How Blogging Made This Investor a Deca-Millionaire — Chris Dixon

How I Write 1h27 5 min #25
How Blogging Made This Investor a Deca-Millionaire — Chris Dixon
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Summary

  • Chris Dixon is a venture capitalist and author of Read Write Own who built his career through blogging—writing roughly 500 posts over several years—and argues that long-form writing is an underused strategy for establishing intellectual credibility and advancing a career in tech. He traces his path from philosophy student to internet entrepreneur to investor, crediting blogging with transforming him from an unknown New York startup founder into a recognized voice in Silicon Valley.

How blogging built his career

  • Dixon started blogging around 2008–2010, initially with no audience, motivated purely by enjoyment and a desire to synthesize one interesting idea per week into a short post—typically around four paragraphs, which he found was the optimal length for engagement.
  • His breakthrough came when prominent VC Fred Wilson linked to one of his posts, driving traffic and creating a comment community; from there, blogging became his primary vehicle for career advancement.
  • He emphasizes authenticity: writing only about ideas genuinely sparked by real conversations during the week, not manufactured cleverness. Memorable phrases like “come for the tool, stay for the network” emerged organically from meetings and intellectual sparring, not from sitting down to coin slogans.
  • He wrote roughly 500 blog posts over about four years, of which only around 10 went viral—but those 10 defined his public reputation, illustrating a self-regulating quality of blogging where weak posts simply get ignored.

Why long-form writing still matters

  • Dixon argues that social media (Twitter, TikTok) has lulled people into thinking short-form content is sufficient, but complex ideas genuinely cannot be communicated well in a few sentences.
  • He sees a surprisingly underused “hack” in tech: someone early in their career who writes a series of thoughtful blog posts on a topic like AI can become a recognized thinker in that area within months—something that doesn’t happen through tweets alone.
  • He acknowledges social media’s positive role in democratizing publishing and helping creators find initial audiences, but believes the ease of short-form platforms has crowded out the deeper career and intellectual benefits of sustained writing.

Writing philosophy: simplicity, clarity, and voice

  • Dixon’s style is heavily influenced by his study of analytic philosophy at Columbia, where he learned to value economy, simplicity, and jargon-free expression—the best philosophy, he says, is just one new idea, clearly stated.
  • He also draws on engineering principles: modularity (his book is structured in 3–4 page sections that can stand alone), directness, and economy of expression.
  • A key insight from his experience: most people can recognize good writing in others long before they can produce it themselves. For years, his editorial ear was far ahead of his actual writing ability—he could sense something was “off” in his prose but couldn’t diagnose it. Writing the book closed that gap through sheer repetition and practice.
  • He advises writers to “write like you talk”—to capture the best version of their natural speaking voice rather than adopting a formal, artificial tone.

The book-writing process

  • Dixon spent roughly 12 months actively writing Read Write Own, working in focused morning sessions and using exercise time to mentally simplify concepts.
  • His first draft was completed in a month or two but was too abstract, too passive-voice-heavy, and relied on “crutch words” (adjectives and adverbs like “genuine,” “strong,” “very”) that papered over insufficient explanation.
  • He shared drafts with about 20 readers—technologists, general readers, and lawyers—who gave paragraph-level feedback via Google Docs. He then did a major rewrite removing crutch words, converting passive voice to active (which required researching who actually did what), and steel-manning counterarguments rather than dismissing them.
  • After incorporating feedback, he discovered the structure was ruined—layering comments had made it incoherent. He spent four more months refactoring the entire structure, which he describes as the hardest part: tracking what the reader knows at each point in a 200-page argument.
  • He hired an outside fact-checker (War Fox) who caught date and attribution errors and found useful historical quotes, including a reference to the original “Read Write Web” manifesto that validated his naming framework.
  • His North Star throughout was the reader: every choice—titles, charts, section breaks, word choice—was evaluated for simplicity and clarity. He avoided jargon and defined the few technical terms he used.

Structure and analogies

  • The book is organized into short, titled sections (2–4 pages each) rather than long chapters, making it modular and skimmable.
  • He relies heavily on analogies to make abstract concepts concrete: “software is Lego bricks” for composability; “don’t be evil” (Google’s motto) versus “can’t be evil” (blockchains encode rules in verifiable code so trust isn’t required).
  • He debated the title extensively—others suggested “blockchains” or “Web3”—but he insisted on Read Write Own because it captures the three eras of the internet (read-only, read-write, ownership) and signals accessibility through simple words.

Business models for writers and the “death of the middle”

  • Dixon wrote a book partly because books still carry cultural gravitas that blog posts don’t—they get reviewed, appear on shows, and function as “meme delivery vehicles” that can become “Canon events” in people’s lives.
  • He is critical of the “1000 True Fans” thesis (Kevin Kelly’s influential essay): the promise that the internet would let creators go direct and serve niches profitably has been hijacked by big tech platforms that reinserted themselves as intermediaries, taking 100% of ad revenue on Facebook, for example.
  • This has produced a “death of the middle” pattern: the extremes thrive (massive scale like Amazon/Walmart or ultra-premium boutiques like Gucci; in media, blockbuster books and viral TikToks) while the middle—magazines, mid-length writing, independent bloggers—has been hollowed out.
  • He expects AI to accelerate this pattern, killing the middle of writing: high-end human writing will survive because people value human connection, status, and community (just as chess is more popular than ever despite AI being stronger), but mid-tier writing will be commoditized.

How creators should think about the future

  • Dixon advises creators to focus on two things AI cannot replicate: (1) a genuine insight that AI would disagree with (using AI as a “consensus calibration mechanism”), and (2) deep firsthand knowledge expressed through personal stories and authentic voice.
  • He sees a future where AI acts as a co-pilot—helping with tactical editing, recalling notes, tracking whether a concept has already been explained—while the human provides voice, judgment, and humanity.
  • He is personally experimenting with rules to counteract social media’s “recency bias” (algorithms favoring new, sensational content): he reads 50 pages of a book every day, treating books as “protein for the mind” and social media as “sugar.”

The core problem he wants to solve

  • Dixon’s broader mission is to close the gap between domain experts who have valuable knowledge and the public who could benefit from it. He calls this helping people identify and share their “core idea”—the one counterintuitive, earned truth they know from decades of experience.
  • He believes the internet’s current architecture—dominated by algorithmic feeds optimized for engagement and recency—actively works against this, making a great piece of writing visible for only 48 hours when it deserves to be found and read for years.
  • He envisions protocol-based networks (like the web itself, which doesn’t have the same recency bias as Twitter) where great work persists and is consistently discoverable, enabling millions of profitable niches and a richer intellectual culture.
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