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Tim Urban: How "Wait But Why" Grew to 600k Readers; AI's Revolutionary Impact on Media | E1048

Tim Urban is the writer/illustrator and co-founder of Wait But Why, a long-form, stick-figure-illustrated website with over 600,000 subscribers and a monthly average of half a million visitors. He has produced dozens of viral articles on a wide range of topics, from artificial intelligence to social anxiety to humans becoming a multi-planetary species. Tim’s 2016 TED main stage talk is the third most-watched TED talk in history with 66 million views. In 2023, Tim published his bestselling book What’s Our Problem? A Self Help Book for Societies. Huge thanks to Tobi @ Shopify for the intro today. ------------------------------------- Timestamps: (0:00) Intro (0:49) Tim Urban’s Early Life (5:20) Making Money from "Wait But Why" (11:27) Tim Urban Considers Being a Venture Capitalist (17:03) Tim Urban’s Selection & Research Process (29:55) Analyzing Content Performance (36:26) Tim Urban’s Writing Process (41:54) How to Grow Your Social Media Following (47:15) How to Build Your Brand (50:31) How to Motivate Yourself (53:54) How to Handle the Critics (58:16) AI Will Shake Our Civilization (1:06:14) Are you optimistic about the future? (1:09:00) Quick-Fire Round ------------------------------------- In Today’s Episode with Tim Urban We Discuss: 1. The Founding of Wait by Why: What was the a-ha moment for Tim that Wait but Why should be his life’s work and sole focus? What does Tim know now that he wishes he had known when he started? What does Tim believe he is running away from? Why is he so fearful of constraints? 2. Wait But Why: The Scaling Journey to 600,000 Subs: What was the first piece to really go viral? How did that change the trajectory? What single piece is Tim most proud of? What piece is he least proud of? What has been the hardest element of scaling Wait But Why? What was the most surprising and unexpected elements of Wait But Why’s scaling? 3. Topic Selection: Choosing What To Write: What does the process look like for Tim when deciding what topic to write about? How does Tim know what his audience will want to hear about vs what they will not? What topics has Tim thought would be interesting but post initial research, are not? 4. The Writing Process: How does Tim approach the writing process? How has his changed over time? What mechanisms does Tim put in place to avoid writers block? What are some of Tim’s biggest tips to aspiring writers and authors? 5. The Distribution Process: How does Tim approach distributing the content once produced? What works? What does not? Why did Tim choose newsletter, Twitter and Instagram as his channels of choice? How important has the newsletter been to the growth of the business? 6. AI: Super-Intelligence and The Future: On reviewing his pieces on AI back in 2015, what does he believe he got right? What would he change with the benefit of hindsight? Is Tim more or less positive looking forward at AI proliferating through all of society? What is Tim most concerned about in the world right now? ------------------------------------- Subscribe on Spotify: https://open.spotify.com/show/3j2KMcZTtgTNBKwtZBMHvl?si=85bc9196860e4466 Subscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast/the-twenty-minute-vc-20vc-venture-capital-startup/id958230465 Follow Harry Stebbings on Twitter: https://twitter.com/HarryStebbings Follow Tim Urban on Twitter: https://twitter.com/waitbutwhy Follow 20VC on Instagram: https://www.instagram.com/20vc_reels Follow 20VC on TikTok: https://www.tiktok.com/@20vc_tok Visit our Website: https://www.20vc.com Subscribe to our Newsletter: https://www.thetwentyminutevc.com/contact ------------------------------------- #TimUrban #WaitButWhy #HarryStebbings

Tim UrbanguestHarry Stebbingshost
Aug 13, 20231h 15mWatch on YouTube ↗

At a glance

WHAT IT’S REALLY ABOUT

Tim Urban on Curiosity, Creative Freedom, AI, and Media’s Future

  1. Tim Urban discusses how he built Wait But Why into a large, loyal audience by obsessing over deep research, clear explanations, and protecting his creative freedom from traditional business pressures.
  2. He breaks down his topic selection, research, and writing processes, emphasizing excitement-driven curiosity, intuitive metaphors, and aiming for a 'sweet spot' of depth that delights smart general readers.
  3. Urban and Stebbings examine trade-offs between growth and autonomy: monetization choices, not scaling a big team, resisting side ventures like VC funds, and using lightweight systems to manage his own procrastination.
  4. They close by exploring AI’s impact on civilization and media, with Urban arguing AI will both solve huge problems and destabilize shared reality, making trusted brands and verification more critical than ever.

IDEAS WORTH REMEMBERING

5 ideas

Build your career around genuine curiosity, not just market demand.

Urban only writes on topics that feel 'delicious' to him—things he’d research for fun anyway—which sustains multi-week deep dives and leads to uniquely engaging explanations.

Aim for the “sweet spot” of depth: from 2–3 to a 6 out of 10.

He deliberately avoids both shallow overviews and hyper-technical detail, targeting a level where a reasonably smart layperson keeps getting 'dopamine hits' of insight without being lost.

Use systems and external pressure to beat procrastination.

Urban sets modest daily quotas (e.g., 800 words), lets friends see his live progress, and creates penalties for missing targets—preferring consistent '4/10' days over sporadic zeroes and heroic sprints.

Monetize in ways that don’t corrupt the core creative mission.

He rejected intrusive ads in favor of Patreon, merch, speaking, and books, and has avoided building a big team or a VC fund because he doesn’t want schedule obligations to crowd out deep work.

Exploit one strong format, then repurpose across platforms.

Rather than chasing every channel natively, he focuses on A+ blog posts and books, then extracts drawings, quotes, and ideas into tweets, Instagram posts, and other formats as efficient distribution.

WORDS WORTH SAVING

5 quotes

I just want total freedom. If I have anything on my schedule at 5 p.m., I’m in a bad mood the whole day.

— Tim Urban

My job is to get from a two or three to a six on a topic, then explain it so readers get a dopamine hit every minute.

— Tim Urban

I don’t want to turn around in ten years and realize the business got big but I lost what I cared about.

— Tim Urban

If you’re doing something with a strong point of view, especially on politics, it will piss people off. That’s inevitable.

— Tim Urban

AI is like a spaceship of super-intelligent aliens coming toward us. They’ll solve our problems, but we don’t know what their deal is.

— Tim Urban

Tim Urban’s personal journey and desire for extreme autonomy in workCreation, growth, and monetization strategy of Wait But WhyTopic selection, research methodology, and writing workflowManaging procrastination, snags, and productivity as a creatorTension between virality, audience data, and intrinsic curiosityHandling criticism, politics writing, and audience pushbackAI’s transformative risks and opportunities for civilization and media

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