31: Gabe Whaley - Playing the Crowd & Outlasting the Hype
Episode 31
Wednesday, October 15, 2025 • Duration 02:03:50
Gabe Whaley is co-founder and CEO of MSCHF (Instagram, Wikipedia), the art collective, fashion and footwear brand, startup, and fill-in-the-blank, famous for its viral products and cultural interventions.
A few notable works include Jesus Shoes (Nike Air Max filled with holy water), Severed Spots (a "decentralized" Damien Hirst print), Museum of Forgeries (One original Warhol and 999 perfect forgeries), and of course the Big Red Boot. This conversation was heavily influenced by MSCHF's recently released Made by MSCHF, a "textbook," through which the team peels back the curtain and shows us inside the black box that has produced more viral hits than one can count.
Gabe had a sheltered childhood and went to two years of army academy at West Point before eventually finding his way to New York City to intern at Buzzfeed around 2014. In his spare time, he started releasing weird internet projects under the name "Miscellaneous Mischief." After tasting virality a few times, he started collaborating with likeminded creatives and eventually formalized MSCHF in 2019.
I've known Gabe for many years (and even did a small collaboration with him from my seat at 100 Thieves). We sat down to reflect on the last 15 years and the arc of MSCHF, what made it special, and where one goes next when virality makes you feel nothing and the internet feels mature.
The conversation includes MSCHF's eye-of-the-beholder legibility, their obsession with value, the power of mystery, and how the product doesn't culminate with release, but after the audience has made it their own (in MSCHF parlance, "playing the crowd"). We also discuss the creative process behind the hit factory, how acting as a label rather than individuals changes their relationship to the work, whether the cultural future is actually canceled, how the internet has changed, and how real world experiences offer something to the creator and the consumer that digital life simply can't. We wrap-up by speed-running through many of MSCHF's internal values, from "always punch up," to "death is just as importance as birth," to perhaps its defining frame: "nothing is sacred."
I hope you are inspired toward play, originality, embracing discomfort, and having the courage to burn it all down and start anew.
David Senra (Website, X) is a podcaster and loves that title more than anyone. He hosts Founders, where he teaches the lessons of history's greatest entrepreneurs by way of the biographies he reads of them. This week, he launched a second show, David Senra, where he talks to the greatest living entrepreneurs (often about the lessons from Founders). The first episode with Spotify Founder & CEO Daniel Ek is available now, and the show is in partnership with Scicomm Media, the team behind Huberman Lab.
David is an enthusiast about four things: entrepreneurship, reading, history, and podcasts. His two shows are the articulation of those obsessions in a form of service for the rest of us. He is following Charlie Munger's advice: "take a simple a idea and take it seriously."
David is one of the most energizing people I've ever met and has greatly inspired my work. I've had several multi-hour conversations with him that left me buzzing afterward, and I'm pleased that this is no exception. We cover many of his favorite lessons and founders, his process, biographies, focus, fear, endurance, service, and legacy.
I hope you are inspired to commit yourself to something worth your days and years.
Special thanks to Josh Kale for producing this episode. Please check out his show Limitless on frontier technology and AI.
Timestamps:
(0:00) - Open
(1:49) - Intro
21: Geoffrey Litt: Software You Can Shape
Episode 21
Thursday, June 19, 2025 • Duration 02:29:17
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.
20: Yancey Strickler - Constellations of Creativity
Episode 20
Thursday, June 12, 2025 • Duration 01:54:53
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.
, a private, highly vetted membership for founders. Hampton surveyed over 100 members with net worths of $1M-100M to create its They asked about financial goals, spending habits, how much founders themselves, investment portfolio breakdowns, risk tolerance, estate planning and philanthropy, and more. Visit to access the report.
19: Henrik Karlsson - Cultivating a Life that Fits
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 , as he is fully reader-supported.
18: Tom Morgan - Wisdom in the Woo
Episode 18
Wednesday, May 28, 2025 • Duration 01:42:26
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.
, a private, highly vetted membership for founders. Hampton surveyed over 100 members with net works of $1M-100M to create its
17: Alex Danco - Innovation Begins with Gifts
Episode 17
Wednesday, May 21, 2025 • Duration 03:09:25
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.
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 to learn more and apply.
16: Anjan Katta - A Sunrise Over Computing
Episode 16
Monday, May 5, 2025 • Duration 02:37:02
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.
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.
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 to learn more and apply.
14: Alex Zhang - Curating Cultural Playgrounds
Episode 11
Monday, April 21, 2025 • Duration 01:51:47
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.
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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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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Timestamps
2:12: Agency in a Digital World and Geoffrey's Creative Medium: Software
12:17: Intro to Malleable Software
20:42: "Popping Open the Hood" & The Nightmare Bicycle: A Case for Understanding How Systems Work
27:47: Computational Media, Spreadsheets, and Digital Informality
34:01: Legos and Home Cooking as Metaphors for Software
42:30: Two Types of Malleable Software: Modular-by-Design and Hacking
48:35: Hampton
50:13: Designing for a Smooth Slope
58:20: Unbundling Apps into Environments and Tools
1:17:58: Why Do the Work at All When AI Can Do It? When Should We be in the Details?
1:29:22: Empathy & Design: Enabling "Local Developers" Who Know Their and Their Community's Needs
1:38:23: A Case for Optimism About Human Agency
1:51:09: AI's Impact on Malleable Software
1:59:03: Commercial Incentives and Ecosystem Change
2:04:17: Research and Ink & Switch
2:11:46: ChatGPT as a Muse
2:15:34: Working at MUBI and Solving the "Too Many Things to Watch" Problem
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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Timestamps
2:36: Self-Cultivation, Introspection, and Larry Gagosian
8:46: Writing to Think
16:05: Using Strong Opinions as an Opportunity to Learn (and Willingness to Look Stupid)
21:53: "Not That" vs. "Maybe this?": Creativity and Formulating a Positive Possible Future
25:12: Self-Criticism and Kindness to Your Past Self and Ideas
28:44: Eclectic Interests (Poetry, Programming, Music) and a Winding Path to Becoming a Writer Pulling on the Threads of "Dead Ends"
33:10: Introspection, Agency and Being Sentenced to Freedom
38:09: "Fit," Unfolding, Making Contact with Reality, and Designing Your Life with Experiments
49:06: Seeing Past Blindspots and Listening to Feedback the World Gives Us
1:04:16: The Role of Ambitious Goals in the Context of Unfolding
1:10:06: Hampton
1:11:41: Escaping Flatland and People Who are "Spheres": Meeting People Who Help You Expand What is Possible
1:26:53: Asking Questions that Push People Past their Cache
1:31:12: Embracing, Being Seen By Strangers, and Finding Your Corner of the Internet
1:48:55: Ruthless Prioritization and Making Time to Get Better
1:57:05: Initial Spark and Connecting with People
2:05:58: Collaborating with Henrik's Wife Johanna
2:09:46: Living a Barbell Life Inside and Outside of the Computer and Henrik's Scale of Ambition
2:16:48: Sacrifice
2:18:57: Pseudonymity and Playing with Identities
2:20:57: Self-Organizing Systems
2:22:51: Learnings from Homeschooling His Kids, Reading Adult Books with the 3-Year-Old, and Becoming a Mentor to Help Them Unfold
2:33:13: Writers Who Help Us See Ourselves
2:35:13: Writing and Thinking in Swedish vs. English
2:37:44: Kindness and Gratefulness to Our Past Selves and Generosity to Our Future Selves – And Modeling That For Others
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:
2:03: Following Your Energy and Positive-Sum Games
6:04: Curiosity and Complexity: Differentiation and Integration
8:12: Entropy & Syntropy: Unpacking Curiosity, Love, and Desire
12:34: Emergence and What All the Mystics Point to: Integration
15:14: Left Brain & Right Brain: A Primer on McGilchrist's "The Matter with Things"
28:58: Hampton
30:34: Discovering Your Gifts
37:35: Creativity and Sustaining Curiosity
43:12: Life Pivots, Especially When You Aren't 22
50:24: A Challenge vs. A Grind: When to Keep Going or Try Something Else
56:19: Synchronicities
1:00:58: Openness and Wisdom
1:04:19: Error Correction, or Something Else?
1:06:02: Tom's Mission and The Meaning-Mortgage Question: Can you really do what you love?
1:08:45: Fear, Faith, Love, and Seeing Reality
1:12:59: "Minimum Viable Woo" and Exploring Out There Topics with a Pragmatic Lens
1:16:10: Stories
1:18:51: Love, Emergence, and Intelligence Beyond Us
1:22:52: A Looming Meta-Crisis, Global Consciousness, and Earth School: Blowing Out the "Woo" Rating
1:33:41: Lightning Round: Pseudoscience as the Streisand Effect, Mystics, What Would Rattle Tom’s Worldview Most, Joseph Campbell, Fred Again
1:40:41: Tom's Encouragement for His 20 Year Old Self
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
(0:05): Hampton: Dialectic's First Partner
(4:09): Commerce & Culture, Patronage, and Constraints
(12:17): Curating People, Spaces, and Art: "Host Energy"
(19:44): How to Throw a Party or Start a Scene
(27:05): Unlikely Intersections and Authentic Marketing
(35:36): Returning to Powder and Building a Unique Mountain Resort
(42:31): Utah and Mountain Living
(47:27): Randomness & Emergence: Christopher Alexander, Jane Jacobs, and Cities
(52:24): Creating a Digital Feeling of Place
(55:15): Network States and New Cities
(1:00:42): "Community"
(1:08:27): Organic Leadership Opportunities, Partnership, and Trust
(1:15:12): Focused Leadership and The Power of Memetic Language
(1:20:02): Learning from Reed Hastings as a Leader
(1:29:09): Getting into Rooms and Finding Serendipity
(1:32:58): Playfulness and Elon
(1:36:25): Intuition and Career Decisions
(1:39:10): Curating Music and a Life Goal of Refining Taste
(1:42:56): Music's Role in Creating Great Spaces
(1:44:08): Photography
(1:46:02): Beginning, Learning to Ski and Scuba
(1:48:10): Improving Los Angeles and What Makes it Special
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