Today I walked with Packy McCormick (@packyM), founder of Not Boring (@notboringco) and Not Boring Capital. Packy built Not Boring into a top newsletter on Substack (@Substack), spent years in finance before leaving to write full-time, and now invests in the same kinds of companies he writes about through Not Boring Capital. He gets into the moment his growth flatlined during the 2022 market crash and what it freed him to do, and why he considers Not Boring's founding mission basically complete. We get into: - Why he passed on investing in the friend who now runs a robotics company valued at $1 billion - The real "nobody gives a s***" moment that came after Not Boring's meteoric growth crashed in 2022 - The clay pot experiment behind why he still writes 30 imperfect essays a year instead of a few polished ones - Why he thinks Anthropic's (@AnthropicAI) careful, downside-focused posture on AI is a little too pessimistic - Why he doubles down on his strengths instead of trying to fix a below-average memory So much more! TIMESTAMPS (00:00) Packy McCormick, Founder, Not Boring & Not Boring Capital (01:02) Weekly business coaching calls with his mom (06:15) Passing on the friend who built a $1 billion robotics company (20:19) The moment nobody gave a s*** anymore (31:02) Being scared of infinity as a kid (34:50) Why Anthropic's pessimism wears him out (36:19) Retiring Not Boring's founding mission (41:09) Telling his pregnant wife he was starting over (45:27) The clay pot experiment behind his writing process (56:00) Double down on strengths, not weaknesses (58:52) What made Colossus's writer profiles so good (1:03:18) $470 million for micro nuclear reactors (1:04:19) The GLP-1 side effect nobody saw coming (1:07:58) What brought him joy this week