31: Gabe Whaley - Playing the Crowd & Outlasting the Hype
Dialectic15 Loka 2025

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-whaley Timestamps (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,...

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62: Quinten Farmer - Technology That Helps Us Be

62: Quinten Farmer - Technology That Helps Us Be

Quinten Farmer (X, LinkedIn) is a co-founder and the CEO of Tolan, which makes voice-first AI characters designed to be a friend and guide. He previously co-founded Even, a fintech company for workers...

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61: Josh Miller - A Good Rectangle

61: Josh Miller - A Good Rectangle

Josh Miller (X, LinkedIn) is co-founder and CEO of The Browser Company, makers of Dia and Arc. The Browser Company was acquired by Atlassian last year. Before The Browser Company, Josh was an investo...

22 Loka 1h 54min

60: Patrick Hsu - Speedrunning the Infinite Game

60: Patrick Hsu - Speedrunning the Infinite Game

Patrick Hsu (X, Website, Arc lab) is co-founder and core investigator of Arc Institute, assistant professor of pathology at Stanford, and venture partner at Thrive Capital. Patrick has always been pr...

15 Loka 1h 56min

59: Joe Gebbia - Design We Deserve

59: Joe Gebbia - Design We Deserve

Joe Gebbia (Website, X, LinkedIn, Wikipedia) is the first U.S. Chief Design Officer, leading the National Design Studio. He is also the co-founder of Airbnb and Samara. The NDS and this role were cre...

8 Loka 1h 49min

58: Adam Mastroianni - Let Me Be Useful

58: Adam Mastroianni - Let Me Be Useful

Adam Mastroianni (Website, X) is an experimental psychologist and the writer of Experimental History. He earned his PhD in psychology at Harvard before leaving academia to pursue research and writing ...

1 Loka 2h 6min

57: Immad Akhund - The Art of Irrational Effort

57: Immad Akhund - The Art of Irrational Effort

Immad Akhund (⁠X⁠, ⁠LinkedIn⁠) is the co-founder and CEO of ⁠Mercury⁠. He is also a prolific angel investor and co-hosts the ⁠Founders in Arms⁠ podcast. Mercury is a fintech banking platform used by ...

24 Syys 2h 1min

Independent Study: Personal Renewal by John W. Gardner (Speech)

Independent Study: Personal Renewal by John W. Gardner (Speech)

Independent Study is a series of bonus episodes to accompany the interviews on Dialectic. I read essays and other writing that has influenced me. "Personal Renewal" was given as a speech by John W....

16 Syys 29min

56: Miles Grimshaw - Back Down the Mountain

56: Miles Grimshaw - Back Down the Mountain

Miles Grimshaw (X, LinkedIn) is an investor at Thrive Capital. He’s spent most of his career there, there, partnering with founders at the early stages of company building, including Cursor, Turbopuff...

1 Syys 1h 53min

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