Not Boring Radio

I recently sat down with General Catalyst CEO Hemant Taneja to understand how his firm is deploying and building during this incredible period in the private markets. He believes that AI has changed how ambitious both founders and investors can and must be. We get into why a billion-dollar company may no longer feel big, why VCs need to stop treating markups as progress, and why the next era will require entirely new ways of financing ambitious companies.Hemant explains General Catalyst’s “living labs”, including Summa Health and Janus Henderson, where they’re trying to turn century-old institutions into AI-native organizations. We also discuss GC’s evolving view of Anthropic, the economics of frontier models, sovereign AI, and the growing tension between technological abundance and human agency.We don't agree on everything, and that's what made this one so fun. Timestamps(0:00) AI has completely changed what “scale” means(2:14) The controversial markup game thesis(5:15) Reinventing the venture capital playbook(8:51) General Catalyst’s “living labs”(14:03) Turning Janus Henderson into an AI-native institution(17:35) Why GC changed its mind about frontier models(20:46) How Anthropic and other AI labs can make the economics work(24:24) Abundance means nothing without human agency(26:55) Sovereign AI and the global resilience thesis(29:28) How Hemant pushes founders to think much bigger(31:25) Public fear may become AI’s biggest bottleneck(33:03) AI as a tool—and the road toward a post-work society(35:57) What CEOs owe their employees during the AI transition(38:20) How living labs change the way GC invests(42:28) Hemant’s ultimate measure of success at General Catalyst

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 Taste, kicked off the craze. She even worked at Dandelion Chocolate just to make something with her hands.
But I'm talking to her today because she wrote a phenomenal, personal, and original essay on her day with Kevin Kelly, who's career is even more varied than Brie's.
She called it Flounder Mode.
Flounder Mode is a way of building a career by following your curiosity. It's winding, weird, and often illegible. I know something about this - I've been in Flounder Mode without having the words for it before reading Brie's essay.
The essay itself is unique. Brie spent a day at Kevin Kelly's house and had the chance to interview her hero. Instead of just writing a bunch of Kevin Kelly quotes, though, she writes about her own career, how odd it feels to be in Flounder Mode when your peers are climbing a sturdy ladder, and how comfortable Kevin Kelly seems to be working this way.
I would never have thought to write this essay this way, but it's perfect. Kevin Kelly has impacted so many peoples' careers. So it's only appropriate that Brie's profile is about how he impacted hers. By putting Kelly's words into the background, she infuses the whole essay with him.
In our conversation, we talk all about how to Flounder Mode, what it feels like, the difference between Flounder Mode and laziness, what it takes to do it well, and much more.
I've been a fan and admirer of Brie's for a long time, and I'm so happy we had a chance to get to chat.
At the end of our conversation, Brie makes a couple of recommendations:
Her favorite of her own essays: Notes on Taste⁠
One essay everyone should read: Being basic as a virtue by Nadia Asparouhova
And she gives a one-sentence takeaway from her time with Kevin Kelly: "Have fun!"
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 for a free trial and get all Hyperlegible articles automatically added to your account: https://readwise.io/hyperlegible
Big thanks to Jim Portela for editing!

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 favor and read them here: The ProphetThe Disciples The GospelThe Kingdom In the series, which Mario worked on for 18 months, and in our conversation, which spans almost an hour and a half, you will learn about Founders' Fund's origins, its team of high-horsepower partners, its investments in Facebook, Airbnb, and SpaceX, among many others. You will learn the 12 Commandments that drive Founders Fund, and why they are impossible to copy. You will learn what it takes to 26.6x a $227 million fund and nearly 14x a $625 million fund. And you will learn how Mario wrote what I believe is the best and most comprehensive exploration of a single venture firm ever written. At the end of our conversation, Mario makes a couple of recommendations:His favorite of his own essays: AI & the Burden of KnowledgeTwo essays everyone should read (although Mario doesn't much like essays):Amis on NabokovHalf-Safe And he gives a one-sentence takeaway from his deep study of Peter Thiel and Founders Fund:"More people should give themselves the permission to follow a thought to its furthest conclusion, even if it leads somewhere really uncomfortable."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 for a free trial and get all Hyperlegible articles automatically added to your account: https://readwise.io/hyperlegibleBig thanks to Jim Portela for editing!

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 building a product at the intersection of American Dynamism and the American Dream, how farm economics work, how she's grown her business to over 2,500 customers, and where the company plans to go from here.
Mackenzie mentions a few essays:
- 2022 Founder's Letter
- Moving past skeuomorphic AI by Michael Akilian
- Could AI Actually Help Rebuild the Middle Class? by David Autor

You can find Mackenzie's new Founder's Letter, America, the Beautiful, at Not Boring.

Thanks to Jim Portela for editing and Matt Marlinski for letting us use The Manhattan Lab's studio.

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 this video. While a lot of people are talking about what AI means for humans, Sari is one of the few people I actually want to talk to about that topic.
A few weeks ago, she gave a talk she titled "Becoming unLLMable" at the Sana AI Summit in Stockholm, and then she summarized it on her Substack: Becoming unLLMable
Because of the format in which she originally presented these ideas, we did this one a little differently. To kick us off, Sari gives the presentation that we gave in Stockholm, and then we dig in on questions I had and things I've been thinking about.
It's characteristically Sari: optimistic but practical, grounded in facts but unafraid to imagine, and informed by her perspective as someone actually using AI to build a product and voice that stands out in a sea of undifferentiated slop.
We discuss a bunch of though-provoking ideas, my favorite of which is that average is now attainable by everyone, which means to stand out, you need to be way better than average. She is a case study on how to do that.
At the end of the conversation, Sari makes a few recommendations.
Her Favorite of Her Own Essays
What matters most in the age of AI is tasteLetter to a friend who is thinking of starting something new
One Thing Everyone Should ReadOn Bullshit by Henry G. Frankfurt
One-Sentence Takeaway: "Make yourself unLLMable"
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 for a free trial and get all Hyperlegible articles automatically added to your account:
⁠https://readwise.io/hyperlegible⁠
Big thanks to Jim Portela for editing!