Jul 11, 2022 · 59m · news
Matt Mullenweg: How I Founded WordPress; Storytelling Tips; How to Give Feedback | 20VC #905 · 20VC with Harry Stebbings
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this episode of 20VC, host Harry Stebbings interviews WordPress co-creator and Automattic CEO Matt Mullenweg, exploring the early open-source origins of WordPress, the unique operational mechanics of fully distributed companies, and the psychological frameworks essential for high-performance leadership.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Harry holds 21.2% of the talking time here. How this is scored →
Harry as informed peer 2.4 Guest teaching 2.5 Guest disagreement 0.6 Harry pushing back 1.6
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 17:57 Defending Automattic's risk profile and capital deployment
Mullenweg firmly counters Stebbings' premise that Automattic plays it too safe, explaining their deliberate contrarian strategy of taking on primary capital only when market conditions dictate.
Hardest push from Harry ▶ 17:57 Direct challenge on Automattic's risk tolerance and capital strategyStebbings directly confronts Mullenweg, challenging whether Automattic's reliance on cash flows from profitable businesses indicates a lack of aggressive risk-taking.
Biggest teaching moment ▶ 38:10 Engineering first-principles reframingMullenweg educates Stebbings on first-principles problem solving by breaking down server migration speed constraints into megabytes, drive speeds, and gateway rerouting.
Harry holds his own ▶ 39:58 Calling bullshit on the trope that leadership never gets easierStebbings forcefully rejects conventional wisdom, arguing authoritatively that leadership definitely gets easier with experience and pattern recognition.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| The Origin of WordPress | 2 | 3 | 0 | 0 | Stebbings introduces a specific quote from Tony Schneider about Mullenweg's multi-decade vision, demonstrating deep research. Mullenweg warmly explains the mechanics of open-source software and how WordPress was created by forking B-2 Cafe Log. | |
| Defining High Performance through Communication | 2 | 2 | 1 | 1 | Stebbings introduces the topic of radical candor and asks whether real-time feedback is superior to delayed feedback. Mullenweg gently reframes the conversation around how feedback is received, citing Frank Luntz and Maya Angelou. | |
| Trust, Optimism Tax, and Storytelling in Product Marketing | 2 | 2 | 1 | 1 | Mullenweg describes his default trusting nature and introduces the concept of paying an optimism tax. Stebbings asks about storytelling in product marketing, and Mullenweg candidly admits it is an area he struggles with compared to others. | |
| Balancing Accountability with Autonomy and Wartime Leadership at Tumblr | 2 | 3 | 1 | 2 | Stebbings pushes on whether executives can practically switch between wartime and peacetime leadership. Mullenweg explains taking over Tumblr in command-and-control mode and cites Ben Horowitz's leadership framework. | |
| Communicating Without Email and Reclaiming Tumblr as CEO | 3 | 3 | 1 | 3 | Stebbings directly challenges Automattic's internal blogging system (P2) by asking how underperformance is handled without email transparency. Mullenweg educates Stebbings on how Automattic uses P2 as an organizational blockchain while maintaining private performance management. | |
| Balancing Growth, Profitability, and Outside Capital | 4 | 3 | 2 | 5 | Stebbings delivers his strongest pushback, asking if Automattic is under-indexed on risk by using cashflows from profitable assets rather than aggressive growth bets. Mullenweg counters by highlighting their contrarian capital strategy and the scale of WooCommerce. | |
| The Secret to Successful M&A Integration | 2 | 3 | 1 | 2 | Stebbings asks Mullenweg about M&A integration difficulty, delegation, and past mistakes. Mullenweg outlines mental models including reversible versus irreversible decisions and managing benefit ratchets. | |
| Money, De-risking, and Maintaining Zen-Like Calm | 3 | 2 | 0 | 2 | Stebbings asks whether long-term thinking is a luxury granted by personal wealth and cites Tim Ferriss praising Mullenweg's zen-like calm. Mullenweg details the 2008 secondary transaction that allowed him to de-risk personally. | |
| Vulnerability, Body Insecurity, and Subconscious Healing | 3 | 2 | 0 | 1 | Mullenweg opens up about body insecurity from childhood swim meets and T-ball, while Stebbings shares his own history with bulimia to establish a deeply personal peer dialogue. Mullenweg explains using hypnotherapy to uncover subconscious memories. | |
| The Value of Naivety and First Principles Thinking | 2 | 4 | 1 | 2 | Stebbings asks about balancing naivety versus experience in founders. Mullenweg schools Stebbings on first-principles thinking by explaining how Automattic engineered sub-15-second server migrations for WordPress.com. | |
| Does Leadership Get Easier Over Time? | 3 | 3 | 1 | 3 | Stebbings explicitly rejects common wisdom by declaring 'it is bullshit' that leadership does not get easier over time. Mullenweg agrees using Ray Dalio's Principles and discusses executive coaching with Joe Hudson. | |
| Practical Time Management and Productivity Tips | 3 | 3 | 0 | 1 | Stebbings demonstrates deep preparation by referencing Mullenweg's appearance on Tony Conrad's podcast in Antarctica discussing his father's passing. Mullenweg explains pre-grieving and Kübler-Ross's five stages of grief. | |
| Quick-Fire Round: Books, Strengths, and Advice to a Young Self | 1 | 1 | 0 | 0 | A rapid-fire exchange covering favorite books, personal weaknesses, and advice to a 19-year-old self. The tone is casual and agreeable. | |
| Shaq's Superpower and the Future of the Open Web | 1 | 1 | 0 | 0 | Stebbings and Mullenweg reflect on Shaquille O'Neal's superpowers and discuss the future of an open, creative web over the next five years. |
Statements from this episode (25)
Mullenweg: WordPress originated from forking the abandoned b2/cafelog software
“I started using some software called B-II Cafe Log, actually from a developer out of Corsica, France, and you know, started volunteering on the farms, forums, helping other people out, contributing code, and then what happened was that software actually was ab…”
Mullenweg: Early Google survey showed WordPress on 0.8% of websites
“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 they found this weird header in HTTP responses that they were like, we're not sure…”
Mullenweg: Defaulting to trust is worth the occasional 'optimism tax'
“I personally am very default trusting. And that also means that sometimes you pay what I call an optimism tax. 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 ta…”
Automattic uses zero internal email, relying entirely on internal blogging
“We have no email. We communicate via blogging and yeah, it's very global.”
Mullenweg: Automattic has been fully distributed since 2005 across 97 countries
“So we've always been totally distributed from the beginning since 2005. So I have colleagues in 97 countries.”
Matt Mullenweg took over day-to-day CEO duties at Tumblr in February 2022
“In February, I took over as the CEO of Tumblr. I've been running that personally day to day since then.”
Automattic's internal blog acts as an organizational blockchain of decisions
“The system's called P two, the letter P is in pool and then the number two. What's cool about this is it becomes like a organizational blockchain, like a history of basically every decision we've made in the company for the past dozen years or so, including ev…”
Mullenweg: Tumblr was mismanaged by Yahoo, AOL, and Verizon
“It had been mismanaged, I think under Yahoo and AWOL and Verizon, and we felt like we could turn it around.”
Mullenweg: All Automattic business units besides Tumblr are very profitable
“Now, fortunately at our business, all the other businesses are doing very well and very profitable.”
Mullenweg: 60% of Tumblr users are under 25 and majority female
“60% of Tumblr's users are under the age of 25. They're majority female. They're, you know, primarily mobile.”
Automattic ran on $11 million in outside capital from 2005 to 2014
“So between 2005 and I think 2014, all of automatic was done with about eleven million in outside capital.”
Automattic raised $160 million in all-primary capital for Series C in 2014
“We ended up doing our series C, which we raised, you know, we went from eleven million dollars to raising one hundred and sixty million. It was all primary capital.”
Mullenweg: WooCommerce will likely equal all other Automattic businesses combined
“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.”
WooCommerce processed $31 billion in GMV in 2021
“It did thirty one billion and a GMV sold last year.”
Mullenweg: Two-thirds of Tumblr was in a New York office at acquisition
“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 an office in New York.”
Mullenweg: Rotate top existing talent into acquired companies to integrate culture
“So one of the best things we can do when we buy something is take some of the best people at automatic, the best engineers, the best designers, et cetera, and we rotate them in to the acquired business. And that builds a lot of bridges, you know, it's kind of …”
Mullenweg: Open source is the future of humanity
“Open source is the future of humanity and it's important that we create more of it.”
Automattic gives employees up to $250 monthly for coworking spaces
“We do give them an allowance of two, of up to 250 dollars per person per month to go to a coworking space or to go to a coffee shop”
Mullenweg: Employee benefits ratchet; removing unused perks still causes outrage
“Benefits ratchet, meaning that people appreciate when you add them, but they're very unhappy when you remove them, even if it wasn't something they were using.”
Mullenweg: Automattic received a $200M acquisition offer in 2008
“In 2008, the company was only about 20 people, just about two years old, and we got an offer to sell for a two hundred million which, you know, I owned a majority of the company.”
Mullenweg: Automattic investors provided $10M primary and secondary liquidity in 2008
“What the investors did is they said, okay, let's take that two hundred million, make it a new valuation. We'll invest money in that and we'll put, you know, ten million to the company and then we'll allow you and Tony and other employees to like take a little …”
Mullenweg: Automated site migration under 15 seconds drove WordPress.com growth
“And we got it down to where most of them take now under 15 seconds. And that feature's been working really well, and it actually drove, like many years of enhanced growth for WordPress.com.”
Shorts cut from this episode
▶ POV: Turning down $200 MILLION 😲 #shorts · 20VC with Harry (@29:15)
▶ Wartime vs Peacetime CEO · 20VC with Harry Stebbings (@11:01)
▶ Automattic's $250 coworking allowance - Part 2/2 · 20VC with (@28:06)
▶ Automattic's $250 coworking allowance - Part 1/2 · 20VC with (@27:01)
▶ The key to giving NEGATIVE FEEDBACK · 20VC with Harry Stebbi (@6:10)
▶ YOU WON'T BELIEVE this Leadership style! · 20VC with Harry S (@8:59)
▶ CEOs and Founders have insecurities too · 20VC with Harry St (@33:12)