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.

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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

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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?

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