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