Dialectic

All links and transcript at dialectic.fm/ryo-luRyo 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, where simple rules and patterns endlessly recombine to create emergent complexity. For Ryo, design is consciously participating in this process: seeing through the surface to understand the underlying structure and rearranging it into new forms. This means constantly moving between simplicity and complexity, chaos and order, bare material and highest levels of abstraction.We discuss how his process has evolved with AI. In the past, designing in tools like Figma felt like painting; now, working in Cursor feels like sculpting clay or finding David in the marble. So much of his philosophy is about getting closer to the material—in this case, code—and letting it provide feedback. There is no better example of this than his personal project, ryOS, a nearly full-on operating system he built entirely in Cursor. It is soulful, deeply personalized, and the opposite of "AI slop."This is a philosophical discussion about designing things that feel "true" or even "inevitable," but it is also a practical one. We talk about balancing agility and quality, allowing for "slack" in systems, and how to create soulful things with AI. Ryo is a profound thinker, but he is also a prolific doer, and it is this marriage that makes him so effective. I hope you are inspired to get closer to your own material, to be more flexible and dynamic, and to expand the boundaries of what you can personally create.---Dialectic is now presented by Notion. I am now focused on Dialectic full-time, thanks to their support. You can read more about why Notion embodies Dialectic's values and our partnership announcement here.Notion is an AI-powered connected workspace where teams build their best work. Notion is also where I compile research for episodes and the home of my new site where you can find all links and transcripts. Timestamps0:00: Notion Announcement & Dialectic's Future4:45: Intro7:46: "It's all the same thing!"17:25: Technical and Conceptual Readiness and How AI Helps us Deal with Complexity20:58: Designing for true-ness and inevitability27:28: Practicality and False-Compromise33:45: Working with Material and Different Ways of Thinking44:06: ryOS and Designing for the Full Spectrum of Users59:39: Allowing for Slack and Some Amount of Chaos in Design1:04:55: What is Cursor, Conceptually?1:10:33: How Using Cursor Evolves1:15:50: Designing for Power While Not Alienating Users1:19:59: How Ryo Designs at Cursor: Abstractions, Writing, Prototyping1:23:57: Process, Creating Soulful Things with AI, Refining Taste1:31:08: Balancing Agility and Quality, Chaos and Order1:37:00: Great Teams and Great Products1:39:41: Grab Bag: Human Tech, Why Tools Need Stories, Why Cursor Isn’t a Slot Machine, Notion & Cursor, Steve Jobs, Liquid Glass1:56:16: Tenderness & Empathy

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 podcast and youtube ad network. We cover the origins of TBPN, or the Technology Business Programming Network, from its beginnings as "Technology Brothers" to the interplay between John's love for technology and Jordi's for business. They share how they've built a media business in an era of infinite competition by leaning into high volume and constant iteration, all while treating media as the "main thing." We discuss brand building and innovating on form by borrowing ideas from outside the tech industry—from Formula One and SportsCenter to Hollywood films—to avoid tech's tendency toward circular references. We also talk about their focus on X/Twitter and a niche, highly informed audience, rather than trying to go too wide. We also chat about what makes their partnership work and how they take the work incredibly seriously while not taking themselves seriously at all.Transcript and all links available at https://dialectic.fm/tbpnTimestamps00:00: Opening Highlights03:18: Intro & Background06:08: Technology vs. Business and the Strategy behind TBPN12:08: Building a Media Business when Distribution is not Scarce22:26: Being Entrepreneurs and Talent30:33: Avoiding Audience Capture35:57: Why Advertising is a Good Model44:04: Technology's Circular References and Borrowing Ideas from New Places53:20: Narrow vs. Wide Appeal59:44: X (Twitter)-First Content and Other Platforms1:14:35: Making Content People Want to Share and Taking Yourself Seriously and Unseriously1:20:28: Valuing Brand1:30:10: Balancing Focus and Iteration1:35:25: Endurance & Evolution1:40:34: A Day in the Life of TBPN & Learning to be Newscasters1:49:59: Jordi & John as a duo, Will Manidis, and the beginnings of TBPN2:02:57: Grab Bag: Bias to Action, 15 Minute Interviews, Not Journalism, Talent, and Domination of SpiritDialectic with Jackson Dahl is available on all podcast platforms.⁠Join the ⁠telegram channel for Dialectic⁠⁠⁠Follow ⁠Dialectic on Twitter⁠⁠⁠Follow Dialectic on Instagram⁠⁠Subscribe to Dialectic on YouTube

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, Lowercase I. Lowercase I is one of if not the best performing VC funds ever, by multiple, at 214x, and included Twitter, Uber, Instagram, and more.Toward the end of Lowercase, I had the pleasure of working with Chris. Around that time, he was also a Guest Shark on Shark Tank. Chris was heavily involved in both Obama campaigns and was a large supporter of Hillary Clinton in 2016. When Trump won, he wound down new investing at Lowercase and "hung up his spurs" to focus on political and democracy related efforts. Then, in 2018, Chris started Lowercarbon Capital to invest in "un-f*cking the planet": carbon removal, climate science, cooling the planet, and eventually nuclear fusion.We talked about writing and storytelling, keeping people around who keep you honest, having a good taste in "weird," playing rigged games, taking the right kind of risks, and how even billionaires have imposter syndrome. We also get into how great founders embody inevitability, what makes the people at Lowercarbon special, how much Chris thinks about AI, and the many chapters of Chris's life, including whatever might be next.Authenticity is a moving target for all of us, but one of the things I most admire about Chris is his ability and desire to shamelessly play his own game.Timestamps:(0:00): Open: The Common Thread Amongst The Best Founders(1:20): Intro(3:42): Coast to Coast(12:29): Leaning into Weird & Investing in Fusion(24:35): Having People Who Keep You in Check(32:00): The Power of Language and Stories(1:03:03): Investing, Risk, and Wild Confidence(1:27:57): Imposter Syndrome and Making Companies Better(1:38:03): Lowercarbon's Team and Culture(1:57:47): Chris's Life Chapters, AI, and Creative Outlets(2:22:04): Drifting Back Towards RealAll links and transcript available at https://dialectic.fm/chris-saccaDialectic with Jackson Dahl is available on all podcast platforms.Join the ⁠telegram channel for Dialectic⁠Follow ⁠Dialectic on Twitter⁠Follow Dialectic on InstagramSubscribe to Dialectic on YouTube

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, Lowercase I. Lowercase I is one of if not the best performing VC funds ever, by multiple, at 214x, and included Twitter, Uber, Instagram, and more.Toward the end of Lowercase, I had the pleasure of working with Chris. Around that time, he was also a Guest Shark on Shark Tank. Chris was heavily involved in both Obama campaigns and was a large supporter of Hillary Clinton in 2016. When Trump won, he wound down new investing at Lowercase and "hung up his spurs" to focus on political and democracy related efforts. Then, in 2018, Chris started Lowercarbon Capital to invest in "un-f*cking the planet": carbon removal, climate science, cooling the planet, and eventually nuclear fusion.We talked about writing and storytelling, keeping people around who keep you honest, having a good taste in "weird," playing rigged games, taking the right kind of risks, and how even billionaires have imposter syndrome. We also get into how great founders embody inevitability, what makes the people at Lowercarbon special, how much Chris thinks about AI, and the many chapters of Chris's life, including whatever might be next.Authenticity is a moving target for all of us, but one of the things I most admire about Chris is his ability and desire to shamelessly play his own game. Timestamps(0:00): Open: The Common Thread Amongst The Best Founders(1:26): Intro(3:49): Coast to Coast(12:36): Leaning into Weird & Investing in Fusion(24:42): Having People Who Keep You in Check(32:07): The Power of Language and Stories(1:03:10): Investing, Risk, and Wild Confidence(1:28:03): Imposter Syndrome and Making Companies Better(1:38:10): Lowercarbon's Team and Culture(1:57:54): Chris's Life Chapters, AI, and Creative Outlets(2:22:11): Drifting Back Towards RealAll links and transcript: https://dialectic.fm/chris-sacca

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. Full transcript and all linked references: https://dialectic.fm/gabe-whaleyTimestamps(0:00): Intro(2:21): Value and Legibility(13:24): Is the Future Canceled?(20:00): We Create as a Result of What We Believe In(26:11): What Makes a Good Remix(29:08): How MSCHF Relates to the Current Thing and Evolves What Game it Plays(38:31): Creating Something the Crowd Can Play(44:59): Emphasis on Craft and Objects Rather than Creating "Lifestyle"(47:27): Keeping Up in a World That Demands Constant Production(53:11): Resisting The Internet's Scale and Lack of Friction(1:03:15): Accidental World Building, Process, Creative Inputs, and Focus(1:14:09): Creating as a Collective and Gabe's Role in Enabling the Team(1:22:30): Trust, Shedding the Black Box, and Staying Original(1:30:35): Applied MSCHF – Doors are Open(1:34:21): Sarah Andelman, People Who are Still Excited, and Long Time Horizons(1:41:52): Buzzfeed(1:44:41): MSCHF ValuesLinksMade by MSCHFSean Monahan11. Eugene Wei - Amusing Each Other to Death - DialecticBig Red BootMSCHF WholesaleTax Heaven 3000Chair SimulatorMaurizio CattelanBirds Aren't RealDavid Bowie interviewBlurJesus ShoesAthletic Aesthetics - Brad TroemelLil MiquelaTrevor McFedriesHow Twitter Gamifies Communication - C Thi. NguyenDisney diagramEva & Franco MattesComedian - Maurizio Cattelan#13: Gabe Whaley - Making MSCHF - Scott NortonSarah Andelman ColetteEmmanuel PerrotinKAWSATM LeaderboardOpus 40Key4AllPT Cruiser from Key4AllSatan ShoesSuper BabyMSCHF on InstagramDialectic is on all podcast platforms.Join the ⁠telegram channel for Dialectic⁠Follow ⁠Dialectic on Twitter⁠Follow Dialectic on InstagramSubscribe to Dialectic on YouTube