Gabe Whaley - Building MSCHF - [Invest Like the Best, EP.398]
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What is Mischief and how does Gabe define its unique creative purpose?
I know firsthand how complex the tech stack is for asset management firms. And seemingly every new tool and data source makes the problem even worse, adding more complexity, more headcount, and more risk. Ridgeline offers a better way forward, one unified platform that automates away the complexity across portfolio accounting, reconciliation, reporting, trading, compliance, and more, all at scale. Ridgeline is revolutionizing investment management, helping ambitious firms scale faster. Faster, operate smarter, and stay ahead of the curve. See what Ridgeline can unlock for your firm. Schedule a demo at ridgeline.ai. Hello and welcome everyone. I'm Patrick O'Shaughnessy and this is InvestLike the Best.
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My guest is Gabe Whaley, founder and CEO of Mischief. What began with viral internet pranks in 2014 has evolved into one of the most singular creative companies I've encountered. Mischief's work ranges from microscopic handbags, literally 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. Mischief is hard to define. But Gabe says its goal is to monopolize a feeling where subversion is the rare constant. Their most viral creation, the big red boots, took over the internet in 2023. Our conversation explores how Gabe dropped out of West Point and 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 this episode inspires you to think about what your version of mischief could be. Please enjoy this fascinating discussion. with Gabe Whaling. So one place we have to begin is just what this thing is. I was trying to put it in a sentence for my friends and what I came up with was an ode to subversive creativity. Whoa, cool. I wonder how you would describe in more than a sentence what mischief is. Just a level set for anyone that hasn't heard of it.
It really depends on who I'm talking to. Mischief means so many different things to so many different people. I think selfishly for me, it is my excuse and my friend's excuse to make whatever it is that's in our heads at any given moment. But if you ask someone in like the art world, they're gonna compare it to, for better or worse, Banksy or Warhol or Duchamp, all of whom I've learned a lot about in the last few years. If it's someone in the fashion world they'll make comparisons to like Supreme or Balenciaga or Loueve, also things that I've learned a lot about in the last few years. Everyone's actually when they look at mischief, I think they just see a reflection of themselves and the worlds they inhabit a little bit.
And that doesn't mean they always like it.
But that is what they see. Another way of asking it would be what do you do over and over again? Maybe even spend some time getting into the structured process for creativity. One of the things you told me when we first met that I found fascinating was how far in advance some of these things are baked. But maybe just describe like the repeated action that you take.
If you really had to think about like what we're doing here, we're manufacturing cultural output.
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Chapters
8 chapters
1
What is Mischief and how does Gabe define its unique creative purpose?
0:00–12:18
2
How did Gabe’s early internet pranks and viral websites shape the origin of Mischief?
12:18–21:51
3
What prompted the shift from digital tricks to physical products like the tiny handbags?
21:51–32:02
4
How did the Big Red Boots become a cultural phenomenon and what did it teach the team?
32:02–42:08
5
What is the structured brainstorming and idea‑vetting process that powers Mischief’s output?
42:08–53:29
6
What lessons did Gabe learn from interacting with venture investors and raising capital?
53:29–1:02:27
7
How does Mischief approach fashion, utility, and the tension between fantasy and function?
1:02:27–1:12:13
8
What strategies does Gabe use to protect his creativity and navigate the crossroads ahead?
1:12:13–1:16:00
Speakers
1 identifiedMore from Invest Like the Best with Patrick O'Shaughnessy
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