations which CNET was a little bit more traditional. Self blog was like a more amateur thing or not as valid.

Even though they were using WordPress to publish some of these sites, the idea of enabling millions and millions of bloggers to have their own voice, which was my passion, It didn’t resonate as much with the company. I stayed probably three or four months extra to finish off some projects. I wanted to show some loyalty to them because they helped me move away from Houston. After that, I wrapped up some of those projects. I left to start Automattic, which is the company behind WordPress.com, Jetpack and other services for WordPress.

[00:03:34] Cory: What was that like? How old were you?

[00:03:36] Matt: Twenty. [laughs] Wait. Yes, 20 when Automattic started, either 20 or maybe just turned 21.

[00:03:42] Cory: Was it just you at the time? Or were there a few other people that you started Automattic with?

[00:03:47] Matt: What I was able to do was actually started the company, I had the first employees before I left CNET. The first I think two employees, I just paid out of my CNET salary and credit card debt. [laughs] That was also partially because I was finishing up the kind of projects that I want to finish up with CNET. They were supportive of everything. That was the very beginning but I was technically a sole founder.

[00:04:10] Cory: Was it pretty scary when you left your job that you’re getting a salary at for no salary?

[00:04:16] Matt: Because it was bootstrapped, we found some early revenue and different partnerships and our anti-spam products and things like that. Automattic definitely made revenue almost from the first month of the business. That definitely removed some of the fear. I would say most of my fear was just tied to having never done it before. It was one of those things where I don’t actually know what I’m doing.

I read a ton of books. [laughs]. I tried to meet with a ton of people. Eventually, I found a business partner, Toni Schneider, who joined and became CEO the following year, who was really super fantastic.

[00:04:47] Cory: Before you found Toni, what were some of the biggest things you learned in that first year? If you can go back in time to the early days of WordPress, what would be some of the things you would do differently?

[00:04:57] Matt: Some of it was actually prior to founding the company. I’d actually sort of pre-announced the formation of the company even when nothing existed. That was a little bit of a mess. That was definitely a pre-Toni mistake. What else did I learn? Toni joined pretty early on. I had met him already but he sold a company to Yahoo! So he was finishing up that. He was a great counsel from early on.

I would say one other thing is that, when you get a legal bill, I thought a legal bill was an electricity bill. If you don’t pay it, you go to jail or something, but it turns out they’re totally negotiable. I was getting all these really huge legal bills, I was just paying them. Toni came in and he’s like, “No. You don’t have to — that’s like the starting point. You can negotiate that down.” That was one very key thing that might be useful for some other entrepreneurs who are listening.

[00:05:40] Cory: What are some of the other things you’ve learned from Toni?

[00:05:42] Matt: Oh, man, so much. Toni was CEO for about eight years and it was really like a master class. In music, you often study under people who have done it before. Toni had been part of startups for 20 years. He had a ton of experience. He’s Swiss-German and then moved to America when he went to college.

The joke was that Switzerland is a neutral country — he was very measured in the way he approached things, which I feel was a good match because Automattic from very early on was very low drama, not a lot of scandals or things. We’d talk a ton and then figure out the best way forward, and through that course of going back and forth we would discern the best path.

I think something I still learn from him, Toni is actually still with the company; he runs a smaller team now, he can approach things and really connect with people in a way that makes everyone feel really included, and I think it’s one of his superpowers.

[00:06:33] Cory: What would you say your superpower is?

[00:06:35] Matt: Probably hiring and the non-hiring parts of hiring, which are finding great people to work with. I’ve been very lucky or good at finding great partners within the investment side and other folks I worked work with like Toni, who I’m still able to work with now 12–13 years later since I meet him. To me, it’s been really special because coming into San Francisco from Houston, I felt very much like an outsider.

Everyone already knew each other and they all worked together at previous companies, or all went to Stanford together or something like that. So being able to develop these long working relationships with folks, that now has been over a decade, has been really, really special.

[00:07:11] Cory: What would be your advice to someone who is moving from another city into San Francisco right now? What would be your recommendation for those types of people who don’t find great people to work with?

[00:07:21] Matt: I think a lot of it was just I tried to help as many people as possible. For me at that time, that was partially doing a lot of WordPress tech support. I would help a lot of people with setting up their sites. I used to host upgrade parties at my apartment. I released a new version, everyone could come over to my house. I would upgrade their sites for them, so just stuff like that.

I felt I kind of put some good karma out there, allowing me to meet some really interesting people. The thing was I would just go to any event I was interested in. It was a micro-format, some web standards events or whatever it was that was around that time like a blogger events. I would just look at meet-up in the different calendars, and on MySQL events. You would go to all sorts of random stuff.

It’s funny now, sometimes I ran into the people who I met there much, much, much later who are running multi-hundred-million-dollar companies, but we met because we had booth next to each other at the MySQL open source conference in 2005. What I see what I was intimidated by when I first moved there, is now something that works to my advantage because that is some folks I’ve been able to know over long periods of time.

It’s really just because I would go out there and I’d show up and just meet people, be friendly, treat everyone well without thinking what they could help me with or give me, but just trying to know them as a person and helps them out if I was able to.

[00:08:36] Cory: What about now? How are you meeting great people either to invest in or to work with?

[00:08:40] Matt: Well, I paused new investments because I have taken back over some core WordPress stuff, so some of the open source site, so to make time for that I paused new investments. I feel I meet good people now. I don’t know. It could be anywhere. I think it’s really just about the state of mind. If you’re open-minded, you can meet great people on the airplanes, you can meet great people at the subway.

I meet a lot of folks through WordPress, at WordPress events, at Word camps around the world. I guess through events I go through, yes. I still go to events sometimes ones that are outside of my comfort zone. It’s probably been four or five years ago, but I went to TedMed, which is the medical version Ted, focused on Health Sciences, not because I work in Health Science or anything like that but just because I was curious about it.

What is the edge of technology in design for things that affect our bodies?Go to things outside of your comfort zone are really helpful there. This is a struggle for me because I’m naturally very much introvert. I usually afterwards appreciate going out even if getting myself out the doors sometimes is difficult.

[00:09:36.] Cory: What are some interests that you have outside of technology?

[00:09:39] Matt: I’m still really passionate about music, and I love Jazz in particular. I’ve become pretty into food, but less on the cooking side and more on the eating side. But because I travel a lot, and I’m finding a good local restaurant or top chef in the areas, always a thing you can do no matter where you are. Finally, I love picking our new technology whether it’s blockchain stuff.

I just joined the board of a company called GitLab which makes — it’s an open source GitHub and source control, but also combining a ton of developer tools. As long as it’s for fun, I’ll just — even though my job day to day is more on the managerial side and being more of the CEO and everything, I still at heart love geeking out with things. It could be development tools. It could be something as simple as re-doing the network at home so that my WiFi is faster.

[00:10:28] Cory: What’s something that you know you should do but you haven’t done yet?

[00:10:31] Matt: One thing that’s on my list for this year, it has nothing to do with technology. But a friend, I can’t remember who it was actually, challenged me to do the Wim Hof 10-week program, which is like he’s the Ice Man guy. He climbs Everest on his bare feet. He’s some crazy guy. He has this breathing 10-week program, where you like take ice baths and do this type of breathing. I haven’t done it, [laughs] but I would like to.

[00:10:56] Cory: What would you say the most embarrassing moment starting Automattic?

[00:11:00] Matt: Probably one of the most embarrassing moments was the first check we got, that was from this guy named Phil Black, who’s now one of the guys at True Ventures, but at the time, it was before True existed. So, he wrote this check, and where the other investors in our first round wired the money, he actually wrote a physical check. It was like $400,000 or $500,000.

I was expecting it to be like a Publishers Clearing House check, like really large that you could carry into the bank like you were carrying a giant sign, but it was just a small, normal sized check, like the one you would write at the grocery store or something. I misplaced this check. [laughs] I wasn’t sure what to do about that.

Luckily, the other investors, they wired money, so we weren’t short for money. But there was this pretty large chunk, like a third of the round that I didn’t know where it was. [laughs] So obviously, I couldn’t deposit it. I wasn’t sure if I could tell him because then he would think that I was really irresponsible or had just lost his money or something like that.

So, I just didn’t do anything for three to four months, maybe longer actually. But I was on a flight back to Houston for Thanksgiving and I opened up a paper book. I think it was a biography or something that I had in my backpack. When I opened it up, it turns out I had used that paper check as a bookmark. So on the plane, the check fell out onto the little tray table, and I was like, ‘’This is amazing.’’ The first thing I did when I landed was go to a bank and deposit it.

[00:12:25] Cory: That’s amazing. That’s amazing. When did you tell Phil?

[00:12:27] Matt: I think I told him probably a couple of years later. He tells that story now too. That was pretty funny.

[00:12:33] Cory: Do you have any tactics for coping with setbacks — negative experiences? I imagine WordPress has been through its ups and downs, so what would be your advice there?

[00:12:44] Matt: Something that I usually find helpful is just reading about how other companies have had a lot of trouble, whether it’s Elon Musk almost going bankrupt or how badly Amazon was panned afterwards. All the companies that we now think of as golden and unassailable actually went through some really, really tough times and almost went out of business at various points in their history.

The Press in particular, Tech Press, they only tell the good side of the story usually, or they tell the bad side as the company is going out of business, [laughs] so that doesn’t really help you a lot. But if you dig in, whether it’s a biography or a deep history on a company, you can usually see that, even the ones you think of as totally golden and having a straight up into the right rise, have often gone through some really tough times or almost gone out of business or not existed, if not for like a very lucky thing along the way. So, knowing that it’s not just you that’s going through a tough time is really helpful.

[00:13:41] Cory: What were some of those tough times at WordPress?

[00:13:43] Matt: We’ve just gone up into the right. There’s been no tough times. There’s been any numbers throughout the years. I think something else that helps now is that WordPress is — is it 14-years old? I’ve seen a couple of the cycles, meaning I’ve seen points when the Press and everyone else, investors, et cetera, where you could do no wrong.

Everything was interpreted in the most positive way, and then a couple of times when everyone is predicting you were going to go out of business because of Blogger, Posterous, and Tumblr, whatever it is that’s hot at the moment. A few years ago it was Medium. All these things, sometimes they come and sometimes they go. So, if you can survive the cycles, that also gives you a lot more confidence in the future ones, to really follow your principles versus being too worried, and your customers, following your principles and your customers versus about being too worried about whatever is kind of the meme of the moment.

[00:14:36] Cory: How do you make hard decisions? Do you have any tactics around that?

[00:14:39] Matt: Yes. I mean probably the number one thing is just talk to people about it. I know that sounds like the most obvious, dumb thing, but sometimes I will realize that I have been agonizing over something for a few days or a week, and I’m like, ‘’I should just tell a friend about it,’’ whether it’s a friend or a colleague or whoever it is. And sometimes in 10 minutes of talking about it, you overcome something that you had been struggling with for weeks. The second thing which I think is super, super useful and I believe everyone should do, is keeping a decision journal. There’s actually a great blog post about it on Farnam Street. I think you just Google decision journal, they’re actually one of the top couple of hits. They have a little template for it, which is really good.

So, the idea of a decision journal is, when you come to a decision, write down about it, write down what you expect the effects to be and sort of your context and thinking forward. This gives you an audit log of all your previous decisions. You can look at it later and see how you done without sort of succumbing to the normal cognitive biases that typically affect our retrospective analysis of the decisions we’ve made.

[00:15:38] Cory: I like that. Do you keep a decision journal?

[00:15:40] Matt: I do. Yes.

[00:15:42] Cory: How often are you writing in it?

[00:15:43] Matt: I only started this year. So, I’ve really only been doing kind of major, major decisions, and a couple dozen entries.

[00:15:51] Cory: What would be an example of one of the more recent major decisions that you could share?

[00:15:55] Matt: It could be high-level hire. Like a big hire that you’re making and maybe you’re deciding between a few good candidates. It could be a direction for a business, whether to do a partnership or not. Now, I’m speaking a little bit in the abstract because they’re all recent. I can’t speak exactly to what they are. But these are kind of classes of things that I think would be good to put in decisions journal.

[00:16:14] Cory: Got it. Do you have any stories about controversy, either with WordPress, first-hand or second-hand?

[00:16:18] Matt: I mean, yes. We’re going through some controversy right now. We’re working on a new editor experience. Basically, the place where people can write and create post and pages for WordPress. We’re taking a pretty radically different approach, like kind of breaking up the structure instead of having like one big box that you write into, kind of break it into blocks. It might be a text block, or amount block, a contact form block, a shopping block, whatever.

Because this changes the editing experience of WordPress so much, it’s going to — well, even if we provide backwards compatibility to work really well on these two interface, some other tens of thousands of plug-ins that are out there for WordPress or people who have built WordPress sites, custom in the past, will need to update it to work in this new interface, or just shine in this new interface.

That’s been hugely, hugely controversial. Because a lot of people, I think, are really scared of that investment in work, in time, and development, and are really advocating for us not to change it at all. [chuckles] There are some very heated discussions around the WordPress world now. The new project’s called Gutenberg. So, if you search for Gutenberg stuff, you’ll see some posts saying it’s wonderful, and you’ll see some posts saying it’s going to cost WordPress to essentially lose all its market share.

[00:17:24] Cory: How do you think entrepreneurs should deal with controversy? Do you think you should shy away from it, seek it, or just not back away when it comes up?

[00:17:31] Matt: I’m a believer in engaging with things. I will counter that by saying that sometimes it’s good to just to lay low [laughs] and let things pass. But with this in particular, people posting about it or some of the fears are rooted in some uncertainty. What we try to do is read every single criticism, every single bad review, everything, and extract out what’s really useful from that.

Look at what might be behind what people are saying and try to understand what they mean, what they really need, which isn’t always what they say. By diving in there, both it makes people feel heard, understood, and gives us the chance to address the issues or counter them. Because some of the things people are saying are just wrong. Usually, if there’s a blog post about it, we’ll come in in the comments and say, “Thank you for your feedback, first and foremost.” Because one, people are writing long post about it, it means they care. That’s kind of a blessing that people care in the first place.

Then two, try to really engage them on the issues and the points and make sure that we understand their point of view, also that they understand what the actual goals and vision and timeline and roadmap Gutenberg is.

[00:18:33] Cory: Got it. What’s something controversial today that you think will be commonplace tomorrow?

[00:18:38] Matt: Anything involving stem cells, the application of machine learnings, non-data task. Self-driving cars are really controversial. I think that will be pretty common place in the future. The world I live in today, I think it’s a little controversial to imagine — This is kind of funny to say actually now that I’m saying it, but that you don’t necessarily need to develop or to make a website.

It’s funny because it was kind of the founding premise at WordPress, was to marketize publishing, make it accessible to a lot of the people. But there’s also hundreds of thousands of people that make their living building WordPress websites. It can sometimes be challenging or scary if we improve the usability of WordPress where it leads to a point where you might not need a developer to build a pretty good-looking site. Although that is a little bit controversial now, I just can’t imagine anything that’s going to reverse that flow.

[00:19:27] Cory: Do you think distributed workforce — do you think more companies will have that in the future?

[00:19:30] Matt: You know what? That’s a really good one. [laughs] I totally forgot about it because I live it everyday. But distributed work is very controversial now. In fact, some companies like Yahoo! or IBM are pulling back to distributed workforce. I think it’s 100% the future work where talent will be all over the world and people will be able to coordinate really well virtually.

So there’s no reason to geographically limit yourself with just people who are going to be able to live or commute to one fixed point, or a couple of fixed points which are opposites. It’s just really trying to find the best people in the world. I truly believe that distributed work is the future.[00:20:06] Cory: Do you think some of those companies that are — Yahoo and IBM, do you think they should be distributed right now?

[00:20:11] Matt: I mean those aren’t exactly companies that are doing super well. Maybe their core issue is attracting the best people in the world.

[00:20:19] Cory: For a startup, what would be your advice to them to setup a distributed workforce? Any tools or tactics to making that efficient?

[00:20:27] Matt: Yes, if you’re starting something new, I would say the key is to do it from the beginning. I think it’s important for teams to get together sometimes, so especially if you’re small. When we were five or 10 people, we used to get together twice a year. But then, really try to be as efficient as possible when you’re not together.

As you scale up the company, make sure that you’re not using those in-person times as a crutch but you’re really investing in the communication skills for being distributed and being apart so you can be just as effective then. If not more effective, then you are the weak or two a year you happen to be together.

[00:21:00] Cory: What are some ineffective things you see first-time founders do?

[00:21:05] Matt: Probably the number one thing I see first-time founders doing wrong is being a little too precious about the idea, either to the point where they don’t want to tell you or where the kind of idea is worshiped as a sacred thing that is the heart of creation. If you get down to it, for every company that you can think of or admire, the idea was usually the least interesting thing.

In fact, when they started, there were probably either big companies doing the same thing or lots of other startups doing that exact same idea. It really comes down to iteration and execution in terms of what I see being successful in the long run. I also tend to see often the ideas that people hide aren’t necessarily really strong ones. The ideas that you tell everyone and they think it’s not worth it, are sometimes the ones that are really, really good. Also knowing that it’s okay to tell your idea and it’s also okay if people besides you think it’s a terrible idea.

[00:21:58] Cory: What would be your advice to young people trying to figure out what they want to do, those who may not have that idea yet?

[00:22:03] Matt: Just to try lots of stuff. That’s the number one thing. It’s impossible to sit down with a notepad and figure out exactly what you’re going to really enjoy doing or be passionate about. You have to try a bunch of things that don’t work out, then know enough to follow the one that really resonates with you.

[00:22:19] Cory: How many things did you try before WordPress?

[00:22:22] Matt: Oh, a ton. I built lots and lots of websites. Actually, WordPress originally wasn’t going to have any content management features. I was going to make a separate system called Content Press or something. WordPress would just be for blogging and these separate systems for content management. I tried lots and lots and lots of stuff, and still to this day, I try things. I think that’s really key to figuring out what’s going to work and what you’re going to enjoy and be excited about.

[00:22:45] Cory: Growing up or now as an adult, did you do things that you’re family thought was crazy?

[00:22:51] Matt: Well, dropping out of school was definitely challenging to my family. I definitely felt like I was squandering a little bit of an opportunity. My dad actually also went to U of H. But he went there and he also worked a job at a factory and was married to my mom and had a kid. [laughs] He worked way, way harder.

When I went to U of H, I had a full scholarship and made money from websites and stuff, so it wasn’t a huge struggle. Dropping out, I was wondering, I’m working so much less than my dad did for the same opportunity and I’m walking away from it. But I was walking away for it, one of the things that reassure, my mom in particular a lot.

She wanted me to go work for Google when I had spoken to them at the time, because I have free food and everything. But I seen it was better because they allowed me to retain the intellectual property rights. I was going to go see and she was like, “Oh, you want to be in Apollo company,” into it having healthcare was a really, really big deal to her. About a year later, when I was like, “Oh, I’m leaving and I’m not going to have healthcare anymore,” and stuff like that. It was definitely a bit of a challenge.

[00:23:46] Cory: If there is one thing you could pinpoint that has contributed to your success more than anything, what would that be and why?

[00:23:54] Matt: I’m not sure if I could pick just one thing. I definitely think it’s not just one thing but it’s a system. It’s working with great people but it’s also giving them autonomy. It’s being persistent but also being self-aware and knowing when you’re heading down the wrong path. Usually, for anything that you can pick, there is a important opposite that you have to keep in mind. It’s not necessarily the one thing but it’s how you navigate between two things. It’s mutually exclusive that allow you to find the path which is the most optimal.

[00:24:24] Cory: How do you manage your life and time? Do you have any specific morning, or afternoon, or evening routines?

[00:24:31] Matt: Yes, definitely. I would say the things that have been really, really effective for me in the mornings in particular is doing at least a little bit of exercise, even if it’s the seven-minute workout, and meditation. If I can do those two things and read in the morning, I found my entire day is really set up. The others, minuscule is just reading a ton. It can be fiction, it can be non-fictions, anything that’s not the news or Twitter.

Longer things and books in particular is definitely one of those things that I find — it’s one of those universals. Almost everyone you find who is successful reads or listens to audio books or just consumes a lot of that longer information on a regular basis.

[00:25:06] Cory: Which couple of books or podcasts do you think, and this is young people, should absolutely read or listen to right now?

[00:25:12] Matt: Now, I’ll name three blogs that are really, really excellent because they’re long form blogs. Once is called Farnam Street. It’s F-A-R-N-A-M street. The second is called Brain Pickings by Maria Popova and Krista Tippett on Bing, which is both a blog and a podcast. Krista Tippett’s is a little bit more of the spiritual side, Maria Popova’s kind of like on the classics, and then Farnham Street is more of like, kind of Warren Buffet, Charlie Munger, Tim Ferriss kind of newer, figuring out the ways of life that are — where the things that people have figured out before.

Those are really, really excellent ones and they refer to a ton of books, including books like Poor Charlie’s Almanac by Charlie Munger, who’s the partner of Warren Buffet. They’re some really good ones. I also enjoyed Tim Ferriss’ last two books. Tribe of Mentors is the latest and the other one is called Tools of Titans. Both Tools of Titans and Tribe of Mentors contain so much good advice and so many good references. Almost any one of the interviews or any of Tim’s podcasts, you can usually go down a rabbit hole of things to learn about and investigate.

He does a pretty good job of showing some of the commonalities between them. You can also just pick up your own patterns and the interviews or the sections that you resonate with most. Tools of Titans is really good not just because I’m in it, but the other things were good. I’m reading through Tribal Mentors right now and it’s also super excellent.

[00:26:34] Cory: Nice. Very cool. I’ll have to check that one out. What would you say your biggest challenges are right now?

[00:26:39]Matt: Right now, I think our big challenges are that we’re trying to figure out marketing for the first time. WordPress has always grown through word of mouth. I think that we’re now starting to look at doing more advertising online, offline, TV, billboards, radios, all sorts of stuff that is not native to me, not something that I’m personally wake up every morning thinking about it or really passionate about. But it’s important for as we scale the business.

The other thing is just building a great team, particularly the executive level. Automattic has been a pretty flat organization historically. I think that we could probably do to hire some more senior people or elevate some of our current people in the more senior roles than they currently are in, so it’s something that’s on my mind a lot right now. We’re about I think 620 or 630 people so it’s really getting kind of big now.

[00:27:25] Cory: Wow. Is there anything that you are trying to learn right now? Are there any — whether it’s on the web or going to different events?

[00:27:30] Matt: Definitely meditation is something that I’m working on a lot and trying to learn more. I’m also trying to learn French. [laughs] I almost hate to say it because I’m doing such a bad job. But this year, I started doing some of that Duolingo, and some Memrise MEM, RSC sort of programs. I’ve never really been able to learn a foreign language before, even growing up in Houston which is super multicultural. It’s just been an interesting way to stretch my brain.

I was able to spend six or seven weeks in Paris this summer. It was nice. It was actually pretty cool to be able to get some rudimentary phrases out. But I am still really fearful of it. I don’t know how to describe it. Obviously, in many parts of life, I lead large groups or talk in front of thousands of people. But I’d just be at a restaurant talking to a waiter and freeze up and I would like break out my rudimentary French. I’m hoping with some continued stay there, I’ll be able to pass those mental blocks.

[00:28:22] Cory: Do you have a tutor or are you doing it on your own?

[00:28:24] Matt: I’ve just been doing online stuff so far, so all apps. But it’s probably a good idea to work more with a person on a regular basis.

[00:28:31] Cory: Speaking a little bit of tutoring, do you think it’s a 100% necessary that you go to college?

[00:28:34] Matt: I think it depends on what you get out of it. Some people definitely waste their time there or squander it. I also have many, many friends that did the dropout thing that I did is a little bit of a cliche. But lots of people will drop out and do fine. I have lots of friends who’s taking an all four-year or got Masters or PhDs that are doing really awesome companies or entrepreneurial things.

I don’t think there is any one path which is right. It’s more about not where you are, but how you spend that time. I would definitely say that, don’t just drop out for the sake it. If that’s not something that you feel like you have to have to do, take advantage of the incredible luxury, which is just to push yourself to learn it. Because if you speak to anyone in their 30’s or 40’s or older, or anyone running a company, they will all tell you that the thing they wished they could just do the most is that kind of uninterrupted time devoted to learning.

[00:29:19] Cory: What excites you most today? Any exciting ideas?

[00:29:23] Matt: We’re really, really excited right now by the sort of Cambrian explosion of the open web. We had a sort of Facebook, Twitter phase where people really thought that everything was going to be on this cool social networks and Google made Google Plus. There was all this sort of stuff that was happening. We’re starting to swing around, like it’s just beginning where people find they spend most of their time online. Maybe they’re inside the Facebook app or maybe they’re looking at links, things on the web.

There’s really cool stuff going on around progressive web apps and other technologies that Google is pioneering, but lots of people are contributing to that meld the best of both worlds between what you would think of as the web and open web standards, and the best that native apps can do. These sorts of things I think we can create some really great user experiences around them. Even though it seems like these companies are huge and all the opportunities have passed, there’s still billions of people that don’t have a smartphone yet, and billions of people who have a smartphone that are still perpetuating to be more and more and publish more app.

Even hundreds of millions of small businesses still don’t have a website. There’s a ton and ton of opportunities. I’m surprised by that because I, a little bit, expected that by now, all the fruit would be picked from the tree. It really feels like we’re at the beginning of a hundred-year cycle or how technologies got transformed or how they interact with each other in the world.

[00:30:39] Cory: Cool. I want to talk a little bit about how you interview people. You have an interesting way of doing it. Can you share what that is and why you do it differently than what’s common?

[00:30:47] Matt: There’s a bit about it. I think it’s not just the interview but it’s the whole hiring process. I actually have an article. There’s an article on HBR. If you Google HBR, which stands for Harvard Business Review and my name, you’ll find it. What we try to do — I’d say what’s distinct and really important and the magic sauce of what we do is that we do a trial project with everyone, whether it’s an incoming C-level position like a CFO or a CMO, or whether it’s someone doing support or managing the offices, we find some way to replicate the real work that they’re going to do.

And just do a short a couple-day or couple-week project with them where they’re working alongside the people that we’re working with. There’s really no approximation that I’ve found through interviewing or resumes or anything that shows what it’s actually like to work in the trenches alongside someone.

[00:31:34] Cory: Got it. I read that you conduct all of your interviews over text chat. Is that right?

[00:31:39] Matt: Yes. I do a few that might be on the phone or in person but it’s only if it’s going to be someone whose job involves [laughs] doing things in person. Then obviously, you want to see if they’re good at that. If they’re going to be pitching to big enterprises and doing multimillion-dollar installations of WordPress, you probably should meet them and see if they’re good at that. For say 98% of the positions at Automattic, we really interact primarily over text and chat.

To evaluate them most fairly and see how they’ll do within the company, text is actually a really good medium for that. It also takes some of the pressure off, because if someone wants to Google something or take five or 10 minutes to compose an answer or something or edit, you could do that. Where if we were in person, I asked a question and they waited five minutes to answer, that would be a little awkward.

[00:32:26] Cory: [laughs] It would be. I have a couple more questions. I know we’re running a little bit over time. What motivates you?

[00:32:31] Matt: At this point, I really get motivated by the joy of creating things that work well, with good people. There’s really a camaraderie to working alongside folks who care about the same things that you do and who are really good at their job and bring that dedication and passion to whatever it is that you’re working on.

Then, the impact on the world just as a way to see whether what you’re doing is really working or not. To me, that’s really valuable. I find it very, very motivating.

[00:32:58] Cory: We spoke a little bit earlier about Tim Ferris’ new book, Tribe of Mentors. Who would be in your close tribe aside from Toni?

[00:33:04] Matt: I have a lot of Toni’s in my life. There’s Toni Schneider, Tony Conrad, Tony Hsieh are definitely three people who have been huge influences on me. I thought I saw you recently at a Tony Hsieh thing. That’s why you asked about that.

[00:33:15] Cory: Yeah.

[00:33:16] Matt: I get a lot of inspiration from people I’ve never met like Warren Buffett and Charlie Munger. I’m reading the Ray Dalio book right now, Principles, which I find really, really good. Laszlo Bock at Google. These are all people I’ve never met. Often through their books or their writings or their talks, I can learn a lot from. Then the people in my life, I try to find something really inspiring about everyone. Now, I get inspired by mom, by my late father.

One of my good friends is Om Malik who’s a favorite tech journalist. One of my other best friends is this guy, Rene Ornelas. In Houston, he was a firefighter. If you really spend time with people and try to understand them, you can often find something you can learn or be inspired by, for just about anyone and certainly anyone that you are investing in and having as part of your life.

[00:33:58] Cory: I’m really curious. Quick game, maybe saying one thing you’ve learned most from or been inspired by with some of these people. From the firefighter, for example, what have learned most from him?

[00:34:08] Matt: I can’t pick one thing. He’s a really amazing guy. I’ll pick two things. One, on the personal side, he’s just a guy of such incredible integrity. The way he interacts with his wife and his family, I just find super inspiring. He really is very emotionally aware and really invested in it. It’s cool to know. We both play saxophones so I met him one of the first days of high school. We were both really immature. He’s such a great father and a great husband now. I find that really inspiring.

Then from his work, how firefighters do triage when they either approach a scene, an emergency medical response, or how it works when they get to a fire. The first truck that arrived, that’s point. Then there’s a hierarchy and this incredible training. There’s a way when a higher ranking person come in later and there’s a pass off between who — like the field commander and the later person. There’s ton of protocols there that I think that actually work really well for any emergency management, even though it’s like the site going down or whether it’s a literal fire like what they deal with.

[00:35:13] Cory: What about Tony Hsieh. What have you learned in this from him?

[00:35:16] Matt: Tony is a really cool guy. One of the things that — Zappos sells shoes. But really what Tony is passionate about is finding how people work together, and whether that was all the stuff he talks about in his book Delivering Happiness for the early days of Zappos. It’s pretty much they’re doing it with Holacracy and they really evolved to the point where it’s something different than Holacracy now.

He’s just kind of an endless experimenter. It’s something I really admire of like Tony Hsieh or someone like Steve Jurvetson, is that they’re just endlessly curious. They’re always learning and trying to look if there’s a different way to think about things and trying a lot of stuff out, being comfortable with a lot of that stuff not working. When you see a criticism over the Downtown project or Zappos with Tony Hsieh, it’s usually, “because the stuff didn’t work.” That’s part of the genius of it, is that a lot of it is not going to work but that’s where you often learn the most.

[00:36:02] Cory: What about Tony Conrad?

[00:36:04] Matt: Tony Conrad I think is one of these guys who just has off-the-charts emotional intelligence. He’s really good at understanding people and thinking about the context for whatever it is they’re doing, like what motivates people, what do they want out of life or out of their work or out of the deal or out of a relationship or anything, and not like it’s intrinsically like in a transactional way but maybe what kind of motivates their core or what was part of their upbringing, or the thing that is really key to them, like you asked what motivated me earlier.

He can often figure that out about someone after meeting him just for a few minutes and then use that context to better understand them. I have always been really impressed with that.

[00:36:46] Cory: I know earlier we spoke about Toni Schneider and some of the early things you learned from him. What about some of the more recent?

[00:36:01] Matt: I think I’ve already spoken about some of the biggest ones. But I think something that Toni demonstrates really daily and I take inspiration from is just a really no-ego approach to really everything. He’s got a great family, great kids, a long relationship with his wife. Those are all inspiring.

Also in business, he’s a super, super, super smart guy. He’s very, very accomplished. He has every reason to be very egotistical. But he still approaches everything with a very open mind and especially when I was younger, but still to this day. Sometimes I’ll be very certain that I’m correct and it always inspires me that Toni is both patient with me when I feel that way.

But then also, even when he’s right, he listens to all sides of an argument or an idea and really considers it. He really listens as much. He’s not just waiting for his turn to speak. He’s really thinking about everything you say. It’s probably one of the reasons he has successful personal relationships and everything like that. Yes, it’s something that even just the last time I hang out with Toni I thought about.

[00:37:56] Cory: Very cool. That’s awesome. My last question is, I’m curious, what did you want to be when you grew up like when you’re young? You went to HSPVA. Did you expect to be on this path or when you were in elementary school or middle school or high school there’s something different?

[00:38:10] Matt: [laughs] I would say like elementary through high school, I really wanted to be a musician. Then at some point, kind of late high school, early college, I wanted to be an economist and luckily I did not go down that path.

[00:38:23] Cory: Well, I appreciate you taking the time.

[00:38:24] Matt: It was good to chat. I hope you’re doing well, in general.

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