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Invest Like the Best with Patrick O'Shaughnessy
Gabe Whaley - Building MSCHF - [Invest Like the Best, EP.398]
01:16:53
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- [00:00]
Patrick O'Shaughnessy
Two fun facts about our newest sponsorship partner, Ramp. First, they are the fastest growing fintech company in history, reaching a level of revenue in five years that I can't quote exactly but is eyebrow raising. Second, they are backed by more of my favorite past guests, at least 16 of them when I counted, than probably any other company that I'm aware of. A list that includes Ravi Gupta at Sequoia, Josh Kushner at Thrive, Keith Raboy at Founders Fund and Coastal Ventures, Patrick and John Collison, Michael Ovitz, Brad Gerstner. The list goes on and on. These facts demand the question why? Having been personally obsessed with the great businesses through history, one clear lesson is that the best of them are run by disciplined operators. These operators manage costs with incredible detail and they are constantly thinking about how they can reinvest every dollar and every hour back into their business. This is RAMP's mission to help companies manage their spend in a way that reduces expenses and frees up time for teams to work on more valuable projects. First on expenses. The average American business has a profit margin of 7.7%. This means saving 1% on costs is the equivalent of making 13% more revenue. The average ramp customer is able to save 5% on their expenses each year. Of course, every entrepreneur is looking for ways to grow revenue by 50%. They should just as seriously seek to save 5% on their expenses. Second on time. Unnecessary complexity is why most finance teams spend 80% of their time doing operational work and only about 20% of their time on strategic work. Ramp makes spend management very simple by handling your company's expenses, travel, bill payments, vendor relationships and even accounting. It's notable that some of the best in class businesses today, companies like Airbnb, Anduril and Shopify and investors like Sequoia Capital and Vista Equity are all using Ramp to manage their spend. They use it to spend less, they use it to automate tedious financial processes, and they use it to reinvest save dollars and hours into growth at both Colossus and Positive Sum. My businesses, We've used Ramp for years now for these exact reasons. Go to ramp.com invest to sign up for free and get a $250 welcome bonus. That's R A M p.com/invest. As an investor, I'm always on the lookout for tools that can truly transform the way that we work as a business. Alpha Sense has completely transformed the research process with cutting edge AI technology and a vast collection of top tier reliable business content. Since I started using it, it's been a game changer for my market research. I I now rely on Alpha Sense daily to uncover insights and make smarter decisions. With the recent acquisition of Tigis, Alpha Sense continues to be a best in class research platform delivering even more powerful tools to help users make informed decisions faster. What truly sets AlphaSense apart is its cutting edge AI. Imagine completing your research five to ten times faster with search that delivers the most relevant results, helping you make high conviction decisions with confidence. AlphaSense provides access to over 300 million premium documents including company filings, earnings reports, press releases and more from public and private companies. You can even upload and manage your own proprietary documents for seamless integration. With over 10,000 premium content sources and top broker research from firms like Goldman Sachs and Morgan Stanley, Alpha Sense gives you the tools to make high conviction decisions with confidence. Here's the best part. Invest like the Best Listeners can get a free trial now just head to alpha-sense.com invest and experience firsthand how Alpha Cents and Tigis help you make smarter decisions faster. Trust me, once you try, you'll see why it is an essential tool for market research. Hello and welcome everyone. I'm Patrick O'Shaughnessy and this is Invest like the Best. This show is an open ended exploration of markets, ideas, stories and strategies that will help you better invest both your time and your money. Invest like the Best is part of the Colossus family of podcasts and you can access all our podcasts including edited transcripts, show notes and other resources to.
- [03:51]
Gabe Whaley
Keep learning@joincolossus.com Patrick O'Shaughnessy is the CEO of Positive Sum. All opinions expressed by Patrick and podcast guests are solely their own opinions and do not reflect the opinion of Positive Sum. This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions. Clients of Positive Sum may maintain positions in the securities discussed in this podcast. To learn more, visit Psum VC.
- [04:24]
Patrick O'Shaughnessy
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 Whaley. 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.
- [05:30]
Gabe Whaley
Whoa, cool.
- [05:31]
Patrick O'Shaughnessy
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.
- [05:37]
Gabe Whaley
It really depends on who I'm talking to, because 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 going to 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 supreme or Balenciaga or Loewe. 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.
- [06:26]
Patrick O'Shaughnessy
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 the repeated action that you take if you really had.
- [06:45]
Gabe Whaley
To think about what we're doing here. We're manufacturing cultural output. And so with that statement alone, it removes the need for sticking to a category or having these arbitrary lines set up that dictate and define what you do over a long period of time? For us, it's just purely cultural output. How can that live in whatever format, medium, device makes sense to resonate the most in culture, both now and in the future? And so if you look back at our body of work, what that has yielded is everything from most obviously very viral pieces of footwear to, maybe more interestingly, software that helps you do your Taxes via going on virtual dates with a cute anime girl in a cafe. It can be anything. But the through line that ties it all together is this underlying feeling of subversive creativity. So how do we do that? We're constantly thinking. We've assembled a group of people here who are not just thinking about these ideas, but they speak the language of these ideas. It's just part of a common understanding that we have here of seeing the world in terms of opportunities for subversion. Most people will look around this room that we're in right now and they'll see, oh, here's a cup of water and here's a roll of tape, and here's some paper and a pen and leave it at that. But for us, we're like, wait, I can take this tape and wrap it around this cup and turn the cup upside down with the water still in it, which means you can't remove it without spilling water everywhere. That's how we see everything. It's an opportunity to flip something upside down and give it a new perspective that other people will react to, I guess. To get back to your question, though, with all of these ideas, how do you actually turn it into something real? And I knew that would be a big challenge when we started because I think it's really easy for a creative or artistic person to have their head so far in the clouds in a good way that it makes it very difficult to actually do the dirty work, to be productive, to create work, to make new outputs. So we actually had to build a process and a system that would allow us to constantly generate these ideas, document these ideas, vet these ideas, and then ultimately slot them for production on a timeline that allows us to effectively organize our resources, organize our time, organize our abilities. And what that ended up yielding is sort of like a creative sweatshop here in Brooklyn that we have all extremely consensually signed up to be a part of.
- [09:21]
Patrick O'Shaughnessy
It's so funny, when you literally walk into the building on your left hand side, you see lots of computer monitors, some code. It feels almost like a startup. On the right hand side, you see, like Willy Wonka's creative workshop. It feels very much like a dichotomy. That's really interesting. And I want to talk about how it got to here. Maybe going back to the very origin Days of Mischief. It's way organized now. We'll come back to that process and go into it in detail, but maybe talk us through, like the Origin, whether it's at Buzzfeed or however far back you want to Take it. And the first couple of things that you did, which were more bespoke, more just you and a small group of people versus this big thing.
- [09:57]
Gabe Whaley
Yeah, yeah. This really all started with me just running away from real life. I think there's like a longer story here of me dropping out of the military academy and not being able to hold down real jobs at real call centers, that I was expected to make 80 phone calls a day. All of these things just kind of weren't working out for me. And I guess in protest, or more accurately, procrastination of these things, in 2011, 2012, I started teaching myself how to make websites because I had these ideas for funny projects that I wanted to build because they sort of made fun of this world that I was not allowed to really participate in. I had this a bit of a sheltered upbringing that ended up culminating in West Point, where you're even more sheltered. And so by the time I got out as a 20 year old, I was seeing the real world for the first time and not really knowing where my place was or who my friends were or how am I supposed to dress. I talked to a lot of college kids these days and they've already got it all figured out. They're more networked than I am now. So for me, I had nothing. I was a blank slate. And I really just didn't know where I belonged. So I would make these websites that kind of made fun of everything that I was observing. And somehow these websites would get a ton of attention. And I started to learn about the relationship between like concept, production, execution and audience purely by accident. One of the first things that I ever did, if you use an iPhone, you know that when someone's typing to you, you see the three dots animate. So in 2012, I made the first GIF of those three dots, formatted in a way where if you saved it to your camera roll and messaged it to someone over imessage, it would resize itself to look perfectly as if someone's typing at the forever and one. I never knew how to make a gif, so I taught myself how to make a GIF in Photoshop. And then I had to figure out how to make that available by building a website for it where I could explain what it was, how it works, how you should use it, what its intention is. And that was the first or second miscellaneous mischief project, which it's mischief now because no one can spell miscellaneous. But that thing got like a million hits overnight. It was one of the craziest things I'VE ever seen. And this is back at a time where virality was not so cheap. These days, brands can buy it. Anybody can get lucky on TikTok. It's a numbers game now, but back then it was magic. You get the right idea to penetrate the right audience, or not even the right audience, the right initial core, that could be five people, that could be 100 people. But if they saw something so compelling that they had no choice but to share it, that was magic back then. And I got to experience that. And that was a crazy feeling. And as soon as I got that feeling, it's an addiction. I don't do drugs. But that must be what drugs feel like, because you get this high and then like anything else online, the world moves on and then you find yourself in withdrawal and you need the high again. And so if you manage to channel that lust that you've gotten from this experience, if you're able to channel that with a desire to learn and a desire to create, it creates something really potent. And I think that's what mischief ended up becoming.
- [13:06]
Patrick O'Shaughnessy
What happened next? What was immediately after, we'll call that the first era or something. So you have a couple of these website based experiences of virality.
- [13:14]
Gabe Whaley
Just kept doing it.
- [13:15]
Patrick O'Shaughnessy
You just kept going, kept going.
- [13:17]
Gabe Whaley
One thing led to another and it brought me to New York. And I bounced around a lot of jobs here in New York trying to figure out how to crack this. Because I knew deep down in my core there has to be a way for whatever this is to be sustainable. How can I basically find a way to do mischief forever? Because I can't imagine a life where I do anything else. It's not even that I want to, it's that I must. I don't have a choice. This has to happen. And so being in New York was a real blessing. Coming from the woods of North Carolina, like being in New York was wild. Every three blocks that you walk, you're in a different world with a different type of person and a different culture and a different sense of style. The diversity of New York City was such an eye opening experience for me that you really kind of felt like anything was possible. And so between the years of, I'd say 2013 to 2017, I continued doing these projects, but I also started to meet other people who spoke this similar language. We all sort of like were aware of each other online because just not a lot of people think like this. Not a lot of people go that extra mile to deliver a punchline that you probably could have just said. And these people had very different backgrounds that were so complimentary. I'm talking people who were like, true software engineers and hackers, people who were like real artists and real craftspeople who knew how to make things with their hands. We would spend a lot of time talking, and I think the dream and the vision was always the same, which is, how do we only do this? Even not only that, if there is a world where we are only doing this, what can that become? Because there is no playbook for this. There is no precedent for this. We are flying blind. But it feels so fun. It's such a fun thing to explore. At the end of the day, all of this boils down to how does this pay for itself? How do you make money? And there's a lot of different routes that you can go with this. And I think people have tried different things in the past. People have taken the gallery approach, where you are a true artist and you get represented by a gallery and you create works and you show up at Art Basel and you sell artworks. People have taken the services approach, where you are effectively an agency with clients and you do, like, design work and creative consulting, so that at night, when you have free time, maybe you can make something that feels somewhat spiritually fulfilling. People have taken the media approach, trying to create content with existing distribution on networks like Netflix, but also maybe even YouTube. People have tried a lot of stuff. We had no idea what we were doing because none of us came from these worlds. So we did all of them, which ended up looking like we raised money from venture capital. We got represented a lot of money. We raised a good amount. Yeah, that's a whole story in and of itself.
- [16:18]
Patrick O'Shaughnessy
We'll get there.
- [16:19]
Gabe Whaley
We got represented by the blue chip gallery. We're creating content that's going to live on these networks. We even tried the client services thing for a hot second, and that failed spectacularly. So we killed that. But it was all sort of, what is that perfect thread the needle through line of doing the thing that you would do if money were no issue? And what do you need to do to make money?
- [16:41]
Patrick O'Shaughnessy
My guess is when you started, you didn't have the ambition to make this a historically important company or entity. In what direction has that evolved?
- [16:51]
Gabe Whaley
Yeah, I mean, back then it was like a very selfish thing. We were just bandits.
- [16:55]
Patrick O'Shaughnessy
We were like.
- [16:57]
Gabe Whaley
I mean, honestly, it was just. It looks like there's a lot of money floating around New York City. How do we get just enough? Maybe we're smarter to get some of that.
- [17:05]
Patrick O'Shaughnessy
And.
- [17:05]
Gabe Whaley
And let's make the best work of our lives, and then inevitably we'll run out of money. But it looks like that's celebrated these days. Maybe there's a way to spend that too. And then we'll run out of money and we'll just leave. We'll just change our names and leave. That was the plan. But then things started to work, and they were really working. So we raised some money in 2019, and that gave us the ability to start making, like, our first physical products. And somehow everything that we had learned from the prior five, six, seven years of creating things online, these digital experiences or websites or apps or whatever, that would get so much attention, these concepts would take a life of their own. Somehow that same phenomenon happened to the physical objects that we were creating. I think there was like a confluence of the nature of virality on the Internet with the nature of hype culture, with the nature of people's attention spans being way more volatile. There were like a lot of different universal factors that were at play that I think the timing lined up really well for us. But ultimately it was just working. People were buying the things that we were selling for better or for worse. They were reselling them, usually for like, multiples higher than what we were selling them at. Our audiences were growing really, really fast because none of us came from any of these worlds. We started learning the playbooks of all of these worlds that we dabbled in, but on sort of like a flat spectrum. So instead of someone coming from finance and then trying to transition to, like, another industry with all of their finance knowledge, we're just taking on both industries at the same time. Finance, startups, art manufacturing, fabrication, fashion. Like, we're learning all of them as one collective discipline. And so I think without knowing better, we pursued a strategy of just doing it all.
- [19:01]
Patrick O'Shaughnessy
Can we give an example of something pre physical product just to really nail home the sort of thing that you were doing in a purely digital sense, and then your favorite early example of a physical product. And just like the vignettes of each of those stories.
- [19:14]
Gabe Whaley
Sure, sure, sure.
- [19:14]
Patrick O'Shaughnessy
I'm sure we'll tell lots of stories, but just to ground people in those two.
- [19:17]
Gabe Whaley
Yeah, yeah. Well, the imessage gif is definitely like a great first example. Another one would be. So the day that Donald Trump announced that he was going to run for president, I guess this must have been 2016. There were like rumors in 2015, but I think this really went down in 2016. Obviously that was just shocking to a lot of people. And the first thing that I Did was I went and bought the URL friendswhich trump.com and I set it up to auto forward to the Facebook open graph URL that would load up anyone's list of friends who have liked Donald Trump. This is back when people use Facebook. This was maybe one of the first truly recorded instances of widespread cancel culture happening. Because that URL in a matter of hours was hitting the tens of millions of hits. There were no tricks. All I did was I shared it on my Facebook and I was like, check this out. Everyone started clicking it and then sharing it saying, I just unfriended 200 people. I just unfriended 30 people. I just unfriended everyone I went to high school with. Truly actually alarming in hindsight. This was going to happen regardless. So I didn't do anything to incur it. It just expedited a little bit. But that's another example of a digital thing. It's not like I'm trying to make a website with a bunch of cool graphics and parallax scrolling. No, it's not that. That's just a wrapper around a concept. It's about the concept. How can you use something digital to change someone's perspective or give them that.
- [20:47]
Patrick O'Shaughnessy
Experience where the virality is baked itself into the concept.
- [20:50]
Gabe Whaley
Right? And it's not even about going viral. Virality is not the goal. Virality is just distribution of the goal. You know what I mean? And I think that's a big difference that people probably miss a lot with mischief, where they're like, oh, the point is going viral. It's actually not. It's all about communication of a concept. So that's one digital thing. I guess I can tell you one more. This is kind of funny. I guess I can tell you about this one. I might not have ever spoken about this before.
- [21:16]
Patrick O'Shaughnessy
Perfect.
- [21:17]
Gabe Whaley
There was a time where there was the early AI personal assistant craze, x AI where people were CCing Amy at x AI into emails and saying, I would literally be emailing with someone, coordinating a meeting. And they're like, yeah, yeah, I'm CCing my assistant Amy. She's going help us find a time and spot. And then I'm reading the dialogue and I'm like, oh my God. They just cc'd me onto a thread with like a bot and they expect.
- [21:47]
Patrick O'Shaughnessy
Me to engage the bot.
- [21:48]
Gabe Whaley
It felt disrespectful, actually. I was like, this is so stupid. I hate this. So I made my own. I made my own competitor. It was called Reginald. Same premise. You Cc Reginald into your thread and Reginald will handle it for you. The thing is, I never built a bot. It was just me basically, like chained to my computer for 24 hours a day for literally water and food, going through my mouth in a tube. And I was responding in real time to everyone ccing me into their email threads as an AI bot because they didn't know that it wasn't AI. Which really makes you think the day that we all realize there is no AI assistance, they're all just people overseas.
- [22:25]
Patrick O'Shaughnessy
In the Philippines or something.
- [22:26]
Gabe Whaley
Yes, exactly. Looking back, and I've talked to some people in like the R world about that. They're like, oh, that was like a performance art piece. And I guess it was. The interesting thing about that though, is I got cc'd into the craziest proprietary email chains.
- [22:41]
Patrick O'Shaughnessy
Wow.
- [22:41]
Gabe Whaley
I got cc'd into mil email chains. I got cc'd into corporate email chains at MasterCard and other places. People would lose their jobs if anyone found out the information that I had access to. I got cc'd into Craigslist casual encounter email chains of a guy looking for a blowjob in Times Square. Really wild. So anyways, those are some examples of digital interventions. Mischief Lite, they're like predecessors to a lot of the things that we've done. Now that, where I would say anything that we do digitally now is significantly more complex and high production value and typically is designed to handle scale from the beginning.
- [23:23]
Patrick O'Shaughnessy
What do you think is a perfect example of an early physical product that had some of the same features of the purely digital?
- [23:31]
Gabe Whaley
I'll just tell you the first two. So the first one, and this was crazy because again, we're not fashion people or hype people or sneaker people by any means. We're truly just outsiders to all of these spaces. But we had this idea to take a Nike Air Max shoe and inject water into the air bubbles. Because then you can say you're walking on water like Jesus. And so we were like, okay, well, which Nike shoe should it be? And we narrowed it down to the classic Nike Air Max 97, all white. And we had it here in our studio. Some of us had some needles. I don't know why, but we took the needles, got some water, injected the water into the air bubbles, and we looked at it and we're like, oh my God, it actually looks really good. And there's the whole walk on water thing. But then we're like, okay, if we're going to do this, how do we build as much symbolism into this as possible. Well, okay, how many do we make? Let's make 12. One for each disciple. What do we price it at? What's the Bible verse where Jesus walked on water? It's Matthew 14:25. Okay, $1,425. Let's add this cross amulet that you can buy off of Amazon to the shoelaces because that'll just make it look good. Let's create packaging where when you open the box, the interior is a waterscape so it looks like the shoe is actually walking on water. We basically took a no holds barred approach to just jam packing as much religious symbolism into the product as possible. We actually didn't really know what was going to happen. Just looking at the shoe itself and the imagery of all the context that we designed around it, it was very compelling. We had the right feeling, and I think that's our biggest predictor even to date, of is this going to perform well or not? It's just, do we still get that feeling? There's a sort of shared electricity that jolts through all of us when we see it and we're like, oh, okay, this is going to be interesting. We built a website for it and like we do for everything. It's always like a bespoke website because that's the best way to control every aspect of the story possible, versus an Instagram post or a YouTube video where they control the constraints and the dimensions and the timing and everything. And we set the product live for sale, and the 12 sold out immediately. And that was the most money we'd ever made in our lives. It was like $25,000. And we're looking at the Shopify like, oh, my God, we're rich. This is crazy. But in the meantime, we checked the site traffic and it's just continuing to climb. It's climbing and climbing and climbing and climbing. And then we're checking the news and this thing is all over the news. And then someone messages us and is like, wait, you guys are on Late Night with Seth Meyers right now? And they send us the clip. And Seth Meyers is talking with the shoe in his background. He's talking about the shoe and how this is taking over the Internet. And then he closes out by saying, don't forget, Jesus rose from the grave three days later. And when he said that, we all looked at each other like, oh, my God, let's do it again in three days. So over the next three days, we went and bought every single Nike Air Max 97, all white in New York City, went to Every single store. I remember going into the flight club and I was like, I have five credit cards. I will take. How many do you have? And they were like, for real? And I'm like, yes. We ended up getting 67 pairs, brought them back to the studio, made all of them in three days, got the packaging, and we're ready to go. Three days later, we set it live again to go for sale. And we're just praying, let these sell, please. We don't want to be stuck holding the bag on 67 pairs. They sold out instantly again. So we're looking at some $100,000 in our bank account. And this is where my recollection of the story gets a little bit hazy, because it's in the movies where time slows down a little bit and everything's blurry and hazy. I remember the guys were not really celebrating, but yelling and stomping around, like, pulling their hair out, like, oh, my God, this actually happened. Is this real? Are we dreaming? It doesn't seem real, but I was the one still on the computer and the shopify. Apparently during the 30 seconds between when the shoes sold out and 30 seconds later, I started increasing the inventory on the back end until 30 seconds later, we hit a million dollars in sales. And then I shut down the store and I closed my computer and I looked at the guys and I'm like, we have to make 700 pairs as fast as possible. It was 11:30 in the morning on a Tuesday. I remember we walked down to the only bar that was open at that time in Brooklyn. We had a drink for an hour in silence. No one talked. We were not celebrating, but we also weren't fighting. And then we walked back in silence to the studio. And as soon as we got through the door, credit cards started flying and phones started dialing. We were hitting up every big box retailer in the tri State area. We needed to buy 700 pairs of these shoes, make all of them, and deliver on the sales that we had done because we had just never seen anything like that. And while the guys did that, I hopped on the first flight to San Francisco and raised more money.
- [28:40]
Patrick O'Shaughnessy
Wow.
- [28:41]
Gabe Whaley
So similar sort of feeling, vibe and energy from the digital outputs that we had cut our teeth on getting started. But when it comes to a physical product, it's just so much more visceral because you're touching things with your hands, putting things in boxes, you're shipping them to real people, and there's real money involved. It's intoxicating.
- [29:01]
Patrick O'Shaughnessy
I have to ask a question that's probably hard to answer with words. You've already said it. But it feels key to this, which is you talked about it as a language before, that everyone kind of speaks the nature of the feeling. When you know you have something, what else can you say about it that is in the things you create that allows this sort of thing to happen? Because it's amazing how consistent it is across the body of work. And I'm going to start diving into different. The art world, the fashion world, they're all different. But you've been able to do it in enough places now. This is not random. Maybe now's the time to talk about the process that leads to one of these outputs. Because I just want to understand more about what is imbued in that shoe and the million other things that you've done that just have this quality to capture imagination.
- [29:51]
Gabe Whaley
Yeah, yeah. If I knew how to articulate the magic, people would have probably tried to figure it out by now. And I think they are trying to. And not to dumb it down, but I think a big part of it is at the end of the day, I don't even think what we do is that profound or new. It's actually like pretty simple. It takes something that people are generally familiar with, whether it is a shoe or an existing artwork or an existing system, the imessage dots. These are systems that people are already deeply familiar with. We just have to like tweak it a little bit, inject our point of view into it and then push it back at you. And so really, at the end of the day, I think the greatest mischief projects are ones that are this multi angled mirror that are just reflecting a slightly distorted version of your own reality back at you. And we have a pretty good sense of when we've done that well. And we have a good idea of even before it goes out to the world. This is tapping into not the zeitgeist, because mischief actually doesn't exist in the Zeitgeist, because we do these things a year in advance. There's a term that often comes up in conversations around Warhol and Duchamp of cultural readymades, which is this idea of taking an existing object and culture that is known for one thing and then putting it in a new context that will give it a new meaning. So Duchamp did that with the toilet. Toilets are designed for what we all know toilets do. But then he puts it in a gallery setting or a museum setting and it really just shocked everyone. I think we do that in a way, but in a way that's more relevant to just the way that the world works right now.
- [31:34]
Patrick O'Shaughnessy
What did you do at Art Basel at the atm?
- [31:37]
Gabe Whaley
So this is actually a funny story because it was never about going to Art Basel and this was never about us being in the art world. This was about us finding the best way to distribute an idea that we had. So we had this idea a while back of creating an ATM machine with a digital leaderboard as part of the ATM machine. Totally normal, functioning atm. You can withdraw cash, you can check your balance. But the twist is if you do any of those things, it will take your photo and then rank you on a leaderboard with other people based on who has the most amount of money remaining in their bank account. So it's gamifying the flaunting of wealth. We were like, okay, this is amazing. We have to do this. But the concept is never enough for us. You also have to think about, where does this concept show up? How does it show up? So we were like, okay, this could go maybe somewhere in Brooklyn outside of our studio. Maybe we find a way to put it in Times Square for, like, the foot traffic there. But then the more that we kept thinking about it, we're like, we've heard of Art Basel Miami, and it seems to sort of be like the armpit of the rich people world. And the more that we, like, poured into it, we're like, this really seems like the best place for this ATM machine. So how do we get it there? What is Art Basel? We don't even know what it is actually, right? So we find artbasel.com or whatever and start cold calling the people who run Art Basel. Actually, I remember calling their head of North America or something. And I was like, okay, I'm with this group called Mischief. We have this art piece that we want to display at your art fair. How do we get a booth? And they sort of like laughed me off saying, that's not how it works. Only galleries get the booths here. Artists can't just submit random pieces. And I'm like, okay, sounds good. So two weeks later, I come back and I've incorporated Mischief Gallery. And I'm like, we have a gallery. We'll pay, we'll do it. How much does it cost? We'll do it. And they're like, no, no, no, again, that's not how it works. We have like a pre vetted list of galleries that are known to us a long time in advance. I'm like, oh, wow, I wish you just told me that. Where is this list of galleries. So I get the list of galleries, and this is where I start learning about the art world. From the beginning of that ecosystem, between the art fairs and the art advisors and the blue chip galleries and the more experimental galleries and the museums and the auction houses, it's a very interesting ecosystem of smoke and mirrors and lies and deceit. But back to the original point of the story. I started cold calling all these galleries because I realized I need to go in through them, and so I'm cold calling. I don't know how much you hang out in the art world, but Gagosian and Pace and Hauser and Wirth and White Cube and Zwerner, I was just going down from the top of the list, and none of those panned out. But somehow, through a different avenue, I ended up meeting Emmanuel Perotin, who represents a lot of artists that a lot of people are familiar with, like Maurizio Catalan, who had the banana at Art Basel a few years prior. So of course he was going to take our call because it makes sense. And now we're good friends with Maurizio. Anyways, Emmanuel was like, yes, let's do it. The ATM machine sounds great. So we take the ATM machine, we get into Art Basel. Funny thing, the first day is the most exclusive preview day for, I guess, the richest but shadiest people. They were so not into this project. They would walk past it, and you know when someone walks past you, but you know they're paying attention to you, but they're clearly not looking at you. Like they're working really, really hard to not make eye contact. That was our ATM machine. That whole first day. People were just not having it. But as the week progressed, it started to open up a little bit more to the public with each day. Until, I guess, like day three, it was fully open to the public. And by that point, this thing was truly like the talk of the town. It was the piece of art Basel Miami 2022, to the point where the fair made us relocate it. Because the crowd was getting so big. It was blocking fire escapes. They assigned five extra security guards just to man the crowd. Because the crowd was also getting. Not rowdy necessarily, but they were bumping into the art of the other galleries, which is not good. And then the most interesting thing happened, which was a new group behavior started to occur around this ATM machine. There was always a big crowd around it, and people, once they would muster up the bravery, they would go do it. And at that point, it's a performance. You are performing in front of a Captive audience willing to sort of show where you stand among the wealthy and the poor. And what ended up happening was there were two types of people who would engage and two types of responses that these people would get. There would be, like, normal people, like students or younger people who would go up and they would have a remaining account balance of $27. And when they would do that and get sunk to the bottom of the leaderboard in front of everybody, the crowd would erupt into applause. Kind of a wholesome thing. We see you, you see us, we are one and the same. And then you juxtapose that with the really rich people who are also. If you're engaging with this, it really says all that you need to know about this type of person. The wealthiest person who engaged with this actually did it twice. He was probably like late 30s, early 40s, athletic build. He had on a suit with an oxford shirt that maybe was unbuttoned one too many times. 5 o'clock shadow, gold chain, Gucci loafers, and a very attractive girl on his arm. He came and swiped and clocked in at like five and a half million. And the couple turns around to the audience expecting the same reaction. And it's crickets. Complete silence, honestly. So excruciatingly awkward. But that's not the end. Three hours later, they come back and he swipes again and clocks in at nine and a half million and then turns around and still the same reaction. And so maybe at the end of the day, the outcome of the experiment was quite wholesome. It was good, which is, I think normal people get it.
- [37:49]
Patrick O'Shaughnessy
One of the progressions that I'm most interested in for mischief is that at first it's sort of isolated thing. You buy some shoes, you do some things here, outside the door we're sitting, you send it in packages. And it's a pretty tight loop. As you've entered more big worlds. Art, fashion, maybe hospitality, other big things where there's all these different stakeholders you've described to me before that you get sucked into and begin to be shaped by the world. And I think there's lots of perversions that you've learned about in these worlds. Maybe go to fashion next, since we talked about art there for a minute, how does that feel to enter into, like, an alternate reality where there's all these different rules and there's all these different players, and what do you learn and how do you avoid getting sucked into the game and staying independent as the outsider?
- [38:37]
Gabe Whaley
Not by choice. We're all outsiders because just somehow we never landed inside of these institutions. It's not like we really made a conscious decision. It was just never accepted. So you don't really know what you're signing up for. When you start to get not just accepted by these worlds, but pulled, I will say it's fun. You are able to learn from a fire hose so quickly about the social dynamics, the hierarchies of the power players, how the products and the manufacturing and the distribution works. What are the cultural symbols that are important, what are the pockets of these people, how do they operate? Where do they hang out in the city, where do they hang out globally? How do they view each other? What's the existing drama within all of these worlds? It's actually really, really fascinating. I think the cool thing is from our vantage point we're able to see all of these worlds at the same time and pick and choose what's meaningful to us and also what's not meaningful to us and maybe what's harmful to us. But you do have to be careful because it's a vanity thing. At the end of the day you're like being accepted by people in high positions that we're just not from those places. So part of it, it does feel good. It feels good to be accepted. It feels good to be recognized, feels good to be validated for being good at something. And it's a slippery slope because we have to remind ourselves we didn't do this to be validated. We never did this to be accepted by these worlds. We did it because we think it's all absurd, all of it. And so how do we keep our sanity? Like how are we able to look in the mirror each morning and still see who we were originally versus this new person that we could become? And it does get hard. It is tricky.
- [40:18]
Patrick O'Shaughnessy
Is it fair to say that there is both from an ingredients sense, some nihilism and some like incredible hope and generative?
- [40:26]
Gabe Whaley
I think you nailed it. It's nihilism in the sense nothing matters. And we're not necessarily going to make the world a better place, but maybe this will ease your fall. And in that sense it's a little bit hopeful too. We're not mean spirited, we're not edgelords necessarily trying to take the piss out of an institution or something like that. I think there's just a hidden way of seeing the world. Subversion can be a higher form of creative output. It just fuels us for some reason. There isn't even necessarily a higher calling beyond our personal desire to make the most creative work of Our lives.
- [41:04]
Patrick O'Shaughnessy
Let's talk about process in detail now. How, if I take anything that's coming off the line next week, how far back does it go? Who contributes ideas and how? What role do you play? How does the team work together? In as much detail as you can. Like, what is the process?
- [41:20]
Gabe Whaley
The most important thing that I think I've done here was create a system where people are not afraid to have ideas. So if you think of any other creative workplace or creative industry, typically junior people are pitching to senior people. Jobs are on the line, pride is on the line. You're afraid to be wrong, you're afraid to be judged for a bad idea. To me, those are the killers of creativity. So from the beginning, I did a lot of work a curating the right type of people, where ego is not an obstacle to having a good idea or preventing someone else from having a good idea. Creating an environment where people can feel a little bit reckless, they can make mistakes, they can make a mess. And that's very straightforward. You look around at the space, it feels like you can make a mistake. Being in a warehouse is really important, actually. If we were in a white box in soho, you wouldn't want to mess it up. And then creating also this culture where it doesn't feel like it's just my ideas getting made or the ideas that I like, that really boils down to creating a certain sense of codes and sensibilities that we all sort of agree on culturally. And you see that come through in the work. So that was the most important thing that I ever did. Because at the end of the day, the people who come up with the ideas at Mischief are actually everyone. You can work on the finance team, you can be our general counsel, you can be on the manufacturing production team. Anyone here can come up with a good idea. Anyone is capable of coming up with a good idea. And in fact, it's more valuable to get good ideas from people who aren't in the business of good ideas, because their vantage point is real versus people who. There are people whose jobs are to come up with ideas, but they don't exist in a space that they can actually reflect on. It's fake. We choose to exist in real spaces. And then as a result, you create ideas that are able to exist in these spaces as well, in a way that's very interactive and almost experiential in a way. So that's the vibe part. But then brass taxes, you brainstorm rigorously, multiple times a week. They're timed on the same schedule every single time. There's a curriculum planned in advance. It's almost like designing a school curriculum. So, like, every quarter, there are topics and concentrations and themes that we think are important for mischief in the future. And then also topics, concentrations and themes that we have no idea about. Just to like, challenge ourselves with new information and keep challenging ourselves to not just exist in our own bubble that we've created. The brainstorms happen. Every idea is documented. We have an entire library of these ideas. And then over, I'd say, like a three to six month period, all of these ideas are run through a fairly long tail vetting process that involves evaluation based on normal things like, can we afford to do this? How much money are we going to lose doing this? Will we make money on this? Is it even possible? Or does it need further research? But then also things like, does this shape the personality of mischief in the way that we want? It's almost like mischief is a child and we're like, raising it. As soon as we land on concepts that we feel really good about, we actually put them in a pile and then forget about them. And that part is what makes this take six months. Because then we will open that pile six months later, look at them and be like, okay, I already forgot about these ideas, but now that I'm looking at them again, do I still feel very excited about them? Have they survived the test of time? And if they do, then they're ready to slot for production. And typically that's done about 12 months in advance. So even now we know all of next year's calendar already.
- [45:03]
Patrick O'Shaughnessy
Wow.
- [45:03]
Gabe Whaley
Yeah, we're already working on it.
- [45:05]
Patrick O'Shaughnessy
You've talked to me before about the value of rules. I think something you said was, rules are interesting because they let you know where people, before you drew the line, say everything you've learned or think about rules and the role that they play.
- [45:18]
Gabe Whaley
That line is specifically something I remember writing down when I was at West Point because there were just so many rules. They typically drove most people crazy while they were there. Because, I mean, it's the army, if you break rules, you're going to get in a lot of trouble. It's as simple as that. And there are so many rules for everything that it's impossible to not break a rule. But for me, and maybe this is my problem, but every rule was an opportunity to create some sort of absurdity that I thought was just really entertaining, even if it meant I had to do a thousand pushups for it. This is my coping mechanism. I'm going to put a copy of The Communist Manifesto on my bookshelf during the inspection just to see what happens. And of course you get destroyed for that. But it's so funny when they see that on my shelf. And so very similarly with Mischief, you look at these institutions, you look at how these herds of people operate in different worlds and different concentrations and you understand where their lines are. But we really see the lines as opportunities, not constraints. They're just creative opportunities.
- [46:24]
Patrick O'Shaughnessy
So you're playing with boundaries is the bottom line.
- [46:27]
Gabe Whaley
Yeah, and I think in the most, I guess, concrete sense of the word, we even look at the law as a creative opportunity. And when you really think about the law, and hopefully all of us know this by now, the law is clearly not objective and it is not set in stone and it can be changed on a whim based on who's in power at any given moment. So for us, we actually embrace that as a very creative opportunity to maybe change the way that the law is interpreted or even create new laws. And I think that's very interesting actually.
- [47:04]
Patrick O'Shaughnessy
I want you to not hold back on the answer to this question. What impression and lessons did you learn interacting with the world of venture investors?
- [47:12]
Gabe Whaley
Honest answer. Just like any other industry, there are good ones and then not so good ones. I think this is less about venture investors and more of just the nature of all of these different variables that have descended on the world in the last, I'd say five to 10 years of a lot of capital and hype being way more valuable than long term sustainability. I think venture capital in many ways became a quick fix to someone's vanity. And when we realized that, we were like, well, we should raise money because we can play this game. But what I didn't realize is a, there are good ones, people who are down to embrace the long term vision, even one as ambiguous as Mischief, and also have our back through all of the crazy things that we've been through. And I think we've had really, really good ones. But I'll say the bad part, which is I think VC and also tech in general are just so self important and so insular to their world that they forget about the rest of the world and how real people think and what real people care about. Maybe that's fine because I think most people in various industries do that too. The other part is generally these people don't really have good tastes. And so there was a time where I think mischief was being pretty celebrated by Silicon Valley, at least in the early days. Like every early stage company, when you raise money, it's like, wow, this is the next hot thing, and whatever. But then we started doing things that maybe didn't really speak to the tech world or the VC world as much. It was speaking to other worlds. And then you started to sense some tension and lose that early fan base. And there was an aha moment where I was realizing, I'm really paying attention to their feedback. I'm seeing what they're saying online, reading Twitter and LinkedIn and seeing people do the big threads, analyzing what our new move was and what they think we're doing wrong. And I was like, holy shit, I almost fell for this. I almost started creating exclusively for that world because it's where the money came from. So I deleted my LinkedIn and Twitter and Facebook. I got off cold turkey, sent my Instagram to Private, and I was like, I will never let, not even just vc, but I will never let any specific world have that much influence on the things that I choose to do.
- [49:34]
Patrick O'Shaughnessy
If you think back on the project that got the biggest, which one comes to mind?
- [49:40]
Gabe Whaley
Definitely the Big Red Boots.
- [49:42]
Patrick O'Shaughnessy
For better or for worse, say more.
- [49:45]
Gabe Whaley
A year ago, we made these big red boots that just look like a Astro Boy. I mean, that's it. There's nothing really that profound about it, but I think we made them at a time where there were a few things happening. One, in the fashion space, there was this movement towards the absurd, absurd pieces. So that was happening additionally in the fashion space. And sort of just like in general, we live at a time where people aren't sharing new information, they're actually just sharing content of them reacting to new information. That's another thing that was going on. We were sort of at this peak of the hype cycle around sneakers and footwear and resale and all of that as well. And we're at a time where the algorithm is what dictates virality. But the alternative is still true, which is when human beings see something that resonates with them, they will find a way to share it or share their reaction to it. Oh, and then one other thing was there had been a lot of talk of AI and metaverse, and I don't know, the Big Red Boots looked like it was photoshopped onto people, like it existed in this strange, uncanny valley of is it real or not real? So all of these factors combined to create this perfect storm that we had no idea was coming. We made them, and we only made a couple hundred pairs. I remember looking at my partner here running around in the studio with them, and we're like, those look kind of cool. Let's make some. But nobody's going to buy these. And they were really expensive to make because we made them at a really high level of quality. So we're like, we'll make a couple hundred and we'll just sell them. And I think it'll be cool. I think people will talk about it. And it's interesting. It got so big, everything hit. The algorithm smiled upon it. And then as soon as people realized that, they were like, wait, if I do content with the big red boot, I'm going to get 100x the views that I usually get. And then in addition to that, people were sharing it. Like the old days, people were literally finding screenshots of this boot online and sharing it with their friends on their platforms. So you're getting old school virality, pure, emotionally driven sharing with new school virality. The algorithm has smiled upon this, creating the perfect storm of a pretty iconic image. Not in the sense that I think it's important or not, but it's just so recognizable. Never seen anything like it.
- [52:10]
Patrick O'Shaughnessy
Have you ever felt the feeling like the Shopify store feeling with the Jesus shoes sense?
- [52:16]
Gabe Whaley
The feeling is we've looked at each other when it's happening in the past and we're like, literally what we say to each other is, all right, buckle up, because this is no longer in our hands. We don't control this anymore. It has taken a life of its own. The narrative is going to change. It's going to find different audiences, they're going to reshape it to fit their perfect image. That's what happened with the big red boot at the beginning, the first few days of it starting to really pop off. It existed in these niche underground creative fashion spaces. A cool underground thing that not that many people knew about, that you could style creatively. And it was cool. And we were like, this is amazing. We want to be in these underground spaces. But then it hit mainstream so fast that it became basically like a tool to go viral. And I'm not saying that's a good or a bad thing. It just changed shapes. It had a different meaning at that point. And you just can't control it when it happens. You don't control it. You just pray.
- [53:15]
Patrick O'Shaughnessy
How do you think about the fact that if you had turned that store back on with the Jesus boots or something, maybe you could have sold $10 million worth? Talk a bit about supply and demand and that line, and if that's something you mess with too, or what you think about it and have learned about it there's so much written now about luxury products and always having supply be 1 less than demand. How do you think about this topic?
- [53:38]
Gabe Whaley
The up close micro perspective, not selling enough compared to your demand makes sense. You want to hold that over for later or something. But for us it's not really about that. It's about every two weeks we release something new and they're all going to spike at different levels. Some are going to be bigger than others, but we're at a point right now where they will all be a spike. But every time you do a spike, it builds off the foundation that was left by the prior spike because there is continuity, there's retention. And so when you zoom out from the past five years, it's actually just one big upwards curve because you're building on what was held over from the prior. Now the tricky thing for us when we're doing that is we are not selling out quickly of big Red boots so that we hold over an audience to sell them big red boots. Again, we are holding them over and then we need to educate them to be okay with the idea that the next thing after the Big red boots is anime dating tax service software. And we churn a ton of people from that because they're like, I was here for these shoes. Why are you sending me TurboTax competitor anime dating Cafe? But what that does is we're building the world for ourselves that we want to exist in, where creativity is that ultimate North Star from a value perspective. And so supply and demand isn't as much of a tool to move more of the same. It's more of a way to generate attention that helps us distribute an idea and a concept that can hopefully educate a significant enough percentage of those people to stick around with us for the ride.
- [55:21]
Patrick O'Shaughnessy
You said something to me before which I loved, which I've used a lot since, which is that you can't define mischief just as you couldn't at the beginning, but you can think about how you are trying to monopolize a certain feeling for the person interacting with mischief. How would you describe that feeling that you're trying to monopolize? And I love that framing. Anyone can ask that question of themselves, right?
- [55:41]
Gabe Whaley
Right. I love that it will be different things to different people. But I think there is this feeling of subversion. There is this feeling of levity. It's kind of funny, but not funny in the way that you see on Saturday Night Live. And hopefully it also just makes you pause and think a little bit like, oh, interesting. I never thought of it that way, but it's totally true. This is just a reflection of a phenomenon that already exists. And then at the end of the day, hopefully you just see it and embrace this idea of pure, unbridled creativity. That's what it is at the end of the day. It's the idea that nothing that you see in front of you is what it may seem. It can be an opportunity for something like so much more. And hopefully people are seeing what we do and they feel inspired to break some rules, make something or do it in a different way. The rules are all fake.
- [56:35]
Patrick O'Shaughnessy
One of the things that's so important here is protecting that creativity. And I know sometimes you do that with legal work, with technology, work with capital that can fund these things. Protecting that core raw thing seems like the heritage that you're building up. If you were giving a sermon on how to protect one's creativity based on everything that you've learned and all the times you've felt the siren song pulling you away from it and wanting a certain world to give them what they want versus express yourself creatively from all that added together, what would you say about protecting one's own creative potential?
- [57:12]
Gabe Whaley
It's a tricky one and it's something that I couldn't even say I've nailed perfectly. It's something that I'm just constantly working on. And every time you feel it slipping, you have to be so alert, acknowledge it and deal with it immediately. But there are like tactical things that you do, and this is probably all of the MBA business school, self help book type stuff. Choose the right people, fire the wrong people, set the right vision. These things are cheesy, but they're true. There's more to it as well. How do you create an environment where fear isn't the primary motivator for someone to get their job done? How do you curate a physical environment where people feel like they can make mistakes? How do you celebrate the act of creation and not the act of virality? For example? We never celebrate when something hits. We don't celebrate when something goes live. If anything, we'll celebrate the day before just to acknowledge the act of creation, which is to us the most holy act. A lot of these little things build up to preservation of this feeling.
- [58:15]
Patrick O'Shaughnessy
Why is it a holy act? It's quite a phrase.
- [58:17]
Gabe Whaley
We make stuff from nothing. It is literally like an act of God. There was nothing and then there was something. It's been that feeling ever since the beginning. Even making my first website, it was such a eureka moment for me where I Was like, holy shit, it wasn't there. And then I literally spoke. And now it is. That's a crazy feeling. We can never forget that feeling.
- [58:38]
Patrick O'Shaughnessy
The stark contrast is West Point. In my mind. What is the most good and bad things that you remember or take from the couple years that you were there? I think you left right before the obligatory service kicked.
- [58:50]
Gabe Whaley
Exactly. So I did the hardest part, which was the first year, and then I stuck around for one more year, which was about how long it takes to quit. So, I mean, personally, I probably needed my ass kicked a little bit. I wasn't a fully formed human being yet. So there is something to say about the discipline and the work ethic that you get from it. I think the biggest thing is West Point to train you for what you're going to do later. They get you really comfortable with the impossible task. So the best example is the rule for the academic curriculum is for every hour that you're in class, you're assigned three hours of homework. But West Point isn't run like a normal college where you choose your schedule and stuff like that. No, you're in class for seven hours a day. So if you do the math, the math doesn't add up. Not their problem. You just have to figure it out. It's impossible. Let's say you get in trouble, you have to do a thousand pushups. Not many people can do a thousand pushups. Most people cannot. Only a few in the world. Ever. Again, not their problem. You just have to find a way to get through it. And I think that was really valuable because mischief is used to taking on things where it's like, there's not really a playbook on how to do this. It's not straightforward at all. And you just figure it out. You roll your sleeves up and you figure it out. And I think that was a really valuable thing for me personally. And then. Sounds so cheesy. The leadership lessons are also really good. I remember being out in the field during your summers, out doing patrols for months. We were out in the field and there was a simulated mortar attack. So you see the things flying in, you hear the sounds, and it's like, all right, we got to get out of here. And I remember my platoon leader was like, all right, we need to run this way. Grab all your stuff. So it's like you have an 80 pound bag, you've got your weapon, you're running. And there was someone on the team who was a lot smaller. I mean, she was probably like £70 and she had an 80 pound bag as well. And she had a pretty bad trip because we're just running. You got to go. Without hesitation, he picks up her bag as well, hands her her weapon and is like, let's go. So he shoulders close to £160 and books it. And then once we get to safety, hands her back the bag. No questions asked, no issue. And I remembered seeing that, I was like, I like that you take care of your people, you don't make a big deal of it and then you move on. I thought that was really good. Those were a couple of things that stuck with me. The bad things, I don't know. I think it's all pretty good experience, actually. It's more so if I stayed, I was going to just keep getting in trouble and then that's when really bad things would happen.
- [61:26]
Patrick O'Shaughnessy
Do you think the fact that you came out of that, because I know prior to that you really didn't have a lot of culture experience. My understanding is you were not allowed to do a lot of stuff as a kid. Played a lot of piano and were.
- [61:36]
Gabe Whaley
Incredible, pretty good classical pianists, incredibly focused.
- [61:39]
Patrick O'Shaughnessy
Do you think that emerging as a 20 year old without any influence on you ended up being a major part of why you're able to.
- [61:47]
Gabe Whaley
I think it was huge.
- [61:47]
Patrick O'Shaughnessy
View the world this way.
- [61:48]
Gabe Whaley
Yeah, it was huge because I learned about culture, Culture all at once on a flat spectrum. I was learning about Urban Outfitters at the same time of learning about Kanye west at the same time of learning about Marvel. And also Instagram had just been bought and the Social Network had just come out. I was getting all of these things as if they were part of the same core curriculum. I do think that was very valuable. And you just have such an open mind because you're like, the world is so big and I don't really know where I belong here. I think that was everything, actually.
- [62:21]
Patrick O'Shaughnessy
The point you made about impossible tasks, the hours of homework or the pushups, what's the best analog in the projects that you've done, which project was the most impossible task that you've tackled and gotten through? And I ask because it seems like every story I've heard, and I've heard so many now of people creating incredible things, this kind of ends up being a. Or the key ingredient.
- [62:44]
Gabe Whaley
Yeah, yeah. I should have specified earlier. I think most people in their careers do hit this wall and they learn how to deal with the impossible TAS task. The thing about West Point is I got it on day one as an 18 year old. Super valuable for us. I Mean, mischief is the impossible task. We shouldn't even be here, right? On paper, this doesn't make any sense. There's a good friend of mine who is. Actually, he spent some time in VC, and I remember talking to him in 2019 when I was trying to figure out if I was going to race for this or not. And he was like, honestly, I like you, but I don't think you can do it. And it has nothing to do with you. It just doesn't work this way. This kind of thing doesn't work. You need such a repeatable hit rate. You need such a strong understanding of audience and retention and a nose for culture. It can't work. It can't last. Actually, I hung out with him a few weeks ago, and he said, yeah, I remember that conversation. And honestly, if someone came to me today pitching what you were pitching, I would tell them the same thing, like, it shouldn't exist. I agree, it shouldn't. This is the impossible thing. And then every project has also got its impossibilities, too. And you just figure it out.
- [63:52]
Patrick O'Shaughnessy
Tell us what you've learned about fashion.
- [63:54]
Gabe Whaley
I think fashion is two things. I think on one side, fashion is utility, basic needs, shelter, protection. And then the other side is fantasy costumes. Human beings love costumes. Personally, I hate Halloween, but people fricking love Halloween. And then I go to these fashion Runway shows, and I'm like, wait, they're just celebrating Halloween early? This is crazy, right? It does come down to fantasy. And the fantasy is not just tied to aesthetics, but it's also tied to value and legacy and symbolism and cultural readymades. And because of that, I think it is such a rich space to play in, because also it is so tied to identity. These are symbols that are created by designers that are created by brands that you wear on your body. And in some ways, they kind of serve the same function as a painting in your home might. So I think it's interesting when Mischief sees that we're like, okay, you can try to focus on creating things that are aesthetically pleasing, and that's one way to go. But you can also seek to exploit the tensions that people have between these objects, not just from an aesthetic perspective, but also like a value perspective, an identity perspective. Last summer, we made a handbag that was the size of a grain of salt because we noticed this pattern of the smaller the handbag gets, the more expensive it seems to become. And we're like, well, let's make one really, really, really small. And then it's sold at auction for $64,000.
- [65:22]
Patrick O'Shaughnessy
What?
- [65:23]
Gabe Whaley
So most expensive handbag of all time. By volume, for sure.
- [65:26]
Patrick O'Shaughnessy
How did you do it?
- [65:28]
Gabe Whaley
So my best friend from childhood, he's a postdoc at Columbia and Biomedical engineering. So he helped us basically identify and then modify a manufacturing process that allowed us to create this handbag at a microscopic level. We made it. There was an image of a little green speck on a thumb that just spread like wildfire last summer. And it said everything that everyone is already thinking about fashion, which is. It is absurd, but not in a hateful way. It just. It is.
- [66:01]
Patrick O'Shaughnessy
What do you make of the fact that only fans has orders of magnitude more revenue than Patreon?
- [66:08]
Gabe Whaley
We're just humans at the end of the day. That's all it is. There's nothing profound about it. It's just whatever Maslov's hierarchy of needs, it's all bullshit. All human beings care about is being able to eat, sleep and reproduce and flex on your neighbor. That's like the true. Those are the only things that matter to us as human beings. And obviously OnlyFans takes like a huge one of those, and then TikTok Instagram, social media takes a huge one of those, and then the rest is just fun and games.
- [66:38]
Patrick O'Shaughnessy
Have you ever played into the flex on your neighbor? Very directly and specifically?
- [66:41]
Gabe Whaley
Oh, that was the ATM machine. Yeah, of course. Yeah, yeah, yeah. There was a website that we made a long time ago where it was first person social media footage of dining experiences at the finest dining establishments in New York City. So, like, imagine like vertical videos of, oh, I'm at Carbone, here's my meal. Or like Noma or 11 Madison or Per Se, or Le Bernardin. And then we created a website that published all of this footage so that you could download it and post it to your stories. So it looks like you're eating at all these places and people did it. So many people use this.
- [67:17]
Patrick O'Shaughnessy
One of my friends has this great saying, we're not searching for meaning, but for the feeling of being alive. Is that what you are chasing, do.
- [67:24]
Gabe Whaley
You think, for ourselves or for the people who interact with our stuff?
- [67:27]
Patrick O'Shaughnessy
Both.
- [67:28]
Gabe Whaley
Definitely not meaning. I don't think we're smart enough to even know that for ourselves, much less other people. The feeling of being alive. Yeah, maybe. The truth is, I just don't even think we're that profound about it. At the end of the day, it's a lot simpler. We see the world in a very particular way, and then we communicate it in a very particular way. And I think in some senses, Music is the best analogy, I think. Mischief is a band and we have a very particular sound, we have a particular set of instruments, and we've been on tour for a few years now, and it's going pretty good, which is great, because when we first assembled, we were only playing at weddings to really, like, continue this analogy. But then it started to work. We just have a sound and people seem to be into it.
- [68:14]
Patrick O'Shaughnessy
I know you have the right people, you've recruited the band members. What have you learned about doing that effectively? Like, what is great recruiting, abstracting away the kind of person you're recruiting? What have you learned about getting ridiculously good at that?
- [68:28]
Gabe Whaley
The initial core group. So there's like a founding team of four others. We started jamming together back in 2018, I think, and there was no sense of recruitment there. It was just the vibes, vibes. And we all had nothing to lose because we had nothing going for us. This was pure luck. But we're still so tight and aligned even today, even though we've grown and our own context has changed and Mischief's place in the world has changed. But there is something so magical about being in a room with that initial group of people where you're just grooving. We were just so remarkably on the same page, but had such complementary skill sets. Nothing like it. But then, of course, you have to grow and you have to find your team, and I think you place a lot of value on things that probably end up reflecting yourself a little bit. I think like attracts like. And for us, we have a high emphasis on the ability to, like, roll up your sleeves, to be scrappy, to get through that impossible task. We have a big emphasis on being a good person, which I know everyone says, but for us specifically, that means you're humble, you don't bring in ego. And what that usually ends up also meaning is that people here are nerdy and introverted. So even though I think we're pretty well known now, you might even say famous. If we really wanted, we could start showing up in these circles with these socialites at these clubs and parties, but we don't. No one here does. No one here cares. In fact, I think a lot of the people here, when some of our stuff really pops off, they actually don't know, because they don't even care if it's big or not. They just care that they made it. And I think that sensibility is really valuable. That's why this place exists even today, and that's why we really haven't had many People quit ever under five, I think in five years people stick around.
- [70:24]
Patrick O'Shaughnessy
Does it feel like you're at any sort of crossroads right now?
- [70:27]
Gabe Whaley
Yeah, yeah, it totally does. There are a few things that are going on. One, our context has changed. We're not unknown, underdog as much anymore. I wouldn't say we're establishment, but we're just a lot more well known. That changes how we see the world a little bit and that also changes the type of work that we can do a little bit because we're just bigger. The other part that that also impacts is it changes a little bit about how we see ourselves and how we talk about ourselves and how we like communicate with others. There was a time where we were a huge black box. I would never be doing this interview with you because there was value in the secrecy when nobody knew who we were and they couldn't understand our intentions or our motivations or our goals. But now that we're more visible, I think we're hitting a point where it makes sense to share a little bit more in hopes that other people see this and walk away rethinking their own perspectives on creativity and the act of creation and doing things, which I think is really good. So those are sort of the philosophical internal struggle crossroads. But then there are other crossroads too in the world right now I think virality is increasingly just a cheap tool. Like I said earlier back in the day, the act of going viral was black magic 10 years ago, but it's not the case now. Now it feels artificial, cheap, kind of gross. So we're thinking a lot more about almost how to suppress virality, actively fight that, which is a crazy thing to think about. That is not what a real business would say to do right now. It's continue to hemorrhage as many free eyeballs as you can. No matter where they come from or what the intention is, just keep doing it. For us, I think it's an important time for us to think about how do you make that a little bit harder for people? How do you create more secrets? So that's another crossroads that we're at. And then I guess from a business point of view, we also have to think about the difference between quick short term cash and long term cultural importance. Where our motivations are the opportunity to make money tomorrow exists. But then we have to remind ourselves was that the goal when we started or has our goal changed? What is that now? And I think where we're ultimately navigating to is when we started this, it was always how do we create a world for ourselves where we can just make all this stuff in our heads and then do it with our friends. And I think that very much continues to be the case. And then the other part is, for better or for worse, we want to see this last as long as possible. And we don't really know what that means or what that looks like.
- [73:03]
Patrick O'Shaughnessy
Are you surprised by that? When you started, did you think that you would end up caring that this thing last for a very long time?
- [73:09]
Gabe Whaley
Nope. No. Not at all. Not at all. I think we're, like, 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. Five years is not enough. Ten years is not enough. It probably needs to be closer to 20 years. Sure. Part of this is vanity driven, for sure. But the other part is, I think it's the highest caliber of personal challenge, which is, how do you make sure that what you did was actually important? How do we make sure that we survived this test of time so that it was important enough for kids to actually learn about this in art school or their history classes in the same chapters of Duchamp and Warhol? And maybe we're creating a new area of study altogether. Who knows? Part of me, I'm also getting older. I'm in my mid-30s now, and I spend a lot of time talking to students. I'm so excited when they are inspired by what mischief does. Because unlike most kids in design school or art school or fashion school, you get the degree and you go get the job. And typically it's some sweatshop at an ad agency or a fashion house or a design studio, and you have to politic your way up to creating more bullshit work that you don't really care about, so that maybe in your spare time, you do something that's creatively fulfilling. When they see mischief, they believe that it's all possible. That's cool. So I'd like to keep that going as long as I can.
- [74:36]
Patrick O'Shaughnessy
A strange challenge for you. Imagine an open area of a big bookshelf in which I want to place an object, a mischief object, that when I look at it, will remind me of everything you've told me today. Which object do you think would do that best?
- [74:56]
Gabe Whaley
It's got to be the tax software. It's the box set of our TurboTax competitor. It's got the CD ROM and the booklet inside, but on the outside it's just anime. I think that's a really, really good example.
- [75:08]
Patrick O'Shaughnessy
Where did that come from? You've mentioned that twice. Tell that story in closing here.
- [75:12]
Gabe Whaley
Yeah, it sort of has all the right ingredients. There is adversary, which is TurboTax, and there's plenty to unpack with TurboTax, their monopoly and their dark UX patterns and how it's just a questionnaire at the end of the day, but they upsell you for all these random things through fear. Plenty to unpack there. So good adversary. We also believe it shouldn't cost you money to file your taxes. So there's that as well. And then there's this other observation that everything is becoming anime or everything is becoming. If you want to consider Metaverse, avatars, games, everything is heading in that direction. One of the things that we love to do here more often than not is jam 2 completely polar opposite worlds in together to create something new. And that led to TurboTax 3000, which is our version, our free competitor to TurboTax.
- [76:05]
Patrick O'Shaughnessy
You started on the Internet in the days when it was heady and fresh and new and like a frontier. It feels very different today. Do you think the Internet still has a sense of place?
- [76:15]
Gabe Whaley
I don't know. Personally, it feels a little bit depressing because I don't know if people are creating as much newness versus, and this sounds so jaded and cynical, but I think people are just creating what their gods are telling them to create. And the gods are TikTok, the gods are Instagram. And any moment where the algorithm changes or there's a new platform update, people change their behavior, feed that algorithm exactly right. They're not creating gross. And then you look at what performs well and then you mimic it, you copy it and then ultimately when you zoom out, everyone is just feeding into this frenzy, which is a bummer, but I think everything moves in cycles. And I also think at the end of the day, human beings are a deeply creative species. I'm bullish that we're going to figure it out. The pendulum will swing in the other direction before too long.
- [77:10]
Patrick O'Shaughnessy
The last question I ask everybody, what is the kindest thing that anyone's ever done for you?
- [77:16]
Gabe Whaley
I don't know if it's the kindest thing, but I remember this meant a lot to me and it meant a lot to a lot of us here. There's a very well known artist named Paola Pivi. She's represented Italy at the Biennale very, very far along in her career. She's also represented by Perotin, who we're represented by, and she wrote us a note. I think six months into that time where we were starting to get accepted by that world. I paraphrased. But her notes said something along the lines of of all of the greats that I've gotten to know over my career, mischief is the one that seems to represent the future that they would have wanted to see. But then she also accentuated with that make sure that you don't create for them at the same time. And that kind of stuck with us. That's just the first thing that came to mind when you asked the question.
- [78:05]
Patrick O'Shaughnessy
Gabe, I think this thing that you and your team have created is so singular. It's so obviously incredible form of self expression for you guys. I hope that people take a little bit and just wonder about what something similar could mean for them and go.
- [78:24]
Gabe Whaley
Create some stuff and hopefully someone creates like a competitor and we have beef someday because that would be good for.
- [78:31]
Patrick O'Shaughnessy
Business so you could dunk on your neighbor.
- [78:33]
Gabe Whaley
Exactly. Exactly.
- [78:34]
Patrick O'Shaughnessy
Thanks so much your time.
- [78:35]
Gabe Whaley
Thank you.
- [78:37]
Patrick O'Shaughnessy
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