Geoffrey Litt (Website, X) is a designer, engineer, writer, and researcher at Ink & Switch, where he champions malleable software: the idea that ordinary people should be able to mold the digital tools they rely on every day.

Ink & Switch is an independent research lab focused on how computers can help us think and work. While researching and writing, Geoffrey and team also build products and prototypes to explore how their ideas can exist in practice. Geoffrey got his PhD at MIT CSAIL, where he built on his inspiration around computational media like spreadsheets, hoping to push more software toward the ethos of end-user programming, but without the technical complexity. In a sense, why should using software and changing it be any different? Previously, he built software for teachers at Panorama Education, which he joined out of school as one of the first employees.

Geoffrey and collaborators recently published a definitive piece on malleable software and we discussed it in detail. We dig into why most modern apps feel like sealed boxes rather than flexible tools and environments, and what changes when your app, document, or workspace, feels more like Lego than machinery. Geoffrey makes his case that we want software tooling to feel like a chef knife, not an avocado slicer, and we talk about how the best designed tools help users up a smooth slope of learning and ability. He argues in favor of deeper understanding, illustrated by one of my favorite ideas: The Nightmare Bicycle. We talk about how LLMs are enabling malleable software and how local tinkerers might be able to build systems for themselves and their team or communities that understand their needs more deeply than any professional designer could. Finally, Geoffrey lays out a call to arms for founders: build products that treat users as co-authors who understand their own needs, not just consumers.

On one level, this is a conversation about software and design. But it is really about agency. I hope it inspires you to pop open the hood on various aspects of your life, look at what's inside, and trust yourself to tinker. As Steve Jobs said many years ago, "the minute you can understand that you can poke life, and if you push in, then something will pop out the other side; that you can change it, you can mold it—that's maybe the most important thing."

All links and transcript: https://dialectic.fm/geoffrey-litt

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Yancey Strickler (Website, X, Metalabel) is a writer, entrepreneur, creative, and founder of Metalabel, a network and platform that allows creative people to release work together. He is also a board member, co-founder and former CEO of Kickstarter and is currently working on establishing a new kind of corporate structure, the Artist Corporation.

Yancey's life and work has revolved around what it means to be a creative individual, and how to improve the cultural and mechanical forms that enable artists and creatives.

We talk about how much of modern society is rooted in individualism, how that wasn't always the case, and how the internet is evolving our sense of self. We get into creativity, the term's surprisingly recent origins, and why Yancey believes the 21st will be the "Creative Century." Then, we go beyond the individual and discuss the deeply-rooted longing that all of us have to be a part of something bigger than ourselves. Yancey suggests that is not simply about being subsumed by a collective, but by maintaining our individual star while becoming part of larger constellations—like the labels that have empowered the distribution of ideas for centuries. Finally, we discuss the forms Yancey has or is helping to build and imagine a future where even more of the world creates professionally.

May we all shine more brightly and find others who inspire us to make wonderful things.

Full transcript and all links available at https://dialectic.fm/yancey-strickler.

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This episode is brought to you by Hampton, a private, highly vetted membership for founders. Hampton surveyed over 100 members with net worths of $1M-100M to create its 2024 Wealth Report. They asked about financial goals, spending habits, how much founders themselves, investment portfolio breakdowns, risk tolerance, estate planning and philanthropy, and more. Visit https://joinhampton.com/community to access the report.

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Key Links & References (all available at dialectic.fm)

Full transcript and all links: dialectic.fm/henrik-karlsson

Henrik Karlsson (Substack, X) is an independent writer focused on "writing a few good essays." Two of them are among my most consistently recommended: on designing your life and finding your wife (or husband).

Henrik's always written, but lived a winding path across software programming, music, poetry, biology, an art gallery, and other odd jobs. A few years ago, Henrik and Johanna picked up their life in Sweden to move to a small island farm in Denmark so they could homeschool their daughters. He now writes on Substack full-time and lives an unusual dual-life: one is remote and intimate; the other is connected and wide.

My favorite theme of his writing is self-cultivation: introspection and action, designing a life that fits you by experimenting, how to think and how to learn, embracing being wrong and seeing past your blindspots, and living in concert with past and future selves.

I also love his writing on relationships: how to find your life partner, why writing helps others see the inside of your head, how to use the internet as a serendipity machine for finding your people, teaching and parenting, and what its like to be around exceptional people who make your world bigger.

He also writes about education, self-organizing systems, AI, exceptional childhoods, and more. But I find the topic rarely matters—all of his writing expands me. What a gift. I hope you enjoy the conversation as much as I did. May we all embrace the burden of freedom—freedom to iteratively unfold into a life we never could have imagined. If you enjoy the episode, please consider supporting Henrik's writing, as he is fully reader-supported.

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This episode is brought to you by Hampton, a private, highly vetted membership for founders. Hampton surveyed over 100 members with net worths of $1M-100M to create its 2024 Wealth Report. They asked about financial goals, spending habits, how much founders themselves, investment portfolio breakdowns, risk tolerance, estate planning and philanthropy, and more. Visit https://joinhampton.com/community to access the report.

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Tom Morgan (X, Substack) is a "curiosity sherpa," writer, and podcaster who runs The Leading Edge, a community for leaders focused on personal transformation and authenticity.

I first encountered Tom and his ideas during his talk at Sohn on Iain McGilchrist, left vs. right brain, and curiosity. Tom writes about complexity, curiosity, and consciousness, and wades into the deep end of various topics that most of us would place in "woo," mystic, and spiritual territories. He spent most of his career on Wall Street and brings a scientifically-inclined, rationalist approach to researching and amplifying some of the most surprising modern and ancient ideas about the nature of humanity and the universe.

With this conversation, I aimed to create a primer on Tom's writing, approach, and the ideas he returns to most. We discuss following your energy, how curiosity is a guiding force, complexity and emergence, and why the world is overrated toward left-brain rationalism. We explore practical questions—How do you know your gifts? When should you pivot or persevere? What does real exploration look like when the world offers no safety nets? And then we wade into much stranger, or even heretical ideas—at least for a modern, intellectual, western audience—including the notion that consciousness is much vaster than what we've come to understand, and how we are just a small part of a much bigger whole.

I hope you enjoy the conversation and consider some ideas that are much more fringe than you're used to. I definitely left it with more questions than answers. And more than that, I hope you are inspired to attune yourself to your curiosity. Perhaps, you may even have the faith to follow that thread pulling you toward what appears today only to be a wall.

Episode transcript.

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This episode is brought to you by Hampton, a private, highly vetted membership for founders. Hampton surveyed over 100 members with net works of $1M-100M to create its 2024 Wealth Report.

They asked about financial goals, spending habits, how much founders themselves, investment portfolio breakdowns, risk tolerance, estate planning and philanthropy, and more. Visit https://joinhampton.com/community to access the report.

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Timestamps:

Alex Danco (Website, X, Substack) is a writer and Product Director at Shopify. Alex rose to prominence while writing his Snippets newsletter while at VC firm Social Capital in 2015. He wrote prolifically—about markets and financial systems, venture capital, startups, cities, culture, the technology-driven shift to a world of abundance, to name a few topics—through 2020, when he joined Shopify. Since then, he's had his hands full with Shopify and young kids, but recently published a flurry of new pieces on his blog while on paternity leave.

This conversation starts with one of Alex's most insightful ideas: that a culture of gift-giving underpins technology, innovation, and creative work, and is the key to solving many of capitalism's coordination problems. We then talk about what businesses will look like in a world of abundance: AI agents, massive and accessible infrastructure, and where moats might actually lie. Alex shares why AI-enabled creativity may resemble musicians finding their sound and how and where we might find internet-native subcultures in 2025. Then he explains what "the medium is the message" actually means across different content formats and why audio continues to thrive. We wrap up with Alex's thoughts on the U.S and Canada as someone who identifies with both places and by taking a peek into some of the books that have most influenced his thinking.

I've read Alex for years and I've always been impressed by how generative he is. That comes through in this conversation and I hope you are inspired to—like Alex—be more curious, creative, and most importantly, generous.

Transcript and all links available at dialectic.fm/alex-danco.

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Anjan Katta (X) is Founder and CEO of Daylight, a new type of computer company.

Having a conversation with Anjan is a bit like trying reign in a wild animal: his horsepower, wide-ranging philosophical interests, and unbelievable depth in the areas he cares about make him one of a kind. Fortunately, all of that energy is being channeled into his life's work, Daylight Computer Company. Daylight's mission is to build a computer that amplifies our humanity. That starts with Daylight's first product: The DC1, a tablet that combines the power and functionality of an iPad with the screen of a kindle. Anjan has been building Daylight for seven years across extensive research on screens and hardware, many near deaths, and mission-driven motivation.

Anjan sees computers as a "magical medium" that we're in relationship with, unlike other tools. Unfortunately, "optimization of the means, yet confusion of goals" has led the technology industry to building hardware and software that sits in what he calls a "messy medium." With devices that can do anything and everything, they often fail to empower us toward the vision Steve Jobs called the bicycle for the mind.

Throughout, Anjan and I discuss a philosophy toward life, career, design, and creating meaning that I hope will inspire you, whether you work on technology or not. May we all aim to get closer to ourselves and our humanity.

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This episode is brought to you by Hampton, a private, highly vetted membership for founders. Hampton makes entrepreneurship less lonely by matching you with a core group of likeminded founders along with community, events, retreats, and more.

Visit https://joinhampton.com/community to learn more and apply.

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• (0:04): Hampton

D.A. Wallach (Website, X, Substack, Spotify) is an investor, musician, writer, and polymath. Today he co-runs Time BioVentures, backing frontier life-science and healthcare startups. Before that, he was an investor in in SpaceX, Spotify, Emulate, Beam Therapeutics, and Ripple, among others, and toured the globe as half of Chester French. He also released music as a solo artist and was Spotify’s first Artist-in-Residence.

Our conversation moves from engineered serendipity—the art of a well-aimed cold email & surfing the web—to complexity science, the Santa Fe Institute, and what better systems might look like. We dive into markets and medicine: investing with a creative mindset; timing in biotech including CRISPR and GLP-1s; and the tension between free-market innovation and healthcare as a human right. D.A. unpacks how incentives shape everything from venture bubbles to hospital billing and how LLMs might move us closer to a universal standard of care.

In the back half we talk creativity, beauty, art, and performance. We discuss whether AI makes us lazy or amplifies originality, DA's many lives across art, tech, and business, and end on his plea for artists to reclaim their throne of "cool". I hope you're inspired by D.A's combination of curiosity and depth and are reminded that you don't have to stay in one lane, regardless of how impressive it might be.

Full episode transcript and all linked references available here.

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This episode is brought to you by Hampton, a private, highly vetted membership for founders. Hampton makes entrepreneurship less lonely by matching you with a core group of likeminded founders along with community, events, retreats, and more. Visit https://joinhampton.com/community to learn more and apply.

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Alex Zhang (Website, X, Instagram) is a cultural curator, community builder, and creative director. Currently, he's Chief Creative Officer of Powder Mountain, a where he's working with Reed Hastings to create a globally unique ski experience that combines art, architecture, and lots of fresh tracks.

Alex loves people and curating spaces and experiences for them: whether that means parties, music festivals, or mountain towns. He joined Summit Series out of school, throwing large scale events around the world and working on Powder Mountain, a Utah mountain resort the ownership group had acquired. He then joined one of the first social DAOs, Friends with Benefits (FWB) as Mayor/CEO, after being tapped by its founder Trevor McFedries to scale the tokenized social club beyond a Discord Server. He launched FWB Fest, an annual in-person music festival and crypto conference with past performers including James Blake, Charli XCX, and Caroline Polachek. Most recently, he joined Reed Hastings to return to Powder Mountain after the Netflix co-founder acquired a controlling stake in the resort. Alex leads brand, art, architecture, and marketing.

Blending culture, commerce, and "cool" is anything but a science, but Alex has made a career of it. I've known him for a decade and it's been a thrill to watch him continue to find strange intersections, blending worlds like music and tech, crypto and culture, and skiing and art. We talk about this, how to create spaces and events, living in the mountains, large scale art experiences, Christopher Alexander and Jane Jacobs, challenges in creating new cities, learning from Reed Hastings, and a life of deepening one's taste.

I hope you enjoy and are inspired to life a more connected, playful, and present life.

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This episode is brought to you by Hampton, a private, highly vetted membership for founders. Hampton makes entrepreneurship less lonely by matching you with a core group of likeminded founders along with community, events, retreats, and more. Visit joinhampton.com/community to learn more and apply.

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Full episode transcript and links available at dialectic.fm/alex-zhang.

Timestamps

Nabeel S. Qureshi (Website, X, Substack) is a writer, entrepreneur, and former Palantir product lead known for his writing on technology, AI, Palantir, culture, and learning. After a brief hiatus writing and researching and spending nearly a decade at Palantir working across government, healthcare, and intelligence, he's now founding a new company.

The first half of the conversation focuses on two big ideas. First: the growth of "slop" across media and culture and how "care" is its opposite. Then: how to think, learn, and understand more deeply across domains over a lifetime. We discuss how both of these sit against the backdrop of AI's rapid challenging of what it means to make and what it means to think.

Then we discuss Palantir and "grey areas" that many technologists avoid working on or thinking about, government bureaucracy and DOGE, and how technologists are pursuing and accumulating power. We also chat about Nabeel's idea maze ahead of the new company, art and what it is for, and a range of other topics that showcase how curious, polymathic, and considerate Nabeel is.

As the world changes at a breakneck pace thanks to technology and AI, Nabeel embodies a deeply humanistic approach that also accepts change as the default. This conversation inspired me to embrace surprise and strangeness, especially in creativity; to push through the friction and temptation to accept the answers at face value and instead yearn to more deeply understand; and to pursue a life of growth, practice, and care.

Full transcript with all linked references available here.

Timestamps:

Che-Wei Wang and Taylor Levy are the founders of CW&T (Website, Instagram, X, TikTok), a Brooklyn-based studio creating products that exist somewhere between art, design, and engineering.

The husband-and-wife team met at NYU ITP and shares a background across industrial design, architecture, computer science, film, including time at Pratt Institute and MIT. They won the 2022 Cooper Hewitt National Design Award for Product Design. They design and manufacture everyday objects including clocks, pens, tools, and other strange objects that challenge our relationship with time, attention, and materiality. Their most recognizable products include the Pen Type-A, Pen Type-C (my favorite), Time Since Launch (a one-time-use, 100-year timekeeper), and Solid State Watch, a remix of the classic Casio F-91W.

Our conversation explores their fascination with time, their commitment to creating heirloom-quality objects in a disposable world, and how they've built a sustainable creative practice on their own terms. We discuss their prototyping-centered approach, the tension between digital and physical creation, and how they navigate collaboration as partners in life and work.

Throughout, Che-Wei and Taylor reveal a philosophy that treats making as its own reward—they create what fascinates them first, trusting that others will connect with their vision. In a world increasingly dominated by disposable products and digital experiences, CW&T offers a refreshing counterpoint: a workshop where physical objects are thoughtfully conceived, meticulously crafted, and built to accompany us through life's journeys. Their work invites us to reconsider our relationship with the objects we use daily and the passage of time itself, offering a refreshing counterpoint to our increasingly digital, ephemeral world.

Full transcript with all links and references.

Timestamps