Episode summary
Re-run: Midnight Madness: Ryan Patch and Jon Seale | Money Stuff: The Podcast
Money Stuff The Podcast
· · 41 min · Hosts: Matt Levine, Katie Greifeld · Guests: Ryan Patch, Jon Seale
Summary
The hosts revisit their 2025 conversation with Ryan Patch and Jon Seale of The Great Gotham Challenge as Midnight Madness returns on October 10th. The discussion explains what a puzzle hunt is, why it differs from a scavenger hunt or escape room, and how the best puzzles require a logical leap rather than a simple task. The guests describe their design philosophy as building difficult but fair experiences that feel brutal in the moment and satisfying in retrospect.
A big theme is why finance people are drawn to Midnight Madness. The guests say Wall Street teams like intense, overnight competition, strong hinting, and the chance to test teamwork under pressure. They note that Goldman Sachs remains the biggest source of teams, but that the event now attracts many firms and serves as a charity fundraiser for Good Shepherd Services, with teams of up to six people.
They also talk about the production side: landmark New York locations, elaborate props, and yearlong planning. The guests say the appeal is making something memorable for people who can buy most experiences already, and they compare the culture differences across clients such as Goldman, Bridgewater, tech firms, and AI companies.
Key takeaways
- The guests define a good puzzle as one that requires a real logical leap, not just a task or scavenger hunt clue.
- They say Midnight Madness works because Wall Street players want intensity, difficulty, and a controlled amount of torment.
- They say the event is a charity fundraiser for Good Shepherd Services, with teams of up to six people and roughly 25 teams competing.
- The guests say Goldman still supplies about 30% to 40% of teams, but the field now spans 15 to 20 firms.
- They say their best events use landmark locations and physical objects to create an experience that feels impossible to repeat outside New York.
Notable quotes
“A puzzle hunt in definition doesn't have to be location based, but in in our case and in many cases, it's a location-based hunt”
“each one should involve a logical leap. So, there's typically a mental connection that you make between two different types of information”
“a really well-designed puzzle should be able to be completed by a good puzzler without needing to be hinted in any way”
How the episode opens
Bloomberg Audio Studios podcasts radio news. Hello and welcome to the Money Stuff Podcast. This week we have a rerun of an interview that we first aired back in May 2025.
It's a conversation that Katie and I had with Ryan Patch and John Seal, the guys who run Midnight Madness, the huge overnight puzzle hunt across New York City. Midnight Madness is happening again in just a couple of weeks on October 10th. So, we thought it was a perfect time to revisit this conversation.
Enjoy. I 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.
Our second and third guests. — Second and third guests. They are Ryan Patch and John Seal of The Great Gotham Challenge. two creators of Puzzle Hunts. Welcome. — That's about uh all you need to say. We make puzzle hunts. 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 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.
Thank you. Happy to be here. coming soon to New York City Street near you. — This is a podcast broadly about money stuff related to money. — That's what we build it as. — 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.
From the episode’s captions: roughly the first two minutes, lightly cleaned. Keep watching on YouTube →
Topics
- midnight madness
- puzzle hunts
- hedge fund culture
- event planning
- entrepreneurship
Companies and tickers mentioned
- Great Gotham Challenge
Watch the episode
Watch “Re-run: Midnight Madness: Ryan Patch and Jon Seale | Money Stuff: The Podcast” on YouTube
Summary, takeaways and quote selection by Octagon. Quotes are short excerpts; the full conversation is in the episode.
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