Packy McCormick, Not Boring

How writing led to investing in Ramp, Scale AI, Replit, Varda, Fuse, Hadrian, Earth AI

The ‘Not Boring’ Empire

I’m absolutely thrilled to share our conversation with Packy McCormick, Founder of Not Boring and Not Boring Capital. Packy is a prolific writer (scaling his newsletter to 239,000+ subscribers) turned investor (into some of the best Silicon Valley companies), and also just someone I totally admire for his intellectual curiosity and hardcore writing (Packy just completed a 100 page piece! on Meter).

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We cover a wide range of topics, including McCormick's journey from writer to venture capitalist, his unique 'Not Boring' idea maze creative process, ‘Vertical Integrator” investment thesis, why asking ‘great’ questions is super important, and his perspective on what key founder characteristics matter most.

Vertical Integrators: “We did atoms development for all of human history, and then 50 years of software development, and then caught up, and I think that’s amazing.. Now software is pulling ahead a little bit so we’re trying to combine hardware and software, bits and atoms, and build all new infrastructure for the country and the world. And that to me is very exciting.”

We also dive into Packy’s investment philosophy, his approach to following instincts versus over-intellectualizing VC decisions, his best investments in companies like Ramp, Scale AI, Replit, Base, Fuse, Varda, and Hadrian, as well as the dislocation in late-stage funding for hardtech companies.

(*Packy shares the BTS on Ramp’s viral Saquon Barkley Super Bowl ad*)

Last but not least, we get into some spicy topics, like why American Dynamism won, critical takes on Y Combinator's RFS (request-for-startups), what we can learn from DOGE recruiting, and the current hype state of AI (Stargate, DeepSeek, OpenAI).

“There hasn’t been any [AI] leap that I’ve seen that I’m like, yeah, that thing is alive.. I feel like I’m being psyop’d”

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Timestamps

1:30 - Growing to 239k+ Subscribers

5:00 - How Writing Led to Managing a VC Fund

8:00 - The 'Not Boring' Creative Process

13:50 - Top Founder Characteristics

16:00 - Following Instincts vs Over-Intellectualization of VC

22:00 - Packy’s Best Investments (Ramp, Scale AI, Replit, Chroma, Varda, Hadrian, Pipedream)

25:55 - Intro to Vertical Integrators (Base, Fuse, Varda, Hadrian)

38:00 - Why American Dynamism Won

42:45 - YC RFS Hot Take

46:00 - Can Heavy CapX Companies Raise Growth Funding?

49:15 - Packy’s Hot Take On AI - Is It Alive? Just A Marketing Stunt?! DOGE Recruiting?

1:00:00 - What Packy Is Most Excited About in 2025

Read more on Not Boring, Not Boring Capital, & Packy’s Podcasts below

Not Boring

Written by Packy McCormick, the Not Boring newsletter sends in-depth analyses of the tech and startup landscape to over 239k subscribers every week. Telling the stories of the most ambitious and complex startups as clearly as possible to give readers a glimpse into the future they’re working to build. Diving into technology, business models, and markets.

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Not Boring Capital

Not Boring Capital, has invested in and written about companies like Ramp, Replit, Hadrian, Primer, Capital, Composer, Braintrust, NexHealth, Fount, ScienceIO, Unit, Scale, Varda, Earth AI, Fuse Energy, Base Power Company, Cuby +more