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All links and transcript: dialectic.fm/cab Are.na channel for this episode: are.na/jackson-dahl/dialectic-cab Charles Broskoski ( Website , Are.na , X ), aka Cab, is an artist turned entrepreneur and co-founder & CEO of Are.na , a platform for collecting, connecting, and self-directed learning. I created an are.na channel for all of the references I used in preparation for this episode. Charles began as an artist before becoming a software engineer, and started Are.na with many collaborators...
Full transcript and links: https://dialectic.fm/andrew-reed . Andrew Reed ( X , Website , Sequoia ) is a growth investor at Sequoia Capital , where he has invested in companies including Robinhood , Figma , Klarna , Phantom , Vanta , and ElevenLabs . He is quietly one of the best growth investors of his generation. We begin with how Andrew's competitiveness and humanity coexist—the twin brother rivalry, the football player who also did musicals, the Goldman analyst who came to value people over ...
Transcript and all links: dialectic.fm/mmm Molly Mielke McCarthy ( Website , X , Substack ) is an investor, writer, and founder of Moth Fund , an early-stage fund focused on backing "moths": quirky, quiet, mission-driven founders who are often underpriced by traditional venture capital. Molly's career has been a dance between "peopling" and making. She's held design, product, and editorial roles at Figma, Notion, Stripe Press, and The Browser Company, and explored film, photography, and the arts...
All linked references & transcript available at dialectic.fm/trevor-mcfedries . Trevor McFedries ( X , Instagram , Wikipedia ) is a musician, technologist, and entrepreneur. Today he is the founder of Runner and 1/2 of electronic dance duo SoFTT . Previously, Trevor was co-founder and CEO of Brud , the company behind Lil Miquela that was acquired by Dapper Labs ; Founder of FWB (Friends with Benefits) ; early artist in residence at Spotify; and a touring DJ who performed as DJ Skeet Skeet, w...
In this episode, C. Thi Nguyen explores his book "The Score," examining how scoring systems in games foster playful value exploration, yet in real-world institutions, they lead to "value capture" by flattening nuanced values into measurable metrics. He discusses the critical difference between recognition and perception, arguing that a focus on quantifiable outcomes often blinds us to deeper, context-sensitive values. Nguyen emphasizes that technology is never value-neutral, embedding ethical decisions and biases, and encourages listeners to adopt a more playful, humble, and perceptive approach to life to cultivate richer meaning.
Full transcript and all links: https://dialectic.fm/brie-wolfson Brie Wolfson ( X ) is a marketer, writer, storyteller, and curator. She’s Chief Marketing Officer of Positive Sum & Colossus , where she works closely with CEO Patrick O’Shaughnessy across investing and media and spearheaded Colossus Review , their new print publication known for superb long form profiles. Brie also recently joined AI-programming behemoth Cursor as Head of Employee Experience and wrote about the company’s c...
All links and transcript at dialectic.fm/ryo-lu Ryo Lu ( Website , X ) is the head of Design at Cursor . Prior, he was a designer at Notion, Stripe, and Asana, working on some of the most influential software tools of the last decade. He is now focused on building the next generation of tools for making software. Our conversation is an extensive exploration of Ryo's design philosophy, which is anchored in his recurring mantra: "it's all the same thing." He sees the world as fundamentally modular...
John Coogan & Jordi Hays are the hosts of TBPN ( X , YouTube , Spotify, Substack ), a daily live show covering the technology business. TBPN was launched only about a year ago, but has become a mainstay in tech culture and a center of gravity forterminally online technologists. John was previously an EIR at Founders Fund and tech YouTuber . He co-founded Lucy Nicotine and Soylent . Jordi has co-founded and invested in many business including Party Round / Capital and Branded Native , a podca...
Chris Sacca is an investor and founder of Lowercarbon Capital and Lowercase Capital . Prior to becoming an investor, Chris grew up in Buffalo, NY; studied around the world by way of the Georgetown School of Foreign Service; turned his student loans in $12M in the tech bubble of 2000 before losing it all and then some; and broke into Silicon Valley before eventually landing at Google, where he won the founders award. Then Chris started angel investing, which led to his first venture fund, Lowerca...
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 recen...
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 ...
Billy Oppenheimer ( Website , X ) is a researcher and writer who works closely with Ryan Holiday and Rick Rubin , and publishes the “Six at 6” newsletter . Billy is also working on his first book, The Work is the Win. We kick off by discussing one of my favorite new ideas: " looking for clues ," a process and philosophy for creativity that Billy learned from Rick Rubin. He shares the story Rick told him when he learned and adopted this language, which is so representative of how Billy (and I!) r...
Maxwell Meyer ( X , Newsletter ) is the founder and editor of Arena Magazine , an "American Propaganda" print and digital publication focused on technology, capitalism, and civilizational progress. Max also works with Joe Lonsdale at 8VC and is the proprietor of his Iowan farm, Henry Hills. He was previously the editor of the Stanford Review. Our conversation is about ideas Max is most interested in across storytelling and media, American values, technology and progress, capitalism, writing and ...
Mackenzie Burnett ( Website , X ) is the co-founder and CEO of Ambrook , financial software for independent businesses starting with farms and ranches. We trace her arc from a policy-first upbringing (USDA household, Congressional internships, climate-security research at Stanford) to a building software for rural America. We talk about why Mackenzie loves America and cares about agriculture, the challenges of aligning sustainability with business and government, and pragmatically building resil...
Cyan Banister ( Website , X , Substack ) is an investor, artist, and co-founder and General Partner of Long Journey Ventures . Previously, Cyan spent four years at Founders Fund and has a legendary angel investing track record alongside her husband, Scott, including early rounds in SpaceX, Uber, and DeepMind. Cyan is as original as they come: she grew up on a Navajo reservation and was homeless by 15, with a series of unlikely serendipitous moments combined with optimism, agency, and love of cap...
Reggie James ( Substack , X ) is a designer, writer, and entrepreneur. Reggie previously founded Eternal and recently edited and published Hardware 2024 , a book highlighting recent attempts at creating a different hardware future. This conversation happened live on stage at FWB Fest 2025 in Idyllwild, CA. We explored Reggie's frame of technology as a mirror and the Kevin Kelly-inspired notion that technology has an agenda of its own. Reggie has a fresh perspective on brand and "feel" as they re...
Linus Lee ( Website , X ) is a builder, engineer, and writer who explores how software can amplify our abilities, humanity, and agency. He builds, researches, and advises on AI at Thrive Capital , a venture capital firm, and continues to write and hack on personal projects. Previously, Linus held research or engineering roles at Notion , Betaworks , Replit , and others, and has built over 100 personal projects on the side--including his own programming language and ...
Tamara Winter ( X ) is the Commissioning Editor of Stripe Press , where she exercises her taste to identify the knowledge and "ideas for progress" that matter most in alignment with Stripe's mission: to increase the GDP of the internet. "Tammy" worked at the Charter Cities Institute and the Mercatus Center at George Mason University, which is chaired by Tyler Cowen . Tammy is obsessed with tacit knowledge and the illegible parts of the world that actually support so much of our lives, work, and ...
Nadia Asparouhova ( Website , X , Substack ) is a writer and researcher who has spent much of her career in service of the question: 'what's happening here?' across various parts of the internet. Nadia recently published her newest book, Antimemetics: Why Some Ideas Resist Spreading . She explores why consequential ideas, unlike memes and supermemes, fail to spread. She also recounts the last several years of online public and private life and how we're all less naive than we were in previous er...
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 CS...
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 e...
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 i...
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 ...
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...
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 produ...
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...
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...
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....
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 c...
Eugene Wei ( Website , X ) is a writer, product thinker, and cultural observer best known for his essays on technology, media, and social networks, including Status as a Service , Invisible asymptotes , and TikTok and the Sorting Hat . Eugene spent seven years at Amazon in its early days before following a brief detour to pursue filmmaking at UCLA. He then led product, design, editorial, and marketing teams at Hulu, co-founded Erly, and worked at Flipboard and Oculus. Today, he works on his own ...
