November 26, 2024 • 1hr 16min

Gabe Whaley - Monopolizing a Feeling - [Invest Like the Best, EP.397]

Invest Like the Best with Patrick O'Shaughnessy

Gabe Whaley is the founder and CEO of Mischief, a creative company that releases new products every two weeks challenging assumptions about art, commerce and culture. What began as viral internet pranks has evolved into one of the most unique creative enterprises, spanning digital experiences, physical products, art installations and fashion items. The company aims to "monopolize a feeling" where subversion is the constant thread through all their work.

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Key Takeaways

Mischief's Core Mission: To monopolize a feeling of subversive creativity and challenge assumptions about art, commerce and culture through bi-weekly releases
Creative Process: Highly structured with brainstorming sessions, 6-month vetting periods, and projects planned 12 months in advance
Business Evolution: Started with viral internet pranks in 2014, evolved into physical products, art installations, and fashion items while maintaining creative independence
Cultural Impact: Projects like the Big Red Boots and microscopic handbag demonstrate ability to create viral moments while making commentary on fashion, commerce and culture
Team Building: Focus on hiring humble, intrinsically motivated people who care more about the act of creation than virality or recognition

Introduction

Gabe Whaley is the founder and CEO of Mischief, a creative company that releases new products every two weeks challenging assumptions about art, commerce and culture. What began as viral internet pranks has evolved into one of the most unique creative enterprises, spanning digital experiences, physical products, art installations and fashion items. The company aims to "monopolize a feeling" where subversion is the constant thread through all their work.

Topics Discussed

Origins and Early Digital Projects (11:09)

Mischief began with Whaley teaching himself to build websites in 2011-2012 after dropping out of West Point. His first viral creation was a GIF of the iPhone typing indicator dots that could be used to make it appear someone was perpetually typing.

Early viral success came from understanding the relationship between concept, production, execution and audience
Digital projects focused on subverting existing systems and expectations
No formal business plan initially - just a desire to continue creating subversive work
"It's not even that I want to, it's that I must. I don't have a choice. This has to happen," says Whaley about the creative drive behind Mischief

Evolution into Physical Products (20:33)

The company's first major physical product was the "Jesus Shoes" - Nike Air Max 97s injected with holy water that sold out instantly and generated massive media attention.

Initial release of 12 pairs (one for each disciple) priced at $1,425 (Matthew 14:25)
Second release three days later (playing on resurrection theme) led to $1 million in sales
Manufacturing challenge of producing 700 pairs demonstrated early operational learning curve
"We looked at each other like, 'all right, buckle up because this is no longer in our hands. We don't control this anymore,'" says Whaley about viral moments

Creative Process and Structure (42:37)

Mischief has developed a highly structured creative process while maintaining space for unbridled creativity.

Regular brainstorming sessions with specific topics and themes planned quarterly
Six-month vetting process for ideas to prove staying power
Projects planned 12 months in advance
Environment designed to remove fear of mistakes and encourage experimentation

Navigating Different Industries (33:07)

The company has successfully entered multiple industries while maintaining outsider perspective and creative independence.

Art World: Created ATM machine displaying users' bank balances at Art Basel
Fashion Industry: Produced viral Big Red Boots and microscopic handbag
Technology: Developed anime dating tax software as TurboTax alternative
"Everyone's actually, when they look at mischief, I think they just see a reflection of themselves in the worlds they inhabit a little bit," notes Whaley

Team Building and Culture (1:09:47)

Mischief has built a unique culture focused on creativity and humility.

Key traits sought: Ability to be scrappy, handle impossible tasks, remain humble
Team composition: Primarily "nerdy and introverted" people who care more about creation than recognition
Low turnover: Fewer than 5 people have left in 5 years
Focus on creation: Celebrate the act of making things rather than viral success

Future Challenges and Vision (1:11:56)

The company faces several strategic crossroads as it grows and gains recognition.

Identity evolution: Balancing increased visibility with maintaining mystique
Virality management: Actively working to suppress rather than chase viral moments
Long-term impact: Aiming for 20+ year legacy and historical importance
"We're getting to a point where this can be important from a historical point of view, but to do that we need to last a bit longer," reflects Whaley

Lessons from West Point (1:00:11)

Whaley's military academy experience shaped his approach to impossible tasks and leadership.

Comfort with impossible tasks: Learning to handle assignments with no clear solution
Leadership lessons: Importance of taking care of team members without fanfare
Discipline foundation: Provided structure that later enabled creative freedom
"You just have to figure it out. It's impossible. Let's say you get in trouble, you have to do 1000 push ups... Again, not their problem. You just have to find a way to get through it," says Whaley

Conclusion

Mischief represents a unique experiment in sustained creative subversion, successfully building a business around unbridled creative expression while maintaining independence from the industries it disrupts. Through structured processes and careful team building, the company has created a repeatable system for generating cultural moments while protecting its core creative mission. As it faces new challenges of scale and recognition, Mischief's ability to balance growth with creative integrity will determine its legacy as a historically important creative enterprise.

The company's success demonstrates the possibility of building sustainable businesses around pure creativity, providing an alternative model to traditional creative industries. Their approach of "monopolizing a feeling" while maintaining creative independence offers lessons for other creators and entrepreneurs seeking to chart their own path.