20VC Matt Mullenweg on Relationships to Risk, Money and Insecurity as a Leader Lessons from a Parent's Passing and the PreGrieving Process What is High Performance in Leadership Today

Summary Notes


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.

Summary Notes

Introduction to Matt Mullenweg and Automatic

  • Matt Mullenweg is the founder of Automatic, the company behind WordPress, Tumblr, WooCommerce, Jetpack, and more.
  • WordPress began as an open-source blogging platform and now powers over 43% of sites on the Internet.
  • Matt also invests through Audrey Capital, backing companies like Stripe, SpaceX, GitLab, and Sendgrid.
  • The episode promises unique insights from Matt Mullenweg, sharing content he hasn't discussed publicly before.

"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 Origin of WordPress and Automatic

  • WordPress was born out of the open-source movement; Matt Mullenweg did not invent blogging but desired an open-source tool.
  • He started with B2/Cafelog, which was abandoned by its original developer, prompting Matt and Mike Little from the UK to fork and continue the project.
  • The name "WordPress" was suggested by a friend in Houston after the forking required a new name.
  • The initial user base of WordPress was small but grew as the platform was translated into other languages, notably Japanese, which was a pivotal moment for Matt, recognizing the potential impact on the web.
  • WordPress's growth was confirmed when it appeared in Google's survey, showing 0.8% of websites using it, a milestone moment for the developers.

"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.

Matt's Long-Term Commitment to WordPress and Automatic

  • Matt knew early on that he wanted to commit decades to WordPress, evident from his enjoyment and the global collaboration involved in its development.
  • His commitment was solidified by the international adoption and translation of WordPress, as well as its recognition in broader Internet statistics.
  • The anecdote of the Japanese translation of WordPress illustrates the dedication of the global community and the potential reach of the software.

"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.

High Performance and Communication

  • High performance to Matt Mullenweg is fundamentally about communication, collaboration, accountability, and a shared mission.
  • He emphasizes the importance of alignment and clarity in communication within teams.
  • Matt believes in improving communication skills continuously to enhance team performance.

"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.

Feedback and Trust in Leadership

  • Matt discusses the balance of giving feedback immediately versus waiting for the right moment, highlighting the importance of trust and ensuring feedback is perceived as constructive.
  • He defaults to trusting people from the start, acknowledging an "optimism tax" where occasionally this trust can be taken advantage of, but overall it leads to a better life experience.
  • Trust is essential for effective communication and collaboration.

"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.

Storytelling and Product Marketing

  • Matt acknowledges his struggle with storytelling and the need to improve in this area.
  • He admires others in the WordPress community who excel at storytelling, linking personal stories with broader themes and circling back to core messages.
  • Effective storytelling is an important aspect of communication and product marketing.

"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.

Matt Mullenweg's Leadership Style

  • Matt describes his leadership style as nontraditional, with Automatic being a flat organization that values transparency and global distribution.
  • He balances giving teams space with occasionally diving into details, moving between high-level and ground-level perspectives.
  • The leadership style at Automatic includes clear goal-setting and flexibility in methods, with Matt sometimes taking a direct approach in times of crisis.

"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.

Explicit Communication in Leadership

  • Harry Stebbings discusses the importance of being explicit in leadership communication.
  • Explicit communication sets clear expectations and reduces resistance.
  • Matt Mullenweg agrees and emphasizes that stating intentions openly can guide teams during transitions.

"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.

Wartime vs. Peacetime Leadership

  • Matt Mullenweg discusses the concept of wartime and peacetime leadership.
  • He believes individuals can adapt to both roles based on behavior, not identity.
  • Mullenweg mentions the ability to switch leadership styles within his company, depending on the maturity of the business.

"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.

Communication Without Email

  • Matt Mullenweg explains his company's communication strategy without using email.
  • He values the written, threaded, and asynchronous nature of email but dislikes its private, siloed nature.
  • Mullenweg's company uses internal blogs for transparency and institutional knowledge sharing.

"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.

Transparency vs. Privacy in Communication

  • Matt Mullenweg addresses the balance between transparency and privacy in internal communications.
  • He believes in transparency for team and division performance but maintains privacy for individual performance issues.
  • The approach is to praise publicly and criticize privately, especially for sensitive HR matters.

"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.

Decision-Making in Leadership

  • Matt Mullenweg discusses his decision to take over as CEO and the acquisition of Tumblr.
  • He describes Tumblr as a "generational property" with potential for turnaround despite initial challenges.
  • Mullenweg highlights the strategic importance of Tumblr for reaching a younger, mobile-first audience.

"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.

Balancing Growth and Profitability

  • Matt Mullenweg reflects on the balance between leveraging profitable entities to subsidize growth in riskier assets.
  • He believes in good unit economics from the start and using outside capital for strategic acquisitions.
  • Mullenweg discusses the timing of investments and acquisitions in relation to market conditions.

"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.

Successful Integration in Mergers and Acquisitions

  • Matt Mullenweg shares insights on how his company effectively integrates acquisitions.
  • Being a distributed company helps reduce 'us vs. them' dynamics.
  • He emphasizes the importance of rotating top talent into new acquisitions and prioritizing backend integration.

"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.

Delegation and Leadership

  • Matt Mullenweg discusses his approach to delegation as a leader.
  • He delegates tasks to individuals who are more skilled or passionate about those tasks.
  • Mullenweg views the need to step in personally as a temporary measure and a sign that the right team or strategy has not yet been found.

"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.

Learning from Mistakes

  • Matt Mullenweg reflects on the valuable lessons learned from mistakes made during his journey with Automattic.
  • He acknowledges the importance of reversible decisions and careful risk management.
  • Mullenweg stresses the significance of sustainability and growth as indicators of successful mission execution.

"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.

Long-Term Mindset and Risk Management

  • Matt Mullenweg discusses his long-term approach to risk management and decision-making.
  • He considers the long-term implications of benefits and hiring decisions.
  • Mullenweg emphasizes the importance of making reversible decisions quickly and irreversible decisions deliberately.

"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.

Relationship to Money and Compensation Philosophy

  • Matt Mullenweg reflects on a significant financial decision in 2008 regarding Automattic, the company behind WordPress.
  • Investors turned a buyout offer into an opportunity for reinvestment and partial liquidity for employees.
  • The goal was to provide financial security for employees to focus on long-term goals and impactful work.
  • Matt emphasizes the importance of a base salary that allows employees to concentrate on their most important life aspects.

"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.

Coping with Stress and Maintaining Calm

  • Matt Mullenweg discusses his approach to maintaining a Zen-like calm during stressful situations.
  • He utilizes a form of coping by stepping back mentally and focusing on breathing, a technique he relates to his experiences playing the saxophone.
  • Matt considers whether panicking would improve or worsen a situation and usually finds that staying calm is more beneficial.

"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.

Insecurities in Leadership

  • Matt Mullenweg shares his personal and leadership insecurities.
  • He has insecurities about his body image and past experiences of feeling embarrassed.
  • Leadership insecurities stemmed from his inexperience and youth, leading him to read extensively to compensate.
  • Matt still finds it difficult when employees leave the company and reflects on what could have been done differently.

"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.

Balance of Naivety and Experience in Business

  • Matt discusses the balance between naivety and experience when approaching business challenges.
  • He values a beginner's mind but also appreciates the insights gained from experience.
  • Matt illustrates this balance with an example from WordPress.com, where they overcame technical challenges by breaking down the problem and pushing the boundaries of what was thought possible.

"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.

Leadership Growth Over Time

  • Matt Mullenweg believes leadership does get easier with experience as patterns and commonalities emerge.
  • He stresses the importance of team diversity and the benefits of having a team member challenge ideas.
  • Matt finds joy in working with a great team on impactful projects.

"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.

The Meaning of True Friendship

  • Matt Mullenweg defines true friendship as being willing to call each other out and support each other, especially in vulnerable times.
  • He admits to struggling with asking for help and is working on being more open with friends during tough times.
  • Matt values vulnerability and the ability to be heard and understood within friendships.

"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.

Personal Growth and Self-Awareness

  • Matt Mullenweg discusses his use of various techniques, including hypnotherapy, to uncover subconscious memories and insecurities.
  • He sees value in self-exploration tools like meditation and hypnotherapy.
  • Matt emphasizes the importance of self-awareness for leaders and the impact of unrecognized internal forces on their behavior.

"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.

Time Management Strategies

  • Matt Mullenweg uses simple tools like a note-taking app and a journal for making lists to manage his time.
  • He surrounds himself with efficient people, including assistants, to operate at higher levels.
  • Matt embraces the philosophy of "eat the frog," tackling the most challenging tasks first to avoid procrastination.
  • His days vary due to moving between businesses and locations, so he prioritizes tasks (triage) and relies on his fast typing skills and comfort with computers to stay on top of his work.

"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.

Impact of Lifestyle Changes

  • The COVID lockdown halted Matt's extensive travel, revealing excuses he used to justify not doing certain activities, like exercising.
  • The stop in travel forced him to confront issues he may have been avoiding.
  • Matt learned the importance of consistency in activities like exercising, meditation, and investing in relationships.
  • He values the long-term development of friendships and working relationships.

"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.

Pre-Grieving Process and Personal Growth

  • Matt Mullenweg went through a pre-grieving process during his father's illness, which led to him seeking control in areas like diet and exercise.
  • He learned about the five stages of grief from Elizabeth Kübler-Ross's book "On Grief and Grieving."
  • The grieving process is personal and varies from individual to individual.
  • Matt now understands the importance of supporting others in their unique grieving processes.

"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.

Lessons from Matt's Father

  • Matt's father demonstrated a strong work ethic by waking up early and being the first person in the office.
  • His father's straightforwardness and integrity in all aspects of life have been a source of inspiration for Matt.
  • Matt's father was supportive of his success with WordPress and showed pride in his achievements discreetly at work.

"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.

Matt's Personal Insights and Future Outlook

  • Matt considers the people he works with as his greatest strength and pride as his biggest weakness.
  • He struggles with feeling stretched thin due to the growth of his company, Automatic.
  • Matt advises others to meditate but finds it challenging to follow his own advice.
  • He wishes he knew earlier that challenges would be okay in the end.
  • Matt appreciates Shaq's ability to think through every angle of a situation and plan accordingly.
  • Looking ahead to 2027, Matt hopes the web will reflect more individual creativity and control, moving away from cookie-cutter profiles.

"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.

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