31: Gabe Whaley - Playing the Crowd & Outlasting the Hype
Dialectic15 Okt 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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38: Molly Mielke McCarthy - The Art of Peopling

38: Molly Mielke McCarthy - The Art of Peopling

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...

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37: Trevor McFedries - Creative People Should Be Rich

37: Trevor McFedries - Creative People Should Be Rich

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 Runn...

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36: C. Thi Nguyen - Measurement, Meaning, and Play

36: C. Thi Nguyen - Measurement, Meaning, and Play

Full episode transcript and all linked references available at https://dialectic.fm/c-thi-nguyen. C. Thi Nguyen (Website, Philpeople.org, X) is a professor of philosophy at the University of Utah foc...

13 Jan 2h 21min

35: Brie Wolfson - Loving Attention & Ease in Craft

35: Brie Wolfson - Loving Attention & Ease in Craft

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...

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34: Ryo Lu - It's All the Same Thing

34: Ryo Lu - It's All the Same Thing

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 soft...

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33: TBPN (John Coogan & Jordi Hays) - Inside Tech's Water Cooler

33: TBPN (John Coogan & Jordi Hays) - Inside Tech's Water Cooler

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 i...

17 Nov 20252h 22min

32: Chris Sacca - Drifting Back to Real

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 Sch...

5 Nov 20252h 36min

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