Powered by RND

Dialectic

Jackson Dahl
Dialectic
Latest episode

Available Episodes

5 of 33
  • 32: Chris Sacca - Drifting Back to Real
    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
    --------  
    2:36:01
  • 32: Chris Sacca - Drifting Back to Real
    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
    --------  
    2:36:08
  • 31: Gabe Whaley - Playing the Crowd & Outlasting the Hype
    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
    --------  
    2:03:50
  • 30: David Senra - The Clarity of Commitment
    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.Transcript and extensive linked references: https://dialectic.fm/david-senraSpecial 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(3:02) - Podcasts are Energy Transmission(7:52) - People Buy Simple Stories(12:38) - Repetition Doesn't Spoil the Prayer(16:11) - Trust in Brands and Products (and Podcasts)(19:40) - Continuous Improvement and Speaking to a Moving Parade(26:18) - Confidence and Simplicity(34:55) - What Makes a Great Biography and Biographer(42:17) - Humanity in Context: Why Biographies are So Practically Helpful(48:52) - Fear(54:32) - Self Reflection and Commitment(1:06:52) - Considering Stuff Beyond Podcasting(1:10:40) - Focus and Making Time for Relationships(1:14:00) - What Should David Delegate?(1:24:36) - Advice for 2017 David(1:28:21) - Storytelling and Clear Thinking(1:32:19) - Defying Rationality and Creating Magic with Obsessive Details(1:38:09) - Self-Deception and Understanding Who You Are(1:45:01) - Intuition(1:48:34) - Being Easy to Interface With(1:52:26) - Biography Most Founders Would Benefit From: James Dyson's Against the Odds(1:57:05) - Simplicity and Edit Before You Make(2:02:42) - Lesson for Tech People: Learn from History(2:06:14) - What David Hopes His Kids Say About HimDialectic 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
    --------  
    2:17:16
  • 29: Billy Oppenheimer - Attuned to Clues
    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!) research in our work.From there, we talk about Billy's robust research process and how he has created an external brain of the ideas and patterns that inspire him rather than relying on memory. We also talk about the importance of time as a filter and a series of maxims that underpin his work and creativity. We discuss the importance of inputs over outputs and his big idea and book title, "The Work is the Win," as well many related ideas on success, complacency, compounding, standards, initiative, local maximums, and more. We finish with some lessons from Billy's favorite people.This conversation is a field guide for making things, pushing through the messiness of progress, and attuning yourself to the richness of the world that often takes the shape of clues.Full transcript and all links: https://dialectic.fm/billy-oppenheimerTimestamps:0:00 - Intro 1:20 - Looking for Clues with Rick Rubin 17:42 - Billy's Own Clue-Seeking 24:26 - Balancing Listening to the Market and Finding Unique Influences 31:17 - Memory, Notecards, and Billy's External Brain 37:13 - Making Notes for an Ignorant Stranger, or Leaving Clues for Your Future Self 45:09 - Lingering and Time as a Filter 52:51 - Billy's Book and Big Idea: "The Work is the Win" 1:00:07 - Be Great Regardless 1:04:31 - Following Up Even When Your Abilities and Standards Don't Match 1:10:10 - Fending Off the Wolf at the Door1:15:55 - Unfolding and Planting Seeds 1:18:17 - Taking Initiative and Opening Doors: "He Who Hesitates is Lost" 1:24:58 - Stupid Bravery and Getting Past the Sewage 1:30:16 - Local Maximums and Resisting Personal "Folklore" 1:36:14 - Some of Billy's Favorites: Ryan Holiday, Rick Rubin, Steve Jobs, John Mayer, Greta Gerwig, Jerry Seinfeld, Ralph Waldo Emerson 1:56:45 - Side Quests 2:02:26 - "I Know What We Do Here" and Creative Environments 2:05:28 - Bringing Familiar and Unfamiliar Together 2:09:26 - Mastery and Compounding 2:12:44 - The Real Life of Appearances 2:15:43 - "Ton-goo-ey" and The Gifts We Give Ourselves Links:‎McCartney 3, 2, 1 (2021)The Way of the Tracker: The Path of “not this” - Boyd VartyEddie Murphy Is Tracy Morgan's Favorite | Comedians In Cars Getting CoffeePoetry UnboundWhen We Cease to Understand the World- Benjamín LabatutFill Up To Pour Out - Billy OppenheimerThe Subtle Art of Not Giving a F*ck - Mark MansonThe Psychology of Money - Morgan HouselLeBron James shows off photographic memoryThe Notecard System - Billy OppenheimerRobert GreeneMike Nichols: A Life - Mark HarrisThe Journal of Eugene Delacroix - Lucy Norton19. Henrik Karlsson - Cultivating a Life that Fits - DialecticStadium of selves — Steph Ango8. Steph Ango - Tools for Amplifying Our Light - DialecticThe third chair - Henrik KarlssonSecrets of the Creative Brain - Nancy AndreasenSetting down the snow globe - Jackson DahlBilly on RESTFace it: you're a crazy person - Adam MastroianniTennessee Williams – The Catastrophe of SuccessCritique of Pure Reason - Immanuel KantBilly on Constraint, Gide, and Kant's Dove‎There Will Be Blood (2007)The War of Art - Steven PressfieldBilly on unfoldingHe who hesitates is lost - Joe Rogan & Jordan PetersonUnfolding - Henrik KarlssonBilly on John Mayer, HubermanSteve Jobs on folkloreThe Making of Prince of Persia - Jordan MechnerMake Something Wonderful - Steve Jobs‎Lady Bird (2017)‎Frances Ha (2012)Billy on Greta GerwigBilly on "I know what we do here"The Art Spirit - Robert Henri
    --------  
    2:20:43

More Business podcasts

About Dialectic

Conversational portraits of original people, across technology, media, business, and creativity. By Jackson Dahl.
Podcast website

Listen to Dialectic, Insurance Tomorrow and many other podcasts from around the world with the radio.net app

Get the free radio.net app

  • Stations and podcasts to bookmark
  • Stream via Wi-Fi or Bluetooth
  • Supports Carplay & Android Auto
  • Many other app features

Dialectic: Podcasts in Family

Social
v7.23.11 | © 2007-2025 radio.de GmbH
Generated: 11/5/2025 - 11:25:16 AM