Not Boring Radio

About Not Boring Radio

For the smart, curious listener. Shows: Age of Miracles Hyperlegible Not Boring Founders Deeper Dives Anton Teaches Packy AI

Publisher

Packy McCormick

Category

technology

Language

en

Explicit

Yes

First episode

5 Mar 2025

Latest episode

30 Jul 2026

Latest episodes

17 of 17 episodes have a transcript.

1. 

   30 Jul 2026TRANSCRIPT

   A Conversation with GC CEO Hemant Taneja

   Host [Host Name] interviews GC CEO Hemant Taneja about how AI redefines scale and necessitates new venture capital strategies for ambitious companies.

2. 

   17 Jul 2025TRANSCRIPT

   Brie Wolfson: Learning to Love Flounder Mode from Kevin Kelly (Hyperlegible 013)

   Brie Wolfson discusses Kevin Kelly's concept of "Flounder Mode" and how it encourages individuals to build careers by following their curiosity, as she describes in her essay, in this interview.

3. 

   8 Jul 2025TRANSCRIPT

   Mario Gabriele: The Gospel of Peter Thiel and Founders Fund (Hyperlegible 012)

   Writer Mario Gabriele discusses Peter Thiel's influence on Founders Fund, exploring its origins, investment strategies, and unique principles in this interview episode.

4. 

   3 Jul 2025TRANSCRIPT

   American Dynamism Meets the American Dream with Ambrook CEO Mackenzie Burnett

   Ambrook CEO Mackenzie Burnett discusses building a business at the intersection of American Dynamism and the American Dream, farm economics, and company growth in an interview with Not Boring Radio.

5. 

   18 Jun 2025TRANSCRIPT

   Becoming unLLMable with Sari Azout (Hyperlegible 011)

   Sari Azout, founder of Sublime, discusses becoming "unLLMable" in the age of AI, emphasizing the need to surpass average to stand out, in an interview with Not Boring Radio.

6. 

   2 Jun 2025TRANSCRIPT

   Crossing the Cringe Minefield with Cate Hall (Hyperlegible 010)

   Host Dan Shipper interviews Cate Hall, CEO of Astera, about her essay "Crossing the Cringe Minefield," which explores how facing uncomfortable feelings leads to personal growth and reveals areas for improvement.

7. 

   28 May 2025TRANSCRIPT

   How Wander Went Asset-Light and 100x'ed its Locations: A Deeper Dive with John Andrew Entwistle

   Wander CEO John Andrew Entwistle discusses the company's strategic shift to an asset-light model, which enabled them to scale rapidly and maintain high customer satisfaction, in an interview with Not Boring Radio.

8. 

   23 May 2025TRANSCRIPT

   A Tale of Two Vaticans (OpenAI & the American Pope) with Reggie James

   Reggie James, founder and author, analyzes OpenAI's structure in comparison to the Catholic Church and discusses the search for meaning in modern times in an interview with host, exploring Silicon Valley's history.

9. 

   1 May 2025TRANSCRIPT

   Golden Age with Mike Solana (Hyperlegible 008)

   Mike Solana, founder of Pirate Wires, discusses Walt Disney's futuristic city vision and China's ability to execute it, exploring the potential for a modern "Golden City" in this interview.

10. 

    27 Apr 2025TRANSCRIPT

    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 (https://x.com/_brianpotter), the author of Construction Physics (https://www.construction-physics.com/). 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 czar job or something." So I was thrilled to get the excuse to talk to him about a bunch of his essays by talking to him about this one specific one, 50 Things I've Learned Writing Construction Physics (https://www.construction-physics.com/p/50-things-ive-learned-writing-construction). Here's the one overarching theme he's discovered writing over 600,000 words in Construction Physics: "Things are always more complicated than they seem. Simple explanations very rarely exist." We discuss that and other lessons by digging into pre-fabbed and manufactured homes, jet engines, gas turbines, windmills, nuclear reactors, batteries, Nobel Prizes, skyscrapers, and even Titanium. Just reading that list, you can probably tell why I like Brian's writing so much. He writes in-depth about all of the topics I love, and I learn so much from him each time. What impressed me most is just how humble Brian is. He knows 1000x more about this stuff than I do, but when he's not entirely certain of an answer, he says so. That's probably in part due to his background as a structural engineer, and in part a response to the lesson that everything is more complicated than it seems. I hope you learn as much from our conversation as I did, and that you go back and read everything he's written. To get you started, here are some of the essays we discuss and that Brian recommends, both his stuff and others'. Potter Essays - How to Build 3,000 Airplanes in Five Years - Why It's So Hard to Build a Jet Engine (https://www.construction-physics.com/p/why-its-so-hard-to-build-a-jet-engine) - What Learning by Doing Looks Like (https://www.construction-physics.com/p/what-learning-by-doing-looks-like) - How California Turned Against Growth (https://www.construction-physics.com/p/how-california-turned-against-growth) - Another Day in Katerradise (https://www.construction-physics.com/p/another-day-in-katerradise) - The Birth of the Grid (https://www.construction-physics.com/p/the-birth-of-the-grid) Recommended and Discussed Essays - Reality Has a Surprising Amount of Detail (http://johnsalvatier.org/blog/2017/reality-has-a-surprising-amount-of-detail) - John Salvatier - Timing Technology: Lessons From The Media Lab (https://gwern.net/timing) - Gwern - 100 Tallest Completed Buildings (https://www.skyscrapercenter.com/buildings) - Boom: Bubbles and the End of Stagnation (https://www.amazon.com/Boom-Bubbles-Stagnation-Byrne-Hobart/dp/1953953476) - Byrne Hobart & Tobias Huber You can find this and all of the articles we discuss on Hyperlegible in one place thanks to our sponsor, Readwise - Visit readwise.io/hyperlegible (https://readwise.io/reader/view/hyperlegible) for a free trial and get all Hyperlegible articles automatically added to your account. Big thanks to Jim Portela for editing!

11. 

    13 Apr 2025TRANSCRIPT

    Forsaking Industrialism with Conrad Bastable (Hyperlegible 006)

    In this timely conversation, Conrad Bastable (https://x.com/ConradBastable) joins Packy to break down his epic essay Forsaking Industrialism (https://www.conradbastable.com/essays/forsaking-industrialism-the-most-expensive-thing-you-didnt-buy) 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 (https://www.conradbastable.com/essays/forsaking-industrialism-the-most-expensive-thing-you-didnt-buy) Conrad has been planning this essay for months, and he couldn't have dropped it at a better time. It's a comprehensive look at what China got right and what real reindustrialization would mean. We dive into how EU regulations inadvertently benefited Chinese manufacturing, why tariffs alone can't solve America's industrial challenges, and what it would take to rebuild America's manufacturing capabilities.Conrad explains the concept of "platform economies" that China has mastered, why capital markets naturally push against long-term industrial investments, and the uncomfortable trade-offs between principles and prosperity that nations must navigate.From electric dirt bikes to BMW's battery dilemma, this wide-ranging discussion offers a fresh perspective on the most urgent debate in America. Conrad's reading recommendations: - Alexander Hamilton's Report on Manufactures (https://founders.archives.gov/documents/Hamilton/01-10-02-0001-0007)Conrad's other essays: - Full Stack of Society (https://www.conradbastable.com/essays/the-full-stack-of-society-can-you-make-a-whole-society-wealthier-full-version) - Escalation Theory (https://www.conradbastable.com/essays/escalation-theory-compliance-violence-and-overachievement-in-society) - Monetization & Monopolies (https://www.conradbastable.com/essays/monetization-amp-monopolies-how-the-internet-you-loved-died)Sponsored by Readwise - Visit readwise.io/hyperlegible (https://readwise.io/reader/view/hyperlegible) for a free trial and get all Hyperlegible articles automatically added to your account.Big thanks to Jim Portela for editing!

12. 

    8 Apr 2025TRANSCRIPT

    Skittle Factory Dementia Monkey Titty Monetization with Parakeet (Hyperlegible

    Pseudonymous writer Parakeet (https://x.com/parakeetnebula) joins me to discuss her viral essay "Skittle Factory Dementia Monkey Titty Monetization (https://parakeet.substack.com/p/skittle-factory-dementia-monkey-titty)." 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 immediately, and saw why. Parakeet describes universally applicable ideas with the color turned up to 11 so they stick. We explore the "dementia personality" - how our core thought loops shape who we are and might one day define us. Parakeet shares insights from working at a dementia facility, explains her Skittle Factory metaphor for personality (and researching Skittle Factories), and reveals her unconventional productivity hack that's transformed her writing output. We talk about her writing process, gifs, why more people should read George Orwell's Politics and the English Language, and what she learned from her once-half-paralyzed dance teacher. Plus, hear the bizarre true story behind the "Monkey Titty" portion of the essay title and why Parakeet believes everyone should re-read Atlas Shrugged as an adult. Key moments: (5:35) Origins of the dementia personality concept (10:30) Can we change our core mental loops? (15:18) Skittle Factory Mass Extinction Events (21:50) Rewiring your brain through Luigi Jazz (30:05) Why this essay got shared by so many smart people (31:50) Using gifs(40:31) Parakeet's productivity hack Reading Recs from Parakeet: Parakeet: YOUR EYES ARE LEAKING CORPORATE CUM™ (https://parakeet.substack.com/p/your-eyes-are-leaking-corporate-cum) Parakeet: ALGORITHMIC GROOMING OF YOUR INNER CHILD™ (https://parakeet.substack.com/p/algorithmic-grooming-of-your-inner) George Orwell: Politics and the English Language (https://www.orwellfoundation.com/the-orwell-foundation/orwell/essays-and-other-works/politics-and-the-english-language/) Ayn Rand: Atlas Shrugged (https://www.amazon.com/Atlas-Shrugged-Ayn-Rand/dp/0451191145) Hyperlegible is sponsored by my friends at Readwise, who build software that helps you get the most out of your reading. If you want to give it a try, go to readwise.io/hyperlegible (https://readwise.io/reader/view/hyperlegible) where you start a free trial and get all the articles discussed here on Hyperlegible automatically added to your account. Thanks to Jim Portela for editing and getting the parakeet animation to work!

13. 

    4 Apr 2025TRANSCRIPT

    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 this conversation, we talk about his new essay, which is an update to some of his older pieces, Scarcity and Abundance in 2025 (https://alexdanco.com/2025/03/27/scarcity-and-abundance-in-2025/). If you want to understand how to think about everything that’s going on right now as a result of AI in a really thoughtful, grounded way, read the essay. There’s so much here. What did Clayton Christensen get wrong? How does tech make things that, contra disruption theory, make things that are both cheaper and better? Is Apple in trouble? Will the vibe coding apps maintain their growth and revenue? What has become scarce? We talk about the shift from Code as Capital to Code as Labor, Tokyo zoning regulations, Red Queen’s Races, whether this time is actually different this time, why big company AI products suck because they’re trying to squeeze everything out of their existing assets, Steve Ballmer Trutherism, and why crypto + agents might actually be a thing. This summary just scratches the surface. Just listen. At the end, Alex gives some great essay recommendations: Book/Essay Recommendations Alex Danco, The Audio Revolution (https://alexdanco.com/2019/10/17/the-audio-revolution/) Alex Danco, Can Twitter Save Science? (https://alexdanco.com/2020/02/15/can-twitter-save-science/) Simon DeDeo, Information Theory for Intelligent People (https://wiki.santafe.edu/images/a/a8/IT-for-Intelligent-People-DeDeo.pdf) Thomas Mann, The Magic Mountain (https://www.amazon.com/dp/0679772871/?bestFormat=true&k=magic%20mountain&ref_=nb_sb_ss_w_scx-ent-pd-bk-d_de_k0_1_14&crid=2MDWEZR5MTLIE&sprefix=magic%20mountain) C.S. Lewis, The Inner Ring (https://www.lewissociety.org/innerring/) Hyperlegible is sponsored by my friends at Readwise, who build software that helps you get the most out of your reading. If you want to give it a try, go to readwise.io/hyperlegible (http://readwise.io/hyperlegible) where you start a free trial and get all the articles discussed here on Hyperlegible automatically added to your account. Thanks to Jim Portela for editing!

14. 

    2 Apr 2025TRANSCRIPT

    Julian Lehr, The Case Against Conversational Interfaces

    In Episode 003 of Hyperlegible, host Packy McCormick (https://x.com/packyM) talks with Julian Lehr (https://x.com/julianlehr) about his recent essay The Case Against Conversational Interfaces (https://julian.digital/2025/03/27/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 most creative writers on the internet. Go read his work at julian.digital (julian.digital). Hyperlegible is sponsored by our friends at Readwise (readwise.io/hyperlegible). You can find links to all of our conversations, and all of the episodes we discuss, at readwise.io/hyperlegible. Episode Highlights: (00:10) - Julian summarizes his essay on conversational interfaces and why they're inefficient (02:31) - Why writing is different: "a thinking process" rather than a speed-optimized workflow (03:08) - The "Pass the Butter Test" and the ideal human-computer relationship (05:04) - The privacy vs. experience trade-off with AI interfaces (07:10) - How Julian's visual approach to writing differs from traditional writers (10:07) - Julian's unique writing process: starting with pen and paper, switching between tools (11:22) - Using Figma as an underrated writing tool for visualizing content (12:24) - How Julian incorporates AI into his writing process, using ChatGPT as a thinking partner (15:18) - Discussion of AI at the OS level and predictions about browser development (18:38) - AI as a complement rather than a replacement, inspired by StarCraft gaming interfaces (21:01) - Sam Altman's always-on AI workflow and potential applications for writers (30:58) - Why Julian took a two-year break from writing and his publishing goals for this year (32:31) - The status-signaling aspect of the "thanks to" section in essays (36:12) - Julian recommends reading his essay "The Power of Defaults" (36:55) - Recommended reading: Kevin Kwok's "The Arc of Collaboration" (38:15) - Key takeaway: Think of AI as a complement that unlocks new possibilities rather than replacing existing workflows Essays and Podcasts Mentioned: Julian Lehr: The Case Against Conversational Interfaces (https://julian.digital/2025/03/27/the-case-against-conversational-interfaces/) Julian Lehr: ⁠The Power of Defaults⁠ (https://julian.digital/2021/12/20/the-power-of-defaults/) Kevin Kwok: ⁠The Arc of Collaboration⁠ (https://kwokchain.com/2019/08/16/the-arc-of-collaboration/) David Perell: How I Write with Sam Altman (https://www.youtube.com/watch?v=6pxmdmlJCG0) Big thanks to Jim Portela for editing!

15. 

    31 Mar 2025TRANSCRIPT

    Hyperlegible 002: Utsav Mamoria, How to live an intellectually rich life

    Utsav Mamoria recently wrote How to Live an Intellectually Rich Life (https://utsavmamoria.substack.com/p/how-to-live-an-intellectually-rich?r=1ftlg&utm_medium=ios&triedRedirect=true) 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 intellectually rich life. He takes us on a journey through Moradoom, Igamor, and Evermore, before arriving at Luminspere, the Mountains of Knowledge. His one sentence takeaway: Consistency trumps everything. I loved reading the essay, and was pleasantly surprised to enjoy our conversation even more. You can find Utsav on X at @utsavmamoria (https://x.com/utsavmamoria) and subscribe to Tumse Na Ho Paayega here (https://utsavmamoria.substack.com/). I asked Utsav for some recommendations. Substack to Follow: Ted Gioia’s The Honest Broker (https://www.honest-broker.com/) Favorite of his own pieces other than this one: Why we understand time wrong (https://utsavmamoria.substack.com/p/why-we-understand-time-wrong) If you enjoy Hyperlegible, subscribe and leave us a rating. We have some great conversations scheduled and I want to bring this to as many people as we can.

16. 

    26 Mar 2025TRANSCRIPT

    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 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 work more, not less. Since you can now do more with each hour, the opportunity cost of each hour not worked is higher! The treadmill spins faster and faster. Read it, and subscribe to Fakepixels while you’re there: https://fakepixels.substack.com/p/jevons-paradox-a-personal-perspectiveIf you're wondering how (or whether) to compete in the age of AI, Tina's personal perspective will help. Please let us know what you think and share your favorite essays with me @packym on twitter.

17. 

    5 Mar 2025TRANSCRIPT

    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-ambitious (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 from a software-focused company to a vertically integrated Microschool model. He also addresses regulatory hurdles, the market potential for innovative educational solutions, and the vision for making quality education accessible to all families. If you want to build a vertically integrated company to solve a really big, important problem, you need to listen to this. Chapters 00:00The Importance of K-12 Education Reform 02:18The Shift from Software to Microschools 04:04The Pivot to Microschools 06:28Building a New Education Model 09:03Scaling and Integrating Education Solutions 11:43Balancing Control and Innovation in Education 14:18The Role of Software in Education 17:15Future of Education and Personalization 21:56The Future of Education Funding 24:14AI Tutors and Their Limitations 26:12The Shift in Educational Structures Post-COVID 28:59Addressing Concerns About School Choice 31:19Breaking the Narrative of Private Schools 33:58The Vision for Free Education 36:49Navigating the Incumbent Education System 39:15Market Opportunities in Education 41:19The Future Landscape of Education 43:09Growth Projections for Primer

Inside a recent episode

A Conversation with GC CEO Hemant Taneja

Published 30 Jul 2026 · Transcript excerpt

[…] It's not going to go kill us. It's not going to, you know, whatever. But you just have a lot of really smart people competing to deliver the best product. But hopefully, you know, they compete to the point where the prices are good. I share your optimism. Like, you know, at Suma, we have a, you know, one of the companies we incubated was Hippocratic, which is, you know, it's got a nurse that is 10x lower price than a human nurse and is a genetic nurse. And they can change their care model with it. The fact that all these people can get care in their home that they weren't before, that's what AI is for. […]

Who has been a guest on Not Boring Radio

Names identified in recent episode analyses. Showing up to five guests.

• Hemant Taneja
• Brie Wolfson
• Mackenzie Burnett
• Sari Azout
• Cate Hall

Reach and audience

Public platform figures. Ratings count people who left a rating, not total listeners.

YouTube views

184,806

Score snapshot 15 Sept 2025

Apple Podcasts (US)

5.0 / 5

1 ratings

Spotify

5.0 / 5

5 ratings

Podcast Authority Score: 62 / 100

A composite of feed quality, social presence, YouTube performance and engagement. Read the methodology.

Quality

56

Social presence

0

YouTube

86

Engagement

81

Contact Not Boring Radio

Guest appearances

Books guests

Based on episode analysis; this does not confirm that the show is currently accepting guests.

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