31: Gabe Whaley - Playing the Crowd and Outlasting the Hype
Timestamps are as accurate as they can be but may be slightly off. We encourage you to listen to the full context.
Podcast Summary
In this wide-ranging conversation, Gabe Whaley, CEO and co-founder of Mischief, reflects on his company's evolution from a viral content machine to a more mature creative enterprise. Mischief, known for spectacle marketing and viral drops like the Big Red Boots and Jesus Shoes, built their reputation on releasing provocative projects every two weeks for nearly six years. (03:00) Now, Whaley discusses a major pivot away from constant content creation toward fewer, more ambitious projects that can stand independently without Mischief's brand attached.
- Core themes include the democratization of creative tools through the internet, the tension between virality and lasting cultural impact, and how to maintain creative authenticity while building a sustainable business in an attention-driven economy.
Speakers
Gabe Whaley
Gabe Whaley is the CEO and co-founder of Mischief, a cultural phenomenon that defies easy categorization as startup, fashion brand, performance art, or virality machine. A former West Point cadet who left to pursue an undefined creative path, Whaley has built Mischief into what many describe as "Mischief for X" when discussing spectacle marketing. Under his leadership, the company has created viral sensations like the Jesus Shoes (Nike Air Maxes filled with holy water), Big Red Boots, and numerous other provocative cultural interventions that blur the lines between art, commerce, and social commentary.
Key Takeaways
Embrace the Black Box Strategy
Whaley reveals Mischief's deliberate approach to maintaining mystery around their creative process. (04:24) Rather than being transparent about their methods, they cultivate an air of mystery because "the mystery lends more to the imagination than reality ever could." This approach serves two purposes: it's efficient (letting others tell the story for you), and it creates larger spectacles as different communities form conflicting narratives around the work. The black box isn't about hiding anything malicious—it's about giving the audience space to project their own meaning and become co-creators of the cultural moment.
Create Cultural Ready-Mades Through Cross-Industry Moves
A core framework at Mischief involves taking established moves from one industry and applying them to completely different categories. (27:31) Their TurboTax competitor in the form of an anime dating simulator exemplifies this approach—it became the number one game on Steam and was actually used by 20,000 people to file taxes. The key is selecting moves from worlds that don't typically communicate with each other, creating that crucial "eureka moment" that makes people stop, engage, and share. This strategy requires identifying long-term cultural mechanisms rather than responding to daily news cycles.
Design for Audience Completion, Not Consumption
Rather than creating finished products for passive consumption, Mischief designs experiences and objects that require audience participation to reach completion. (32:12) Their early mantra was "never fall into the trap of building for your community"—instead, they create polarizing work that forces audiences to either love it or hate it, then tell them to "shut up, love it" if they hate it. This paradoxical approach creates authentic engagement because audiences can sense the conviction behind the work. The sock queen example demonstrates how this strategy can transform customers into active participants who create their own narratives and business models around Mischief products.
Virality Is No Longer Enough—Permanence Is the New Goal
After years of viral success, Whaley admits the dopamine hit from going viral has worn off entirely. (33:54) He describes feeling nothing when a piece got 30 million views on TikTok, while feeling deeply moved by 3,000 people at a physical gallery opening. This realization has led to a dramatic shift in strategy: abandoning their famous biweekly drops to focus on 3-5 annual projects that prioritize permanence over virality. The goal is creating work that can stand independently without Mischief's name attached, reversing the creator-audience dynamic that has trapped many in the content creation cycle.
Cultivate Systematic Creative Input Through Structured Processes
Despite their reputation for spontaneous creativity, Mischief operates with rigorous creative discipline. (68:00) They employ someone full-time to create "the equivalent of a collegiate curriculum" for creative inputs, mining topics from diverse sources and maintaining boards of random inspirational words. The team engages in daily structured brainstorming sessions that Whaley calls "going to the dark place"—the necessary struggle of creative work. This systematic approach to novelty-seeking is combined with mandatory use of public transportation to ensure exposure to diverse real-world inputs, recognizing that consistent creative output requires intentional exposure to friction and new perspectives.
Statistics & Facts
- Mischief released new drops every two weeks for nearly six years, totaling 40-50 new projects annually. (52:54) This relentless schedule helped them build cultural momentum but eventually became constraining rather than liberating.
- Their TurboTax anime dating simulator became the #1 game on Steam for two weeks and was used by 20,000 people to file their actual taxes in 2024. (27:30) This demonstrates their success at cross-industry creative applications.
- A video of one of their art pieces received 30 million views on TikTok, but Whaley felt nothing from this viral moment, contrasting sharply with the meaningful impact of 3,000 people at a physical gallery opening. (60:08)
