My guest today is Gabe Whaley, the founder and CEO of MSCHF. What began with viral internet pranks in 2014 has evolved into one of the most singular creative companies in modern culture. MSCHF’s work ranges from microscopic handbags—the size of a grain of salt—to tax software that helps you file your returns by going on virtual dates with anime characters.

Every two weeks, they release something new that challenges our assumptions about art, commerce, and culture. MSCHF is hard to define but Gabe says their goal is to “monopolize a feeling” and subversion is the rare constant. Their most viral creation, the Big Red Boot, took over the internet in 2023.

Our conversation explores how a West Point dropout built a company that thrives on breaking rules, but it's also about something bigger - the power of unbridled creative expression and what happens when you build a business around it. I hope it inspires you to think about what your version of mischief could be. Please enjoy this fascinating discussion with Gabe Whaley.

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This episode is brought to you by Ramp. Ramp’s mission is to help companies manage their spend in a way that reduces expenses and frees up time for teams to work on more valuable projects. Ramp is the fastest growing FinTech company in history and it’s backed by more of my favorite past guests (at least 16 of them!) than probably any other company I’m aware of. It’s also notable that many best-in-class businesses use Ramp—companies like Airbnb, Anduril, and Shopify, as well as investors like Sequoia Capital and Vista Equity. They use Ramp to manage their spending, automate tedious financial processes, and reinvest saved dollars and hours into growth. At Colossus and Positive Sum, we use Ramp for exactly the same reason. Go to Ramp.com/invest to sign up for free and get a $250 welcome bonus.

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Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 

Follow us on Twitter: @patrick_oshag | @JoinColossus

Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com).

Show Notes:

(00:00:00) Welcome to Invest Like the Best

(00:06:50) Defining Mischief's Unique Creativity

(00:11:09) The Origin Story of Mischief

(00:12:53) Early Digital Projects and Virality

(00:20:33) Transition to Physical Products

(00:33:07) Navigating the Art World with Mischief

(00:39:52) Entering the Fashion World

(00:42:37) Mischief's Creative Process

(00:44:51) Structured Brainstorming and Idea Vetting Process

(00:46:38) The Role of Rules and Boundaries in Creativity

(00:48:39) Interacting with Venture Investors

(00:51:07) The Big Red Boots Phenomenon

(00:54:48) Supply and Demand in Creative Projects

(00:58:08) Protecting Creativity and Overcoming Challenges

(01:00:11) Lessons from West Point

(01:05:25) Fashion as Utility and Fantasy

(01:09:47) Recruiting and Team Dynamics

(01:11:56) Navigating Crossroads and Future Goals