Matt Mullenweg built Automattic into a $7.5B company

coming up on Venture Voice. So we got that bill. And by the way,

that was a substantial part of all the money we had at the time. I thought it was like a light

bill. You just pay it. And then Tony came in. He was like, no, this is actually a lot. They

should give us a break because we're brand new. And they know that we're going to be a customer

for a really long time. So I'm going to go negotiate this down. I was like, what? You

can negotiate a bill? Never even occurred to me that that was something you could do.

And sure enough, he went there and he was like, hey, we're starting out. We're five people now.

We're going to be a lot more in the future. So can you give us a break on this? We'll have

more money in the future too. And the company, they're just down. They reduced the bill quite a

bit. Welcome to Venture Voice. This is Greg Gallant. I am so excited to bring you this

interview with Matt Mullenweg, the CEO of Automatic.

And pretty much founder of WordPress. WordPress now powers a good chunk of the internet.

He employs over 1,700 people across 91 countries. And even more interesting than all of Matt's

business accomplishments, and I should say Automatic, his company now also owns Tumblr,

SimpleNote, Parsley, a bunch of other products that I personally love using.

But the really interesting thing about Matt is that he's

pioneered remote work. His company's pretty much enabled remote work for the 16 years that

they've been around. Matt has been an inspiration for me and my own company called MuckRack,

which is a PR software platform. We have over 100 employees. We used to be half remote,

half in person. And during the pandemic, we decided to commit to being fully remote.

We actually launched the Work Remotely Forever pledge. You can check out workremotelyforever.com

to see it.

And Matt was the first person to sign on. Having him signed on gave us such confidence to go out

and get dozens of more companies representing thousands and thousands of jobs to agree to

let their employees work remotely forever. I've done my business for 10 years. It's hard to keep

motivated and to stay fresh. Matt has pretty much ran WordPress for 16 years, eight as president,

working with the CEO, but still the founder and largest shareholder.

And then eight as CEO, he took it over and put in a lot of really forward-thinking strategies,

made a super interesting capital structure. And for someone like me,

who loves running his business and hopes to run it for many years to come,

there are very few entrepreneurs to point to have done it in this way without taking lots of venture

money and going public or committing to doing things the traditional way in a physical office.

So,

Matt has broke the molds in many ways. I was really excited to talk to him for this interview.

I hope you enjoy it as much as I did.

Matt, welcome to Venture Voice.

Hello. Thanks. Have a good morning.

Usually, I love to start by asking people when they started their first business. Sometimes

it's from childhood, but in your case, it all started with a blog. So, I'd love to hear how

old you were and just where you were in life and what inspired you to want to start blogging.

How old was I? I was probably still in high school, but the later part, maybe 17 or 18.

It would have been probably around 2000, 2001. And I was just reading blogs and loving them.

Some that are still going today, like Tyler Cohen's Marginal Revolutions,

which is blogging on WordPress today and I think almost daily. So, I was just reading these blogs

and I was so impressed by how they were doing what I was doing, which was reading the internet,

but then they would curate the best for their friends and they'd share about it and share

their opinions and use it.

It was like a personal journal. So, those early bloggers really influenced me to start blogging

myself, made it very accessible.

Cool. And how do you go from actually just writing a blog to actually thinking about

the blogging software?

I think every blogger tinkering with a blog is as much time as writing itself,

at least for the ones that like me. And so, I was always tweaking the software,

trying to make it just represent myself more personally because I didn't want my site to

look like every other site out there on the internet. And so, I wanted to be really custom.

What I felt like represented me. And so, that customization led me to switch software.

My first blog was probably on LiveJournal, then I switched to MoveableType or Blogger,

then MoveableType. And then finally, I found this software called B2,

which was an open source blogging software written in PHP. So, it was very easy to modify

and also to community. So, that was really the one I took to. The long story short is that

was what was the base for what became WordPress later.

Cool. And it's so funny to think back when I started this podcast in 2005. I also started

out as a blogger. I started out as a blogger. I started out as a blogger. I started out as a blogger.

And at the time, it just seemed like they were the dominant force.

They were?

It seemed hard to imagine unseating it. When you switched off MoveableType,

how much of it was just a personal desire? How much of it, I know people can get very

passionate about what open source platform they're on, but to what degree did you foresee like,

hey, maybe MoveableType won't be it forever? Or was it just really you thinking that you were

going off to the fringe?

For me, it was a philosophical decision as much as anything. MoveableType was not open source.

And so, I was really beginning to understand the importance of, you know, if you're using software,

if it's open source, it increases your freedom. If it's not open source, it decreases your freedom.

And so, I was trying to increase my freedom as much as possible. And so, opting into open source

wherever I could was great. So, that was part of what drew me to be too.

And then also the customization. You know, MoveableType was written in Perl.

It would generate these static pages, not unlike some static state generators today,

but that to me felt very clunky. I loved with PHP. I could just change one file and instantly

my entire site, thousands or even millions of pages would be up to date. So, that was very,

very compelling to me about the PHP fully dynamic approach to blogging. But did I expect others to

care about that stuff as much as me? No, probably not. And what we focused on though,

that I think ended up being a big strategic advantage, was the installation process. At the

time, the company behind MoveableType, which was called Six Apart, you could pay them 50 bucks or

something to install the blog for you because it was kind of difficult to set up. But that also

created the incentive for them to not make the setup that much easier. I don't think consciously.

No one sat down in a meeting and said, we're going to make it hard to install.

But just subconsciously, it just wasn't their first priority when they were working on things.

We had no users. So, getting people to install it was really, really important.

So, it focused a lot on the installation process. And I think that's what made it so important.

On making that installation process as clear as possible. It actually wasn't easy,

but we tried to make it clear. And then, I think I had gone to some diner that had some milkshake.

It was like, this is the famous milkshake. The famous Mel's milkshake or something.

And I thought to myself, like, is it really famous? I've never heard of this before.

This milkshake doesn't have like an encyclopedia entry or anything like that.

They just call it famous. And then you're more likely to order it because they call it famous.

So, for WordPress, I called it the famous five-minute install.

Even though it was certainly not famous at the time.

I just branded it as famous. And you know what? It became a self-fulfilling prophecy.

People really would talk about that five-minute install as something that was a huge contrast to others.

That's a prophetic fame. The fame came first before the notoriety.

When WordPress, you were starting it as an open source movement,

did you have any idea back then that there could be a business around it?

Or was it purely kind of that feeling of hobby and just wanting to build an online community?

It was much,

much more just wanting the software to exist.

There were some open source businesses, but the models weren't as well developed yet

and hadn't had the idea for things like Akismet or other SaaS services that could plug into WordPress.

So, it was just early days of the internet too, at least to me.

It had been around, but to me, it was still pretty new.

And so, tell me then, what was going on in your life at the time?

Like, where were you? How are you thinking about your need to make money?

Where you wanted your career to go as you were building WordPress?

As an open source community?

I would have been finishing up my high school, which was, I went to a special performing arts

high school where we had no sports, no gym, no anything, but we would do three plus hours of

our art area per week, which for me was jazz saxophone. I ended up deciding to stay in Houston

to go to the University of Houston, where my father went actually. I was making money at the

time. I moved out as soon as I could when I was 18. And I would make money two ways by playing

gigs for the saxophone, often union gigs.

Which was great, because we'd get a check in the mail later. Or building computers, like buying

parts and putting computers together, mostly for other musicians. And I guess the third way,

which is making these really terrible websites. Using like Dreamweaver and Frontpage. And like,

I didn't really understand what it was to make the web then, but I liked figuring out software.

So that was my income screams. The computers were honestly a lot better than the websites.

So, but over the time, the websites became to be more and more of a focus. It was more fun to me,

because it,

it was about community. There were other people on the websites.

And what was the moment where you realized that WordPress, the open source

project, that there could also be a business to build alongside it?

I don't think I would notice that or realize that for many years to come.

A year, year and a half in the WordPress, I gained some notoriety for writing it. And then

that caused me a job offer at a media company called CNET Networks, which ran news.com and

download.com and a bunch of big media properties.

At the time, but getting the job was kind of my, my business model. I was like, oh, great. I got a

job. I'm a 20 year old kid from Houston without a college degree. So that was cool. And that also

allowed me to move out to San Francisco, which was really where I felt like I found my tribe

in Houston. I had, you know, a handful of people, part of like the open source, not the nonprofits

there, the tech support groups or others that felt like they were passionate about the same

things I was, but San Francisco, it was just in the water. So WordPress was your resume more than a

business.

Yeah.

It was your, your calling card to get noticed by employers.

Yeah. And in fact, you know, something that my co-founder of WordPress, I had a co-founder,

he chose not to focus on it full time. He had a job and a life and kids and things. And so he

kind of went a different direction. We were all just volunteers and all, I think not,

didn't have a strong sense of any commercial possibilities.

Yeah. And I remember right at the time there was this feeling kind of open sources,

almost anti-business or that it was not compatible with the idea of making money.

And literally we were giving the software away. So what all of our competitors were charging for,

we were doing for free. So it just seemed like we would need to figure something else out if we

wanted to have a business. I would say our grand aspirations were, I was getting paid, you know,

20% of my time for working on WordPress. It's like, if I can ever get that to 50 or a hundred

percent, that would be golden. So our business wants are also really modest. We just wanted

kind of the people working on it to be able to work on it full time.

What was that moment at CNET that let you leave there?

And be able to focus full time on WordPress?

Well, I'd started to figure out some business models for WordPress and running some advertising,

partnering with some web hosts on sort of sending people to them. And then they chair back the

revenue from the people who signed up for the hosting was just starting to kick off. And so

that started to be a lot of money, a couple hundred bucks a month, a couple thousand bucks a month

to where we were able to bootstrap the company through the first three or four hires full time.

Including myself.

Were you even your first own hire? Did you start hiring people before you left CNET?

No, I actually started paying people just out of my CNET salary. And in fact,

I over leveraged myself. I got a little over my skis there, maxed out all my credit cards and

everything. But I was just, yeah, I think I ended up being the third person to join full time,

even though I was the founder. Part of that as well was, even though I told CNET I was going to

leave, they asked if I could finish up some projects. So I stayed on a couple of months,

actually.

To wrap up some things I've been working on. I had so much appreciation to them for moving me out,

taking a chance on a kid from Houston. I really want to make sure that all the things I had set

out there to do, I'd finished. And actually, I was really proud. I ended up doing some software

that saved them. It made them millions of dollars more than they would have because they were paying

a lot of licensing fees and things out. So I was proud of my tenure there, even though it was short,

just a little under a year.

So you do the year there and now your credit cards are maxed out. You actually,

you have a payroll. Was that scary at that moment? I mean, I know a lot of people,

I got freaked out when I first had a payroll to support much less all the credit card debt.

Totally. And to me, it was just a responsibility of these other early folks who had put their

trust in me. They left a job that was from a real company and joined me. And I'd already

kind of over-extended myself once. I wanted to make sure that even if everything went to zero,

I could still give all these folks some time to find another job and not miss a paycheck and

everything like that. So that was really what led me to raising our first round. Even though we were

break-even at the time, I thought, well, let's have some money in the bank. It was like a rainy

day. So if anything happens, I can make sure these folks who have entrusted me, I'm repaying that

trust. Two things I find really fascinating about your story. One, obviously, the early adoption of

remote work, and you were very gracious in joining us.

Signing the Work Remotely Forever Pledge. And it's been a big inspiration for how we grew

MuckRack and being a remote-first company. And the other is how you've done your financing with it

all to let you be flexible enough to still be an independent private company. I guess there were a

couple of pivotal things happening back then. But just to go back to the start, those first two or

three people, my understanding was they were all remote. They weren't in San Francisco.

Yeah. So first couple of people were...

People I was already working with on the volunteer open source project. And open source projects

attract people from all over the globe. It's not just people in one city using WordPress. It was

very much a global phenomenon. And so first person was in Larney, Ireland. Second was, I think, in

maybe Vermont, if I'm remembering correctly. Maybe Seattle. I was probably third in San Francisco.

We had someone join in Texas. So it was from the very beginning, really, really spread out,

including time zones.

So you've got this totally spread out company. And now, it's so funny to look back at it now when

that'd be totally normal since it's the pandemic and everyone's just accepted their remote work

works. But at the time, and that was before easy video chat and all that, what was it like going

out to investors? Because I just remember being in Silicon Valley around then, and there just being

this idea that like, hey, if you're a startup, there's some office I can go to and I'm going to

see a bunch of people sitting around. And I was like, I'm going to go to a company that's going to

coding. And a startup was an office of a bunch of people or a garage or whatever the cliche was,

or somewhere in Soma, just like a bunch of people working. And here you are, probably just meeting

with people alone in your apartment or in a coffee shop and saying, we have no office. I don't have

anyone else here in San Francisco for you to meet. A little weird and definitely turned a lot of

investors off. I found investors basically fell in two camps. There was one camp, which often who

had operated a company before, who were very concerned about how you were building the

company, which to be fair, I was a 20-year-old kid, so they should be. It wasn't like I knew

what I was doing. But then there was a second class that was just concerned with what you

were accomplishing. And so the ones that were seeing what we were accomplishing were the ones

that ended up investing and the ones who would sort of say how we were doing it and saw that

we were doing it different from every other company they had done or invested in that had

been successful. I think pattern matched to say like, okay, maybe this is not,

a good fit, or maybe this is a little too weird.

And at the time, were you just kind of like everyone else in Silicon Valley where you're

like, hey, I've got something working. And of course, the next step is to raise venture. Or

was there any part of you that was thinking like, you know, going more of that 37 signals

based camp route and unsure if you wanted to take on outside investors?

I was very much not sure to take on outside investors. In fact, didn't want to for the

first part. And I don't think I was going to take on outside investors. I don't think I was going to

necessarily needed to. Because at the time, the model was not founder led companies, but

bringing in adult supervision. So the model that most people would look at was Larry and Sergey

on themselves geniuses who found a Google, they brought in Eric Schmidt as like the adult

supervision to run the company. So I knew if we raise money, they would want to bring in adult

supervision. And that didn't sound like fun to me. Until I met this gentleman, Tony Schneider.

Tony had been a CEO of a company that just sold

Yahoo. He was introduced to me by someone who's still one of my best friends, the journalist Omalek,

who had written a business, a cover story on him for a magazine. And when Tony and I met,

it was like we're two sides of the same brain. And he was someone who was a really amazing guy,

a great person, understood open source and everything I was doing, and that we wanted

to accomplish, got the vision immediately, but also was an experienced executive. And so when

I was like, I would, I would love to work for this guy. You know,

I was like, well, if I can choose the adult, adult supervision, isn't that bad?

And so that's how Tony and I ended up partnering in the beginning. I can see myself so incredibly

lucky that I met him and that he was, you know, that we were able to hire him a CEO

to join the company. And he was CEO for the first eight years of the company.

Ah, so choose your own babysitter.

Yeah. And this, you know, Tony and I are still so close to this day. So it's one of those things

where it's not often that you meet someone and you click so much on that first meeting and it's

still going strong.

You know, 16 years later, but that's definitely Tony and I. And so I just can say, again,

I've met thousands of people. Tony's kind of one in a million for me and how well we mesh

then and now.

And how's your dynamic work? And I, you know, like, like you were saying, I'm sure,

you know, it's probably somewhat similar to the Google dynamics where, you know, you have,

you is the founder who I imagine owned more of the company and was thought of as synonymous

with WordPress, but then you had Tony come in whose title?

The CEO and in a corporation, the CEO is the, uh, the top dog.

Well, a lot of things I'd read at the time made it clear that when reporting lines were uncertain,

or if executives were, you know, having the two parent effect where people go to one and then

get one answer and another get the other answer that wouldn't work well. Right. And so I always,

it was very clear in my mind that Tony had the final call on things.

And that was why I was hiring because I wanted him to have the final call on things and, uh,

that we'd want to, we'd want to, we'd want to, we'd want to, we'd want to, we'd want to, we'd want to,

and, you know, always be in agreement or consensus within the company, even when we were small,

you know, five or six people. So we would talk and debate endlessly, including with the rest of

the folks in the company, but we'd always make sure that we ended up agreeing on a path, even

if it was sort of what is now called like disagree and commit. Like maybe we disagreed, but we commit

on what we were going to do. And then whatever that was, we would go fully into it with no

hesitation, just like really try to make that as successful as possible.

So that is very basic advice, but I probably got it from some book, but it ended up being very,

very helpful. I think in Tony's mind as well, he might be better asked about this as well,

is he was thinking, well, you know, Matt's writing the code, he's, you know, working with

engineers. So he really tried to set up clear areas of responsibility. So I was the president,

but he ended up giving me a ton of responsibility for a lot of things within the company. And that

really grew over time to when we did actually do the handoff where

took over our CEO. It was very, very natural. It was really like a very smooth baton pass

because he had done such a good job grooming me and teaching me and passing more and more

responsibilities on. So by the time we did that handover, it was, you know, very friction-free

within the company. Cool. So it wasn't one of these situations where you were just chairman

and had no direct reports and was floating around. Like, did you actually have reports

and divisions rolling up to you and kind of a span of control? Yeah, more the latter. So

I think my title as president and the engineering and the product all reported into me,

which ended up being a big part of the company as a rule.

And now for Tony, he was already a successful CEO. I didn't actually get a chance to research

this, but I imagine his prior company, it was in a non-remote company and an office company.

Is that true? And if so, you know, was it hard to get him on board with the remote work train?

They did have an office.

They might've had people remote. I don't remember. It was called Allposts and they

were a very forward, progressive company in so many ways. But Tony also fully got the remote

thing. So there was never any hesitation or issues there. He also, though, knew the importance of

getting people together. So at the time, I think those first, the first year we flew everyone in

twice to where we all got together, brainstorm, hang out, share a meal. And that was really key

to the culture then. And now, you know, pre-pandemic, we would tell people who

joined Automatic to expect three to four weeks of travel per year. And that means probably three,

four, maybe five times you're meeting your colleagues. Maybe it's at a conference,

maybe it's at a whole company meetup, but like you're seeing people pretty regularly.

What are the biggest things that you learned from Tony that you didn't,

kind of weren't on your radar prior to hiring him? Like you knew this concept of like,

oh, experienced CEO, adult supervision, but like, what did you see him do where you were like,

I would have never, never thought to do that or never,

expected that next move from him.

It's countless, but I'll share one antidote from the very, very beginning, which I thought was

funny. Tony joined at the perfect time because we hadn't had to like pay taxes or do a lot of

things yet. And I first incorporate the company on LegalZoom, but then we hired some lawyers to like

redo it and make it clean and everything like that to be venture backed. And that cost, gosh,

who knows, $20,000 or whatever it was that they billed to incorporate the company. Because it

wasn't like a template.

It was still like they would do everything from scratch, or at least bill you like it was from

scratch. And so we got that bill. And by the way, that was a substantial part of all the money we

had at the time. I thought it was like a light bill. You just pay it. And then Tony came in,

he was like, no, like this, this is actually a lot. They should give us a break because we're

like brand new. And they know that we're going to be a customer for a really long time. So I'm

going to go negotiate this down. I was like, what? You can negotiate a bill? Never even occurred to

me that that was something you could do. And, uh,

and sure enough, he went there and he was like, Hey, we're starting out. We're, we're five people

now and we're going to be a lot more in the future. So can you give us a break on this? We'll have

more money in the future too. And the company did just that. They reduced the bill quite a bit.

So you're getting to kind of watch someone in action, like getting to kind of skip maybe what

would normally take an entrepreneur two, three, four years to learn. You're just getting to watch

all this, uh, for a pro. Yeah. There was no blog that I had ever read that said that no book,

and certainly the lawyers weren't going to tell me that I could negotiate the bill down.

Okay. I'll tell the lawyers for everything. And so, uh, along that way of working with,

um, working with Tony, how, how do you learn yourself to be, you know, kind of go from that?

Uh, you obviously knew how to collaborate really, really well, which is what open source is all

about. How do you become a manager yourself and know how to deal with performance issues of people

on your team and structure your teams and just everything that goes along with the business

of management? For better or worse, I would say that was largely trial and error over the past 16

years. Um, the good news is, as you said, we were really great at collaborating around the product.

So the team, I think because we were coming from open source, we worked together before

and we were so in touch with the users and we were users ourselves of WordPress.

We never had any issue making products that really resonated with people

and that every iteration, it would appeal to a wider and wider audience.

But everything else in management, you know, I really had to learn largely through reading books.

A lot of seeing the example of Tony, the example of other more experienced people who joined,

which was by definition, pretty much everyone joining the company had more experience than me.

And, uh, and like I said, some trial and error, including, you know, being not the best manager

for some people or reacting from a place of fear or ego when something was happening,

but then seeing, you know, that doesn't work as well as when you can do the opposite.

Do you remember any specific,

specific examples where you just had a management issue and just had no idea what to do or wanted to

run away from it as, you know, I think all of us did as you were learning to be managers?

I think some of it because we were, we were pretty frugal and we were getting started and

we were really tight knit team that was high performance.

Some of the stuff that we ended up doing, which ended up with being innovative

was kind of just working from first principles of what was working.

So hiring engineers.

We did the interviews and we did the thing that we had seen other companies do where we brought

them in for a panel and they would write on a whiteboard and like, they would talk to seven

different people. I think we over-indexed for people who had like masters or PhDs in computer

science and like really tried to go for that. And then some of those early hires really didn't work

out. And so we just kind of looked around the table and we're like, well, we're all really good.

And we don't have similar backgrounds. Like I did political science and I didn't finish.

I was a dropout.

Maybe like indexing on college degrees is not the best thing because obviously we don't all have

these fancy college degrees from Stanford and MIT and stuff. And so we're like, well,

what did allow us to work well together? Well, we actually did the work. So we worked well together.

And so we knew we would work well together. There was a little bit of a truism, but it was true as

well. Like people who were referred, someone was like, oh, I worked with this person at a previous

company. They usually end up working really well. But it was like, well, we're tapping out the

people we've worked with before and we can't afford some of those people.

So how do we make it so for anyone who shows up to the door in the world,

we can see whether they would be someone we work well? Like, well, let's just figure out a trial

project. Let's figure out like a small project that could take a couple of days that, you know,

could be even like a bug on the open source. Like just send them a bug and say, hey, this is a bug

in WordPress. Do something to it. And so that evolved to become our trial project, which I

think was, and actually still to this day, a huge competitive advantage for us in hiring because

we almost,

don't look at the resume at all. All we look at further in the resume is typos.

Like, is there attention to detail? But other than that, go to college anywhere, have any

previous work experience, be a barista, be a team master. It doesn't matter to me. Have a 10-year

gap in your resume. Who cares? I'm looking at the quality of your application, the quality of

writing in your cover letter. So are you a clear writer? And if that's true, you know, let's chat.

And then if the chat's good, let's do some little project together. Over time, we've gotten

better at making those projects really good at predicting someone's future success. But that

allowed us to really tap into talent that was, came from non-traditional backgrounds or had

kind of a non-traditional work experience. How do you manage that tension? Like you'd

mentioned, you kind of first did it the Silicon Valley conventional way. Then you did the more

kind of first principles, let's just figure this out way. And I've heard kind of two schools of

thought. There are a lot of people who are like, hey, what we do is the product that's unique.

You know, WordPress is going to be unique and everything else that's been figured out before.

So we can just hire people from Google or now Facebook or whatever, and implement the playbook

way of doing things versus the idea of like, hey, we could do everything from first principle. But

of course, you know, if you do that, it could be so much work to get going that it'll take forever.

What's your learning bit on like when to go for the playbook and when to

figure it out first principle? I guess if the playbook's working,

keep doing it, right? But for us, the playbook wasn't working.

And maybe it's because I hadn't worked at a Google or Microsoft or Yahoo or the big companies at the

time. So I didn't know who were the right people in those companies. Or we were all coming from

like outside of Silicon Valley. So yeah, the playbook just wasn't working for us. We tried it.

You know, we had investors and friends at other companies were like, here's what you do. So we

tried that first. But then we're like, okay, let's try something else. And that ended up being a real

competitive advantage for us because almost everyone else was working out of the playbook.

So by using our own book, I think we,

we're able to build something with a lot more staying power and a lot stronger foundation.

Another thing is like the people we were hiring stayed, you know, we had so much still to this

day have a much, much lower attrition rate than almost every other technology company I'm aware

of the numbers for. And so that allows you to build a stronger culture, allows you to build more

expertise and sort of pass along knowledge from more tenured people to newer people,

which I think is, again, a really huge competitive advantage for our company.

So let's fast forward now eight years to when Tony's does the transition and the adult

supervision's no longer needed and you get the, the keys to the company. What was there a specific

event that precipitated it? You know, not why it wasn't seven years in or nine years in what,

what was it at that eighth year that kind of triggered that discussion?

There was kind of a, an arbitrary milestone, which was my 30th birthday.

So I was exiting.

I was in my twenties. I was into my thirties. Yeah. Tony was in his thirties when he was,

was the CEO of the company. So that was kind of the arbitrary one. That was also kind of fun.

I think we officially did the handoff, did a fun party down in Mexico. Tony was there. And then

like the Monday after that, we did the official handover, but I'll say the conversation that

started a few years before. And it was just, you know, Tony is a very aware and conscious person.

And he was like, yeah, I really enjoy working with small teams. So it automatically getting bigger.

And over time I had become really passionate about what it would take to scale.

I got really into that idea of like, okay, how would you go from 15 to 50 to 500 to 5,000

and became kind of obsessed with learning about that. And so that was a very, very natural thing.

And the fun thing about it was Tony just took a different job within the company.

He was like, I'm going to take off the CEO hat, but now I want to run some teams. I want to work

with some of these small teams again, which also created this,

this amazing legacy of kind of like how the best thing that George Washington did

when he was the first president of the United States was I stepped down, you know,

it sort of made it. So there was this orderly transition of power. It's actually very,

very key and automatic that when people become leads of a team or division or something like

that, if ever they feel they're not getting energy from it or passionate about it, or the best person

in the world for it, they can step down yet still stay at the company and still have a great job or

find something that they are passionate about. And so I think that's a really, really, really

passionate about within the company. So it doesn't mean they have to leave their colleagues

in this great, you know, kind of a team that we've created together. So Tony was an amazing

example of that. So some of the things he just did being himself have become really key parts

of the culture. Another thing that he did was he took, I don't remember exactly how long it was,

but I think it was at least a month or two in there and did a road trip around the country

with his family. So, you know, he's European, he's Swiss, he's used to longer vacations.

And at one point he was just like, yeah, I want to do this road trip with my family. The kids are

the right age, you know, we're young, we're healthy. And so I'm going to take a few months

off. So Matt, run things while I'm out. So that was also kind of a practice run. But two, like,

yeah, this is a really valuable thing that ended up turning into a benefit that now we offer to

every automatician, which is we call it sabbaticals. So every five years at Automatic, you get two to

three months of pay time off, minimum two, maximum three. And, uh,

it's fully paid. So you get your full salary for that time and you can do whatever you like.

It ends up being a really amazing benefit for people. Often people do life experiences that

they remember and cherish the rest of their life, whether it's with family or doing a backpacking

trip or something like that. So the inspirations were Tony and also this nonprofit I joined the

board of called Grist. And they circulated this white paper that was like, uh, nonprofits become

too dependent on the journal managers, their founders. They become a bottleneck for everything

in the organization. So if you're a nonprofit board,

you should force that person to take a few months off because then the rest of the organization can

figure out how to operate without them. And otherwise it'll just always be dependent and

you'll get all these like inefficiencies. And so the other thing about sabbaticals is it,

it forces the organization to figure out how to operate without that person. It maybe gives a,

someone there, they're grooming to be a successor to their role, like a chance to try it out.

Like it creates actually so many great things for the organization. And so I do incentivize people

to do that. Well, you just pay them.

You say, okay, make your full salary and then do your own thing. And that's an addition to the

normal vacation or other benefits that we have. So again, I consider ourselves lucky that some

of these early things, sort of some serendipity combined with some research ended up being

things that are key to our culture.

How big was a automatic when, when you did this transition at your 30th birthday?

I'd have to look up to see the exact number, but call it on the order of magnitude, like 150, 200.

So you take over at that scale.

But what do you observe kind of before and after, like, what were the,

the kind of biggest moments in scale where you had to change your job as CEO and running the company?

You know, the first thing was actually around fundraising, which is pretty interesting.

The first, I guess that was eight or nine years of the company. We did the whole thing on just

$11 million of outside capital. So like a million dollar round in the beginning,

then like a $10 million round later. So that wasn't very much. It was largely bootstrapped.

So the company was kind of growing as the revenues grew. And Tony had advocated to raise more money

so we could grow faster in the past. But I never got comfortable with that because to me, bigger

companies were less innovative, less fun, less good. But then once I became CEO, even though it

was in some ways just a title change, even more than responsibility change, it became clear to me

how right Tony was. We were capital constrained. And so we went out to, to raise around our Series C.

And that was, I think, 2014 when we closed it. And we became a unicorn in that round. And we've

raised $160 million, both of which now seem like not a huge deal. It like happens five times a

week. But we were one of the very first ones. And I think we're the first to do around that large

because that was kind of what people were raising in IPOs. So it was like we did an IPO, yet we

stayed public, maintained control of the company, and gave ourselves a lot of room to really put the

gas pedal on and accelerate growth.

And so that was very much a turning point for the company because it hadn't been as clear to me,

but we were capital constrained and our opportunity was much bigger than our revenue growth was able

to support at that time.

How do you think you missed that as, I mean, you were working with Tony, you were on the board,

you had this remote company, like what, what was it that getting the CEO title let you see

something that you couldn't see as president and as founder?

Yeah, I wish I knew.

Because then I could tell folks to avoid it. But it was just probably my hard-headedness.

Let me see. Yeah, at that time, WordPress was 21% of the web.

Wow.

So about half as large as it was now. Yeah, but we figured it out eventually.

Cool. Yeah. And you know, it's funny going back to that, because I remember there was this big

idea at the time that you could do so much with few employees, which it sounds like is the idea

you had. I remember looking at, I forget who it was that did a presentation on this, but they

showed the top 10 website.

And, you know, you had Yahoo, which was like the old dinosaur with thousands of employees. But then

you had Craigslist, which then had about a hundred employees or maybe less. And you had Wikipedia,

which had a couple dozen employees. So I remember this kind of feeling of optimism back then that

like, hey, you could have this huge company. We have the internet and technology leverage. You

could have this huge company with very few employees. And maybe we're trending towards

a day when it's just, you know, one person. And, you know, I don't know, I don't know, I don't

remember getting respect for every one of those. I got a server plugged in, and that'll be $106,000

company.

Which happened with like Instagram and WhatsApp and like some really amazing examples.

That's a great point. Yeah, yeah. So we saw that. But then even with those ones,

right, eventually they get acquired. And now there's, God knows how many thousands of people,

you know, within Facebook working on Instagram and WhatsApp. And then you were kind of at that

pivotal point, right? Like you could have decided back then just to make lots of profits, have 150

people and maybe do it. But what happened?

What happened?

do you think it is that you know that like what or what led you anyhow to just decide like hey we

need more humans here i'm not satisfied just having a small relatively small team running

this business that could scale and make lots of profit i think still in an automatic the best

work is done by small teams to this day but just we're doing work on more things so that's where

i don't think the depth of what you do necessarily can expand but the breadth can really go and so

our whole structure and how we try to run things is balancing out how can we create like a sort of

forest of small teams that are fast and iterated quickly and have a lot of autonomy but then just

do more stuff you know we're 2 000 people now in our current roadmap there's enough work for

10 000 people easily and so it's just about how do we grow the business to be able to support that

in the meantime i want to learn about the kind of endurance

that let you know automatic and you keep going for all these years but first i'd love to just

hear with the investors because i think there's this idea that hey if you take vc the vc is going

to be on a whatever you know five to seven year time span and the timetable for sure yeah they

need an exit and i guess the conventional wisdom was always like hey if you take vc in five years

you're going to ipo or you're going to get fully acquired by some bigger company how have you

16 years without either ipoing or getting acquired again we were we're fairly lucky um there's a name

which is very well known now which is tiger global which is a hedge fund out of new york which is some

of the smartest investors of the past few decades no one knew who they were they reached out a

gentleman named leaf excel and i think 2013 he's like hey i've seen your business he actually came

to a sort of de novo where he was on vacation in mexico and thinking about like what is the future

well there's going to be something powering like the operating system and then he came back i was

like let me figure that out then he came across wordpress he was like and then he just reached

out cold and we didn't know what an incredible investors they were but they came in and they

said well we want to be a long-term holder of this company we think you can run it so we're

not trying to like take a board seat or anything like that and we're happy to buy stock from your

existing investors if they're done so that's the thing sometimes funds might need an exit but you

have to be a long-term holder of the whole company and uh tiger was really helped us with that and

they really helped us with that one thing i i always say to every shareholder whether they're

new or existing is if for whatever reason you need liquidity i'll find it for you that's my

commitment to you as the ceo i consider that part of my fiduciary responsibility i can't promise you

it's the right thing for the rest of the company the whole company to sell or to ipo that's driven

by a lot of factors and in fact i'm never going to do it for an external pressure it will only be

what's right for the business but if you your shares you know you want to sell i'll help you

with that and i'll call investors and i'll like pound the streets even though it's not my first

choice of things to do it's kind of like actually at the very bottom of my list of things i love to

do but that's my commitment to anyone joining and that gives people a lot of confidence to hold as

well we definitely have had many early investors that have sold along the way which they needed to

or early employees or things but we have others that knowing that they they can sell at any time

gives them the confidence to hold and they just kind of look at the metrics of the business say

well this is growing faster than other things i could put my money in i'll let it roll i would

say also in this time period in 2005 to now it's much more normal for limited partners to give

extensions to funds sometimes indefinitely when a stock is doing well because they've seen how

many returns they've missed out on by selling early in the best companies this is how you

probably saw sequoia just switch where they can now have public holdings and definitely i think

a lot of venture had some amazing returns the returns could be an order of magnitude higher

if they were allowed to hold longer so now it's now it's a little bit of common wisdom that if

you've got you know if you've caught a tiger don't let go no pun intended yeah if you're on a rocket

ship don't jump off stay on it as long as you can and now we know i mean we have companies

like google and apple at tens of billions hundreds of billions of dollars still growing 30 and 40

so the growth of

a worldwide technology company appears to have no ceiling yet we haven't yet found the most

valuable companies in the world trillions of dollars of market cap is possible so where before

i think people assumed that an exit of a billion dollars was like a once-in-a-lifetime event now

we know you can actually build tons and tons of value that's right and so interesting to think

that the kind of the investors and the mechanisms you're using now to stay private didn't exist or

would have never invested in technology back when you started this

company yeah you know one of our largest new investors of the past few years is actually

bernard arnault who's uh the chairman of uh lvmh louis vuitton white hennessy which is one of the

largest luxury conglomerates in the world he's obviously a super smart guy and understands

the impact of technology on his businesses understands quality understands creativity

understands building businesses and conglomerates over decades so he's an amazing fit for us doing

what we're trying to do which is create essentially a holding company which is automatic

is not unlike a berkshire hathaway or an lvmh or an ic or an alphabet that has products like

wordpress tumblr woocommerce jetpack that can grow to be companies on their own which are really

substantial and in fact could be public if they wanted to and i saw you just did a uh a new raise

of uh 288 million back in february uh congrats on that thank you i was reading as part of it

you provided a uh a buyout for your employees which i imagine is another big

vector of this this challenge of staying private and not having that typical like

hey ipo everyone's stock options are worth money and you can look at the market

how do you structure that and then it sounds like you did it differently than the

the kind of standard model of saying like hey employees you can just sell your shares to this

third party we found it sounded like you're actually from the company buying back the

employee shares from what i read it's very similar to selling to a third party except

you do a tinder offer is because you can aggregate supply and demand so if you own shares in a

company you can sell it anytime you want there might be like a right or first refusal for the

company or something like that but ultimately they belong to you when these transactions happen

kind of one-offs it's not usually advantageous for the seller they don't have the ceo the cfo

of the company out there like sharing financials and information they might not have access to the

best investors in the world or they might not just have enough stock where it's worth writing

a check and doing the work for the best investors in the world they might need to put

in a minimum of 50 or 100 million dollars so it had been a few years since we'd done any employee

liquidity so that was just something that we thought well it's been a while the company's

grown a lot let's um do this tender offer i would say they're pretty standard and i'm actually very

excited by platforms like uh cardax or nasdaq private markets which make this almost like an

ongoing thing create essentially like a stock exchange for a private stock that's probably

the future where this goes to but for the next few years at least we're just doing it kind of like as

where we like say hey we're gonna buy 200 million of employee stock we're gonna sell it to

investors and we'll figure that out as a middle person and you've been big enough now to ipo why

why haven't you ipo'd i mean so many entrepreneurs dream of bringing that opening bell and you can

raise well you raise a lot of capital anyhow but not only do you get capital but you get a lot more

fame and press why not just ipo yeah i think it's just looking at what are the constraints for the

business

we're not constrained by how famous we are how much press we get certainly that's not something

i want more of in my personal life we're not capital constrained we have lots of money in

the bank and even if we need a lot more we have a lot of credibility with investors to be um

intelligent allocators of capital so that means there's a lot more available if we asked for it

and liquidity like we just talked about how we're providing liquidity to shareholders

so that's another big reason to go public as the largest shareholder

and you know with the other largest shareholders and investors in the company i think we're all

pretty happy with the trajectory of where we are in the private track so the advantages of being

public are advantages we largely already have and i think there's another advantage to not having

the scrutiny of quarterly results the public markets and also other people in the world not

knowing your your numbers whether that's competitors or new startups or other things like that so by

keeping that pretty close to our chest by keeping that pretty close to our chest we're not going to

having a very very small set of shareholders you know you can kind of you can fit our whole cap

table on a single page it gives us a lot of flexibility to uh work hand in hand with some

of the best and brightest investors in the world build a team which really thinks long term and

just have a ton of flexibility for when we need to make a very very long-term investment which

occasionally we do it's not that public companies are precluded from doing that and some examples

like amazon where they can build something like the kindle or echo over have it lose money for

five or ten years and then they can build something like the kindle or echo over have it lose money for

years before it really starts to have the impact aws being another good example amazon actually has

a lot of them but you know we have that same flexibility and it's just it's nice we're not

subject to the vagaries of ups and downs of public markets right now and have you optimized your own

endurance to be able to keep running the company after this long without getting bored or restless

or burnt out bored is never a risk because what the company does changes so much year to year

i think that's just a function of scaling evolving growing we have more products now

wordpress is totally different than it was a decade ago or 15 years ago so everything changes in

technology all the time so i think if you're staying relevant you are also changing both

yourself and the product you work on and so the work changes burnout is a factor and i would say

the good news is i i'm very passionate about what we do i would do it even if i wasn't getting paid

so that's nice i get a lot of interest in it and i'm very passionate about what we do and i'm very

from the wordpress community so again we haven't talked about it too much but there's still an

open source community of thousands of volunteers and hundreds of thousands or millions of people

who make a living from wordpress and so you know usually once or twice a week i'll get a email from

those people or meet someone in person they say hey my first job out of college was building

wordpress sites and sometimes it's ceos of like decacorn companies they're like yeah that's how

i bootstrapped myself and so that is very compelling you know i get a lot of reward from that far more

than any

change in monetary stuff at this point but i will also admit that like post-covid i i got hit pretty

i think because i was i was working harder than ever and then just life was really tough and so

it has been something i've been thinking about a lot more over the past year and a half just how

to keep up my own personal energy because i felt it flagging for the first time in my career and

it's given me so much empathy as well for other people who hit a wall or had troubles in their

personal life which then led to like work being a bit more difficult for them and i think that's

a bit tougher so that's i think for me applying the things that i knew were helpful on a daily

basis really doubling down on that meditation diet exercise spending time with loved ones

is maybe like an easy forward list that we all know but like it's sometimes hard to prioritize

doubling down on that also just you know building at a time i hadn't taken any vacation or time off

and actually i have an upcoming trip where i'll be offline for like really offline like in the

middle of nowhere satellite phones only for 13 days so i've been really looking forward to that

trip and it'll just be nice to be out in nature and be disconnected for a little while i'm hoping

that that will also be very restorative nice and if i read right on your blog uh you you i think you

wrote that you uh went down the uh van life rabbit hole and have been uh kind of exploring with

alternatives would love to see us here because i think so many people think working from home is

work

sounds like you've uh you've done more than just work from home i would say i definitely you know

i'm from texas so people think i'm a country pumpkin but i really grew up in the cities

and houston is a a huge thriving metropolitan that really has a ton of energy i think it's

third after new york and la but the pandemic definitely you know may turn cities from an

asset to a liability a little bit and so i really got out in nature a lot more which i'd done

occasionally before i'd been a boy scout and stuff but yeah van life was fantastic and i figured out

that i had a really good connectivity and everything and just being in rv parks or national

parks it's kind of that venn diagram overlap and where you'd still have really great cell phone

connectivity or wi-fi yet you were in some place beautiful and you could you know step outside and

be in a lake or hike to a waterfall or something like that it was funny because at the beginning

of 2020 i do a thing every year where i reach out to some of my closest friends and loved ones and

ask them to assign me a new year's resolution

so i make my own but then i'm like okay make one for me and i'm always just fascinated what

people choose and sometimes i do and sometimes i don't but that year my mom the one my mom had

made for me was like get out of nature more and this was pre-pandemic and everything and it ended

up being incredibly prescient advice for not what i would actually do certainly the sort of like that

first march to september but what i sort of realized through that first lockdown like oh gosh i really

miss that day i really miss the first march and i do really miss the first march so i think i do

really appreciate what you guys are doing right now a place where you can kind of think of bags

and cash and kinda be the best way to look for those kinds of opportunities as well and i guess

that's the last thing that i wanted to tell you because i kind of kind of feel like i can't

get through a month of work that's actually a lot of time and work but i want to make sure that i

still have a good amount of time that i can put in for my friends and family and maybe just sort of

just send them my e-mail and check through my e-mail and see if that's still being everywhere i'll be

stat that we went from 5% of hours being remote in the United States to 60% in the course of about

a month. So a lot of people were doing it for the first time. So some of the things we had learned

at Automatic in 15, 16 years of doing it, we hadn't really necessarily written down or shared

or even really thought about. And so it gave us, you know, I think a big opportunity to get back

in that regard. So that felt good. And, you know, that was, I think, just lucky. And then also

just the health of myself and loved ones was largely safe during that time.

Now, if I could just ask something really practical and a little selfishly, because I'd

love to do it too, but you pick a lake to go to or a mountain to work from, how do you connect

to the internet there? And how do you even know what the connectivity is going to be?

Good question. So there's a ton of sites, particularly for boondocking. So that's often

what I would do is I would have my van RV would be like totally self-contained. So I wouldn't have

to like plug it in. I would just plug it in. And then I would have to plug it in. And then I would

plug it into electricity or grid or anything. I could do that for a few days. And so some of

these sites will actually show here's the number of bars for Verizon. Here's the number of AT&T,

et cetera, at these campsites that sometimes you have to go on like a logging road to get to.

So you can be quite remote physically where there's not another soul there, but still have

pretty good coverage. So that's just, again, it's that Venn diagram overlap. What are some of the

sites? Boondockers Welcome, Harvest Host. If you just Google for like boondocking apps and websites,

there's like five or 10 of them. And I would just use them all, you know, kind of like logging on,

see what was around and see what was there. And then into the van I built, ended up using the

system called Peplink, which is a multi-WAN router. It's a little expensive. It's a couple

thousand dollars, but it can essentially, you can plug in multiple SIM cards and then put an

antenna on the roof. It'll actually create multiple network connections simultaneously,

and it can even combine them. And so if one's not working, like if AT&T is really weak,

it'll use the Verizon.

So I think I set up a Verizon and AT&T and a Google Fi, which is basically like T-Mobile

SIM cards, and was able to do that antenna and everything. And that worked actually really,

really well, even more reliable than Wi-Fi in many situations. And also kind of networking

and like literally networking is kind of my hobby, like Wi-Fi and routers and all that sort of stuff.

So it was also just a fun kind of cathartic activity for me to hack around on this stuff.

I said, were you concerned at all, like when you're doing, I mean, you have obviously an

amazing reputation in remote work and your company speaks for itself, but still when you're talking

to billionaires about fundraising, you're talking to BlackRock and Tiger Global and these kind of,

you know, older school finance people who are probably in their mansions, God knows where.

Did it feel weird at all? Or did you feel self-conscious jumping out and having your

background be somewhere deep in nature? Or do you feel like you're in a place where you're

you think that added to the, or did you just feel great about it and that it added to the charm of

your pitch? Usually my background's pretty nondescript. So I try not to have it be a

distraction to wherever I am, or you can always do the virtual Zoom background. That's just me.

So, and usually when I talk to these folks, we talk about the business.

So they have no idea you're in the middle of nowhere.

They might, I mean, if they asked, I'd tell them, but you know, we usually had lots of other things

to talk about. So it wasn't usually the first or even fifth thing to come up.

That's wild. Yeah. It's funny how some people are at home and they put up the virtual background

of nature and you might've been doing the opposite. You're in nature and you're putting

up a virtual background of an office or of a wall in your home.

Yeah. There was a video broadcast. It was actually a panel I did with

Mitchell Baker from Mozilla and Dries from Acquia, two people I admire a lot.

But just the way it worked out is I ended up someplace very, I wasn't able to make it to

the place where I planned to do the broadcast by the time we had to do it.

And so I ended up just stopping on the side of a road and setting up a little mini studio

outside and on the camera, it looked really nice. Cause like I had this kind of like nice

nature looking background and I have a real camera. So like usually there's a nice bokeh

effect and everything, but then I did a behind the scenes picture. It's actually on my blog.

If you look up, I think streaming set up or something. And I was literally like on like

a folding chair with like a folding table, some yoga blocks, holding up my laptop,

the camera kind of on a tripod with a blanket over me.

Cause it was actually pretty cold. So like I had the suit on top, then like a blanket on bottom.

It turned out that this particular road was right next to a logging station.

So every couple of minutes, this giant logging trucks with like 40 feet of logs would go by.

And in one of the pictures you see kind of like the van and then like a logging truck going by.

But luckily over time and tech is so good, I was able to use things like crisp AI and a good headset

to essentially make it so that there was no perceptible background audio noise.

I use that as an example.

Like you could literally be on the side of a road with a truck going by

and have like a professional quality broadcast. So what a time to be alive.

Going to the new normal. Are you, do you see yourself going back to your old life,

which is, I understand it from checking out your blog was going to lots of conferences and

traveling, traveling the world, staying at hotels, meeting with your employees, your partners,

or do you see, you know, embracing van life or, or, you know, getting out into nature and

living in the world?

Yeah.

This more solitary, uh, you know, nature connected life.

That's a good question.

To be totally honest, since I've been able to fly safely, I haven't been driving around as much.

I mean, the driving just takes a ton of time, even if you're sharing it with a friend, like

you can really only, I can only drive two or three hours at a time before like my back starts

hurting or I get tired. And so to get around, sometimes you might need to cover a thousand

miles. So it can really, really add up.

And there's a lot of uncertainty to being fully nomadic where you don't know how the cell phone

signal will be or what the internet connection will be. And I don't like that. I like to control

variables and minimize risk on things that don't need to be risky. So a lot of the second half of

this year, really 2021, I've been back to either being at a home base. Like I have some home bases

in different cities or staying at every beast or hotels. I know we'll have a great internet

connection. And it's funny, my number one thing,

even when a friend invites me over, like, come stay, I have a guest room. I don't ask about the

bed or anything like that or anything about where I'll be staying. I'm like, how's the internet?

That's my first question. Because I find with great internet, I can be really productive

and run a company of almost 2000 people now. But when the internet's slow or bad or dropping,

it can be really, really frustrating. You or I experienced this a little bit earlier. I think

it was the software we're using, not the internet, but like, it's so frustrating when you're trying

to connect with someone. And it's like, I don't know, I don't know. I don't know. I don't know. I don't

know. I don't know. I don't know. I don't know. I don't know. I don't know. I don't know. I don't

hear me now. Can you hear me now? So that's when I'm when I'm looking at Airbnbs, I'm looking at

the reviews if anyone mentions the Wi Fi. That's great. The only only thing that matters like and

by the way, does it have a roof and a working toilet? But yeah, actually, a fun hack is there's

this thing you buy on Amazon, it's a 50 foot retractable ethernet cord that kind of goes into

like a little thing. And a lot of times if I know I'm going to need to do a professional broadcast,

I'll actually travel with that. Because you can run the cable from wherever the router is

up to 50 feet. And I've actually daisy chained two of them. So I did 100 feet into where I was

broadcasting. And once the funny thing that happened was, I had gotten an Airbnb, and it

turned out the internet connection was like DSL. So I couldn't broadcast and I had to do a company

town hall, which we do once a month. And I take them really seriously, like no matter what I'm

doing in the world, once a month, we get the whole company together, we do a video broadcast,

people can do a q&a, you can ask whatever they want. It's not filtered, it's not moderated,

and it's really important to our culture. So what I ended up having to do was I had set up the sort

of camera station in the in the house, but the internet was so bad, it turned out the internet

through my modem in the RV was better. So I ended up running daisy chaining a couple of 100 feet of

ethernet from the van, through the garage, through the kitchen into this living room

to the broadcast. So it ended up the cell phone connection was much more reliable than the house

one was at that point.

And van life saved you even even when you're getting Airbnbs.

I really like being resilient to whatever happens. So I think of anti fragility for business,

I think of it for personal life, I think of everything. And so there is something to knowing

like your whole life can fit in this car. And that you have you're prepared for many eventualities.

Now you've got axes, I've got things to get the tires out of mud. It's, it's just a really good

lesson and kind of reminding us all the things we take for granted to like running water and

flushing toilets. I think it really makes you appreciate modernity and the luxuries of modern

life as well. When the pandemic started, I think everybody looked to you as the remote expert. And

as you said, lots of people called you up and you really made the playbook that a lot of other

companies have followed. But I'm curious, though, you know, in that shift is just being a pandemic

where it's forced remote, and you can't get on a plane during it. And you can't bring your

company together as you used to put a lot of resources to what would you say?

You personally have learned in the last since the pandemic started about remote work and running a

business. You know, I think what we did so well, and what we've shared is what we figured out and

worked well, which is how to work together. And part of that was us getting together a few times

a year with those meetups. And so when that was taken away, and then you also had the stress of

a global pandemic. I think what we are still figuring out alongside the rest of the world

is exactly what I talked about earlier. Like when,

you can't go out and see friends every day when you can't necessarily have the part of your life,

which allows you to be better at work, and which I think when you work remotely can actually be

really great, because you have total autonomy and control over going for hikes or walking your dog

or going to matinee movie and spending time with your friends and loved ones. All those things that

when you have normal flexibility, weren't available, how to navigate that pandemic life.

And the good news is, at least in America, it's getting better. Cities are open,

restaurants are full, people are vaccinated, feel safe, concerts are happening. So a lot of

things feel back to normal. But you know, we have colleagues in 90 countries, some of them don't

have widely available vaccines yet. So it's really what can we figure out and what can we do to give

people the space to navigate this, you know, hopefully once in a lifetime stress. And if

you're in a country where you don't have vaccines, that also means like your friends and loved ones

might be getting sick more, or you might be getting sick or other things could be really,

really stressful.

So we've been just trial and error. One new thing we introduced was actually

the ability to move to part time work and pay and move back at any time. So we allow people

to go to either 80% or 60% expectations and pay. So the equivalent of being three or four days a

week, even though it doesn't necessarily add up to that, but just sort of like expectations.

A lot of people have opted into that, because they're like, I need an extra day a week because

I need to share child caring responsibilities with my spouse who's also working from home.

You know, there's any number of reasons why people might need that extra time and allows them to do

it without the guilt of feeling like they're not pulling their full weight at work. And also for

the business also allows us to titrate some of our costs as well, which is of course a concern when

so much economic uncertainty in many parts of the world and some parts of our business.

So that's something that we've launched new that's been successful, but that was kind of

trial and error and also just from people asking for it. And we found a lot and some teams did

the experiments with it and it seemed to work. And how do you manage it all? Like in the kind

of Berkshire Hathaway model you described where you have all these kind of different companies

operating within automatic now. And I believe with Berkshire Hathaway, they don't kind of

prescribe how all those companies should work at all. And each one has their own HR departments

and their own policies. How are you thinking about that in terms of like, to what degree are you

kind of like a Google and like, hey, this is a business.

This is how we do things. It doesn't matter if you're in the YouTube division or the

search division, how much of it is, hey, you know, Tumblr can run this way. WordPress.com can run

that way. Parsley can run this way and just show me your P&Ls at the end of the year and don't do

anything illegal. It's definitely more towards, in a lot of ways, more towards the Alphabet or

Google model, where we have some things that work really, really well, like our ability to hire or

share an infrastructure. And in fact, WordPress itself.

All of our businesses are basically built on top of WordPress. The good news is because WordPress

is open source, the coordination overhead of completely disparate businesses working together

is totally possible because the code's open source. I don't need like someone in a different

division to enable me to do something. In fact, any company in the world can build on WordPress

and, you know, many tens of thousands do. So the open source, I think, is our hack for allowing

lower coordination costs among very disparate businesses.

And getting kind of the best of both worlds, where we have the best of being part under the

same roof, but not as much of the overhead of a large company. So that's just what we've been

able to figure out so far. We, of course, look to some of these forebearers, Googles and others,

that have done this for much longer and to a much larger scale. But we also look a lot to

things like military organization or city and federal governments, LVMH, Berkshire,

like other conglomerates, Koch Industries, like others that have done this in other industries.

And sometimes we find more learnings from the non-tech examples, necessarily the tech examples,

because sometimes for like a Google, they did all that innovative stuff, but they had also

stumbled on what appears to be the world's greatest business model in AdWords and search

that's ever been discovered before or since. So that can also forgive a lot of mistakes

and provide a lot of leg room, where other industries like manufacturing, which might

have much tighter margins or be much more competitive. They've had a much tighter margin

of error for what works or what doesn't. And some of the places we compete in are much more like that

than they are like a cash machine. We have some of the best competitors in the world with companies

like Shopify, Squarespace, Google, Adobe, Salesforce. So we really have to be at the top of our game

to stay relevant. Yeah, it's valid to think if the Google guys had worn suits and ties and not

given out free lunch with...

You know, their business could have worked just as well and we'd all be wearing suits and ties

and charging for lunch now.

Yeah. I really appreciate this excellent set of questions.

Yeah, my pleasure. Thanks so much for coming on. I know, sorry, I went a little over,

but this is really great. So I appreciate you taking the time.

No, thank you so much. I hope this is valuable for your audience. And if people want to see more

or see more of these stories, my blog is at ma.tt. I'm photomatt, P-H-O-T-O-M-A-T-T on

Tumblr, Instagram, Twitter. So follow me there.

And yeah, tweet at me or something. If you have another question, I'd love to keep the

conversation going.

Wonderful. And I'll make sure to link to that 50-foot

ethernet cord in the show notes. I think people will need that for their next adventure.

Thanks again, Matt, and enjoy your time off the grid too.

Thanks. Have a good one.

That's all for my interview with Matt. Man, I could have gone on for hours and hours more.

There was so much to dig into, just the way they do remote work,

the way that he's been able to keep his company private and independent, the open source movement

that he has pioneered and continues to be such a powerful force in our economy. So really hope you

enjoyed this. Go out there and check out all of Automattic's products. Make sure you follow

Matt on social media, Automattic. He is just really kind of continually a source of inspiration

for a lot of entrepreneurs. And I hope you tune in for the next Venture Voice.

Your help spreading the word would really mean a lot. Head over to iTunes, leave a good review,

tell your friends. The more people that listen, the more great guests like Matt will be able to

have on this podcast. And let me know what you think. I'm just at Gregory on Twitter and Instagram.

At Gregory, I look every time someone tweets at me, so keep your comments coming.

Until next time, this is Venture Voice. Good luck on your businesses.

Thank you.