The Twenty Minute VCMatt Mullenweg: How I Founded WordPress; Storytelling Tips; How to Give Feedback | 20VC #905
EVERY SPOKEN WORD
115 min read · 23,064 words- 0:00 – 0:40
Intro
- HSHarry Stebbings
Three, two, one, zero.
- MMMatt Mullenweg
You have now arrived at your destination.
- HSHarry Stebbings
Matt, I'm so excited for this show. Obviously, we have to thank the main man, Shaq, for making this one happen. I've wanted to do it for a long time. So thank you so much for joining me first.
- MMMatt Mullenweg
It's really a pleasure to finally connect in this format.
- HSHarry Stebbings
It totally is. As I said, thrilled to make it happen. But I want to start by saying, you know, we see the incredible journey that you've been on with WordPress and Automattic, but I wanna go back just for the beginning to set some context. How did you come up with the idea for WordPress and Automattic? And take me back to that starting ah-ha moment in the early days.
- 0:40 – 4:53
Origins of Wordpress and Automattic
- HSHarry Stebbings
- MMMatt Mullenweg
Yeah. So WordPress was very much born out of open source. So, um, I didn't come up with any idea. Blogging was already happening. There was lots of tools, including, like, LiveJournal, Blogger, et cetera. Um, but I wanted something that was open source, so I started using some software called b2cafe log, actually from a developer, uh, out of Corsica, France. And, um, you know, started volunteering on the farms, forums, helping other people out, contributing code. And then what happened was that software actually was abandoned. The, uh, the developer kind of disappeared. And myself and a gentleman in, uh, the UK named Mike Little said, "Hey, we really like this." Um, we were both kinda contributors and, and part of the community, so we're like, "Hey, why don't we, you know, pick up this torch and keep it going?" 'Cause it seemed like really valuable software. In open source, that's called forking. Uh, fork, like you would eat with. And, uh... (laughs) Now, the, the main thing with forking is... I mean, one of the beauties of open source is you could take all the code, but you need to come up with a new name. So that's, uh, a friend in Houston suggested the name WordPress, and we were off to the races.
- HSHarry Stebbings
I want to ask a question from Tony Schneider, actually. And he asked, when he first met you, he said, uh, "How long do you wanna work on WordPress and Automattic for?" And you very clearly said, within seconds, "Decades." And he was taken aback by your longterm mindset, and he asked the question, "When did you know this was a project that you wanted to commit decades of your life to?"
- MMMatt Mullenweg
I'd say pretty early on. So, you know, first year of WordPress was very small, probably dozens of users. Um, but it was fun in that the developers, myself and the others, were really having a good time working on it and collaborating, and we were all over the world. We'd never met each other, but that's, that's how open source works. Uh, it was probably the second year that, um... One, I got a job offer, so I got basically hired by a company called CNET and moved to San Francisco because of my work on WordPress, so that was pretty cool. That felt like winning the lottery. And then, uh, as WordPress started to get translated into other languages. You know, I am unfortunately quite monolingual. F- I barely speak English that well (laughs) , but I've always been fascinated with other languages. And, um, particularly, uh, WordPress was translated into Japanese. Now, what was... This, nowadays, doesn't sound like a big deal, but what happened was a gentleman in Japan... We had no translation framework, so what he did was he actually went through every single line of the software, which must have been 60 to 80,000 lines at that point, and manually changed all the English text to Japanese (laughs) , which was like... I can't even imagine how many dozens or hundreds of hours that took. And, um, and then I, you know, I downloaded the software, I, I loaded it, and it was just one of the most beautiful things I've ever seen in my life, because it was like this interface in software that we'd been working on, but with the really beautiful, you know, Japanese scripts. Uh, katakana, hiragana, I think they're called. And I was like... I was just totally blown away. And, um, I thought, wow, if this, if this guy would take all this time to do it, maybe there's something bigger on our hands, and, uh, maybe we could have a bigger, bit of a, a bigger impact on the web. And shortly after that, maybe a year or two after that, we started to see WordPress show up in, like, whole internet numbers. And I remember the first time Google did a survey, and, um, they found this weird header in HTTP, uh, responses that, um, they were like, "We're not sure what this is, but it's on 0.8% of all the websites we, we, we looked at." And that was a header that WordPress added. And so, you know, me and the other developers, like, popped some virtual champagne. We're like, "Oh, my goodness, we're 0.8% of the websites out there." And it was just a, an incredible rush and incredible feeling. It's really rewarding, if you love the craft of software, to make things that other people use. And I get a lot of, uh... I get really jazzed from, you know, seeing what people do with the platforms we've created.
- HSHarry Stebbings
That's a pretty special feeling. And, um, I'm gonna be honest. I've stalked the shit out of you for the last few days, Matt (laughs) .
- MMMatt Mullenweg
(laughs)
- HSHarry Stebbings
Now, we knew each other before, but, I mean, I have really stalked you. And it's been fascinating 'cause there's been some real commonalities in, in everything that I've heard actually, which is, is really interesting, and I'm gonna kind of unpack them one by one. And we're gonna start on your leadership. And so when we think about high performance, I wanna just start there and ask,
- 4:53 – 5:55
What does high performance mean to you?
- HSHarry Stebbings
what does high performance mean to you when I say those words, Matt?
- MMMatt Mullenweg
Hmm. I mean, the first thing that comes to mind for me is definitely communication. Uh, feel like all, all great things I've been involved in, at least, were created from collaboration and teams. And communication is fundamentally, you know, taking what's in our respective minds and finding that common ground. And then when you pair it with things like accountability, a shared mission, it, it's, it's really the foundation where everything else grows on. So something that I continue to work on, uh, really every week is, how can I be a more clear, concise, um, communicator, and how we can get our teams really aligned, uh, through clear communication? So, yeah, communication is what comes to mind first.
- HSHarry Stebbings
So what I love is just, like, being able to go off on tangents. I'm always stuck on communication, on radical candor, and, you know, giving feedback in real time. Sometimes you've had a stressful day, you've had a fight with your family member or whoever, and it's not right to do it in the
- 5:55 – 6:59
How to give feedback effectively
- HSHarry Stebbings
moment. But then other people say it is. How do you feel about giving feedback in real time versus delaying it, and knowing when and how to do quite tough feedback well?
- MMMatt Mullenweg
Yeah. Well, there's two sides of communication, and I actually, I go back to a Frank Luntz quote a lot, uh, where he said, "It's not what you say, it's what people hear." And another one I think about a lot, it might have been Maya Angelou, but I'm probably getting this wrong, which is like, "People will forget what you say," et cetera, et cetera, but they'll remember how you made them feel.
- HSHarry Stebbings
Mm-hmm.
- MMMatt Mullenweg
So I think that it's important if you're, particularly if you're gonna be critical of someone, it i- to make sure that they feel it's coming from a place of care and shared misson- mission. Um, and probably doubly so because people naturally become defensive. But I also think it's something that as you build more trust, uh, with, you know, someone you're collaborating with, you can become better and better at- at having that just knowledge that it's from a place of, uh, trying to get better together.
- HSHarry Stebbings
Tru- trust is so crucial there,
- 6:59 – 8:00
Trust earned over time, or theirs to lose?
- HSHarry Stebbings
as you mentioned. Do you start trusting people fully from day one and it's there to be lost? Or do you say, "I'm going to learn to trust you over time?" How do you think about your willingness to trust at the beginning?
- MMMatt Mullenweg
I personally am very default trusting. Uh, and that also means that sometimes you pay what I, uh, call a optimism tax. (laughs) Um, my friend John Sten came up with that, and basically saying that, you know, if you default to being optimistic and trusting, sometimes people will take care of you. Uh, but the rest of the time, the 99% of the time that, um, people are taking advantage of you, i- i- your life will be much better. (laughs) So, so occasionally I pay a optimism tax, but I would much rather, like, live my life in a way that is default trusting and optimistic towards, um, yeah, pretty much everyone.
- HSHarry Stebbings
Can I ask, I think, you know, so much of communication is also in storytelling, uh, and I think actually we've lost the art of storytelling today, especially when it comes to great product marketing.
- 8:00 – 8:45
What makes great storytelling?
- HSHarry Stebbings
How do you feel about what makes great storytelling and what makes great product marketing? Because it is such a core part of communication.
- MMMatt Mullenweg
Hmm. Yeah, this is something I personally struggle with a lot because I feel like I can get very lost in the nuance and the details. And, uh, there's a gentleman in the WordPress community actually named Chris Lema, who is just so incredible. I think he has a background of, like, uh, preaching, where he can really tie it in with, like, a personal story that then goes someplace you didn't expect and then it comes back at the end, and I think it's an incredible form of communication. So probably something I should work on more and think about.
- HSHarry Stebbings
I- i- okay, so if we think about that as something, you know, you'd like to work on and think about, I'd love to be reflective
- 8:45 – 13:12
How would you describe your leadership style?
- HSHarry Stebbings
on your leadership style. How would you describe your style of leadership, and how has it changed over time?
- MMMatt Mullenweg
I'm probably in many ways a non-traditional leader in that Automattic is a very flat organization. Automattic's the company that I ended up building after, uh, WordPress, um, or on top of WordPress. It's, uh, it's a for-profit, about 2,000 people now, and I'm the CEO there. Um, but we're very flat, particularly at the top, hierarchically. Um, everything's sort of ultra transparent. We have no email. We communicate via blogging. And, uh, yeah, it's very global, so we've always been totally distributed from the beginning since 2005. So I have colleagues in 97 countries. So I feel like all these things, when you mix them up, I end up being a leader which, uh, is normally, um, giving folks a ton of space and then occasionally diving extremely deep into the details, as close as to, like, database schemas or, um, code architecture or how we're gonna approach something or a specific partnership. Um, so I like being able to move between the sort of, like, one-foot view and the 10,000-foot view. And a lot of what I'm doing as well is trying to create the environment for people, um, to do well, uh, without me there. (laughs) But then also kind of that maybe trust but verify, that sometimes I'll dive in and really try to learn part of something, uh, very deeply.
- HSHarry Stebbings
Can I ask, how do you approach the element of accountability with independence? You want people to be accountable, you want them to go big, but you also don't wanna let them not be feared of failure, not be willing to engage. How do you think about that challenge of giving them enough accountability but not too much?
- MMMatt Mullenweg
Yeah. I think that where we've done that best is probably having clear goals and giving people a lot of flexibility for how to accomplish them. And where we've done it poorly is probably when (laughs) myself or others get, like, a little too involved in how to do it, uh, particularly if a team's doing well. So... But I think just if you're communicating which mode you're in. So for example, um, in February, I took over as the CEO of Tumblr, and I've been running that personally day-to-day, uh, since then. And I told the team, like, "Hey, we're- we're in a tough place right now, so I'm not gonna be trying to build consistent consensus or other things. We're gonna be in a bit of a command and control, uh, method for a little bit, where, um, let's just try to do, uh, what I'm saying to do as quickly as possible so we can kind of pull out of this, uh, this dive." Um, and I think that's fine if you communicate it, but it also is not sustainable. (laughs) Like, I think that at some point, hopefully when things start going better again, you can then step back and, uh, you know, have just a different kind of leadership style. But much like Ben Horowitz talks about, like, wartime versus peacetime CEO, I think that it's important to vary your leadership style based on who you're working with, the state of the team, and sort of what's going on. I think where we make, or I- where I've made mistakes before is not being explicit about that. (laughs) So I think it was actually really helpful for me to say, "Hey, this is gonna be, like, top down for a little while," and then everyone knew what to expect. And where if I'd just done that without saying that first, I feel like there probably would have been a lot more resistance or, um, or sort of passive aggression.
- HSHarry Stebbings
Do you, do you think it's possible for many people to be both? I totally agree with you in terms of wartime and peacetime leadership and how you need to be both in your tenure. But some people are wartime leaders and some are peacetime leaders, or think they are at least. Do you think many are plastic enough to be both?
- MMMatt Mullenweg
Absolutely, yeah. Because it's about behaviors, it's not about identity. Um, and I feel like I switch between, um, just in working with different businesses within our company. You know, we have some businesses that are very mature, like, uh, WooCommerce, which is our e-commerce platform, or WordPress.com, which has millions of subscribers. And we have some that are very nascent. Um, actually a podcasting app called Pocket Cast, which is a really good podcatcher. If you're listening to this (laughs) and another one, check out Pocket Cast. So you can move between them at different times. And, uh, yeah, I think it's just all about behaviors. Behaviors probably, and self-awareness.
- HSHarry Stebbings
I have to ask, we, we spoke about the importance of communication, and then y- you mentioned not having email. And I, I, I kind of glossed over that,
- 13:12 – 15:37
How do you communicate without emails?
- HSHarry Stebbings
but I'm fascinated. How do you communicate by blog posts and not having email, Matt? Can you just walk me through this? (laughs)
- MMMatt Mullenweg
Yeah, so first I'll say what I like about email is that it's written, uh, it's threaded, and, uh, it can be asynchronous, right? Like you can send something, I can reply on my own time. We don't have to be there at the same place. Now what I really dislike about email is that, um, it's private, meaning that so much intelligence in the company is locked into people's inboxes. And that means when new people join, they don't have access to all of that conversation and decision-making. And when someone leaves, like, in their inbox often leaves a ton of institutional wisdom and knowledge about the business. And so basically everything that most companies do on email we just do on these internal blogs, including, like, you know, you might post something and say, "Hey, Matt, what do you think of these mock-ups?" And then I would give your answer, and then maybe you post some more, and then maybe we do a user test and post that to the thread. Like we can have all that things there. And what's cool about this, the system's called P2, the letter P as in pool and then the number two. Um, what's cool about this is it becomes like a organizational blockchain, (laughs) like a history of basically every decision, uh, we've made in the company for the past dozen years or so, including every partnership meeting, every investor meeting I've had. Like pretty much everything's in there. And, um, and it's, you know, all searchable, indexed, everything. And I try to lead by example. Myself and other executives. Where like, you know, if I met with, um, you know, Scott Schleifer from Tiger, uh, I post about that meeting, and the whole company can see it. (laughs) So we try to be really transparent, including when it might be uncomfortable to.
- HSHarry Stebbings
Are there any dangers of being too transparent? Say I'm on your team and I'm not performing, and you're concerned about my lack of performance. Are you gonna put that on the blog even if I am useless?
- MMMatt Mullenweg
Hmm, not individually. Like, you know, I do believe there is a, to an extent, like praise in public, criticize in private, particularly if it were more like a HR issue or, or personal performance. Uh, but a team performance or a, a division performance could definitely be on the blog, and we'd want to be really transparent there about, um, where people stand relative to our goals. But I think for individual, um, you're, you're right that I think, you know, communicating privately would be better.
- HSHarry Stebbings
Now I chatted to Shaq a couple of hours ago before, and obviously you have many hours of chatting to Shaq about you and, and many stories that you
- 15:37 – 20:45
How did you take over Tumblr?
- HSHarry Stebbings
guys have shared. His, uh, one baller OG move was, uh, the Tumblr, um, acquisition, and then obviously also you taking over as CEO. Can you just help me understand more? What was the decision-making process for you in terms of taking the helm and taking the reins as CEO, you know, earlier this year?
- MMMatt Mullenweg
Yeah. It's, um, it's a good question. So, I mean, we bought Tumblr because it's a, it's a generational property. Like it's really amazing. Um, it had been mismanaged, I think under Yahoo! and AOL and Verizon, and, um, we felt like we could turn it around. Uh, the reason I ended up taking over as CEO is that the first two years of the acquisition it has not turned ar- it had not turned around yet. Uh, so not an ideal circumstance to be honest. But we ended up, you know, a lot of the teams knew, 85 or 90%. And then at some point, um, like I said earlier, I felt like I needed to go in and be a bit more hands-on with the business. Uh, because while we, you know, it's been reported that we bought Tumblr for very little. Um, it has so much usage, it's actually quite expensive to run. So getting Tumblr to where it can be breakeven, um, and sustainable is really critical. Uh, now fortunately at our business, all the other businesses are doing very well and very profitable, so we kinda evens out at a full business level. But I think rightly so. Like, uh, board and others looks at this and says, "Hey, why are we losing so much money on this thing?" Especially when it wasn't growing. Uh, what I'm really happy to say is that the team has done some amazing work over the past few months, and, um, not only is... Tumblr is, like, growing really, in a really interesting way now, both usage and revenue. And we've launched a lot of features that have been really positive in the community. And it's just, I think it's actually super strategic for us over the next decade, because Tumblr has a much younger user base than WordPress. You know, the, um, 60% of Tumblr's users are under the age of 25. They're, uh, majority female, they're, you know, ma- uh, primarily mobile. And so it's amazing on-ramp as well, as if we can get people who start on Tumblr to someday actually be using WordPress. I think it's actually a pretty incredible, um, thing that keeps WordPress relevant for, uh, much longer than we would have been otherwise.
- HSHarry Stebbings
Can I be challenging to your business model? And I hope this (laughs) is okay for me to ask. Given how many profitable entities you have and how successfully they're doing, only having one in Tumblr that is loss-making could suggest that you're actually not taking enough risk, and you could leverage and subsidize more risky assets with the cash flows...
- MMMatt Mullenweg
Mm-hmm. (laughs)
- HSHarry Stebbings
... of your profitable assets, and really go for growth in a ton of more risky assets. Now I appreciate the time that we're in (laughs) now, being a challenging time-
- MMMatt Mullenweg
(laughs)
- HSHarry Stebbings
... to go for growth and not profitability and cash flow, but have you thought about this balance between growth and profitability a lot more in terms of leveraging cash flow here to really subsidize growth here?
- MMMatt Mullenweg
... uh, totally. And we have done that in the past with, um, you know, the money we've raised. It's been primarily through acquisitions, though. Like, we do like to have businesses which have good unit e- economics as you, as you run them from the beginning. So between 2005 and, I think, 2014, all of Automattic was done with about $11 million in outside capital. Uh, those were also the years where Tony Schneider, um, you know, came in as the CEO. In 2014, when we were passing the baton, um, you know, we did a lot, we did about a year or two of work, uh, before that where he was kind of, like, uh, getting ready to pass over the CEO title to me. And one of the things that became clear as we were sort of planning for that and everything was, one, building up the executive team, which we did, but, two, that we were foregoing a lot of opportunities because we were essentially running the business at breakeven and only had, you know, $10 million in the bank or something. Like, we didn't have a, a lot of, uh, a lot of leeway, and the business was, um... I'm trying to remember the size. Probably still sub $100 million, but getting up there. Uh, so that was when, in 2014, we ended up doing our Series C, which we raised... You know, we went from (laughs) $11 million to raising $160 million. It was all primary capital. And that really opened us up quite a bit. It's actually what allowed us to do the acquisition of WooCommerce. Uh, WooCommerce is our e-commerce platform, which, you know, today can be... probably will be as large of all, as all of our other businesses combined. It did 31 billion in, uh, uh, GMV sold last year. So this is, you know, one of the things that I think we've used outside capital for, and we've been very lucky to have investors which are very supportive of our long-term approach. But we're... Try to not follow... We try to do the opposite (laughs) of what the market is doing. So we do a lot of acquisitions and things in, like, 2008, 2014. Maybe we'll start to do some more now. But we try to hang back a little bit when things are getting a little frothy.
- HSHarry Stebbings
What's the secret
- 20:45 – 22:41
What’s the secret to successful integration with M&A?
- HSHarry Stebbings
to successful integration? M&A is fucking hard. Everyone struggles on integration.
- MMMatt Mullenweg
Yeah.
- HSHarry Stebbings
How have you guys done it so well so consistently?
- MMMatt Mullenweg
I think it helps that we're totally distributed, so there's less of, like, a us-versus-them in the office or things. It was actually a big challenge when we bought Tumblr because they did have, you know, pretty large office presence. About two-thirds of the company was in a office in New York, and, uh... So we had to bridge that. Um, a lot of what we do is around, like, internal switchers. So often when you acquire a company they... you're doing it, or they're doing it partially because they want more resources. So one of the best things we can do when we buy something is take some of the best people at Automattic, the best engineers, the best designers, et cetera, and we rotate them into the acquired business. And that, uh, builds a lot of bridges. You know, it's kind of the, again, some of our best folks. So it's painful to remove them from other businesses, but then they give a really good impression of the rest of Automattic, and, um, they can be embedded and essentially, uh, helping transform the culture. Uh, it's very much, though, the culture goes both ways. So, you know, like Tumblr, as a good example, like, influenced the rest of Automattic's culture quite a bit, and now we have them using P2 in, like, all the things that we do. So there's, um... I think that's pretty important. I guess it's kind of geeky, but the other thing is just really backend integrations and making sure that you really prioritize the server infrastructure, how things are running, shared codebases, access. Like, it's surprising, um, sometimes even, like, months into acquisitions we've done that, like, you know, a bug is being posted, and people are like, "I can't access that," and you're like, "Well, that's just silly." (laughs) You know, you need to have that internal transparency and ease of access for any sort of collaboration. So breaking down those, those walls as much as possible is really important for us.
- HSHarry Stebbings
Matt, I, I have to ask you. You mentioned taking over from Tony there in, I think, 2014 or 2015. We mentioned you're becoming CEO of Tumblr.
- 22:41 – 23:52
How do you determine what to delegate?
- HSHarry Stebbings
In terms of delegation, how do you determine what to delegate versus what only you can do? And this is directly advice for me, because I'm shit at it. (laughs)
- MMMatt Mullenweg
(laughs) Um, you know, part of going from 10,000 feet to one foot is I do like to really deeply understand an area, and that, I feel like, helps me hire or recruit someone who's way better at it than me. And so, for me, where, uh, it's very, very easy to delegate is when I find someone who is so much better or maybe just enjoys it so much more than me (laughs) that it's a joy to pass things off. So I'd say that's where it's gone well. And when I come into things, I do see it as a little bit of a, a failure in that it means that we haven't, you know, found the right formula, uh, without me there. So I usually think of it like a temporary thing.
- HSHarry Stebbings
Can I ask? Mentioning kind of the failure and you having to jump in, I think that we learn a lot from lessons or mistakes that kind of go wrong. When you think about kind of painful lessons that you've learned, I do want to ask this one, which
- 23:52 – 26:20
What was the most difficult part of running Automattic?
- HSHarry Stebbings
is, what are the most difficult but valuable lessons you've learned in the Automattic journey that, although it sucks, you're pleased that you went through them?
- MMMatt Mullenweg
Ah. You know, everything we've talked about so far, there's usually an opposite side. (laughs) So we talked about-
- HSHarry Stebbings
(laughs)
- MMMatt Mullenweg
... good communication. Uh, like, remember, I was 19 when WordPress started, so I was a pretty terrible communicator (laughs) for many of those years. Um, so everything that's going right, I've definitely done wrong at some point. And unfortunately, sometimes my head's kind of thick. I, I need to do it wrong before I figure it out. Um, Tony was always really, really great at also... You know, he's very wise. He was a much more experienced executive than me, and, uh... But he'd also give me some fa- some space to make my own mistakes. So, you know, mistakes that come to mind, um...... you know, making capital expenditures when we shouldn't have, or, you know, put us in a tight cash position. Uh, signing a lease for an office for Tumblr in, like, uh, December 2019 (laughs) to move in April 2020.
- HSHarry Stebbings
Ooh.
- MMMatt Mullenweg
Um, so there's just different things. But there is something I learned from Tony, actually, is, uh, to try to make reversible decisions quickly and irreversible decisions very deliberately or slowly. So, uh, and if there is an irreversible decision, like apparently our lease was in New York (laughs) , um, you know, make sure that the, the cost, even if it goes wrong, is not existential. So, I think a tremendous amount about risk management and longevity and sustainability, because-
- HSHarry Stebbings
Mm-hmm.
- MMMatt Mullenweg
... like I said, I do want to do this for decades. Uh, I think that you only get the grace and opportunity to do so if you're executing really well. Um, if you look at folks who have been executives the longest, like, it's typically because they're really firing on all cylinders. So, that's part of why it's important for me for our businesses to do well, because it gives us the freedom and the optionality to run a business in the way that we want, which is, you know, a little bit different than many other businesses. Like, pretty much all the software we make is open source, 'cause I'm a big believer that open source is the future of humanity and it's important that we create more of it. But if we were doing open source and the business was failing, guess what? We would lose that ability to do it. So, the sustainability and the, the growth is actually a trailing metric, but it's a really important trailing metric of how well you're executing
- 26:20 – 30:38
How do you think about risk?
- MMMatt Mullenweg
against your mission.
- HSHarry Stebbings
You mentioned risk management there. Uh, ironically, for a venture investor, I don't love risk (laughs) .
- MMMatt Mullenweg
(laughs) Yeah, same.
- HSHarry Stebbings
Um, how do you think a- how do you think about your relationship to risk?
- MMMatt Mullenweg
Again, I think I got a lot of that out of my system in my 20s, um, so now how I think about it is very much in the long term. You know, what, what are the decisions now? And if you play out a decision that you're doing today, and you say, "Okay, this continues for five years or 10 years from now, what does it look like?" Um, we think about that with benefits, like let's say that, uh, for example, we have a benefit that's a coworking allowance. Um, although we don't have, um, outside this one in New York, we don't really have, like, offices in all the places we have em- employees. Um, but we do give them an allowance of two- of up to $250 per person per month, um, to, uh, go to a coworking space or to go to a coffee shop and, you know, buy coffee so they don't get kicked out and (laughs) things like that. And early on, one of the arguments was like, hey, instead of making this a reimbursable thing, like you go and you reimburse us, let's just, like, give it to everyone. Or maybe an example, like let's pay for everyone's internet. And so... But when we thought about that, we thought, well, right now, this benefit's used only by a small percentage of folks. Um, the cost is rela- relatively reasonable. It can scale up and down. Like during the pandemic, obviously, usage of that coworking allowance went down a lot. But, you know, if you're paying 250 per month, 12 months a year, with 2,000 people, that's now $6 million per year (laughs) , so that starts to add up to be quite a bit of money. And, uh, do we want to commit ourselves to that? Also, just the knowledge that benefits ratchet (laughs) , meaning that people, uh, appreciate when you add them but they're very unhappy when you remove them, even if it wasn't something they were using. So, we think very, very much about, uh, one-way doors. Raises are one-way doors, hiring is somewhat of a one-way door for us, because we, you know, we have people who stay for a very, very long time. We have really high retention. So, on those things, like, make sure you're making the decision in a way that makes sense if it's successful and it happens for many, many years in the future.
- HSHarry Stebbings
Can I ask, and I, I hope this isn't too personal, but, you know, we mentioned kind of the risk in being much more long-term minded. Do you think that comes with increasing wealth? And I don't mean that rudely, but, like, as you make more money, you can afford the luxury of having a longer term mindset than worrying about rent or worrying about heating bills. Do you... How do you think about that in your relationship to money?
- MMMatt Mullenweg
Yeah, 100%, it helps. This was actually something... You know, in 2008, um, secondaries were relatively rare. Uh, they, they just weren't very common. But, you know, a lot of credit to our investors at the time. You know, in 2008, the company was only about 20 people, just about two years old, and we got an offer to sell for 200 million. Uh, which, you know, I owned the majority of the company. That, that would have been obviously life-changing. And of course, we considered it from, uh, a variety of angles. But it felt like that was a small fraction of the impact that WordPress and Automattic would have, um, in the coming years. And so, what the investors did is they said, "Okay, let's take that 200 million and make it your new valuation. We'll invest money in that, and we'll put, you know, $10 million into the company, and then we'll allow you and Tony and other employees to, like, take a little bit off the table." Especially since my salary at that point was pretty low, um, I remember, like, 80 or 100K or something like that, so living in San Francisco. So they're like, "Hey, so, you know, take a little bit off the table, de-risk, and, uh, focus on the long term and what you can build. Swing for the fences." And I think that was really, really helpful for, for me, and I try to think about that now more in our sort of base compensation, is for people who work at Automattic, how can we get them to a base salary where they don't really have to worry about a lot of other things in their life? And so, they can really focus their intention on the things that are most important to them, which hopefully are, uh, you know, having a huge impact, doing the best work of their careers, uh, during their work day, and then, you know, a rich and loving life in their non-work day.
- HSHarry Stebbings
Uh, we... (laughs) W- I'm
- 30:38 – 32:40
How do you retain a zen-like mindset?
- HSHarry Stebbings
really using this just as an advice session. We mentioned kind of risk management there, personal approach to risk, and also challenges when things go wrong. You know, I spoke to Tim Ferriss before this show about you, and he said, uh, "You have two skills, world-class skills." And he said, "One of them is your zen-like mindset and your ability to just stay calm when the shit is truly hitting the fan." Um.
- MMMatt Mullenweg
(laughs)
- HSHarry Stebbings
And he, and he asked, how do you retain this zen-like calm in the midst of challenging environments?
- MMMatt Mullenweg
Hmm. I think it's just a form of coping. So when something is really overwhelming, um, a way for me to try to get a handle on it is to sort of step back mentally a little bit and, uh, just try to dispassionately, um, look at it, uh, breathe. You know, remind myself to breathe and other things, which comes from probably my saxophone days. You're about to walk on stage. Your heart's racing, you're nervous, you gotta breathe. (laughs) Otherwise, you can't blow the horn. Um, and then also something, I don't remember where I read it or who said it, but like, uh, is freaking out right now gonna help the situation or make it worse? (laughs) And you know, 99% of the time, it's gonna make it worse. So if, you know, something's challenging and we wanna get through it, uh, you know the saying, "If you- if you're going through heck, keep going." (laughs) Like, don't stop and hang out there. Like, keep going, and then look at, you know, what would be most helpful. And, um, I find that actually very... it helps me get out of that part where my body, my heart's racing, I'm really stressed out. And so it probably looks on the outside like it's very calm. Um, internally, I'm probably freaking out a little bit. But then, sort of coming back to that sort of centered place.
- HSHarry Stebbings
I, I, I, I love that in terms of, um, (laughs) breathing and ensuring to retain that sense of calm. I do want to ask, you know, when you have those challenging moments and you have to retain that calm, zen
- 32:40 – 34:30
What would you say your biggest insecurities are?
- HSHarry Stebbings
mind, you know, I think insecurity can often creep in, and it stays long term afterwards.
- MMMatt Mullenweg
Mm-hmm.
- HSHarry Stebbings
Uh, it's e- honestly, man, I listened to a lot of your shows beforehand, and you sound so calm and thoughtful that you're like, "Oh, this guy, he's got no insecurities." And I think it's-
- MMMatt Mullenweg
(laughs)
- HSHarry Stebbings
... quite humanizing to dis- (laughs) I think it's quite humanizing to discuss them. So, what would you say are your biggest insecurities in leadership today?
- MMMatt Mullenweg
Oh. Um, yeah. Uh, I will just say that I have all the normal human foibles and follies (laughs) and issues. Um, gosh. Insecurities, what comes to mind is... I've always been pretty insecure about my body. You know? Like, embarrassed to, like, take off my shirt at the swimming pool or something like that. Um, on the leadership side, I would say a lot of my insecurity came from my inexperience and age. It's part of why I would read so many books, 'cause I was like, "Gosh, I really have no idea what I'm doing. I've never done this before. I need to learn something before (laughs) everyone figures it out or, or I mess up this thing I really care about." Um, and I still, like... it still gets to me when, you know, even at our scale, and we've hired thousands of people and, you know, over the years, people, a lot of people have left as well. Hundreds of people have left. Um, that's still is tough for me, even at this level, where, you know, when you hire someone, you have the, all the hopes in the world. And, um, so when that doesn't work out, it still, uh... yeah, it still, still bothers me. It's something I really, I try to think about and also, like, think what could we have done differently. Because it's not really fair to someone else as well to leave their previous job and everything else to come and, uh, and not be in the environment where they feel like they can be successful.
- HSHarry Stebbings
I, I would love to unpack
- 34:30 – 37:34
Where did your insecurities come from?
- HSHarry Stebbings
them. Um, I, I, I've actually said it before publicly. I, I have bulimia for many years, and I was f- I still am have, you know, very challen- it is very tough. You never lose an eating disorder, I don't think. Um, can I ask, where did your, um, insecurity, self-awareness over your body come from, do you think?
- MMMatt Mullenweg
Hm. You know, the, the earliest memory I have there, um, were one, being at a swim meet in a Speedo and just, like, shivering on the side of the pool, and then I was a really slow swimmer so I finished, like, a minute after everyone else, and just everyone, like, standing by the side of the pool, watching me, like, struggle my way through it. So that was definitely an early one. And then the other one I remember was, uh, Little League Baseball (laughs) and you know, go up to the... you know, you wear the uniform and everything and you go up to the bat. I think this was tee ball probably, so the, the ball's on, like, a little stands. And, um, I remember the kids in my dugout, like, really laughing at me because I had some sort of cartoons on my underwear, like Scooby-Doo or something, and it was visible through these, you know, baseball uniform pants. And they started, like, laughing and yelling, and I was like, "Oh, no." Like, so those are two that I, I remember from a, a really young age.
- HSHarry Stebbings
God, this, this interview is so much more than you bargained for.
- MMMatt Mullenweg
(laughs)
- HSHarry Stebbings
On the second one-
- MMMatt Mullenweg
I don't think I've talked about that publicly before, but, uh, thanks for bringing it up.
- HSHarry Stebbings
... you're gonna be like, "Shack, what did you get me into?" (laughs)
- MMMatt Mullenweg
(laughs)
- HSHarry Stebbings
Um, on the, on, on the second one about, um, you know, age and feeling like you hadn't done it before. You know, you invest now as an angel. I, obviously, invest with funds. I'm constantly kind of stuck between the mindset with founders of, great, I believe in the value of naivety, and I believe in not knowing the challenges and then overcoming them 'cause you didn't know they weren't possible. But then I've also been in situations where we've just been fucked because we could have avoided mi- mistakes-
- MMMatt Mullenweg
(laughs)
- HSHarry Stebbings
... and situations that could have been known.
- MMMatt Mullenweg
Yeah.
- HSHarry Stebbings
Where do you sit in that balance?
- MMMatt Mullenweg
Let me say one thing on the last one just before we go, is like, I originally didn't remember those things. I just had the insecurities. But I actually did some hypnotherapy a few years ago.And one of the techniques was they'll be like, "Okay, um, you know, go back. When was the first time you remember that feeling? Or go back and go back." And so those, those memories I just said were actually entirely self-conscious, or se- self subconscious, excuse me. Um, they're self-conscious, subconscious memories, and it wasn't until, like, I did this kinda guided meditation, um, that was able to figure out that that was probably still influencing me, even as an adult, when I haven't worn a Speedo (laughs) in a long time. So, uh, it just, it's, you know, an interesting tool. There's lots of tools for self-exploration. I think meditation and, you know, guided meditations, hypnotherapy can be really good ones for people to explore. Um, and I forgot the question you just asked, so I apologize. (laughs)
- HSHarry Stebbings
N- not at all. My question was where do you... how do you kind of sit in terms of the balance between
- 37:34 – 39:57
Balance between naivety and experience
- HSHarry Stebbings
the value of naivety and not knowing what's ahead of you, versus very experienced, knowing what's coming and being aware of the pathway and the potential challenges ahead which could stop you doing something great?
- MMMatt Mullenweg
I- I've probably fallen the side of I prefer to come into things with a little bit more of a beginner's mind and really try to break down the problem area that you're tackling, whether that's for a social networking, podcasting, web publishing. And, uh, you know, because it's so easy for people to say, like, you can't do something or that's not possible. But it's nice, and it's cliched now to talk about first principles thinking, but, like, I remember there was a technical issue we were, we were challenging w- or struggling with with WordPress.com. Well, WordPress.com is, like, a nationally multi-tenant, kinda shared SaaS application, and people wanted to support plug-ins and themes for WordPress, which meant that we'd need to move you to, like, a, essentially like a virtual private server, where you had your own contained environment where you could run arbitrary code and just have a lot more flexibility that wouldn't affect, you know, the other folks in the multi-tenant architecture. And the design goal was, I was like, well, what if we could do this, just you upload the plug-in and it happens all in the background? Like, while you think the plug-in is uploading, we're actually moving your entire site and server and re-, you know, rerouting it at the, at the gateway and everything to switch you from the multi-tenant to the sort of, um, more isolated architecture. And originally, you know, we were like, "Can't do that 'cause the goal is under 30 seconds." But then we were like, "Well, okay. What, what takes longer than 30 seconds? Like, how much data are we talking about here? Like, how many megabytes? What's the speed of the network connection? What's the speed of the hard drives to, to read this and write it on the new place? Like, could we actually..." And we got it down to where most of them take now under 15 seconds, and, uh, and that feature's been working really well, and it actually drove, like, um, many years of enhanced growth for WordPress.com. But the original sort of reaction was like, "Oh, we shouldn't do that. We should just have, like, where, how a lot of other folks do this, where you click the button that shows like, 'Hey, we'll email you in, you know, 15 minutes when it's done,' and, like, that sort of thing." But, uh, yeah, breaking it down to kinda, like, what raw data is going across the wire and how, what are the speed limits there
- 39:57 – 41:45
Does leadership get easier over time?
- MMMatt Mullenweg
was really, really helpful.
- HSHarry Stebbings
Everyone always says, you know, um, "Oh, leadership doesn't get easier over time." I honestly think that's bullshit. I think it does. (laughs) Um, does leadership get easier over time or not?
- MMMatt Mullenweg
Yeah, a, a book I loved recently was Ray Dalio's Principles, and one of the things, what I loved about it is he says, like, over time, with experience, you start to see, like, oh, this is another one of those things that I've seen before, and particularly if you can extract out patterns or commonalities between otherwise disparate events. And so, you know, I have such incredible respect for experience, and, you know, for most of my career, I've worked with people sometimes much older than me, and that's been, uh, one of the things that I felt like was really, uh, productive about our partnerships, is they could bring in the experience of having seen a lot of these things before that were entirely new to me, and I could bring in, like, just a, a fresh look of, of not knowing what we can't do. And, uh... but you need both sides. (laughs) Like, I think if you have just one or the other, it's probably not great. But that's what's beautiful about building a team. Like, when you put a really great team together, everyone's bringing a different background, a different point of view, different everything, and then that, you know, allows you to, I think saves you a ton of time, avoids you a ton of issues. And I love the idea as well, is, you know, having someone on the team whose job it is even to, like, attack the ideas and to really, uh, force them to defend themselves. So yeah, I, I like, that's why I think I love teams more than anything. Like, for me, happiness is working with a great team, um, on something I feel like is gonna have a impact bigger than just, you know, our job or our revenue, and, uh, that people use. You know, making something that people use is incredibly rewarding. So you give me those three ingredients,
- 41:45 – 43:54
What does great friendship mean to you?
- MMMatt Mullenweg
and like I said, I wo- I would love to do this the rest of my life.
- HSHarry Stebbings
I, I, I listened to you on Tim Ferriss, and you said, you know, you would, um, if you could change one thing or if you knew you were gonna die in a year, it would be, like, spend more time with friends, um, and correlating that to happiness. And I spoke to Hugo Barra, I spoke to Daniel, I spoke to Shaq, I spoke to Tony Schneider, Tim Ferriss, and the depth of their friendship with you was so wonderful to hear. And it, it just made me think on a couple of things, but first is, like, what does truly great friendship mean to you?
- MMMatt Mullenweg
Hmm. You know, a friend is someone who calls you out. (laughs) You know, I always joke that, like, if you have something in your teeth, like, a stranger might not tell you, but a true friend will always tell you if you have something in your teeth, 'cause it's kinda saving you from walking around all day with a poppy seed in there or something.
- HSHarry Stebbings
(laughs)
- MMMatt Mullenweg
Um, I do appreciate, um, vulnerability. I think, uh, you know, uh, being vulnerable with your friends, um, and making space for them to be vulnerable with you is really powerful. Like, we all want to be heard and understood. Um-... what I'm bad at and trying to get better at is actually asking for help when I need it. Uh, if I'm going through a really challenging situation or tough time, I, I tend to kind of go in a cave and, like, withdraw. And (laughs) all my friends are like, "Hey, like that's when we wanna be there for you. Like that's... But we can't if you don't tell us." So that's something that's been on my mind recently.
- HSHarry Stebbings
Wh- why, why do you think you're bad at that? Is it 'cause you don't want to open up and admit that you're struggling? Is it because you think you can do it on your own? What do you think is the reason?
- MMMatt Mullenweg
Yeah, there's probably some, some embarrassment or shame there. There's also just that through my life, I've been able to get through a lot of tough things just by kind of white-knuckling it, you know, like really, like, diving in and working crazy hours or doing something really gargantuan. Um, but that doesn't always work. You know, there's some things in life that you can't white-knuckle that... because they're completely out of your control or influence. So having someone honestly just to talk to about it
- 43:54 – 46:00
Have you ever seen a therapist?
- MMMatt Mullenweg
is really, really valuable, and that's something I really appreciate.
- HSHarry Stebbings
Have, have you ever seen therapists? When I went through, you know, very bulimic kind of schedules and episodes, I, I saw therapists for many years and probably still need therapists for many years. Uh, but- (laughs)
- MMMatt Mullenweg
(laughs)
- HSHarry Stebbings
... um, have you ever spoken to them and, and how did you find that, if so?
- MMMatt Mullenweg
Um, not a formal therapist, but I've worked with a lot of teachers over the years who have done very therapy-like things with me, including a coach I work with now called, uh, Joe Hudson, uh, who actually has a really great... He shares a lot of his stuff online now. So, uh, it's been... I think self-awareness is kinda, you know, know thyself before you can change anything else.
- HSHarry Stebbings
Mm-hmm.
- MMMatt Mullenweg
And where I see leaders struggle the most, including companies I invest in, is typically where they're being driven by some forces which they're not fully aware of, and that might cause them to be snappy, or tense, or act out of fear rather than abu- in abundance. And, um, you know, all these things, some sound really woo-woo (laughs) and sometimes I do these things. Like, a friend will bring me in, I'm like, "This is total, like, (laughs) woo-woo crystal stuff," but I'll try anything at least once. And I try to look for the wisdom in even things that I think are a little ridiculous, uh, particularly if it's, like, from an older modality or something that's been around for a long time. It's like, "Okay. Why has this survived so long?" Or, "Why do people like it?" Or even if I think it's totally, you know, made up, why are people drawn to it? What about... What is it promising that people are drawn to? So, um, yeah, approaching these things with an open mind I think is really, really helpful. For all of this, like, you have to be open-minded for it to work. (laughs) If you just go into it being like, "Oh, this is never gonna work for me," or, "I'm gonna prove them wrong," it- you'll, you'll be right. (laughs) It won't work for you.
- HSHarry Stebbings
On friendship, I spoke to Shaq and he... I'm quoting him here. He said, um, "Matt is always there when it matters. Always. Birthdays, special events. If it's special, he's there." We met at Shaq's wedding. Um, uh, and, you know, seen you obviously at Brilliant Minds and other events. To do this, though, you
- 46:00 – 49:54
How do you manage your time?
- HSHarry Stebbings
have to manage your time very well. And so my question to you, and same from Hugo, uh, in particular, was, first, how do you manage your time?
- MMMatt Mullenweg
That's a good question. Uh, like, I do try to... I make a lot of lists. I use, um, Simplenote and DayOne quite a bit to make, like, extensive notes and lists of things. Um, I manage my time by working with really great people who make me better, um, including, you know, my super amazing assistants, Mo and Shiva, and, and others that, like, really kinda help me operate at a higher level. And, um, yeah, I do like the philosophy of, like, eat the frog, where if there's something really I don't wanna do (laughs) in a day or I'm procrastinating or putting off, I try to do that first. With a joke, that being that, like, if you have to eat a frog on a Tuesday, don't wait until the end of the day, like... (laughs) Do it first thing and then just get it over with. So, uh, that is probably my best time management tip. Everything else, it's, you know, my days are so different, um, because I'm moving between our businesses quite a bit, um, I'm often in different physical locations quite a bit, and so it's not really a typical day. Um, so I just try to really triage. I'm a very fast typist. (laughs) I, I love being on the computer, so those things definitely help for kinda keeping on top of things.
- HSHarry Stebbings
What have you stopped or started recently that's made a big difference? So like, for me, I, I stopped drinking in the week, and I noticed that made a big difference actually. I still drink on the weekends and, you know-
- MMMatt Mullenweg
Mm-hmm.
- HSHarry Stebbings
... have a great time then, but weekdays, no. Is there anything that you've stopped or started that has made a big difference?
- MMMatt Mullenweg
Hmm. You know, the two best things in the past couple years that were interesting for me was actually the COVID lockdown, when I stopped traveling. In 2019, I think I did over 500,000 air miles, uh, so I was really traveling quite a bit. And, um, you know, that went to zero (laughs) for a while there. So that was interesting because I realized that once I was in a single place all the time, all my excuses kinda fell away. 'Cause before I'd be like, "Oh, I'm not exercising because I'm on the road," or like... (laughs) or whatever it is. So, like, when I stopped doing that, I really had to face a lot of things that I think I'd been running away from a little bit. And-
- HSHarry Stebbings
What did you learn about yourself at the time? Because it, it does reveal a little bit about who you are and, and what you really want.
- MMMatt Mullenweg
I found I had a lot of resistance to these things. So, uh, yeah, I would say that the... I think I learned the importance of consistency. So typically, what I've done in the past is, like, you know, I won't work out for a while, and then I'll, like, work out every day, and then I end up hurting myself, and then I stop (laughs) you know? So, like, that kind of feast or famine, um, I think for things like exercise is not the most effective approach. By the way, I know I'm the least- world's least expert on this, but at least that's been (laughs) my experience so far. Um, versus the consistency of doing even just a little bit every day...... I found felt a lot better, was easier to accomplish, and got, honestly, better results. So that, um, consistency, I think, applies to a lot of things, whether it's meditation, you know, investing in your close relationships to make sure you're, um, not just spending time around each other, but really, like, listening to each other, talking to each other. Uh, yeah, the consistency matters a lot. You know, we were talking about friendships. One of my favorite things is also seeing how friendships and people develop over the long term. I feel really lucky that the people I worked with when I first moved to San Francisco, like Phil Black or Tony Schneider, um, Tony Conrad, I still work with today. Uh, so, but seeing how people change over time is also really inspiring to me. But I could change over time. (laughs)
- HSHarry Stebbings
(laughs) I love Phil in particular. A- absolute favorite. What a hero he is. I, I hope it's okay for me to ask,
- 49:54 – 52:22
On grief and grieving father’s death
- HSHarry Stebbings
but I, I listened to your episode with Tony in Antarctica, and in the beginning, you spoke about y- your, your father's passing, and actually the pre-grieving process being a very significant time for you. I was interested when listening and, uh, you know, thinking about it, what did you learn about yourself in that pre-grieving process and, and, and how did that impact how you think?
- MMMatt Mullenweg
Hmm. You know, I only realized it later. So at the moment, I didn't realize what was happening. Um, but I was so searching... You know, his situation and his illness was very much out of my control, so I was really searching for things I could control. Um, so I actually got really strict about, like, my diet and exercise and all these other things 'cause I was just, like, just trying to grasp on to something in the universe. And it was afterwards that I realized that, um, I was going through a grieving process even though he was still there. And I read a, a great book by Elisabeth Kubler-Ross called, uh, Grief and Grieving. She's, you know, one of the, um, academics that came up with the five stages of, uh, grief. You know, like anger, denial, uh, bargaining, depression, and acceptance, I think, are the five. So, yeah, that book sort of revealed both the things I had gone through before but not been aware of, and then also after his passing, 'cause a, a friend from high school actually gave it to me. Um, so I read it and... after he passed, and then just s- kind of seeing how myself, my mom, and my sister were grieving so differently. And originally, that made me kind of angry. Um, you know, one of the anger phases for me is like, "How can the world go on?" You know? "How can people just act like things are normal?" Um, but then sort of understanding that it's a very personal process and, like, people grieve differently at different times. And so I think about that now as well when someone is facing a loss, whether it happens or not, that they are going to respond differently, and that that's okay, and that it's really important to support them in however they're going through that pre-grieving process. So, uh, again, just something that if there is one bright side that can come out of a loss like that, it's that when someone else is going through something similar, perhaps you can be there. And much like my friend gave me that book, like, help them, uh, understand what's going
- 52:22 – 55:12
Lessons from father
- MMMatt Mullenweg
on a little bit better.
- HSHarry Stebbings
I always think our parents shape us in ways that we don't expect or anticipate. When you think about your father, are there one or two big takeaways or lessons that you learned from him in terms of how you think, how you act, how you operate?
- MMMatt Mullenweg
Hmm. You know, one of my, my early memories of my dad were, um, him waking up super early in the morning before the sun was out. This was when I was so young I would sleep in my parents' bed. And, you know, he would shower. He'd put on a suit. He was a computer programmer, but at that time, you had to wear, like, a suit and a tie. And get his briefcase, and just, like, without fail, be super early in the morning, like, first person in the office. And then he would take me sometimes on weekends, so he would go into the office on, like, extra days, which was my favorite thing, because then I... he'd stick me at one of the other workstations and I'd get access to the, you know, T1 Internet or something. Um, but just, like, his just work ethic was really incredible. Uh, that was definitely one. And just he was always incredibly straightforward, you know? The, uh... he would, you'd always know... Yeah. He, he was just a very genuine person, and that sort of high integrity, you would see throughout every single aspect of his life. And just has always been really inspiring to me, you know, both as, as an example, but also just in how much simplicity it adds to life, if you're the same person in all contexts. You know, if you lie, you have to keep track of it. (laughs) Where if you could just tell the truth all the time, um, you have one less thing to keep track of. All you have to keep track of is reality. So I feel like that example, um, yeah, still serves as a inspiration to me today.
- HSHarry Stebbings
Did he see your success with WordPress?
- MMMatt Mullenweg
He did. So he passed in 2016. So, yeah, Automattic, uh, had been around for 11 years. WordPress had really started to become a bigger thing. And, uh, one of the things that really touched me... because he, um, he did start saying, "I love you," kind of in the l- you know, last five or 10 years of his life, where he wasn't overly demonstrative when we were super young. But, um, after he passed, some of his, uh, folks at his office told me how he would, uh... he would never really talk about me, but sometimes when there was a press article or news article, he'd come in and kind of put it on the wall in the break room. Um, they had, like, a little pinboard. And, uh, I never knew that, and that really, uh, made me cry and made me really happy because it helped me see that, yeah, he was following along and, and, uh, and a big supporter.
- HSHarry Stebbings
Man, that's, that's super special. Um, I'm, I'm sorry for, for going deep there, but, um, I really appreciate you opening up and discussing it. I, I, I do want to move into a quickfire round. So I say a short statement, you give me your immediate thoughts.
- 55:12 – 55:38
Favorite book and why
- HSHarry Stebbings
Does that sound okay?
- MMMatt Mullenweg
Sounds great. (laughs)
- HSHarry Stebbings
What's your favorite book and why?
- MMMatt Mullenweg
Uh, my favorite book right now is probably this one, actually. It's called, um, Sum by David Eagleman. And, um, it's 40 tales from the afterlife. And it's, uh... He's actually, like, a science writer, but this is kind of a fiction. And it's sh- all short stories, they're really kind of mind-bending and amazing. And, um, it's a nice bedtime
- 55:38 – 55:59
Biggest strength and weakness
- MMMatt Mullenweg
read, so to read one, like, right before you go to bed.
- HSHarry Stebbings
What would you say is your biggest strength and then your biggest weakness? 30 seconds on each.
- MMMatt Mullenweg
Oh. I think my biggest strength is definitely the people I work with. Um, and my biggest weakness is definitely probably pride, you know. You know, that not asking for help.
- 55:59 – 56:37
Hardest element of role with Automattic
- MMMatt Mullenweg
- HSHarry Stebbings
Totally. Uh, can I ask, what is the hardest element of your role with Automatic today?
- MMMatt Mullenweg
Hmm. You know, this is both in Automatic and my life, is, um, right now and often, I feel stretched very thin.
- HSHarry Stebbings
Mm-hmm.
- MMMatt Mullenweg
So, like, I can't spend as much time or do as much with everything we have going on, especially as the company has now gotten to thousands of people. Um, so yeah, it's my biggest struggle.
- HSHarry Stebbings
What advice do you often give but find it hard to follow yourself?
- MMMatt Mullenweg
I meditate
- 56:37 – 57:54
What do you know now that you wish you knew when you were young?
- MMMatt Mullenweg
(laughs) .
- HSHarry Stebbings
Uh, f- uh, okay. Totally. What do you know now that you wish you'd known at the start of Automatic as a 19-year-old? What would you tell yourself?
- MMMatt Mullenweg
Hmm. That it's gonna be okay. I think there were times when it felt, like, very existential. And, um, just knowing that, like, you know, when it's over, it's gonna be okay, and if it's not okay, it's not over.
- HSHarry Stebbings
What would you say is Shachar's greatest superpower? I always say to him he sees and believes in people before they even believe in themselves. He did with me-
- MMMatt Mullenweg
Mm-hmm.
- HSHarry Stebbings
... and he has done with many others. Um, what would you say his is? You've known him for many, many years.
- MMMatt Mullenweg
I mean, yours I would agree with. Um, let... So let me add another one. Maybe not his greatest, but something I get really inspired by him, is his ability to think of a situation or a problem from every single angle. You know, he talks a lot about loving friction, free logistics. And part of that is, like, anticipating every single possible thing in every interaction and planning for it or countering for it. And, uh, I find that super inspiring and something I aspired to, like, in our experiences or when I host something or, you know.
- HSHarry Stebbings
I mean, it is just exceptional. I
- 57:54 – 59:39
Where do you see yourself in 5 years?
- HSHarry Stebbings
totally agree with you there. I'm always amazed. Um, I want to finish on the final one, which is what do the next five years hold for you, Matt, and what is the plan ahead? If we do this in 2027, where do we want to be?
- MMMatt Mullenweg
Oh. You know, broadly, Automatic's mission is to democratize publishing and commerce. And one thing that's been excited as we've grown is being able to expand into other areas, like social networking with Tumblr, podcasting with Pocket Cast, personal journaling with Day One. So... Um, but all of these things fit together in that kind of, like, making a more open web where people can express themselves. So my hope in 2027 and over the next five years is that the web is a lot more creative, a lot weirder, that people have a lot more control over it versus just being another profile on Twitter or Facebook, and, um, and more fun. You know, I think that when you do these things right, it allows an expression of human creativity and individuality, which, you know, traditional web properties, they really try to fit everyone into the same boxes and very cookie cutter. And that's not how humanity is. You know, the beauty of human- mani- humanity is in the diversity and sh- and uniqueness of each individual. And so we need to be able to express that indi- individually online better. So I hope that we are able to create tools which allow people to do that more, and that the tools get adopted more and more.
- HSHarry Stebbings
Matt, it did take time for us to do this, but it's shows-
- MMMatt Mullenweg
Mm-hmm.
- HSHarry Stebbings
... like this that make me so appreciate doing what I do. Thank you so much for being so brilliant. And I, I really so love this discussion.
- MMMatt Mullenweg
Thanks, Henry. And I hope that we're... next time in London, we'll be able to hang again. Looking forward to it.
Episode duration: 59:39
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