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S1E13 Brie Wolfson: Learning to Love Flounder Mode from Kevin Kelly (Hyperlegible 013)
How do I introduce Brie Wolfson? Brie's website – briewolfson.com – is a good place to start. It's a treasure trove. She launched Stripe Press. She started The Kool-Aid Factory. Today, she's the CMO…
S1E12 Mario Gabriele: The Gospel of Peter Thiel and Founders Fund (Hyperlegible 012)
There is no venture capital firm like Founders Fund, and there is no writer who tells venture capital firms' stories like Mario Gabriele. In their respective crafts, both have No Rivals. That is the…
S1E3 American Dynamism Meets the American Dream with Ambrook CEO Mackenzie Burnett
Mackenzie Burnett is the co-founder and CEO of Ambrook, an all-in-one bookkeeping, invoicing and payment tools that help family‑run businesses improve margins and stay independent.This week, Abrook…
S1E11 Becoming unLLMable with Sari Azout (Hyperlegible 011)
Sari Azout is a former VC, the founder of Sublime, a friend, and a writer whose work I've long admired. We actually co-wrote the first piece I ever wrote on crypto about a company called Fairmint.…
S1E10 Crossing the Cringe Minefield with Cate Hall (Hyperlegible 010)
Cate Hall is the CEO of Astera, one of my favorite organizations and the new home of my friend Eli Dourado, and one hell of a writer.If you've noticed the word "agency" popping up all over the…
S1E2 How Wander Went Asset-Light and 100x'ed its Locations: A Deeper Dive with John Andrew Entwistle
Wander raised $50+ million in a Series B led QED and Fifth Wall. The fun part is, Wander did it by throwing out a lot of what we discussed in the first Wander Deep Dive — which, at the time, I said…
S1E9 A Tale of Two Vaticans (OpenAI & the American Pope) with Reggie James
Reggie James is a founder, the author of the Product Lost substack, one of the most original thinkers I know, and one of my top choices to be the Creative Director of America.In this conversation, we…
S1E8 Golden Age with Mike Solana (Hyperlegible 008)
Mike Solana is the founder and Editor-in-Chief of Pirate Wires, one of my favorite publications on the whole internet and the only one I read every day. You’ll hear this about a lot of our guests,…
S1E7 50 Things I've Learned Writing Construction Physics with Brian Potter (Hyperlegible 007)
Nobody on the internet writes about all of the complexity involved in actually building things -- from homes to jet engines -- better than Brian Potter, the author of Construction Physics.I am a huge…
S1E6 Forsaking Industrialism with Conrad Bastable (Hyperlegible 006)
In this timely conversation, Conrad Bastable joins Packy to break down his epic essay Forsaking Industrialism and explore why the West has abandoned manufacturing while China built a world-beating…
S1E5 Skittle Factory Dementia Monkey Titty Monetization with Parakeet (Hyperlegible
Pseudonymous writer Parakeet joins me to discuss her viral essay "Skittle Factory Dementia Monkey Titty Monetization." I first heard about Parakeet a couple weeks ago when I saw half of my Twitter…
S1E4 Hyperlegible 004: Alex Danco, Scarcity and Abundance in 2025
On Episode 004 of Hyperlegible, I speak with Alex Danco. It was a treat. Alex is on my Mount Rushmore of internet writers. When I’m writing well, his writing has probably had an influence on mine. In…
S1E3 Julian Lehr, The Case Against Conversational Interfaces
In Episode 003 of Hyperlegible, host Packy McCormick talks with Julian Lehr about his recent essay The Case Against Conversational Interfaces and why natural language might not be the ideal way to…
S1E2 Hyperlegible 002: Utsav Mamoria, How to live an intellectually rich life
Utsav Mamoria recently wrote How to Live an Intellectually Rich Life on his Substack, Tumse Na Ho Paayega. It blew up, breaking out of containment in India and spanning the globe to the tune of 1,100…
S1E1 Hyperlegible 001: Tina He, Jevons Paradox: A personal perspective
For the first episode of Hyperlegible, I talked to my friend Tina He (@fkpxls on twitter) who writes the excellent Fakepixels, which she recently brought back to life after a four year hibernation…
S1E1 Ryan Delk: To Fix the School System, Build Schools
In April 2022, Packy wrote a Deep Dive on Primer:https://www.notboring.co/p/primer-the-ambitious-home-for-ambitiousThree years later, a lot has changed. Primer is building schools. The opportunity is…
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Not Boring Radio has published 16 episodes since March 2025, covering topics in Technology.
Not Boring Radio is currently dormant with new episodes every 2 weeks. Average episode length is 55m.
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