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The Art of Foolish Spending

12 min

The Remarkable Power of Giving People More Than They Expect

Golden Hook & Introduction

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Olivia: Alright Jackson, I’ve got a game for you. Review a book in exactly five words. The book is about the world’s best restaurant. Go. Jackson: Okay, five words. "Make customers tell legendary stories." How's that? Olivia: I like it. Very narrative-focused. Mine is: "Giving more is good business." Jackson: Ah, the practical, bottom-line approach. I should have known. So what book has us talking in these five-word epigrams? Olivia: We are diving into the widely acclaimed bestseller, Unreasonable Hospitality: The Remarkable Power of Giving People More Than They Expect by Will Guidara. And his story is just wild. At 26, he took over a struggling two-star brasserie in New York called Eleven Madison Park. Over the next decade, he and his partner, Chef Daniel Humm, transformed it into the number one restaurant in the world. Jackson: The number one restaurant in the world? That’s an insane claim. What does that even take? I assume it involves more than just really good food. Olivia: It absolutely does. And funnily enough, the journey to becoming number one didn't start with a success. It started with a spectacular, public failure.

The Birth of 'Unreasonable Hospitality': From Humiliation to a World-Changing Vision

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Jackson: A failure? That's not what I expected. Tell me more. Olivia: So, it’s 2010. Guidara and Chef Humm are at the World's 50 Best Restaurants awards in London. They’re a hot New York restaurant, they have four stars from the Times, they’re feeling good. But they're also intimidated. All the culinary gods are there—Thomas Keller, Heston Blumenthal. Jackson: I can picture it. The new kids feeling like they don't quite belong at the cool table. Olivia: Exactly. The ceremony starts, and they're counting down from 50. They’re hoping for a good spot, maybe top 30, top 20. The announcer gets to number 50... and it's them. Eleven Madison Park. Dead last on the list. Jackson: Oof. That is a gut punch. In front of all your heroes. Olivia: A gut punch broadcast on a giant screen, which showed their crestfallen faces for everyone to see. To make it worse, another famous chef, Massimo Bottura, comes up to them later and basically mocks them for looking so disappointed. They were so humiliated they just left and went back to their hotel room. Jackson: Wow, that's brutal. So they just drown their sorrows in the minibar and fly home? Olivia: They did drink some bourbon, but something else happened. In that hotel room, feeling like total failures, they had what Guidara calls the "Cocktail Napkin Revelation." They asked themselves, "What would you attempt to do if you knew you could not fail?" And on a cocktail napkin, they wrote, "We will be Number One in the world." Jackson: That is an incredibly bold move. It's one thing to think that, but to write it down after being ranked fiftieth? What actually changed? A napkin can't magically make you better. Olivia: That's the core of the book. They realized they had been focused on being excellent—on perfecting the food, the service, the technical details. But all the other great restaurants were doing that too. They needed to change the conversation entirely. And that's when Guidara added two more words to that napkin: "Unreasonable Hospitality." Jackson: Okay, I need a definition here. "Unreasonable Hospitality." What makes it different from just really, really good service? Olivia: Guidara tells this great story about a job candidate who gave him the perfect answer. She said, "Service is black and white; hospitality is color." Service is technical—did you pour the water correctly? Did you bring the food on time? Hospitality is emotional—how did you make the person feel? It’s the difference between a transaction and a connection. Jackson: Hospitality is color. I like that. It’s about adding something more, something human. Olivia: Precisely. It’s about moving from a monologue, where the restaurant tells you what's great, to a dialogue, where you connect with the guest and give them what they need in that moment. And that philosophy of connection is what they decided would be their path to number one.

The 95/5 Rule and the Art of 'Foolish' Spending: Systematizing Magic

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Jackson: Okay, so this all sounds wonderful and inspiring. But let's be real, "color" and "connection" sound expensive. Especially the "unreasonable" part. How does a business, particularly a restaurant with notoriously thin margins, actually afford to be unreasonable? Olivia: This is my favorite part, because it’s so counterintuitive. Guidara developed what he calls the "Rule of 95/5." The idea is you manage 95 percent of your business down to the absolute penny. You are meticulous, you are disciplined, you cut waste everywhere you can. And you do that so you can spend the last 5 percent "foolishly." Jackson: Spend it foolishly? My accountant just had a heart attack. What does that even mean in practice? Olivia: It means you use that 5% to create disproportionate memories. The perfect example is the gelato cart. Guidara became obsessed with creating a gelato cart for the restaurant's terrace. He found the best gelato, designed the perfect cart, and then he found these tiny, perfect, light blue spoons from a specific maker in Italy. They were absurdly expensive. Jackson: For spoons? Come on. No one is going to remember the spoons. Olivia: That's what a "reasonable" manager would say! But Guidara argued that this was the 5%. He was so tight with the rest of the budget that he could afford this one "foolish" detail. And it worked. The spoons elevated the entire experience. People talked about them. The head of the museum even commented on them. It was a tiny detail that screamed, "We care about everything." Jackson: So it's like a personal budget. You're frugal on groceries and daily expenses all month so you can justify buying that one amazing concert ticket that you'll remember forever. Olivia: That's a perfect analogy. And they applied it everywhere. They'd use slightly less expensive wines for most of a tasting menu pairing, so they could pour one glass of something incredibly rare and special at the end. The goal of the 5% isn't just spending; it's investing in the story the guest will tell later. Jackson: I'm thinking of the most famous story from the book, the one that’s all over the internet. The family from Spain who had never seen snow, and the team sent them sledding in Central Park after dinner. That had to be a 5% moment. Olivia: Absolutely. A completely unplanned, improvisational, and "foolish" expense. But the return on that investment isn't measured in dollars. It's measured in legend. That family will tell that story for the rest of their lives. And that's where Guidara took it a step further. He didn't want these moments to be random. He wanted to systemize magic. Jackson: How do you systemize magic? That sounds like a paradox. Olivia: You create a new position. He hired someone he called a "Dreamweaver." Their entire job was to listen—to overhear conversations, to read reservation notes—and then use a dedicated budget to create these unreasonable moments. A couple's vacation gets canceled? The Dreamweaver fills a private dining room with sand and serves them mai tais. It became a core, budgeted part of the operation. Jackson: Wow. So it’s not just a random act of kindness. It's a deliberate business strategy. That changes everything. It’s not about being nice; it’s about being intentional. Olivia: Exactly. And that intentionality is what makes it scalable. Or at least, that was the next big challenge.

Scaling Culture: From One Restaurant to an Empire of Kindness

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Jackson: Right, that's the big question. This all works beautifully in one elite, four-star, world's-best restaurant. But can you really scale a feeling? What happened when they tried to expand? Olivia: Well, they got the chance. In 2011, they were offered the opportunity to run the entire food and beverage program for a new hotel, The NoMad. At the same time, their boss, Danny Meyer, offered to sell them Eleven Madison Park. Suddenly, they were about to be owners of their own empire. Jackson: That's a massive leap. From running one restaurant to owning it and launching a huge hotel operation. Olivia: It was huge. And Guidara made a classic, ambitious leader's mistake. He thought he could do it all. He decided he would be the general manager of both Eleven Madison Park and The NoMad. He was literally running back and forth between the two buildings. Jackson: Oh, I can see where this is going. That sounds like a recipe for disaster. Olivia: It was. While The NoMad was a huge success, things at Eleven Madison Park started to slip. The team felt a lack of leadership. Decisions weren't being made. The culture they had worked so hard to build was starting to fray because the person at the center of it was stretched too thin. Jackson: Did anyone say anything to him? It can be hard to speak up to the boss, especially a successful one. Olivia: A few senior managers tried, but he was in the whirlwind and didn't really hear them. The breakthrough came from a longtime, trusted captain named Sheryl Heefner. She pulled him aside and didn't accuse him or yell at him. She just calmly and lovingly reflected back to him what his absence was doing to the team he claimed to care so much about. She basically said, "You tell us to trust each other, but you're not trusting any of us to lead this place." Jackson: That must have been a tough pill to swallow. Olivia: It was a wake-up call. He realized he was failing his team at EMP. And in that moment, he did something that many leaders find impossible. He went to the entire staff, all 150 of them, and he apologized. He admitted he was wrong, that he had let his ambition get in the way of his responsibility to them. Jackson: For a leader at that level to show that kind of vulnerability is incredibly rare. That's an act of hospitality in itself, isn't it? Olivia: It's the ultimate act of unreasonable hospitality—directed at his own team. And then he did the most important thing: he promoted from within. He made Kirk Kelewae, the guy who had started as a kitchen server and built their beer program, the new general manager of Eleven Madison Park. He empowered his team to carry the culture forward. Jackson: So the lesson in scaling the culture wasn't about the leader being everywhere at once. It was about the leader learning to let go and trust the people they'd built. Olivia: Exactly. You don't scale a feeling by cloning yourself. You scale it by instilling the values so deeply in your team that they become the new carriers of the culture. You create more leaders.

Synthesis & Takeaways

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Jackson: When you boil it all down, what's the one thing we should really take away from Unreasonable Hospitality? It feels like it’s about so much more than just restaurants. Olivia: It is. I think the central idea is that in our modern economy, your product or service is often just the ticket to entry. Everyone can make a good cup of coffee or a solid steak. The real differentiator, the thing that builds true loyalty and creates stories that people will tell for a lifetime, is how you make them feel. Jackson: It’s about intentionality. It's not about these grand, expensive gestures that most of us can't afford to do. It’s about looking for small opportunities to give people more than they expect. Olivia: Precisely. It’s the difference between a transaction and a connection. Guidara proves that investing in connection isn't just a "nice" thing to do; it's the most powerful and sustainable business strategy there is. It's about choosing to be in the business of making people feel seen. Jackson: I love that. It feels like a challenge, in a good way. Olivia: It is! And here’s a challenge for our listeners. Think of one interaction you'll have today—with a customer, a colleague, your partner, your kids. And just ask yourself, "How can I add 5% of unreasonable hospitality to this moment?" It doesn't have to be a grand gesture. It can be as simple as truly listening. Jackson: That’s a great, practical takeaway. And we'd love to hear what you come up with. Find us on our social channels and share one small, "unreasonable" thing you did today. Let's build an empire of kindness together. Olivia: I love that. A perfect way to end. Jackson: This is Aibrary, signing off.

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