Packy McCormick has built a one-of-a-kind career around curiosity. As the writer behind Not Boring and GP of Not Boring Capital, he’s turned a side project newsletter into a thriving ecosystem that bridges media and venture. In this episode, Packy and Chrissie talk about burning the boats to bet on yourself, how deep research and writing became his superpower, and why the Internet still rewards people who do truly original work.Packy shares the evolution from banker to startup operator to full-time creator, the flywheel between his writing and investing, and what he sees coming next for independent builders in the “great online game.”

Check out Not Boring: www.notboring.co(00:01:18) Thriving Tech Investment Newsletter from Startup Background(00:06:12) Not Boring: From Niche Club to Media Platform(00:08:19) Transitioning to Sponsorship Model in Media(00:18:14) Writing-driven Investment Strategy Synergy(00:21:43) Strategic Writing Shapes Investment Portfolio Over Time(00:25:02) Deep Dive Writing Process with ChatGPT(00:30:03) Navigating Writing Challenges with Generative AI(00:42:34) Value-driven Innovation: Future of Online CreatorsSelf Funded Links:

Substack: https://selffundedbychrissie.substack.com/

Apple: https://podcasts.apple.com/us/podcast/self-funded/id1845157459

Spotify: https://open.spotify.com/show/5u4zA43k4hC183fM0PisKq?si=26bf586458934e49YouTube: https://www.youtube.com/@selffundedpod

The Long Game:

I help growth-stage companies close the gap between strategy and execution for growth or exit through The Long Game. Learn more at longgametalent.com.

My Self Funded Tech Stack:

These are some of my favorite tools I use everyday in my business and podcast (affiliate links):

Collective: Powers my S-Corp from bookkeeping to paying contractors to tax prep. https://share.collective.com/mQHI7Bf

Flodesk: The easiest email platform with clean, easy-to-customize designs and a simple workflow interface: https://flodesk.com/c/19VL1X

Granola: I’ve tried several AI notetakers and this is my favorite. I take my own notes in the interface which are the enhanced after the call: https://go.granola.ai/chrissie-francona

Airtable: I’ve built my business operating system in Airtable, including my CRM, content management tool, and to-do list: https://airtable.com/invite/r/uq7tgTC3