Recorded talk — WordPress.tv

a WordCamp Detroit 2011 talk arguing that bloggers, designers, and developers can build a working career around supporting open-source WordPress development. This is the earliest publicly archived version of a thesis the speaker has now revisited four times across twelve years — see the related talks below for the through-line.

Where and when

Illustration supporting key points in How to Make a Living, Giving It away for Free
a quick visual summary to make the concept easier to understand at a glance.

Watch the talk

One archived viewer comment on the original WordPress.tv page: “This was so inspiring. Shared on twitter and facebook.”

The premise

From the published WordCamp Detroit 2011 schedule:

“a look at how to make a living working with a free product like WordPress. The presentation looks at how bloggers, designers and developers can build authority, revenue and opportunities by supporting open source development.”

What the slides covered

The slide deck for this talk is published on SpeakerDeck under the title “How to Make Money with WordPress” — 40 slides, posted October 1, 2011 (one month before the talk). The deck organizes the argument around five primary income strategies available to WordPress professionals:

  1. Full-time employment as a WordPress developer
  2. Consulting work — both project-based and maintenance-based
  3. Publishing expertise through tutorials and content
  4. Selling solutions (themes and shipped)
  5. Content monetization — including site advertising and working directly for automattic

Two anchor lines from the deck are worth quoting verbatim:

“Free is not a business model.”

and, citing Matt Mullenweg as a then-current data point:

“20,000 people make a living from WordPress.”

Matt Mullenweg, cited in the deck

The deck also flagged the contemporary scale of the platform — that “approximately 19% of alexa’s top 100,000 sites are on WordPress” — as the size-of-market case for the thesis. (alexa is gone; the underlying point about WordPress market share has only grown since.)

What I’d say differently today (15-year reflection)

Retrospective interpretation. The recording and slide deck above are the authoritative record of what was actually argued in 2011. The reflection below is a long-view reading of the thesis from 2026, anchored to three time horizons.

2011 assumptions

The 2011 talk rested on a small set of assumptions about the WordPress ecosystem: that GPL-licensed shipped would remain the cultural default; that the WordPress.org repository would stay open and discoverable; that personal reputation built in the community would translate into paid consulting work; and that “free + supported + plainly documented” would compound faster than walled-garden alternatives. None of those were obviously true at the time. The contrarian move was committing to all four anyway.

Midpoint reality (≈2018–2020)

By the late 2010s the assumptions had aged well. WordPress crossed thirty percent of the web. The plugin economy matured into a viable career path for thousands of developers. Freemium and SaaS models entered the ecosystem aggressively, but the GPL-licensed core remained the gravitational centre. The 2011 thesis turned out to be load-bearing: the people who shipped free, useful work in the early 2010s were largely the same people running independent consulting practices a decade later. The bet on community as a career strategy paid off — not through a single practical improvement but through compounding small returns on every contribution.

2026 perspective

Fifteen years on, WordPress runs roughly 43% of the web, the block editor and full-site editing have reshaped the development model, and aI agents have entered the tooling layer in ways the 2011 talk could not have anticipated. What stayed constant is more interesting than what changed. Plain-language documentation still wins. Free, supported, GPL-licensed work still compounds. Community participation as a career strategy still works — arguably more reliably than any paid acquisition channel a small consultancy can afford. The specific monetization tactics in the 2011 deck have aged unevenly (some affiliate references are dated; ad networks shifted), but the underlying claim — generosity as the long-game positioning play — held up.

What the 2011 talk could not have predicted: full-site editing, the WordPress.org governance debates of the 2020s, aI commoditizing the marginal cost of how-to content, the rise of headless and decoupled architectures. None of those broke the thesis. Each just changed the surface area on which it operates.

Next step

What happens next

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