Midnight Madness: Ryan Patch and Jon Seale

Summary

Money Stuff: The Podcast
Episode: Midnight Madness: Ryan Patch and Jon Seale
Release Date: May 23, 2025

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Introduction

In this episode of Money Stuff: The Podcast, hosted by Matt Levine and Katie Greifeld from Bloomberg, the hosts welcome Ryan Patch and Jon Seale, the creative minds behind the Great Gotham Challenge—a renowned puzzle hunt event. The discussion delves deep into the world of puzzle hunts, their intricate design, and their unique intersection with the financial industry.

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Understanding Puzzle Hunts

Ryan Patch kicks off the conversation by introducing the concept of puzzle hunts, particularly focusing on the Midnight Madness event, an intensive overnight puzzle competition primarily attended by professionals from the financial sector.

Ryan Patch [01:41]: "We get as a podcast proudly about money. Stuff related to money. It's not always true, but that's kind of what we say."

Matt Levine succinctly defines their role in the puzzle hunt arena:

Matt Levine [02:02]: "That's about all you need to say. We make puzzle hunts."

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Designing Engaging Puzzles

Jon Seal provides a comprehensive overview of what constitutes a puzzle hunt, differentiating it from other similar activities like scavenger hunts and escape rooms.

John Seal [03:16]: "A puzzle hunt, in definition, doesn't have to be location-based, but in our case, it's mostly a location-based event where people travel from place to place, solve complex puzzles."

He elaborates on the nature of puzzles, emphasizing the need for lateral thinking and the importance of logical connections between disparate pieces of information.

John Seal [08:24]: "Each puzzle should involve a logical leap, typically a mental connection between two different types of information."

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Balancing Difficulty and Engagement

Katie Greifeld poses a critical question about maintaining the right level of difficulty in puzzles to keep participants engaged without causing frustration.

Katie Greifeld [10:22]: "How do you make them difficult without being infuriating?"

Matt Levine shares insights from his experience, highlighting the delicate balance puzzle creators must achieve.

Matt Levine [10:30]: "The magic sauce is figuring out something that's just hard enough that makes people really feel like they've gone on a journey... but not making it so hard that they rage quit."

Jon Seal adds that rigorous playtesting and community feedback are essential in refining puzzles to this balance.

John Seal [12:57]: "A lot of it is playtesting... we have people that just playtest our puzzles and time themselves to ensure the right difficulty level."

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The Role of Hints in Puzzle Hunts

The conversation shifts to the mechanics of providing hints during puzzle hunts. Ryan Patch inquires about effective hint systems that aid participants without giving away solutions.

Ryan Patch [12:57]: "Can you talk about how you think about [hint systems]?"

Matt Levine contrasts the personalized hinting approach of Midnight Madness with the more structured system used in the Great Gotham Challenge.

Matt Levine [13:28]: "In Midnight Madness, game controllers are a little malicious... whereas, in our puzzle hunts, there's a unified pre-communication system where hints come with a time penalty."

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Midnight Madness and the Financial Industry

A significant portion of the discussion explores the symbiotic relationship between Midnight Madness and the financial sector. John Seal explains the origins and evolution of the event within Wall Street.

John Seal [18:23]: "Alicia designed it for about a decade before the winning team took over and renamed it. Now, it's a major event with around 15 to 20 different firms represented."

Matt Levine provides context on the event's charitable aspect and its high production values, which attract top financial firms.

Matt Levine [24:30]: "Midnight Madness is a charity event for Good Shepherd Services. Instead of traditional fundraising, teams compete, making it a unique and engaging way to support the cause."

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Production Values and Unique Challenges

Ryan Patch is intrigued by the high production standards of Midnight Madness and inquires about the logistical challenges of securing iconic NYC locations for puzzles.

Ryan Patch [28:35]: "How easy is it to get locations like the Intrepid for a puzzle hunt?"

Jon Seal shares anecdotes of both successes and setbacks in acquiring coveted venues.

John Seal [28:59]: "Last game, we did a puzzle in FAO Schwarz where teams had to play the big piano with their feet to solve a puzzle. That was a really fun one."

Matt Levine discusses ambitious but unfulfilled ideas, highlighting the intensive planning and coordination required.

Matt Levine [30:06]: "We tried to set up a giant inflatable obstacle course in an Olympic-sized pool, but it simply didn't fly."

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Clientele and Industry Trends

The hosts delve into the shifting landscape of their clientele, noting a decline in tech companies and a rise in financial and AI firms seeking their puzzle hunt services post-pandemic.

Matt Levine [41:30]: "We've seen a shift... pre-pandemic we did a lot of events for big tech companies, but now it's more hedge funds and AI firms."

John Seal attributes this trend to changes in company culture and employee retention strategies.

John Seal [37:20]: "They like the brutality. They like it to be difficult."

Matt Levine adds humor while acknowledging the intense nature of these events.

Matt Levine [37:17]: "It's a little more suspicious. Sustainable for us, but yes, exactly."

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Puzzles as Indicators of Skills

The discussion touches on how the ability to solve complex puzzles can be a desirable trait in the financial industry, even serving as a lead indicator for a firm's market performance.

Matt Levine [38:19]: "When those same companies three years later stopped doing well, it meant something."

Ryan Patch humorously connects puzzle-solving prowess to hedge fund success.

Ryan Patch [38:30]: "Has a hedge fund ever been like, 'you're good at puzzles, come work for us.'"

Matt Levine confirms this trend, noting that some hedge funds have in-house puzzle creators.

Matt Levine [38:33]: "They do have in-house puzzle creators and have hired our friends as in-house puzzle creators."

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Custom Experiences and Unique Puzzles

Jon Seal and Matt Levine share examples of innovative puzzles that integrate physical objects and immersive experiences, enhancing the overall challenge.

Matt Levine [31:32]: "We distributed a Palantir orb crystal ball that reacts with different colors based on geographical location, creating a dynamic puzzle experience."

John Seal reminisces about elaborate puzzles from past events, emphasizing creativity and participant engagement.

John Seal [28:59]: "We've always wanted to do a puzzle in the Natural History Museum... but it involves costly partnerships."

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Conclusion

As the episode wraps up, Ryan Patch expresses gratitude to Ryan Patch and Jon Seale for their insightful contributions, highlighting the intricate blend of puzzle design and financial industry engagement that makes events like Midnight Madness and the Great Gotham Challenge uniquely compelling.

Ryan Patch [44:57]: "And that was the Money Stuff podcast. I'm Matt Levine."

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Key Takeaways

• Puzzle hunts like Midnight Madness and the Great Gotham Challenge require a delicate balance of difficulty and engagement to keep participants motivated.
• Hint systems are crucial for preventing participant frustration, with different events adopting personalized or structured approaches.
• The financial industry has a strong affinity for puzzle hunts, viewing them as both team-building exercises and indicators of analytical prowess.
• High production values and unique locations enhance the immersive experience of puzzle hunts but come with significant logistical challenges.
• Clientele trends indicate a shift from predominantly tech companies pre-pandemic to more financial and AI firms post-pandemic.
• Innovative puzzle design often incorporates physical objects and immersive storytelling to create memorable and challenging experiences.

This episode provides a fascinating glimpse into the world of puzzle hunts, showcasing the intricate planning, creative design, and deep ties with the financial sector that drive these engaging events.

Transcript

[Matt Levine]

You're listening to an iHeart podcast.

[Katie Greifeld]

Hi, I'm Kelly Cavagnaro, Managing Director, Head of North America Institutional Distribution at Janice Henderson Investors we believe working together is the way to work better. Like combining your portfolio plans and our in depth strategy, your valued assets and our valuable insights. Your mission and our vision working in harmony to seek the right investment opportunities. Janice Henderson Investors Investing in a brighter.

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[Ryan Patch]

Feel like it's going to be weird to do an intro, but like, it's the money stuff podcast. We're here today with, I think our second episode with a guest. Yes, with two guests.

[Katie Greifeld]

Our second and third guests.

[Ryan Patch]

Second and third guests. They are Ryan Patch and John Seal of the Great Gotham Challenge, two creators of puzzle hunts. Welcome.

[Matt Levine]

That's about all you need to say. We make puzzle hunts.

[Ryan Patch]

We got in touch because I am a degenerate puzzle hunter in my way. And Ryan and John are taking over or sort of have taken over the the big financial industry puzzle hunt that I have done occasionally, which is sometimes called Compass, but is mostly called Midnight Madness and runs overnight this year in October. So welcome John and Ryan.

[John Seal]

Thank you. Happy to be here.

[Matt Levine]

Coming soon to New York City street near you.

[Ryan Patch]

This is a podcast proudly about money. Stuff related to money.

[Katie Greifeld]

That's what we bill it as.

[Ryan Patch]

It's not always true, but that's kind of what we say. And it has a listenership that includes a lot of financial industry and tech industry people and the overlap of that audience with people who do puzzle hunts is meaningful, but it's not perfect by any stretch of the imagination. And so I kind of want to explain what a puzzle hunt is. And I feel like you guys might say that you're something other than puzzle hunt guys Exactly. But I really want to explain what puzzles are. So can I prompt you with that?

[John Seal]

I think sometime in the 90s, maybe before the MIT mystery hunt started, I get the sense that that is the beginning of the industry that we are weirdly, a part of. Largely by accident, I would say, because when Ryan and I decided to start designing puzzle hunts, we weren't aware of any of the existing ones. We thought we were making something that no one had ever heard of before. A puzzle hunt, in definition, doesn't have to be location based, but in our case, and in many cases, it's a location based in which people travel from place to place, solve a complex puzzle. And by puzzle, I don't mean jigsaw puzzle, but they receive a series of clues and pieces of information that have to be combined in some way and thought of laterally in order to yield a solution. And that solution will often take them to a new place and they'll kind of repeat that process. Maybe people are familiar with the Amazing Race, combining elements of something like the Amazing Race with elements of an escape room and all into a competition in which people are competing against each other most of the time in small teams to prove their mettle and arrive at the end first or with the highest standing that they can.

[Ryan Patch]

I became aware of puzzle hunts before I became aware of escape rooms. And I don't know if that's like, the actual chronology in the world where, like, people.

[Katie Greifeld]

It's not my experience.

[Ryan Patch]

Yeah, well, puzzle hunts are pretty niche.

[Matt Levine]

But the escape room escape rooms came after puzzle hunts.

[Ryan Patch]

Yeah, that was what I thought. They sort of grew out of the puzzle hunt idea. And, like, you could put an escape room in a place and sell it to people every day rather than do it once a year.

[Matt Levine]

And escape rooms are definitely a little more consumer oriented, whereas a puzzle hunt, you have to be a certain glutton for punishment or at least intellectual stimuli. You know, escape rooms are great because, you know, at the end of 60 minutes, you're done. Whereas at puzzle Hunt, if you fail, you're floundering in the middle of some urban landscape trying to figure out where.

[Ryan Patch]

To go next at 3am often.

[John Seal]

But, you know, what I would say is that I think escape rooms and puzzle hunts share an origin story, I would guess, which is that it's people saying, what if we could be in a video game in real life? So it's kind of taking this idea of a quest and something to be solved and creating a real life experience around that, Right?

[Ryan Patch]

Yeah.

[Katie Greifeld]

What differentiates a puzzle hunt from A scavenger hunt or is that just a meaningless distinction?

[Ryan Patch]

Is it the puzzles?

[Matt Levine]

Absolutely.

[Katie Greifeld]

You get clues and you have to think critically.

[Matt Levine]

In scavenger hunts there's definitely a blurry line between the two. But I think that the puzzle hunts are often once you arrive at a location, you're not just there to find something, you're there to solve a complex situation. And there's pen and paper puzzle hunts where you just go to a location and you're given a few pieces of paper and they of these very crosswordy or language based or math based puzzles that you wind up solving and then they result to a keyword or often the next location that you're going to. And then you go to the next location, you get handed another set of papers. So there's always some very specific activity. Now we came kind of this from more the immersion angle. We kind of asked ourselves the question, what would it look like if people felt like they were in a movie? And then we started creating these quests and then we realized we, well, to kind of unlock the door that kind of lets you into the next thing there needs to be a puzzle. And so we kind of came at it from a little more of an angle saying, well, we need to have a key for that door, we need to have a password for that door. And started slowly integrating puzzles. So we kind of backed into the puzzle hunt community from more of like an immersive angle. Whereas the puzzle hunt community has then kind of been pulled a little more into the immersive community through escape rooms, through, through immersive theater. And then you have, yeah, the scavenger hunt community which is kind of geocaching adjacent and just making hunts for your 10 year old kids. Adjacent and scavenger hunt. The worst version of a scavenger hunt is like take pictures of five out of state license plates or like, you know, get a photo of a person with a beard and is kind of our guiding light that we move away from.

[John Seal]

We draw a distinction in our world between puzzles and tasks. And a puzzle is, it requires some sort of lateral thinking and a task is just an action that you complete. So I think a lot of scavenger hunts are task based versus a puzzle. Requires you to use your brain in a different way.

[Ryan Patch]

Do you have like a classic puzzle or like a form of puzzle or a way to describe more concretely what the puzzles and puzzle hunts are? Because like to me, and I have not, I don't think done your challenges, although I think I did at midnight meta a Compass. That might have been partly your doing. And I have a sense, like an inarticulate sense of what Puzzle hunt puzzles feel like. I've done, I don't know, four or five puzzle hunts on an escape room or two. But how do you think about puzzles and what is a puzzle and what kinds of things are puzzles? Could you give a puzzle that we could talk about on a podcast?

[John Seal]

Sure. I think every puzzle hunt has its own tradition of how it defines a puzzle. And Ryan and I are the first people to be in charge of the Midnight Madness tradition, kind of coming from the outside, not having played and not being from the finance industry. So we had to do our homework and spend a lot of time learning what's a puzzle by the definition of Midnight Madness. And one thing that we identified is each one should involve a logical leap. So there's typically a mental connection that you make between two different types of information. So an example of a puzzle that I think is a good illustration of this from an event that we did a few years ago, was designed by our friend Josh Daviner. And it's a puzzle in which you receive a rap sheet that looks like a police description of several perpetrators of criminals. And each one has a description and then picture of what looks like a fingerprint for each one. But you use clues in the descriptions, and you use clues of what the visual of the fingerprint looks like to actually make a connection that you're not looking at fingerprints, you're looking at topographical maps of mountains. And each one you discover as you kind of read through the text and look for words that might seem out of place and kind of evidence that the descriptions are not quite fitting. Well, to, like, how a policeman might describe a criminal, to recognize that each of the seven is representing the seven highest peaks on each continent. And so then you use that information to go back to the first descriptions. And in there, you work with the information, you have to yield a final solution, which is a key word. But in order to do that, you have to be able to make this mental leap and recognize that one thing is actually representing another.

[Katie Greifeld]

How do you make them difficult without being infuriating? Because this is something different. But Bloomberg has a weekly quiz quiz. Go, Matt. You've played it.

[Ryan Patch]

I have. You've written it. Right.

[Katie Greifeld]

I used to be the curator of the quiz, and one of the metrics on which I judged myself was by how many people who started the quiz, completed the quiz. And there was, like, this fine balance I had to find between making it challenging. But not making it annoy. So how do you find that balance when you're putting together puzzles and make sure that people basically don't rage quit?

[John Seal]

Yes. You're our sister in pain.

[Katie Greifeld]

I see.

[Matt Levine]

I think that's the number one skill of a good puzzle creator. I think that right there is the magic sauce is figuring out something that's just hard enough that makes people really feel like they've gone on a journey and they were just about to quit. But then they had that spark of inspiration that turned it all around for them. And then everything fell into place. And then looking back on it, it's like, of course that was the answer. It could never have not been the answer. And bringing people on that journey and allowing them to go on that journey themselves and then by the end of it having that. I heard it recently described as, I think, secondhand fun or second degree fun, where it's like it sucked in the moment, but when you look back on it, it's a pleasureful thing. And so creating that moment, it's very difficult and we've struggled with it. And the, you know, we created the Great Gotham Challenge. I created the first one by myself. John was a participant. This is how we started working together. And no one finished it. Everyone rage quit. It was in 2009. The stock market had crashed. I just graduated college and couldn't get a job. And so me and another friend created this. And it was supposed to be like a four hour thing. Everyone just texted us after hour four and was like, I am a quarter of the way through. Please put a bullet in my head. And so it's just like, okay, come to the finish line. But anyways, we've gotten better. We've been doing this for about 11 years. And a lot of it is play testing. Like we have a community of people that just play test our puzzles and they time themselves and we make sure we know how long a puzzle should take and what the right deviation is. And. And it's also a lot of argument. Like we've just got people that we really trust and who have done a lot of these things. And someone says, this is way too hard, this is way too easy. And we just go 12 rounds until we find something that we all agree on and we trust each other. So part of it's not working in a vacuum and part of it's just a lot of experience and a part of it's playtesting. John and I are creative by nature and we brought in an operations person to help run our company named Teresa who's brilliant and has saved our company many times. But one of the things she instigated is. No, we play test things, we playtest things thoroughly.

[Ryan Patch]

I feel like another part of the answer to Katie's question is when I've done puzzle hunts, there's some sort of hint mechanism where you can, without fully giving up, you can give up a little and get some sort of help. Can you talk about how you think about that?

[Matt Levine]

Yeah. And it's interesting because we've seen this done different ways in the Midnight Madness puzzle hunt that we stage every other year for the finance industry. There's kind of a bespoke, personalized, what's called game controller who meters out hints.

[Ryan Patch]

It's like your personal tormentor.

[Matt Levine]

Right, right, exactly. And this is actually something very unique about the Wall street vibe, is that the game controllers are known to be a little malicious and a little. Kind of. Because we've been kind of apprenticing with the current creators for the last four years, and we've taken it over this year and so we've watched them and tried to learn and we've been like, this seems weird, this seems mean. And they're like, oh, no, it's what people want. Like, it's what the. It's what the players want. That's done in a very, like, bespoke, handcrafted, concierge way, both the hinting and the tormenting. Whereas, like on our great Gotham Challenge branded puzzle hunts that we do, there's kind of a unified pre communication hand hint system that when you feel like you're at a dead end, you can take a hint and there's a certain time penalty. And we've introduced a fun gamified mechanic where the longer you're on a puzzle, the less penalty time you get. And so, yeah, there absolutely needs to be a hint system, and that's absolutely a way that you keep people within the same universe. If there was no hint system, then you'd see deviations of 200% on times.

[Ryan Patch]

My experience of Compass or Midnight Madness is if you're getting on the subway to go to the wrong boroug, so your game control will be like, hold on.

[Matt Levine]

Right. Yeah, yeah, yeah.

[Ryan Patch]

There's some amount of, like, don't do something really stupid.

[Matt Levine]

And that's the designer's job is to. Yeah. Figuring out how to let people fail enough that they go through those peaks and valleys of emotions, but not letting them fail so much that they're just destroyed.

[Ryan Patch]

Yeah. You want to feel like you can fail so that when you succeed, you feel good about it, right?

[Katie Greifeld]

Hi, I'm Kelly Cavagnaro, Managing Director, Head of North America Institutional Distribution at Janice Henderson Investors. We believe working together is the way to work better. Like combining your portfolio plans and our in depth strategy, your valued assets and our valuable insights, your mission and our vision working in harmony to seek the right investment opportunities. Janice Henderson Investors Investing in a brighter.

[Kelly Cavagnaro]

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[Ryan Patch]

Can we talk about Midnight Madness? I've written about having done one or two Compass Hunts, which my understanding is that at some point a kind of Goldman Sachs affiliated group of Wall street people started a Midnight Madness puzzle hunt, possibly named after a movie of the same name. And it was called Midnight Madness because it started at, I don't know, 4pm and went until 2pm the next day.

[Matt Levine]

Everything you've heard is correct? Yes.

[Ryan Patch]

And it was run by, I think Alicia Wiesel at Goldman. And then it became so overwhelming that my understanding was like the winners got to run it the next time. And I know like Colin Teichelt ran it for a while. And that is like, in my understanding, the premier Wall street puzzle hunt. And all of the teams are like eight Goldman teams and six chain street teams. Is that basically correct?

[John Seal]

Most of that's correct. Alicia designed it for I think maybe a decade or a little Less. And at some point, I think he decided it was too much for him to continue and just decided, I can't keep doing this. I need to quit. And the team that won the year that he called his final year decided that they loved the game too much to let it die. So they said, we'll take over, we'll put it under a different name so that people recognize that it's under new management. They ran it for several years and then they decided, we can't keep doing this. It's destroying our lives and our relationships.

[Ryan Patch]

Because all these people have real jobs in the financial industry and also extracurricularly design these insane all night puzzle hunts.

[Matt Levine]

As opposed to us who have fake jobs in the financial industry. Yes, that's correct. No, we have real jobs in puzzle hunts. Yeah, exactly.

[Ryan Patch]

This is your job. It's not their job.

[Matt Levine]

It's a little more suspicious. Sustainable for us, but yes, exactly. I don't know how they could possibly do it because this is my full time job. It already is so hard for me. I can't imagine working at a hedge fund while simultaneously doing this.

[Ryan Patch]

So you guys are professional puzzle hunt makers and they are professional hedge fund managers. As you look at their work, what do you think? Were they good at it? If you have the regular puzzle hunt community and then you have the hedge fund guys, is there a different style or mindset?

[John Seal]

Yeah, that's something Ryan and I were just discussing. Actually, there are things that are unique to it. There are ways that maybe we look at things a bit differently. For instance, talking about hints, Ryan and I, as puzzle designers, we kind of believe that a really well designed puzzle should be able to be completed by a good puzzler without needing to be hinted in any way. Whereas I think they're coming from a world in which they feel like if it's not hard enough to require someone to take hints, then it's not hard enough. So that's been an adjustment, I think, for us to kind of recognize we're.

[Matt Levine]

A little more breadcrumb. That leap of logic in a way that like at the end of a good murder mystery, you look back and you're like, oh, the hints were always there that it was the butler. And so we're a little more on that end versus. Yeah, they're more like, you have to make this leap of logic with no prior breadcrumbs.

[Ryan Patch]

I'm with you. I've had some midnight madness experiences where you're like, you get the hint and you're. No one would have gotten that. That Makes no sense.

[John Seal]

Yeah. Another big distinction though, that we've come to terms with, though, that I think is really interesting and says a lot. And we didn't believe this to be true when we started, but I think we've come around to the idea that the people who are attracted to this Midnight Madness game, who come from Wall street, they do crave, I hesitate to use the word glutton for punishment, but they, they do crave a certain amount of intensity and some would even say torture. That I think was surprising to us.

[Ryan Patch]

Yeah, I mean, just the fact that it sort of runs overnight is cruel in a way.

[Katie Greifeld]

It's like endurance athletics, but with your mind and your body.

[John Seal]

Totally. Yeah.

[Ryan Patch]

You have a day job running puzzle hunts under your own brand and like puzzle hunt activities for corporate clients.

[Matt Levine]

Right.

[Ryan Patch]

My sense is that a lot of your clients are also in the financial industry and puzzle hunting and finance overlap a lot. Is that right?

[Matt Levine]

Yes. You're onto us. We didn't mean to do it that way, but the market found us.

[Ryan Patch]

What do you think it is about financial people and puzzle hunts? Why do they go together?

[John Seal]

Several things. One is, I think the finance industry and the tech industry have become really closely intertwined and as I said, the tradition of the MIT Mystery Hunt. A lot of these people that come from Cambridge end up in New York, end up doing finance related jobs and so they've crafted a taste for this type of thing already earlier in life.

[Ryan Patch]

Does everyone at MIT do the Mystery Hunt?

[John Seal]

I don't think everyone does it. And a lot of people who do it are also not currently at mit.

[Ryan Patch]

I've been invited on teams and it seemed like more trouble than I was.

[John Seal]

Worth, but yeah, yeah, that's like a three day event or a four day event and it's about 100 people and.

[Ryan Patch]

You can do it remotely. It just seems like a lot.

[John Seal]

It is a lot. You're not wrong about that.

[Matt Levine]

Our coo Theresa, participated this last year and had a fantastic time and we're going to try to go next year. And she went there on a team and it's like how fun can. Like being holed up in a hotel room solving puzzles, you know. But it really seems like the winning teams are. It's not just about puzzle solving acumen, but about organization of brain power. You know, how do you effectively deploy a hundred people to effectively manage problems and contribute and make these lateral leaps? And it seems like that's the key to the MIT Mystery Hunt, which is, I think, such an interesting social management problem.

[Katie Greifeld]

Yeah, I was reading A Quartz article from 2013, I think it was, because Midnight Madness went on a bit of a hiatus and then it came back.

[Matt Levine]

Right.

[Katie Greifeld]

And the article is talking about how originally the thinking, you know, among the Goldman Sachs teams who participated was that they wanted to stack their teams with quants. They just wanted a lot of big brains. But the team that ended up winning was a group that worked together and I think they were client facing and they chalked their winning up to just, we know how to work together. We don't necessarily have the smartest guy in the room, but we all know how to manage together.

[Ryan Patch]

Yeah. And also if it's all quants, you want different kinds of intelligence too, in solving the puzzles as well as in creating the puzzles. As I was thinking about why the financial industry likes puzzle hunts, I mean, I was thinking teamwork is always pretty heavily emphasized when you interviewed a financial firm. And the idea of getting different types of intelligence to delegate responsibility and brainstorm together does seem useful in the job. And then it hadn't even occurred to me that the 100% MIT mystery hunt teams are an enormous management problem. But yes, if you can manage a puzzle hunt team of 100 people, that does seem useful for managing a hedge fund.

[Matt Levine]

They create custom software platforms just to manage the puzzles. It's incredible. I did want to go back to. You were correct in that Midnight Madness grew out of Goldman. And I'd say maybe still less than, I mean, maybe 40% of our teams are Goldman, 30 to 40% of our teams. So they're a huge supporter. And just to give the context for your listeners, this Midnight Madness is a, is a charity event for Good shepherd services. And so the great part is instead of going to a fundraiser where you have to, you know, buy a table and sit through speeches and watch pretty picture videos, you stake a team to compete. And so I'd say, yeah, still definitely a huge, the biggest showing is from Goldman, but there's probably 15 to 20 different firms represented. Everything from, yeah, bigger investment banks to quant firms to really small shops and I don't even know all the different types of shops that are represented there. And it goes from like, places where the CEO is leading the team and to places where the CEO stakes the team and then like puts his best people on the team and shows up at the finish line. Or also places where just like, they just look at it as a donation and, and let the people who want to show up.

[Ryan Patch]

But. Right, the idea is basically Midnight Madness is a fundraiser for Good Shepherd. A team is up to six people.

[Matt Levine]

Correct.

[Ryan Patch]

And it costs something like $40,000 to sponsor a team. So it's a meaningful donation.

[Matt Levine]

Yeah. And so we'll have 25 teams duking it out on October 4th, the early hours of October 5th, duking it out for the title of the most intelligent and really best.

[Ryan Patch]

So in my experience, the production values for Midnight Madness are really high. The year I did it, most recently, it ended on the Intrepid, like the aircraft carrier solving a puzzle on a real Enigma machine. I don't know if you know this, but it's very finance industry coded. Like you're not a hedge fund unless you have a real Enigma machine somewhere. And it was like, you know, you had to get clues, like going to a screening of a movie on a rooftop in Brooklyn and there was a chessboard in the Brooklyn Museum. It was like a real pretty high end experience. I'm very interested in talking about the puzzle aspect, but as designers, I feel like you're more interested in the cool experiences side of it. Can you talk about that?

[John Seal]

Yeah. I mean, that was really intimidating. And it's interesting. When Ryan and I started designing games like this when we were in college, just for our friends and scraping together a couple of bucks from our own pocket and trying to dream as big as we could. And only many years later, we came across an article about the tradition of Midnight Madness and learned that there was a puzzle that year where teams had controls that were actively controlling the lights on the Empire State Building and changing the colors to solve a puzzle. And we were absolutely floored by the kind of production value available to these game designers and thought, like, wow, if we could just do something like that one day, that would be the biggest dream that we could dream for ourselves. And, yeah, so a lot of the fee that people contribute to Stake a Team does go towards the production of a very fantastic and epic game. And that's part of the appeal. It is interesting for us to try to design for the man or woman who has everything, quote, unquote. And if you're super wealthy and you have all these kind of opportunities and experiences available to you on a regular basis, you know what is impressive, what can make an impression on that type of person. I think that's part of where this tradition has come from of like, wow, it has to be bombastic. And having access to landmark locations in New York City that you wouldn't normally have is a big part of it. The scale has changed a bit. I think when Alicia was designing it, maybe a much bigger portion of the Fee went towards the production value of the game. And we're allocating a different kind of percentage to the charity versus the more.

[Matt Levine]

To the charity, to be clear. Yeah, no, we don't, we don't know.

[Ryan Patch]

Do you have a list of, like, here are some cool locations. Let's see if we can get them. And then, like, often get told no or like, absolutely, if you want to, like, get the Intrepid, like, how easy is that? And when you call and you say hi, we run a puzzle hunt with a lot of golden people. Like, does that work? Or people are like, what are you talking about?

[Matt Levine]

It's everything. We didn't get the Intrepid. I think that was the year before we started working with them. So I can't speak to specifically renting the Intrepid, but it's always, yeah, at midnight. Yeah. Or into 2am Some things are, wow, we're never going to get that. And then people come back to us and like, yeah, how about $2,500? And you're like, great, let's do it.

[Ryan Patch]

What's the most surprising location or thing you've gotten access to?

[John Seal]

Last game, we did a puzzle in FAO Schwartz where teams had to play the big piano with their feet to solve a puzzle. That was a really fun one for someone who grew up watching the movie Big with Tom Hanks.

[Katie Greifeld]

We could also ask the inverse of that question. I mean, where have you been turned down from that you really wanted to happen?

[Matt Levine]

You know, every year there's a theme. In 2023, it was the lost cosmonauts, which is a riff on a conspiracy theory that there's cosmonauts that were launched into space that we'd never heard about. And kind of the seed of the idea is that somehow they're still alive and we have to bring them home. And so we were going to do a cosmonaut training course, like in a swimming pool in New York City. And so I was trying to get, you know, one of those huge inflatable, like, water obstacle courses. You know, we're going to like, order this $10,000 inflatable obstacle course from China and then like set it up in an Olympic sized pool in New York City and it just did not fly. And, you know, we had a, a poor good shepherd staffer who was in charge of trying to find me my, my swimming pool. And she was just like, ryan, I don't think anyone's going to let us inflate this giant obstacle course in the pool.

[John Seal]

I've always wanted to Do a puzzle in the Natural History Museum, like with the.

[Katie Greifeld]

The big whale and night at the museum style.

[John Seal]

Yeah, exactly. You have to become like a. An official partner of the museum. And it's like an annual membership that costs $30,000. And then there's all these other hoops you have to jump through.

[Katie Greifeld]

You can get a Bloomberg terminal with that. Jeez.

[Matt Levine]

Some of the best locations we've had are like the rooftop of the Port Authority Bus Terminal. On the north end of the Port Authority Bus Terminal, there's an uncovered parking deck that anyone can access. And you can look down 41st street all the way to the library, through Times Square, through Bryant. Bryant Park. And at night, it's one of the most incredible places in New York City. And it's just sitting there for anyone to come and see. Or we'll like, park a box truck on the side of that street and have people go in. And there's like a speakeasy type establishment with like a live band inside, a box truck, delivery truck just parked on the side of the road. And so the. The venues that we love are those types of unexpected delight that kind of like, are hidden in that New York City is. Is so good at kind of concealing.

[Ryan Patch]

What about best puzzles? Right. So you've talked about the simplest level is you get handed a piece of paper, and you do some piece of paper, certainly at midnight Madness, with production values, what they are. There are some amount of doing puzzles on cool physical objects. What are some cool physical objects that have been purposed as puzzles?

[Matt Levine]

I have one sitting right here. It's like a Palantir orb crystal ball that we distributed. Yeah. Holding up a crystal ball. And it reacts with different colors and flashing patterns based on where you are geographically. And so there was a whole puzzle in 2021 scattered all over Central Park. And as you approach different locations, the globe did different things and flashed different color sequences, and then those were decoded. One of my favorite puzzles from. I think this is an Alicia. I don't know, but I've read about it in one of the many articles that I'm sure you guys said was the circuit board, where you had to assemble C circuit board, and then one of the transistors overheated, and you discovered that the circuit board was actually a map of New York City subway stations. And when you looked at it through a infrared camera, you know, it was identifying which station to go to. So that's another example of something that lives in my head as a. As a great use of a physical object.

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[Ryan Patch]

Just to go.

[Katie Greifeld]

Back to Midnight Madness really quickly. I mean, so you have these three to four to five hour puzzles. I believe you said Midnight Madness seems like a different beast entirely in that it runs overnight.

[Ryan Patch]

Yeah. What is your time expectation for this year's Midnight Madness? When does it start and when do you expect the last team to finish?

[John Seal]

Yeah, about 12 to 14 hours depending on how fast teams are. The idea is to start at early afternoon, one or two and then it ends sometime shortly after midnight. Hopefully not too much longer than that.

[Katie Greifeld]

So it's in early October. When do you start planning for it?

[John Seal]

Typically about a year in advance. So it's about a year in the making.

[Ryan Patch]

Do you design games for a lot of big Wall Street? Can you say your repeat clients or something?

[John Seal]

Yes, we have a lot of Wall street clients. That's our biggest audience and our biggest client base. We have like.

[Ryan Patch]

And so just to be clear, this is in your business you do like Relatively short one day events for team building. Events for companies who hire you to design games, right?

[Matt Levine]

Yeah, three to four hours long based on how much we think that they can take or how much we know that they can take. As we have repeat clients, we start to understand the culture of the company and what they're looking for and what they can handle. And yeah, there's been some.

[Ryan Patch]

And who can handle the most?

[Matt Levine]

Well, there's a difference between who can handle the most and who wants to give off the vibe like they can handle the most.

[Ryan Patch]

Answer both.

[Matt Levine]

We have NDA. All of these companies are so secretive.

[Ryan Patch]

We'Ll bleep them out.

[Matt Levine]

It's really hard. Fortunately, Bridgewater has been very generous that they allow us to talk to say that we have done many hunts for them and they actually came to us only recently in 2021 after they did Midnight Madness, formerly known as Compass with us. And we've worked with them multiple times a year for different teams and they're awesome to work with.

[Ryan Patch]

I do want to know where Bridgewater falls on the can handle things and want to give the impression but it seems rude to make you answer.

[Matt Levine]

They're great. I mean, don't make us pick between our children. You know, we love all of our puzzle children equally and the only thing I'll say is specifically the team we work for does love the puzzly puzzles. You know, there's definitely a gradient of people that love the experience. They love the locations and the feedback we get from Bridgewater, at least the point of contact who helps us plan their event, that they want the puzzles, they want the goods.

[John Seal]

Yeah, they want the brutality. They like it to be difficult.

[Matt Levine]

And it's been really interesting for us as again outsiders. Like we both went to art school figuring out what's the difference between like a quant hedge fund and a Bridgewater and a Goldman and where they all function in this world. It's been quite the education.

[John Seal]

They each have a different culture that manifests differently in our games. And often the culture is kind of inspired by the founder. Like some of them are work hard, play hard and they like to party hard. And that's a culture that emanates from the founder. And some of them are more like about work, life, balance and generosity. And they each kind of have a very distinct culture that we can recognize just in our limited touch points through our games. And also when a lot of our client base was more tech like Google and meta and tech firms, we joke about like making our own private investments based on how well we see people doing in our games because we definitely recognize that companies that are doing well for us were also doing well in the market.

[Matt Levine]

And then when those same companies three years later stopped doing well, it meant something.

[Ryan Patch]

Stopped doing well in the puzzles. The puzzles were like a leading indicator of the stock.

[Matt Levine]

Exactly. Yeah.

[Ryan Patch]

Has a hedge fund ever been like, you're good at puzzles, come work for us.

[Matt Levine]

Not in house, but we know some hedge funds that do have in house puzzle creators and have hired our friends, as in house puzzle creators. So it exists. It's a thing.

[Ryan Patch]

Yeah, I've seen some of that. Right. Because clearly there is a big recruiting dynamic of a lot of these firms like to hire people who are good at puzzles. They like to pose puzzles to them as part of the recruiting process. They like to attract people who like puzzles. It does seem like an overlap in the puzzle creator community. Is there a trend where a lot of people have a certain degree or a certain background?

[Matt Levine]

Certainly, yeah. Stats, math, business, definitely. But then there's also people who do a lot of more linguistic puzzles. There's a whole kind of like the crossword, that whole world is a little more linguistic and they have a different background.

[Ryan Patch]

When I've done puzzle hunts, there's always a cryptic crossword cluing type puzzle and I'm always the guy who solves those. That's my one contribution to the team.

[Matt Levine]

Right, right. A good puzzle creation team has a good puzzle is created by people with a lot of different backgrounds.

[Ryan Patch]

I assume that when you do team building events, it's like a company for like 200 people. But do you ever have like these five people are going to do a puzzle together?

[Matt Levine]

Yeah, I mean, yeah, if you can afford us, we'll do it. And we've done groups as small as four and groups as large as what, 300, 400.

[Ryan Patch]

John, wait, can you tell me about the groups of four? Like, how does that come in?

[Matt Levine]

Either someone's birthday. It's a birthday party usually.

[Ryan Patch]

You know, it's like someone who really likes puzzles.

[Matt Levine]

Someone who really likes puzzles. And either they can afford our, our services because we just like run a past event for them, or they have a ton of money and we do something completely tailored to them that's like all about their life and all about their 50 years and all about their kids. And those are really fun too.

[John Seal]

We've done many birthdays for CEOs of like hedge funds.

[Ryan Patch]

Yeah, I was going to say this feels like a classic hedge fund manager. 50th birthday party.

[Matt Levine]

We did one hedge fund who said that they wanted maybe if you want to talk about our white whale was one of the co CEOs of this is a small fund. And they said, okay, I want to do this across Europe for my 50th birthday. And I was like, yes, let's do it, call us. And then they never showed.

[Ryan Patch]

But did you have a preliminary budget?

[Matt Levine]

No, no, we didn't even get that far. But it was for a fun that was celebrating their 25th anniversary I think in London. And so we got to build a six hour hunt in London and that was one of still our favorite jobs to date. But it could have been the lead in to a cross Europe scavenger hunt. But wasn't to be.

[Ryan Patch]

Yeah. Wait, you said something about like you had a lot of tech clients and now you have fewer tech clients and it's more finance skewing. What do you think is causing that?

[Matt Levine]

Yeah, we've definitely seen the shift when tech was the coolest place to be. And now it's these companies have matured and they're still great places to work, but there's a little less of an edge to them. I think we've seen they're also working a little less hard at employee retention and they're pulling back the perks. And so we've seen pre pandemic specifically we do a lot of like 50 to 80 person events for big tech companies, growing tech companies, that sort of thing. And then post pandemic we've seen a lot fewer tech companies. And when the tech companies do come, this is more of a return to office thing, but it's a much smaller group, so people are getting together in much smaller groups. They're going out with their immediate five to 12 team members and not their full division or whatever. And so at the same time we've seen a lot more hedge funds and AI companies coming in. And so as as the type of company where young, ambitious, really smart people work at kind of shifts, we do see that in our clients as well.

[Ryan Patch]

So it's like if you work at Facebook, 10 years ago you were like, I really want to solve puzzles. I'm motivated to use my brain. And now it's like, yeah, I'm going to rest, invest and not go on a puzzle hunt.

[Matt Levine]

I don't want to say exactly, but yeah, that's a little bit of the vibe I get. One of the reasons that I started reading money stuff was after you wrote that huge crypto article, Matt. And at the same time we were building a completely bespoke kind of Alternate reality game puzzle community for a NFT firm. And we had no idea what we were doing in crypto, no idea what we were doing with NFTs. And so reading your article helped me get my head around this whole concept as we were building out this game community world IP universe that we were hired to do, kind of like as an extension of the Bored Ape yacht club universe. And it was.

[Ryan Patch]

Did you get paid?

[Matt Levine]

We did get paid, yeah. Yeah, we got paid. It was an incredible, incredible experience. And we got to create characters and create stories and sometimes our events are a little more puzzle, puzzle oriented. And this was the most built out we've ever, like, created a whole world. Like we created locations and characters and plot points and betrayals and. And stashed puzzles in lockers at the LAX airport and in bars in London and slipped burner phones. And it was a really fun event. Now, the project as a whole didn't survive more than a few years, but we kind of were in this at one of the crypto bull markets and.

[Katie Greifeld]

That'S a real moment in time.

[Ryan Patch]

I know we've talked about hedge funds and tech firms. We didn't even talk about what does the chart of your crypto exposure look like. Yeah, it was all crypto firms and never heard from them again.

[Matt Levine]

That's pretty much it. Yeah. We haven't done any of our private kind of team building events for crypto firms. This was a kind of like a public facing event for the crypto community and it was led by a guy who wanted to create this series of IP around some of the bored apes, or to be more specific, the mutant apes, which is a whole sub genre of apes.

[Ryan Patch]

And I think we'll end it there.

[Matt Levine]

Yeah, yeah, yeah, exactly.

[Ryan Patch]

John and Ryan, thank you so much for coming on. This was fun.

[John Seal]

Thank you for having us.

[Matt Levine]

Great to be here. Hope to see you on the streets.

[Katie Greifeld]

Thank you guys.

[Ryan Patch]

Yeah, thanks.

[Matt Levine]

Honored to be your second big guest.

[Katie Greifeld]

Yeah.

[John Seal]

Wow, what a distinction.

[Ryan Patch]

And that was the Money Stuff podcast. I'm Matt Levine.

[Katie Greifeld]

And I'm Katie Greifeld.

[Ryan Patch]

You can find my work by subscribing to the Money stuff newsletter on Bloomberg.com.

[Katie Greifeld]

And you can find me on Bloomberg TV every day on Open Interest between 9 to 11am Eastern.

[Ryan Patch]

We'd love to hear from you. You can send an email to moneypodlumberg.net Ask us a question and we might answer it on air.

[Katie Greifeld]

You can also subscribe to our show wherever you're listening right now and leave us a review. It helps more people find the show.

[Ryan Patch]

The Money Stuff podcast is produced by Anna Mazarakis and Moses Andam.

[Katie Greifeld]

Our theme music was composed by Blake.

[Ryan Patch]

Maples, Brendan Francis Newnham is our executive.

[Katie Greifeld]

Producer and Sage Bauman is Bloomberg's head of Podcasts.

[Ryan Patch]

Thanks for listening to the Money Stuff podcast. We'll be back next week with more stuff.

[Katie Greifeld]

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[Matt Levine]

You're listening to an I Heart podcast.