Substack's Strategic Investment

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"