Not Boring Radio

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 of Positive Sum and Colossus. And there's so much more! She told a story on The Moth! She's written two novels. Everyone is now obsessed with "taste." Her essay, Notes on...

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 title of Mario's epic four-part series on how Peter Thiel turned Founders Fund into one of the world's top venture firms, and its most unique. If you haven't already, do yourself a fav...

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 announced that it's raised $29 million, including a $26.1 million Series A from Josh Kushner at Thrive Capital and Figma CEO Dylan Field at Field Capital. In our conversation, we talk about buildi...

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. Sari is one of the most thoughtful and tasteful people on the world wide web, something that comes across in her writing, in the product she's building at Sublime, and even her background in thi...

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 place, you have Cate to thank. Her 2024 essay, How to be More Agentic took the internet by storm and brought agency into the zeitgeist, where it has remained and grown. Now, she's ev...

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 was the absolute right way to do things — and growing insanely fast while maintaining its high quality bar. I started doing these Deeper Dives, following up on companies I’d written Deep Dives on in the...

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 discuss his latest piece, A tale of two Vaticans (or, OpenAI building an unholy spirit) , which you should read before listening, or after. No one but Reggie could have written this piece, which is...

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, because this is why I do Hyperlegible, but Mike is one of the best writers doing it today, one of the few whose name in my inbox gives me a little dopamine hit. His writing is unlike anything out there....

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 fan of Brian's writing. I use it as a reference for a lot of my pieces. I once tweeted, "Construction Physics is a national treasure and the president should give Brian Potter a medal or c...

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 industrial platform over decades. Read it here for the full experience: Forsaking Industrialism Conrad has been planning this essay for months, and he couldn't have dropped it at a better time. It&#3...

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 feed and half of my Substack Notes feed sharing her essay, including a bunch of people I wouldn't expect to share an essay with "Monkey Titty" in the title. I read it immediatel...

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 this conversation, we talk about his new essay, which is an update to some of his older pieces, Scarcity and Abundance in 2025 . If you want to understand how to think about everything that’s going o...

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 interact with computers. Julian explains why conversational AI should complement rather than replace graphical user interfaces, and shares insights about his unique writing process. Julian is one of the...

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 likes at the time of recording.  For good reason: Utsav combines philosophy, mathematics, biographies, personal experience, and hand-drawn sketches to create a map – quite literally – for living an in...

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 and on which she’s dropped gems each week since. Last week, Tina wrote an essay called Jevons Paradox: A personal perspective about something surprising she’s noticed: AI is causing a lot of people to wo...

In April 2022, Packy wrote a Deep Dive on Primer: https://www.notboring.co/p/primer-the-ambitious-home-for-ambitious Three years later, a lot has changed. Primer is building schools. The opportunity is both bigger and more challenging than it was then. In this conversation, Packy and Primer CEO Ryan Delk discuss the need to fix in K-12 education. Ryan shares insights on Primer's transition fro...