1:00 Jason intros Chris Best

3:24 What happened to Kik? (Chris' first startup) What did he learn from it?

5:03 What is it about email newsletters that attracted Chris?

9:41 Chris explains the AI alignment problem and how it relates to content consumption

13:58 What bad behaviors have Google & Facebook's ad algorithms created? How is Chris working to fix them?

18:09 Gamification's impact on startups

23:02 What types of writers are best suited for Substack?

29:25 How did Chris secure a $15M Series A from a16z with only 3 FTEs? Plus explaining the benefits of being "default-alive"

34:33 Are we approaching a flipping of the attention economy?

43:20 How does Substack make money?

49:46 Benefits of writer collaboration & cross-promotion

50:57 How the Deadspin situation relates to Substack

56:01 Most interesting newsletter content so far?

58:19 Dealing with offensive speech & explicit content

1:05:32 When will major publications start losing writers to Substack?

1:10:00 Plans to add audio or video?

1:11:34 What are the top-performing newsletters and what are the price ranges?

1:17:29 Ad-model vs. Paid-model at Inside & Substack

1:30:16 Chris explains the Substack fellowship

1:32:23 Thoughts on "hustle culture"