E1016: Substack CEO & Co-Founder Chris Best empowers writers via his email newsletter platform, shares insights on driving change in the attention economy, raising $15M from a16z, providing value to retain talent & more

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"