In this episode of 20vc, host Harry Stebbings interviews Matt Mullenweg, founder of Automattic and the force behind WordPress, Tumblr, WooCommerce, and Jetpack. Mullenweg shares his journey from contributing to an open-source project to leading a company that powers over 43% of the internet, touching on his investment activities through Audrey Capital. He discusses embracing a long-term mindset, the significance of open source, and the impact of WordPress's global reach. Mullenweg also reflects on leadership, communication, and the importance of trust and accountability within teams. The conversation delves into his personal growth, dealing with grief, and the value of strong friendships. Mullenweg envisions a future where the web celebrates individual creativity and diversity through tools that Automattic develops, aiming for a more expressive and open internet.
"I think he's one of the defining leaders of a generation and I'm so thrilled to welcome Matt Mullenweg, founder of Automatic, the force behind WordPress, Tumblr, Woocommerce, Jetpack, and many more."
This quote highlights the significance of Matt Mullenweg as a leader and innovator in the tech industry, emphasizing his role in creating influential Internet properties.
"The main thing with forking is, I mean, one of the beauties of open source is you can take all the code, but you need to come up with a new name."
This quote explains the concept of forking in open-source projects and the necessity of rebranding the project after taking over the codebase.
"Oh, I'd say pretty early on. First year of WordPress was very small, probably dozens of users, but it was fun in that the developers, myself and others were really having a good time working on it, collaborating, and all over the world we never met each other, but that's how open source works."
This quote reflects Matt's early realization of his long-term dedication to WordPress, fostered by the collaborative and enjoyable nature of the open-source community.
"All great things I've been involved in at least, were created from collaboration and teams. And communication is fundamentally taking what's in our respective minds and finding that common ground."
The quote underlines the role of communication in achieving high performance through collaboration and shared understanding within teams.
"I personally am very default trusting. And that also means that sometimes you pay what I call an optimism tax."
This quote reveals Matt's approach to trust, accepting that while there may be drawbacks, the benefits of a trusting disposition outweigh them.
"I feel like I can get very lost in the nuance and the details."
This quote reflects Matt's self-awareness of his challenges with storytelling and the importance of focusing on the big picture in communication.
"I end up being a leader, which is normally giving folks a ton of space and then occasionally diving extremely deep into the details."
This quote captures the essence of Matt's leadership approach, emphasizing autonomy for his team while maintaining the ability to engage deeply when necessary.
"I've made mistakes before is not being explicit about that. So I think it was actually really helpful for me to say, hey, this is going to be like top down for a little while, and then everyone knew what to expect, where if I'd just done that without saying that first. I feel like that probably would have been a lot more resistance."
This quote highlights that openly communicating a leadership approach, such as a temporary top-down strategy, can minimize resistance from team members because they understand what to expect.
"Absolutely. Yeah. Because it's about behaviors, it's not about identity. And I feel like I switch between just in working with different businesses within our company, we have some businesses that are very mature, like woocommerce, which is our e-commerce platform, or WordPress.com, which has millions of subscribers. We have some that are very nascent, actually a podcasting app called Pocketcast, which is a really good podcatcher, so you can move between them at different times. I think it's just all about behaviors. Behaviors, probably, and self awareness."
Mullenweg's quote suggests that effective leadership can switch between wartime and peacetime modes depending on the context and needs of the business. This flexibility is based on self-awareness and adaptable behaviors rather than a fixed leadership identity.
"So first I'll say, what I like about email is that it's written, it's threaded, 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 it's private, meaning that so much intelligence in a 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 in their inbox, oftenly is a ton of institutional wisdom and knowledge. And so basically everything that most companies do on email, we just do on these internal blogs."
Mullenweg describes how his company replaces email with internal blogs to make communication more transparent and accessible to all employees. This approach ensures that institutional knowledge is shared and preserved within the company.
"Even if I am useless, not individually praise in public, criticize in private, particularly if it were more like an HR issue or a personal performance. But a team performance or a division performance could definitely be on the blog and we'd want to be really transparent there about where people stand relative to our goals. But I think for individual. You're right. I think communicating privately would be better."
This quote emphasizes the company's policy of maintaining transparency at the team or division level while handling individual performance issues with discretion. This approach protects individual privacy while still fostering a culture of openness about collective goals and performance.
"Yeah, it's a good question. I mean, we bought Tumblr because it's a generational property. Like, it's really amazing. It had been mismanaged, I think under Yahoo and AWOL and Verizon, we felt like we could turn it around. The reason I ended up taking over as CEO is that the first two years of the acquisition, it had not turned around yet."
Mullenweg explains the rationale behind acquiring Tumblr and his subsequent decision to take on the CEO role to directly address the challenges in turning around the platform. The acquisition was seen as an opportunity to rejuvenate a valuable asset and strategically position the company to appeal to a younger demographic.
"Totally. We have done that in the past with the money we've raised. It's been primarily through acquisitions, though we do like to have businesses which have good unit economics as you run them from the beginning."
This quote indicates that Mullenweg's company, while open to taking calculated risks, prefers to invest in businesses with sound economic fundamentals and strategically uses acquisitions to drive growth.
"I think it helps that we're totally distributed, so there's less of like us versus them in the office or things. It was actually a big challenge when we bought Tumblr because they did have pretty large office presence."
Mullenweg attributes part of the success in integrating acquisitions to the company's distributed nature, which fosters a sense of unity and reduces office-based tribalism. He also notes the specific challenge of integrating Tumblr due to its significant office presence.
"Part of going from 10,000ft to 1ft is I do like to really deeply understand an area that I feel like helps me hire or recruit someone who's way better at it than me. For me, where it's very, very easy to delegate is when I find someone who is so much better, maybe just enjoys it so much more than me, that it's a joy to pass things off, say, that's where it's gone. Well."
This quote reflects Mullenweg's belief in deeply understanding an area before delegating it to someone more capable, thus ensuring that delegation is a positive and effective process.
"Everything we've talked about so far is usually an opposite side. So we talked about good communication. Remember, I was 19 when WordPress started, so I was a pretty terrible communicator from the of those years. So everything that's going right, I've definitely done wrong at some point."
Mullenweg candidly shares that he has learned from past communication mistakes and emphasizes the importance of learning from all experiences to improve and grow as a leader.
"Again, I think I got a lot of that out of my system in my twenty s. Now how I think about it is very much in the long term. What are the decisions? Now if you play out a decision that you're doing today and you say, okay, this continues for five years or ten years from now, what does it look like?"
This quote illustrates Mullenweg's shift from taking risks in his twenties to adopting a more conservative, long-term perspective on decision-making, focusing on the sustainability and future impact of those decisions.
"And we got an offer to sell for 200 million, which I owned a majority of the company. That would have been obviously life changing. And of course we considered it from a variety of angles, but it felt like that was a small fraction of the impact that WordPress and automatic could have in the coming years."
This quote indicates the decision to reject a lucrative buyout offer in favor of pursuing greater long-term potential with WordPress and Automattic.
"And also something I don't remember where I read it or who said it, but is freaking out right now going to help the situation or make it worse? 99% of the time it's going to make it worse."
The quote conveys Matt's philosophy that panicking is rarely productive, and maintaining composure is preferable in challenging situations.
"On the leadership side, I would say a lot of my insecurity came from my inexperience in age. It's part of why I would read so many books, because I was like, gosh, I really have no idea what I'm doing."
The quote highlights how Matt's inexperience in leadership roles led to self-education as a means to overcome insecurities.
"I probably fall on the side of, I prefer to come into things with a little bit more of a beginner's mind, really try to break down the problem area that you're tackling."
This quote reflects Matt's preference for approaching problems with an open, unassuming mindset while acknowledging the value of experience.
"But what I loved about it is he says over time, with experience, you start to see like, oh, this is another one of those things that I've seen before."
The quote from Matt references Ray Dalio's book "Principles" and underscores the value of experience in recognizing and handling recurring situations in leadership.
"A friend is someone who calls you out. I always joke that 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."
This quote illustrates Matt's view that true friends are honest and caring enough to point out even the minor issues, which is a sign of deeper care and connection.
"Know thyself before you can change anything else. 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."
The quote emphasizes the critical role of self-awareness in leadership and personal growth, suggesting that many leadership challenges stem from a lack of self-understanding.
"I make a lot of lists. I use a simple note in day one quite a bit to make extensive notes and lists of things." "I tried to do that first with a joke, that being that if you have to eat a frog on a Tuesday, don't wait until the end of the day, do it first thing, and then just get it over with."
The quotes highlight Matt Mullenweg's reliance on organization through list-making and his proactive approach to completing unpleasant tasks promptly, which contributes to his time management effectiveness.
"When I stopped traveling in 2019, I think I did over 500,000 air miles. So I was really traveling quite a bit, and that went to zero for a while there." "Consistency, I think, applies to a lot of things, whether it's meditation, investing in your close relationships to make sure not just spending time around each other, but really, like, listening to each other, talking to each other."
Matt Mullenweg reflects on how the interruption of his travel routine due to COVID lockdown led to a greater understanding of the role consistency plays in various aspects of life, particularly in maintaining health and relationships.
"I only realized it later. So at the moment, I didn't realize what was happening, but I was so searching." "That book revealed both the things I had gone through before but not been aware of. And then also after his passing, because a friend from high school actually gave it to me."
The quotes emphasize Matt's retrospective understanding of his actions during his father's illness as a form of pre-grieving and how he learned to recognize and respect the individuality of the grieving process through literature and personal experience.
"One of my early memories of my dad were him waking up super early in the morning before the sun was out... Work ethic was really incredible." "If you lie, you have to keep track of it. Where if you could just tell the truth all the time, you have one listing that all you have to keep track of is reality."
The quotes illustrate the profound influence Matt's father had on him, both in terms of work ethic and the value of honesty and integrity, which Matt continues to admire and emulate.
"That it's going to be okay. There were times when it felt like, very existential, just knowing that when it's over, it's going to be okay. And if it's not okay, it's not over." "The beauty of humanity is in the diversity and uniqueness each individual. And so we need to be able to express that individually, online, better."
These quotes reveal Matt's introspective nature, his awareness of his personal and professional challenges, and his vision for a more individualized and creative internet in the future.