Matt Mullenweg on WordPress, Distributed Leadership and Building for Decades

Matt Mullenweg says WordPress emerged from an existing open-source blogging tool, b2/cafelog, rather than a wholly new idea. When its original developer stopped maintaining it, Mullenweg and Mike Little, both community contributors, continued the code as a fork and chose a new name.

He recalls the first year as small but enjoyable, with contributors collaborating from different places. He began thinking in decades early on. A Japanese contributor’s painstaking translation, before a translation framework existed, made him realize the project might matter to people far beyond its original community.

Mullenweg recalls a Google survey identifying a WordPress-related header on about 0.8% of sites it examined. He describes the result as an exciting early signal, not a current measure of adoption. For him, seeing people use and extend software is a central reward.

High performance begins with communication, he says: teams need shared understanding, accountability and a mission. He tries to be clear and concise. When giving difficult feedback, he wants the recipient to feel it comes from care and a shared effort to improve, with trust built through collaboration.

Mullenweg says he defaults to trusting people, accepting that optimism occasionally has a cost. He also admits that storytelling is an area he wants to improve: he can get lost in detail, and admires communicators who connect a personal story to a larger point.

He describes Automattic, the for-profit company he built around WordPress, as flat and distributed, with colleagues in 97 countries at the time. His style is to give people room, then occasionally dive deeply into a technical or partnership detail. These descriptions reflect his account of the company in 2022.

The best balance of accountability and independence, he says, comes from clear goals and flexibility about how to reach them. He sees mistakes when leaders become too involved in a successful team’s methods. The approach also depends on being explicit when circumstances require more direction.

Mullenweg says he took over Tumblr’s day-to-day leadership in February 2022 and told the team he would initially be more directive because the business was struggling. He regards that mode as temporary and believes leaders can switch behavior between difficult and calmer periods if they explain what to expect.

Automattic uses internal blogs rather than email for much of its work, he says. Written, threaded and asynchronous conversations stay searchable, so new employees can see decisions and institutional knowledge is not confined to departing employees’ inboxes. The internal system is called P2.

He says transparency has limits: team or division performance can be discussed openly, but individual performance and personnel issues are better handled privately. His principle is to praise publicly and give personal criticism privately.

Automattic bought Tumblr because Mullenweg saw a culturally important property that he believed previous owners had mismanaged. He says that, after two years without a turnaround, he became more hands-on. Running a large service was expensive, so he wanted a sustainable path toward break-even.

He reports that Tumblr usage and revenue were growing at the time and says 60% of its users were under 25. He saw the younger audience as potentially complementary to WordPress. These are the company leader’s 2022 claims and strategic hopes, not verified current figures.

Asked whether profitable businesses should subsidize more risky growth, Mullenweg says Automattic has used outside capital primarily for acquisitions while favoring sound unit economics. He recalls the company operating on about $11 million of outside funding until roughly 2014.

He says a 2014 Series C raised $160 million in primary capital and helped make acquisitions such as WooCommerce possible. He reports $31 billion in gross merchandise value for WooCommerce in the previous year. That is transaction volume as he stated it, not Automattic revenue or profit.

For integration after acquisitions, he says a distributed company can reduce office-based divisions, although Tumblr’s New York office required adjustment. Automattic rotates experienced engineers and designers into acquired teams, and he stresses that culture can travel in both directions.

Shared infrastructure, code access and internal transparency also matter, he says: an acquired team cannot collaborate effectively if it cannot see a bug or system. He sees hands-on intervention as temporary and delegates more easily when he finds someone better suited to the work.

Mullenweg says he made many mistakes as a young leader, including spending that tightened cash and a Tumblr office lease signed shortly before the pandemic. He credits Tony Schneider with giving him space to learn and with a rule: make reversible decisions quickly and irreversible ones deliberately.

He ties risk management to the possibility of running the company for decades. In his view, a sustainable business gives Automattic freedom to continue supporting open-source software. That is both a strategic belief and a statement from the company’s CEO.

He evaluates commitments over five or ten years and gives a coworking allowance as an example. An allowance of up to $250 per month for 2,000 people would total $6 million annually if fully used; he says actual usage varies. Benefits and hiring can be hard to reverse, so a policy that seems small can become a lasting cost.

Stebbings asks whether wealth makes long-term thinking easier. Mullenweg agrees and recounts a 2008 offer to buy the company for $200 million. He says investors instead funded the company at that valuation and allowed some employees, including him, to sell a portion of their holdings. These are his historical account and financing figures.

He says that opportunity reduced personal financial risk and helped him focus on the longer term. He now thinks about compensation in similar terms: people should be paid enough to focus on meaningful work and their lives outside it. The account is his philosophy, not evidence that all employees experience compensation the same way.

When overwhelmed, Mullenweg tries to step back, breathe and ask whether panicking would help. He says this can look calm from outside even when he is anxious internally. The technique is his personal coping practice, not a clinical claim.

Asked about insecurities, he mentions discomfort with his body and, in leadership, his early age and inexperience. He read extensively because he feared making mistakes with something he cared about. Even after years of hiring, he says a failed hire remains painful for both the company and the person who joined.

Mullenweg recalls childhood experiences of embarrassment at a swimming event and in youth baseball. He says guided meditation and hypnotherapy brought those memories to mind years later and that he believes they may have influenced him. This is his interpretation of personal memories, not proof of a cause or an endorsement of a treatment.

On experience versus naivety, he values a beginner’s mind that questions assumptions. He describes asking whether a WordPress.com migration could happen during a plugin upload, then breaking the problem into data size and transfer speed. He says the team brought many migrations below 15 seconds; this is his account of the technical work.

Experience can make leadership easier by revealing patterns, he says, while a fresh perspective helps challenge what others consider impossible. He values teams combining both, including someone willing to challenge a proposal. Working with a strong team on something useful is a source of happiness for him.

For Mullenweg, a good friend can be honest, make space for vulnerability and offer support. He is trying to become better at asking for help: his tendency has been to withdraw or work through problems alone. He recognizes that some difficulties cannot be solved through effort alone.

He says he has worked with teachers and a coach rather than a formal therapist. He values self-awareness and an open mind when examining why a leader reacts with fear or tension. His experiences with different practices are personal reflections, not evidence that a method will work for everyone.

He manages time with notes and lists, support from colleagues and assistants, and a habit of doing a difficult task early rather than procrastinating. His days vary by business and location, so he prioritizes rather than relying on one fixed routine.

The pandemic pause in travel exposed habits he could no longer attribute to being on the road. He says he had traveled heavily in 2019. From his own experience, consistent modest exercise felt more sustainable than alternating inactivity with overexertion; he explicitly does not claim expertise.

During his father’s illness, Mullenweg says he tried to control diet and exercise because the illness itself was outside his control. Only later did he recognize his experience as anticipatory grief. A book on grief helped him understand that he, his mother and sister responded differently.

He emphasizes that grief is personal and can unfold differently for different people. The experience made him more attentive to supporting others facing loss. He describes his own reading and feelings rather than presenting a required sequence of stages.

He remembers his father’s work ethic and straightforwardness, and says integrity simplifies life because one need not maintain different stories. His father died in 2016, after seeing WordPress grow. Later, coworkers told him his father had quietly posted articles about his son at work, a discovery that moved him.

In a quick-fire round he recommends David Eagleman’s Sum, identifies his colleagues as a strength and pride as a weakness, and says he often feels stretched thin. He also finds it easier to recommend meditation than to practice it consistently.

He would tell his younger self that difficult periods can pass. He admires a friend’s ability to examine a situation from many angles and anticipate friction, a habit he hopes to apply to the experiences his teams create.

Looking toward 2027, Mullenweg hopes Automattic’s publishing, commerce, social and podcasting tools will contribute to a more open and creative web where people have more control over their expression. This is his 2022 ambition as Automattic’s founder and CEO, not evidence that the outcome occurred.