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!

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 even writing the Book on Agency, which you can pre-order here.

On the first episode of Hyperlegible with Tina He, when I asked who people should read more of, Tina recommended Cate. So I was excited to see Cate drop a new essay that felt like it was written at me (and I think will feel like it was written at you, too) called Crossing the Cringe Minefield:

Crossing the Cringe Minefield

When we want to improve ourselves or our station in life, she argues, we start with the things that come naturally, the easy wins. They don't work. Then, we try things we don't love but don't hate. Those don't work, either.

Finally, we're faced with a choice: give up, or do the thing that feels deeply, incredibly uncomfortable, the thing that makes us cringe. That's where the answer normally is, because the cringe is a sign that we've left that area of ourselves under-developed."

This means," Cate writes, "that existential cringe is actually a signal pointing you to where you can make the most progress quickly."

We all have something we want to get better at. And we all have something that makes us cringe to even think about.

In this conversation, I ask Cate to guide us (OK, me) through the Cringe Minefield. We sprinkle in a little agency, too, of course.

There hasn't been a Hyperlegible with more laughs or more depth. I hope you learn as much about yourself as I did, and come away as ready (as you'll ever be) to face your cringe.

At the end of our conversation, Cate makes a couple of recommendations:

Her favorite of her own essays:

How to be More Agentic

And the upcoming book on Agency

One essay everyone should read:

Dream Mashups by Malcolm Ocean

One sentence takeaway: "The places where you feel that existential cringe are actually the places you can make the most progress as a person really quickly."

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:

Readwise.io/hyperlegible

Big thanks to Jim Portela for editing!

Timestamps

• [3:37] Cate summarizes "Crossing the Cringe Minefield"

• [5:48] Why this essay resonates universally (and why your 30s aren’t too late)

• [7:20] My personal cringe around asking for help

• [8:15] Why cringe exists - the "hot stove" analogy for psychological patterns

• [10:53] How cringe distorts your sense of proportion in normal situations

• [12:19] What percentage of people actually overcome their cringe (less than 1%)

• [13:40] Whether naming your fear publicly makes it easier to face

• [15:54] How to identify your cringe using the Enneagram system

• [22:06] Why personal vulnerability in writing creates audience connection

• [23:23] How Astera's mission connects to Cate's writing on agency

• [25:57] Whether Cate kicked off the "agency trend" before it was cool

• [27:38] Coaching session: applying agency principles to Enneagram 7s

• [32:49] The "gift of desperation" - how addiction led Cate to higher agency

• [34:29] What it feels like to be high agency - seeing constraints as arbitrary

• [35:39] The challenge of figuring out what you want once you can do anything

• [37:05] Facing cringe is more agony than thrill initially

• [40:31] Final Takeaway: "The places where you feel existential cringe are where you can make the most progress as a person really quickly"

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 past to understand what I got right, what I got wrong, and what we could learn from both, in March, with a Deeper Dive on Primer. I gotta admit, I was a little smug: Primer was doing great, in large part because it had gone more vertically integrated, which is exactly my thesis on how these things should be built. “And if you want to fix K-12 education,” I wrote, “you need to build schools.”Welp… over the past two years, Wander shut down the REIT I praised, went asset-light, grew from 13 to more than 1,000 locations, grew GMV 6x over the past 18 months, and is onboarding over $1 billion worth of real estate monthly. And while growing, its NPS has actually ticked up to 85. Being wrong and learning is why I do the Deeper Dives! If companies could be built as cleanly as I can write an essay, I’d be a billionaire. You’ve got to play the game; the lessons emerge from the messiness, and from following the best companies as they evolve. So today, I'm talking to Wander CEO John Andrew Entwistle about what we both got wrong and how Wander has gotten the important things right. You can read the full Deeper Dive at Not Boring.

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 the highest praise I can give to a writer. It combines his deep knowledge of the history of Silicon Valley, his Christianity, and his willingness to "critique the gods."

And it gave me an excuse to cover a topic I've been wanting to talk about for a while -- the rise of Christianity and the search for meaning -- with the best person I know to have that conversation with. We go deep and wide in this one. I hope you enjoy it.

At the end of our conversation, Reggie makes a couple of recommendations:

His favorite of his own essays:

Political Expectations

One essay everyone should read:

How to Find Ideas Worth Building by Matt Hackett

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/reader/view/hyperlegibleBig thanks to Jim Portela for editing!

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. He’s not afraid to tackle tricky subjects, not afraid to form his own opinion, not afraid to be earnest, and he writes the cover off the ball in a way that feels entirely his.

The piece we discuss today, Golden Age, is pure Solana. He starts by copping to having a lovely time in Disney World, before taking us on a tour of Walt Disney’s vision to build a whole futuristic city in the Florida swampland. He talks about why China has been able to execute on Disney’s vision better than America has, and what it would take to build a modern version, what he calls Golden City, a place where houses are cheap and rare earth metals are processed.

Go read it: https://www.piratewires.com/p/golden-age

It makes me nostalgic for this future, and after listening to our conversation and reading Golden Age, I hope you’ll add your voice to the small but mighty chorus calling on President Trump to just give Solana the federal land in California he needs to build this thing.

We talked all about this piece and much more, live from The Manhattan Lab in New York City, where Matt Marlinski was nice enough to let us record.

At the end of our conversation, Mike makes a couple of recommendations:

His favorite of his own essays:

Moral Inversion

One book everyone should read:

There is No Antimemetics Division

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.

Big thanks to Jim Portela for editing!

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 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.

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

- What Learning by Doing Looks Like

- How California Turned Against Growth

- Another Day in Katerradise - The Birth of the Grid

Recommended and Discussed Essays

- Reality Has a Surprising Amount of Detail - John Salvatier

- Timing Technology: Lessons From The Media Lab - Gwern

- 100 Tallest Completed Buildings

- Boom: Bubbles and the End of Stagnation - 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 for a free trial and get all Hyperlegible articles automatically added to your account.

Big thanks to Jim Portela for editing!