The Idea
In January 2003, a 19-year-old Houston student called Matt Mullenweg wrote a short, slightly panicked post on his blog. The software he used to publish it, an obscure tool called b2/cafelog, had stopped being updated. Its developer had vanished. Mullenweg wondered aloud in that post whether he should just fork the code himself, since it was GPL licensed and nobody could stop him.
It got one reply. A programmer in Stockport named Mike Little said that if Mullenweg was serious about forking it, he would help. Two strangers on opposite sides of the Atlantic started patching a dead blogging script. They called it WordPress.
By 2004 it was spreading fast among developers and was useless to everyone else. You needed a server, a database and the patience to configure both. That year Mullenweg left Houston for a job at CNET in San Francisco, and an Irish developer, Donncha Ó Caoimh, merged his own fork into the codebase. They wanted the same thing: a version of WordPress anybody could start in a minute.
On 20 June 2005, Mullenweg, then 21, made Ó Caoimh his first hire. This was the beginning of Automattic.
The Execution
- June 2005: Automattic began as one founder and one employee, with the deliberately awkward business model of giving away all the core IP and selling services on top. Akismet, the anti-spam tool, shipped in October. WordPress.com followed in November, hitting 100 blogs and then 1,000 within weeks, and Mullenweg quit CNET to work on it full time.
- Summer 2006: Roughly ten people gathered in San Francisco for the first Grand Meetup, an event whose main incidents were Mullenweg doing the airport runs himself and everyone living through a small earthquake. There was no office then and there is none now. The first Automatticians, Andy Skelton, Ryan Boren and Mark Riley, all worked remotely, and Toni Schneider joined as the company's first CEO.
- April 2006: The company raised a $1.1m Series A from Polaris Ventures, Blacksmith Capital, Radar Partners and CNET. Mullenweg later wrote that they barely touched it, because revenue grew quickly enough to keep 18 full-time staff at break-even.
- January 2008: A $29.5m Series B brought in the New York Times alongside the existing backers. Internally, email was pushed aside in favour of P2, the company's own blogging tool, so decisions stayed visible. Gravatar had been acquired the year before.
- May 2014: A $160m Series C led by Insight at a $1.16bn valuation, nine years in and only the third real raise. In 2015 Automattic bought WooCommerce for around $30m in cash and stock.
- August 2019: It bought Tumblr from Verizon for less than $3m, six years after Yahoo paid $1.1bn, taking on the entire 200-strong workforce at a post-close cost of roughly 20x the purchase price. A month later Salesforce Ventures put in $300m at a $3bn valuation as sole investor.
- February 2021: A $288m round with BlackRock, Wellington and Alta Park, plus a $250m buyback for current and former employees at a $7.5bn valuation.
- October 2024: After Mullenweg publicly attacked hosting rival WP Engine and cut off its access to WordPress.org, he offered anyone who disagreed with him a way out. 159 people, 8.4% of the company, took $30,000 or six months of salary and left. The following April, Automattic cut 16% of staff, around 280 jobs across 90 countries.
- Today: Twenty-one years on from a fork nobody asked for, WordPress powers over 43% of the web, and the WP Engine case is set for jury trial in September 2027.
The lesson?
Automattic started because a teenager wrote a post admitting he had no idea what to do, and one person answered it. No pitch deck, no market analysis, no co-founder search. The commercial decision that followed looked insane at the time: give away every line of the core product, then sell hosting on top of software your competitors get free. It kept the company break-even at 18 staff with $1.1m in the bank, and it is why WordPress ended up on nearly half the internet rather than in a licensing war it would have lost. Open the door wide enough and the whole web walks through it.