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AI Can Do Everything…Except This (Why Humans Still Win) with Will Guidara | A Bit of Optimism

As businesses race toward faster systems, smarter tools, and total automation, something critical is getting lost: human connection. And ironically, the rise of AI is making that gap impossible to ignore. In this episode, I sit down with returning guest and close friend Will Guidara, former co-owner of Eleven Madison Park, to explore why humanity is becoming the ultimate competitive advantage in the age of AI. Will helped transform a restaurant into the best in the world, not by reinventing the food being served, but by reinventing the experience around it. He calls this philosophy "Unreasonable Hospitality," which is the practice of going beyond what’s expected or required to make someone feel genuinely seen, valued, and cared for to create a memorable human experience. He argues that in a world where people expect excellence, the real differentiator is care. And Will isn’t alone in this belief. His book "Unreasonable Hospitality", which I’m the proud publisher of, is a global bestseller. And his follow-up book, "Unreasonable Hospitality: The Field Guide", comes out April 28, 2026. In this conversation, Will and I unpack why human value will continue to rise in an automated world, how the smallest moments of care can create lasting loyalty, how we can turn automation’s efficiency into better experiences, and why the things that matter most in our lives are the hardest to measure. And fair warning, Will and I do giggle our way through some of this conversation about why technology can’t replace human connection, the hidden cost of achievement, and a story about how a single piece of Basque cheesecake delivered to a hotel room is a gesture thoughtful enough to make someone feel seen. That’s just the kind of friendship we have. So if you’re wondering how to stand out and live a more meaningful life in a world increasingly shaped by AI—and share a laugh with us—this is a conversation for you. This… is A Bit of Optimism. To stay in the loop with Will or purchase his best-selling book Unreasonable Hospitality, head to: https://www.unreasonablehospitality.com/ If you’d like to pre-order Unreasonable Hospitality: The Field Guide, out April 28, 2026, check out: https://uhthefieldguide.com/ + + + Simon is an unshakable optimist. He believes in a bright future and our ability to build it together. Described as “a visionary thinker with a rare intellect,” Simon has devoted his professional life to help advance a vision of the world that does not yet exist; a world in which the vast majority of people wake up every single morning inspired, feel safe wherever they are and end the day fulfilled by the work that they do. Simon is the author of multiple best-selling books including Start With Why, Leaders Eat Last, Together is Better, and The Infinite Game. + + + Website: http://simonsinek.com/ Live Online Classes: https://simonsinek.com/classes/ Podcast: http://apple.co/simonsinek Instagram: https://instagram.com/simonsinek/ Linkedin: https://linkedin.com/in/simonsinek/ Twitter: https://twitter.com/simonsinek Facebook: https://www.facebook.com/simonsinek Simon’s books: The Infinite Game: https://simonsinek.com/books/the-infinite-game/ Start With Why: https://simonsinek.com/books/start-with-why/ Find Your Why: https://simonsinek.com/books/find-your-why/ Leaders Eat Last: https://simonsinek.com/books/leaders-eat-last/ Together is Better: https://simonsinek.com/books/together-is-better/ + + + #SimonSinek

Simon SinekhostWill Guidaraguest
Mar 24, 20261h 5mWatch on YouTube ↗

EVERY SPOKEN WORD

  1. 0:00 – 0:22

    Intro

    1. SS

      I just need to share it with people-

    2. WG

      Yes

    3. SS

      ... that this is how we actually have conversations. [laughs]

    4. WG

      [laughs] Whether we're being recorded or not.

    5. SS

      Whether we're being recorded or not. Like, this is the way we actually talk.

    6. WG

      [laughs]

    7. SS

      We interrupt each other more.

    8. WG

      [laughs]

    9. SS

      We're being polite. We-

    10. WG

      We're trying to, we're trying to interrupt a little bit less.

    11. SS

      We're trying to interrupt-

    12. WG

      We're not doing a great job, but-

    13. SS

      We interrupt each other less, but we actually would have this conversation-

    14. WG

      100%

    15. SS

      ... without cameras. [laughs]

    16. WG

      100%. [whimsical music]

  2. 0:22 – 2:09

    Why AI raises the value of kindness and attention

    1. SS

      AI is the hot topic right now. There are so many people talking about all the tools that can help us do things faster, cheaper, more efficiently than ever before. All of this is true, but it's also revealing something interesting, that the more automated our world becomes, the more valuable the human being is becoming. Being thoughtful, paying attention, being genuinely nice to people, making people feel seen and heard. It turns out things like kindness are pretty much AI-proof, which is why I was so excited to welcome my dear friend Will Guidara back to the podcast. Fair warning that if you listen to this podcast, when Will and I get together, it always turns into what somebody once described as a giggle fest.

    2. WG

      [laughs]

    3. SS

      Will is pretty incredible. He is the former co-owner of Eleven Madison Park, which was the number one restaurant in the world. He is the executive producer of the TV show The Bear, and he is the bestselling author of The New York Times bestseller Unreasonable Hospitality, of which I am the proud publisher, and I'm also the proud publisher of Will's new book, Unreasonable Hospitality: The Field Guide, which is remarkable. Will has accomplished all those things and built his entire career around one simple philosophy, that if we go further than anyone expects, that's when we can make people feel truly cared for. Though usually Will is the one going above and beyond, he recently found himself on the receiving end of his own philosophy in a hotel room in Los Angeles involving a piece of Basque cheesecake, and somehow me. This is A Bit of Optimism. [whimsical music]

  3. 2:09 – 5:32

    The Basque cheesecake story: a masterclass in being "seen"

    1. WG

      Okay, I gotta tell you something. So I got to LA two nights ago, and then I had to go to Anaheim, and then I came back. And the night I stayed here, I stayed at the, the Waldorf in Beverly Hills. Now, uh, you know what this story is going to be about, but other people don't. So when I say Basque cheesecake, what is, what does that mean to you?

    2. SS

      Okay. So a while ago you came to visit LA, and you and I went out for something that I'd never done before. You said, "We're gonna go out for dinner," and you said, "Do you wanna do bang bang?" And I said, "What's bang bang?"

    3. WG

      [laughs]

    4. SS

      And what bang bang is, is you go to a different restaurant for each course.

    5. WG

      Yeah.

    6. SS

      So you and I went to one restaurant for appetizer.

    7. WG

      Yeah.

    8. SS

      We went to a different restaurant for the main course.

    9. WG

      Yeah.

    10. SS

      And while we're sitting in the restaurant having our main course, we were planning where we should go for dessert.

    11. WG

      Yes.

    12. SS

      And you said, "I know where we're going." You said there's this, uh, restaurant called Pageole in Santa Monica.

    13. WG

      Yeah.

    14. SS

      And they have what you described as one of the top five desserts you've ever had in your life. Now, coming from the top restaurateur in the world, that's a, that's a bold statement right there.

    15. WG

      It means something.

    16. SS

      It means something. And you said, "Here's the problem. You can't order it. It's off the menu. They give you a slice if they like you. If you see somebody else getting one and you say, 'Hey, can I have one?' They say no."

    17. WG

      [laughs]

    18. SS

      "You can't pay for it, you can't order it, and they make one a night. That's it."

    19. WG

      Yeah.

    20. SS

      "Let me text to see if they've got a slice. I know the chef."

    21. WG

      Yeah.

    22. SS

      So you text the owner, and he says, "We have one slice left. Get over here." And you're like, " [fingers snap] We're going to Pageole." We went to Pageole. They spoiled us. We had our slice of Basque cheesecake, and it was easily one of the top five desserts I've ever had in my life.

    23. WG

      One of the greatest things in the world.

    24. SS

      One of the greatest things ever.

    25. WG

      Okay. So I've never told that story before. I get to the hotel, I go up to the room, and there's a really awesome note, um, from the guest relations manager. Her name is Abby. She says, "Will, welcome. Congrats on the field guide. Since you probably aren't gonna make it to Santa Monica, we decided to bring a piece of Santa Monica to you. Check the fridge." I open the fridge, and it's a piece of the Basque cheesecake from Pageole.

    26. SS

      No.

    27. WG

      So I'm, like, freaking out.

    28. SS

      But how do they even know?

    29. WG

      Well, so I crush it. I go to bed. I, the next morning, have a breakfast.

    30. SS

      [laughs]

  4. 5:32 – 8:03

    When the secret goes mainstream: Simon’s follow-up cheesecake date

    1. SS

      Anyway, did I tell you the, the follow-on story to the Basque cheesecake at story at Pageole?

    2. WG

      Wait, yes, but you need to tell it. [laughs]

    3. SS

      [laughs] You, so I'm on-

    4. WG

      You need to tell it here

    5. SS

      ... I'm on a date. [laughs]

    6. WG

      Wait, but hold on. So but for context, the bang bang dinner we had was probably two or three years ago.

    7. SS

      Y- y-

    8. WG

      It was a while ago now.

    9. SS

      It was a while ago. Yeah, yeah.

    10. WG

      Three or four years ago now.

    11. SS

      It was a while ago, yeah. So here's the follow-on story to the Basque cheesecake. [laughs] So I'm on a date, and I'm telling the story of our bang bang night and this amazing cheesecake that's off the menu. You can't order it.

    12. WG

      Yeah. [laughs]

    13. SS

      You know, it's a French m- it's a French restaurant. That's why they can't serve Basque cheesecake on the menu. And I said to the girl, I'm like, "I met the owner. I, I'm, I bet we could get a slice."So we go to the restaurant. It's af- you know, it's later n- it's later. It's like 9:30 or something, so dinner service is winding down. We get a great spot at the bar, right on the edge of the bar. I go to the bartender, and I bring up the, the owner's name. I was like, "Hey, is he in?" You know, dropping the hint, you know? And he's like, "Nah, he's not in tonight." I'm like, "Oh, okay. Well, sorry I missed him." And then I sort of like, sort of, sort of surreptitiously go-

    14. WG

      [laughs] Out of the side of your mouth

    15. SS

      ... out of the side of my mouth like, um, "Think we could get a slice of cheesecake?"

    16. WG

      [laughs]

    17. SS

      And the bartender looks at me and sort of like... He's like, "Yeah, I think we could arrange that." And I am like-

    18. WG

      You- you're just the man

    19. SS

      ... I'm, I'm just the man.

    20. WG

      You're the man.

    21. SS

      And they-

    22. WG

      You're gonna look so good on this date

    23. SS

      ... um, so they bring out the cheesecake. The girl is like, "Oh my God, this is one of the top five desserts I've had in my life." I'm like, "I told you, right?"

    24. WG

      Yeah.

    25. SS

      "Isn't this amazing?"

    26. WG

      Yeah.

    27. SS

      And y- and the, the... Like, we got a slice.

    28. WG

      Yeah.

    29. SS

      Isn't this amazing?

    30. WG

      Because I'm, like-

  5. 8:03 – 11:07

    Reinventing fine dining by reinventing hospitality

    1. SS

      This is a treat for me because, um, you've come on the podcast a few times before-

    2. WG

      Yeah

    3. SS

      ... but this is the first time we've ever done it in person.

    4. WG

      I know. I love this.

    5. SS

      And this is what, you know, I, I want people to appreciate, which is you and I are actually very, very close friends. Um, and so any time I get with you is a treat. For the m- many, many reasons I love you, uh, one is how your brain works.

    6. WG

      Hmm.

    7. SS

      Um, and it doesn't work like mine. [laughs]

    8. WG

      Opposites attract.

    9. SS

      I don't know if it's opposite, but it's, it's y- your, your brain doesn't work like a lotta people. You know, for, for somebody who's extremely good at business, I mean, you're a, you're a g- a, a good, shrewd business person who understands the, the levers of business. You're one of the most creative people I've ever met.

    10. WG

      Hmm.

    11. SS

      And I love, I love bragging about Unreasonable Hospitality, and I love telling people, you know, where most restaurants find themselves number one in the world because they reinvented food, to come up with the idea that you can become the number one restaurant in the world by reinventing hospitality.

    12. WG

      Hmm.

    13. SS

      The thing that I found amazing about that is for the hundred years of, you know, we've been rating restaurants, that it was always about the food.

    14. WG

      Yeah.

    15. SS

      Any- anybody could've come up with, "Wait, what about the hospitality?"

    16. WG

      Yeah. [laughs]

    17. SS

      Like, it liter- it's not like, it's not like you're the only person that could've come up with that.

    18. WG

      No.

    19. SS

      And it's both exciting and depressing at the same time.

    20. WG

      Yeah.

    21. SS

      Like, amazing you came up with it, kinda depressing nobody came up with it. When in your restaurant career, 'cause you're a front of house guy, when in your restaurant career did you start to recognize that treating people was the thing that everybody else wasn't focusing on?

    22. WG

      I mean, I think where we did something different was thinking about this approach at the very high end. Like, Danny Meyer, who was my boss and mentor, was focused on hospitality, and I mean, uh, he gave me the foundation upon which I built all this stuff. Where we took it in a different direction was do it at the three-Michelin-star level, and we doubled down on hospitality at that level, I think, uh, uh, for the following reason: It's easy to have a hospitable restaurant when you are less concerned with the details, right? Excellence and hospitality don't necessarily go hand in hand.

    23. SS

      Mm-hmm.

    24. WG

      But when you're so maniacally focused on perfection, hospitality would normally take a backseat because you care more about serving a perfect plate of food and having every detail of the service be executed at a certain level, and that always took precedence over how you made people feel.

    25. SS

      Mm-hmm.

    26. WG

      I, I think our, our thing where we challenged that was to say, "Hey, yeah, we wanna be excellent. We want to have food that is extraordinary and service that is as close to technically perfect as possible in an amazing dining room," and yet those are table stakes. Like, that's just fulfilling the base level obligation you have, the promise you are making when you choose to operate a restaurant like that. We believe that in our hospitality, that's where we can really make an impact.

  6. 11:07 – 12:37

    Table stakes vs. differentiation: how brands confuse excellence with "unreasonable"

    1. SS

      So, so here's where my mind is going, right? Here's where my mind is going, and, and, and, and this is where I think from a brand standpoint, from a marketing standpoint, from a product standpoint, where so many businesses get it wrong is they confuse, uh, excellence and unreasonable.

    2. WG

      Yeah.

    3. SS

      Right? And, and here's where my mind is going, right? The number of companies that offer usually some sort of back office service, whether it's accounting or some sort of organizational software, whatever it is, their value proposition in their marketing is always the same. "We do all the dot, dot, dot so that you can go focus on dot, dot, dot."

    4. WG

      Yes.

    5. SS

      Right?

    6. WG

      Yes.

    7. SS

      Like, "We'll do the accounting so you can focus on building the business," and, and they all kind of have the same, you know, value proposition. And in reality, like, that's what your product is supposed to do.

    8. WG

      Yeah.

    9. SS

      Like, the reason I'm paying you money-

    10. WG

      Yeah

    11. SS

      ... is for you to do the stuff that I don't wanna do. That is why I hired you. [laughs]

    12. WG

      Yes. Yeah.

    13. SS

      Right? Like, and the way you're talking about excellence and service, like, you have to do that minimally.

    14. WG

      Exactly.

    15. SS

      And now, you could argue you do it better than others. Fine. That's a different conversation. But if you accept that that's the minimal standard to do that excellently-Now what?

    16. WG

      It's almost like the-

    17. SS

      It opens up an entirely new door for how to build a brand, how to understand marketing, how to understand customer service. If you accept that doing that brilliantly is the table stakes.

    18. WG

      That's how you should describe the product, not how you should sell it. Like, "This is the product. We're gonna do all this."

    19. SS

      Right.

  7. 12:37 – 13:41

    Hospitality as the only durable competitive advantage

    1. WG

      "The reason you should work with us, though, is this." As I've traveled around, 'cause I've been all over the country, around the world for the last few years, spending time with companies across pretty much every industry, everyone is trying to identify their competitive advantage.

    2. SS

      Mm.

    3. WG

      Right? What is it about their business that will prevent someone else from coming in and, and taking it away? And yet those conversations to that point almost always center around the quality of the product, sometimes the strength of the brand. But here's the thing, it does not just matter how good the product is or how strong the brand is, because eventually, this is not my opinion, it's a fact, time has proven it to be true, someone will build a better product-

    4. SS

      Mm

    5. WG

      ... or they will create a stronger brand. They may be better capitalized. They may be newer and shinier, younger and more innovative. They may just be more talented than we are.

    6. SS

      Mm.

    7. WG

      The only competitive advantage that exists in the long term, in my view, is hospitality.

    8. SS

      Mm.

    9. WG

      Consistently, generously, creatively investing in relationships, because those take a long time to build.

  8. 13:41 – 17:00

    AI and automation: people become a luxury (and a trust signal)

    1. SS

      I think your message is more timely, you know, than I think people realize, which is, was the rise of AI.

    2. WG

      Mm.

    3. SS

      What the technologists all forget is people. They always leave the people out.

    4. WG

      Yes.

    5. SS

      Right? They have these visions of the world that will exist, and they always forget that people fundamentally are legacy machines. We're tens of thousands of years old, older than that, hundreds of thousands of years old, and our software has not been updated-

    6. WG

      Yeah

    7. SS

      ... at all, ever. And, you know, you look at the, the world where technology has attempted to sort of take over. You know, Amazon, uh, is removing all the palm scanners from, uh, uh, Whole Foods because of unbelievably low adoption. The economics no longer make sense.

    8. WG

      Yes.

    9. SS

      Right? Amazon had those stores where you could just walk in, take stuff off the shelf, and walk out. Sounds like a dream.

    10. WG

      Yes.

    11. SS

      They're closing them all 'cause they're not working.

    12. WG

      I mean, yeah.

    13. SS

      Right?

    14. WG

      Because the ones in the airport, it's a disaster.

    15. SS

      It's the worst. And, and what they're forgetting is I don't want to look on an app to find out where the thing is. The reason I like having a guy stocking the shelf is not 'cause I want a person stocking the shelf, it's 'cause I want a person randomly in an aisle that's nearby that I can say, "Where's the peanut butter?"

    16. WG

      Mm-hmm.

    17. SS

      And they either point or take me. Either one, I don't care. But the point is, that tiny little interaction makes me feel seen and heard as a human being. And even if it's a basic thing, talking to another person, even though the AI could do it, is delightful. And the airlines know this, and hotels know this, and anybody in the service industry knows this, but the problem is, is that a person has become a luxury, that you have to earn a person.

    18. WG

      You have to earn access to them.

    19. SS

      You have to earn access to a human being. And, and all the technologists and, and the sort of the AI is like we're taking all the people away. And this is why your work is more prescient and more important than simply being a competitive advantage. It reinforces the importance of the human being in any commercial transaction.

    20. WG

      Well, and yeah. Gosh, I love that. And I, and I think it's only gonna grow in its importance.

    21. SS

      Which is a good thing. Your book is selling gangbusters, and your, your stuff is spreading like crazy, and I think that is a good sign that as, as AI and automation grows, that at least a class of, of, of people are recognizing that we cannot do it at the sacrifice of people.

    22. WG

      Yes.

    23. SS

      It has to be done in parallel with people.

    24. WG

      Well, and by the way, if everything we're saying is true, humans are a form of luxury now. That will only become increasingly so. Like, even you pick up the phone and you call someone, and whether it's one year, two year, five years, who knows how long it's gonna be, we're not gonna know whether we're talking to a human being anymore.

    25. SS

      Yeah.

    26. WG

      That technology is getting so good-

    27. SS

      It's so good

    28. WG

      ... that we won't be able to trust. I'll get off the phone and I'll be like, "I think I was talking to a human. I, I really don't know." Which means I, I really do believe that I've seen enough of it now to feel pretty convicted that, uh, we're gonna get close to that. Which means-

    29. SS

      Yes, and? But go on

    30. WG

      ... I think the moments like this-

  9. 17:00 – 18:59

    The smart AI play: save money, then reinvest in more human moments

    1. WG

      And I think we're at a crossroads in how companies are beginning to adopt the technology. And let, let me finish.

    2. SS

      Yeah, yeah, yeah, yeah.

    3. WG

      Where there are plenty of companies ... Listen, with a lot of the financial pressure people are facing right now, AI represents, like, a pretty good lever that you can pull to get your profitability in line.

    4. SS

      Mm.

    5. WG

      You can adopt some of this technology, you can clear out a bunch of people, you can put some more money to the bottom line, you can get ... You can save the day, and many people will do that. I think the ones that are very, very smart, though, are gonna be those that recognize that, yeah, maybe you need to save a little bit of money. But if you reinvest some of the money you saved into making those human moments even more human-

    6. SS

      Mm

    7. WG

      ... you'll make a little bit less today, but you will make so much more down the road.

    8. SS

      Yeah.

    9. WG

      Because those are gonna be the people we turn to when we are feeling that way.

    10. SS

      And, and when things go wrong.

    11. WG

      Yeah.

    12. SS

      You're like, "Enough with the computer. I need a person."

    13. WG

      And you'll know who you can go to.

    14. SS

      And you'll know who you-

    15. WG

      You'll know who to trust

    16. SS

      ... I think that's right. This is an amazing opportunity for something like Unreasonable Hospitality as a concept, not as a, as a book, is because, um, if people are concerned about job losses, well, why not expand hospitality jobs?

    17. WG

      Yeah. Hang on.

    18. SS

      Why not make more jobs service jobs? And you talk about the nobility of service. And it's not like we're trading in, you know, I used to be a knowledge worker, you know, computer programmer or whatever I was doing, and now, you know-I'm, I'm digging ditches, you know, to build roads.

    19. WG

      [laughs]

    20. SS

      You f- that's not w- that's not what we're talking about here.

    21. WG

      Yeah.

    22. SS

      Which is the sophisticated problem-solving, highly engaged, you know, e- e- emotional intelligence required to be good at service, and the joy that is derived from helping another human being could be way more fulfilling or at least equally as fulfilling as any job you loved. And so why not reinvest some of those savings, as you said-

    23. WG

      100%

    24. SS

      ... and convert some of those jobs in- into service jobs? Let's double down on, on people.

  10. 18:59 – 21:25

    A practical case study: reservations tech and redeploying (not firing) staff

    1. WG

      So listen to this. I wanna tell you a story from the restaurant back in the day, which is pre-AI but analogous to what we're going through now. For a long time, I believed strongly that you shouldn't make reservations over the phone. I wanted every experience with us to begin with a human voice. And so even when OpenTable came around and you could book reservations online, we had OpenTable because an interface-

    2. SS

      You have to.

    3. WG

      Yeah. But we blocked every reservation online. You had to call the restaurant to make a, to make one.

    4. SS

      To make one.

    5. WG

      'Cause I had awesome reservationists. I wanted to start with a human voice. And then thankfully, you know Laura. It was, like, the person on my team that I trusted so much, and she trusted me enough to be able to call me out when I was doing something dumb. She said, "Hey, have you ever even tried to make a reservation here?" And I said, "Well, no." She goes, "Why don't you try?" 'Cause the team was getting upset at me for this decision. So next day at 9:00 AM, 28 days before we opened to the books, I called only to be put on hold, to wait on hold for 30 minutes, to be taken off hold to say, "I'm so sorry. We're fully reserved. Can we add your name to the wait list?" I was like, "Oh."

    6. SS

      [laughs]

    7. WG

      And so she was right. We, I w- I, in pursuit of-

    8. SS

      Yeah

    9. WG

      ... human connection, I was doing something that was definitively less hospitable.

    10. SS

      Mm-hmm.

    11. WG

      So instead I went in the opposite direction. Now you couldn't book reservations on the phone anymore.

    12. SS

      [laughs]

    13. WG

      They were only available online.

    14. SS

      Yeah.

    15. WG

      Which meant you go went on at 9:00 AM, and it was very clear when we had reservations, when we didn't. No one had to waste their time. But here's what I did, and I think ... I didn't write about this in Unreasonable Hospitality, and that was a mistake because I think it's one of the most important decisions I ever made. We did not fire a single person from our reservations team. Now we had no one answering phones all day. They didn't have to do that. Rather, we redeployed them to spend all the same time they were telling people no and adding people to the wait list to spend proper time with people who had gotten a reservation on the phone, getting to know them, and understanding how we could make their meal more special. That's what I'm talking about right now.

    16. SS

      Amazing.

    17. WG

      Like, as we shift ... And now, I, I'm not gonna blame anyone for saying, "All right. If we have 10 people, I'm gonna get rid of a couple people 'cause we're really over budget on a labor perspective. I need a little bit of that back." But keep the eight people, and through a bit of creativity and a lot of intention, figure out how you can deploy them-

    18. SS

      Yeah

    19. WG

      ... so that the experience feels more connective, more memorable, that you can build that loyalty.

    20. SS

      Yeah.

  11. 21:25 – 27:14

    Loyalty is the greatest capital—and it’s slow to build, slow to lose

    1. WG

      Uh, listen, the greatest capital-

    2. SS

      Mm-hmm

    3. WG

      ... we have is loyalty from the people we serve.

    4. SS

      Mm-hmm.

    5. WG

      'Cause it takes a long time to erode.

    6. SS

      Mm-hmm.

    7. WG

      And, uh, I'm sure you've had relationships with companies where they dropped the ball big time, and if they've done enough to earn your loyalty, you're gonna give them one, two, three more chances. I've had people come in who maybe do a little bit better job for less money-

    8. SS

      Yeah

    9. WG

      ... but because this person has been good to me for such a long time, I'm loyal and I'm gonna stick with them. And I don't think that's a uniquely, that's a unique trait to me.

    10. SS

      Well, this is, this is exactly the conversation we're having, which is the technologists b- forget about the people.

    11. WG

      Yeah.

    12. SS

      And there's one thing that every human being on the planet needs, it's other human beings.

    13. WG

      Yeah.

    14. SS

      Right? And we know this. We know that, you know, a solitary confinement is a form of torture, and we know that solitary confinement literally makes people lose their minds.

    15. WG

      At one point, once upon a time, an economist said the words, "What gets measured gets managed." And I understand, obviously, there's a lot of benefit to thinking that way, and yet I think that one idea has been so destructive to so many companies. Because the reality is some of the things that are the most important to do, you cannot measure the return in as easily or immediate a way as these companies have been trained to, to think. Yeah. If you start investing in hospitality, if you start really putting resource to making the people you work with and those that you serve feel truly seen and valued and cared for, will it benefit you over the long term? Yes. Is it easy to measure in three, six, nine-month increments? No. But just because it's harder to measure doesn't mean it matters less. In fact, it means it matters more. And I think that those who don't invest in it because they can't clearly calculate it in the short term are being reckless in the long term.

    16. SS

      Well, let- let's reveal it here. You're operating at a level that's beyond. Like, the amount that you invested in, in Unreasonable Hospitality is more than you're even expecting others to.

    17. WG

      Yes.

    18. SS

      And yes, you became the number one restaurant in the world. Right here on camera, did your company lose money?

    19. WG

      No.

    20. SS

      Exactly. The company didn't lose money. [laughs]

    21. WG

      No. We made more than most.

    22. SS

      You made more money.

    23. WG

      I think we were one of the most profitable fine dining restaurants in America.

    24. SS

      There you go. One of the most profitable fi- ... That's a, that's an important detail-

    25. WG

      Yeah

    26. SS

      ... for the people who are, who question your work, which is you may not have seen it in month one or month two-

    27. WG

      No

    28. SS

      ... but you were one of the most profitable fine dining restaurants in the world, not just number one-

    29. WG

      Yeah

    30. SS

      ... because of Unreasonable Hospitality, right?

  12. 27:14 – 30:15

    The tyranny of measurable metrics: impressions, clicks, and short-term ROI

    1. WG

      100%. The other area this applies to is marketing, and I see this all the time. Like, you, you can see the... I, I remember back in the day, we did a lot of brand partnerships, and the question that drives me crazy whenever I'd go to someone with an idea was, "Okay, how many social media impressions are we gonna get out of this?" And it, like, that is how, still to this day-

    2. SS

      Hmm

    3. WG

      ... a lot of brands are deciding where to invest their money is based on how many social media impressions they're gonna get. Now, why? Because that is the easiest thing to measure.

    4. SS

      Mm-hmm.

    5. WG

      What will the impact be on how much people love their brand for-

    6. SS

      Hmm

    7. WG

      ... having done that thing? It's much, much harder to measure. So they take the easy way out-

    8. SS

      Yeah

    9. WG

      ... which is also the thing that is the most meaningless in terms of people's, like, love for that brand. I'll give you an example. When we did EMP Summer House in the Hamptons, we closed Eleven Madison Park to renovate, and we moved the restaurant for three months to The Hamptons. We needed a sponsor to do that, 'cause the whole point of it was Eleven Madison was what it was because of my team. I could not lose them. So I had to move 120 people to The Hamptons for the summer, which meant housing for 130 people in one of the most expensive places on Earth. So I had the idea to go to American Express and say, "Hey, will you sponsor this? This is how much money I need from you, and what I'll do is I will only accept American Express cards and cash, but no other credit cards." And I had to go through meeting after meeting after meeting with all these people more junior in the company, and they were ready to say no because they didn't think they were gonna get enough clicks. They, they, they couldn't figure out a way to measure it. Thankfully, I had a relationship with someone at the top. I ended up just going to him instead. He greenlit it. They had more people in The Hamptons sign up for an American Express card that summer than ever before. It was one of their best investments ever, and now they're doing stuff like that all the time. But it takes someone with creative vision who's able to look, uh, at things over the long term, who's less concerned with-

    10. SS

      The short-term ROI

    11. WG

      ... the short term.

    12. SS

      The short-

    13. WG

      Which, by the way, is not necessarily even a testament to the, the people I was talking to before.

    14. SS

      Yeah, yeah.

    15. WG

      It's a testament to how their compensation was structured.

    16. SS

      100%.

    17. WG

      Like, they can only operate within the confines of how-

    18. SS

      No, I see, I see it with, you know, with advertisers who wanna come on the, on for this show. They only... You know, it goes through some agency-

    19. WG

      Yes

    20. SS

      ... 'cause nobody does it themselves. They all use agencies. The agencies are all compensated based on just clicks, and they'll compare me to some other podcast that does more clicky-baity stuff that has, maybe has more listeners-

    21. WG

      Yeah

    22. SS

      ... and they're just not interested. They don't think about the brand halo. They don't think about, you know, creative things we could gather.

    23. WG

      Or who are the people-

    24. SS

      Who are the people

    25. WG

      ... that are actually listening or what-

    26. SS

      So yeah, yeah. I mean, it's, it's, it's... I see it in publishing, you know, where y- like, to get a book deal these days, the first thing they're gonna do is look at your social media following.

    27. WG

      Hmm.

    28. SS

      And w- in, in other words, they're looking at your, the quality of your idea after-

    29. WG

      Yes

    30. SS

      ... after they're looking at your social media following.

  13. 30:15 – 34:05

    Why their ideas spread: the "exercise" model and playing the long game

    1. SS

      Right? Your work and my work, you know, I'm very open about the fact that most companies, um, will n- do not use my work. Most companies, even if they know about it, don't care about starting with why. They don't care about the infinite game. Like, most companies do not use my work. I, and I know the reason why. It's because my work, like your work, is much more akin to exercise, right?

    2. WG

      Hmm.

    3. SS

      If you, uh, work out every single day for 20 minutes-100% of people will get into shape.

    4. WG

      Yes.

    5. SS

      100%.

    6. WG

      Yeah.

    7. SS

      Every... Can I take a day off? Yes, you can. How many days can I take off? I don't know. Not too many, right?

    8. WG

      [laughs]

    9. SS

      But if you work out every day for 20 minutes, 100% of people will get into shape. But here's the problem: when? I don't know, and neither does any doctor.

    10. WG

      Yes.

    11. SS

      But if you trust in the process, if you have faith, and the data proves it out, then just stick with it, and it will work.

    12. WG

      Yeah.

    13. SS

      Your work is the same, my work is the same. And the reason most companies are not interested in my work is I cannot guarantee that the result that you want to happen will happen on the day of your financial year.

    14. WG

      Yeah, will happen as quickly as you want it to-

    15. SS

      It, it, it, it-

    16. WG

      ... or need it to based on whatever-

    17. SS

      It may.

    18. WG

      Yeah.

    19. SS

      But because I can't promise, I... and I'm gonna tell you, you're gonna have to stick with it regardless, their incentive structure disincentivizes them to do what is the right thing for their business. And, and I know this because my entire career, your entire career, we are both guinea pigs and experiments we did on ourselves for our own ideas.

    20. WG

      Yeah.

    21. SS

      And we were disciplined, and we did that, that believed in the process and the 20 minutes every day. We didn't know when it would work or when it would pop, but for both of us, we believed in it enough that it... We've made guinea pigs out of ourselves.

    22. WG

      Yeah.

    23. SS

      Like, if you want proof, here you go. I built my brand with a zero marketing budget to prove that if you learn to start with why and you obey the law of diffusion of innovations and you focus on the early adopters, and the way you talk to early adopters is by starting with why-

    24. WG

      Yes

    25. SS

      ... that is, it, that is the way you talk to an early adopter, that at some point, a tipping point will happen. And I, and I literally, when I started in the early days, I restarted my business, I reset, I closed my office, the whole thing. I started from scratch because I wanted to prove the idea could work, and I did it without any marketing budget. And it worked. Not because I'm smarter, not because the timing was lucky. It's because I did the thing 20-

    26. WG

      'Cause you stuck with it

    27. SS

      ... I stuck with it. And there were days that were hard, but I, the discipline to turn down the wrong customers, the wrong clients who weren't early adopters, and say yes to lower-paying clients who were the right, I did those things, you know? I did those things.

    28. WG

      Mm-hmm.

    29. SS

      And people say to me now, "Oh, but you can afford to turn down business." No, no, no. I was turning down business when I couldn't afford to.

    30. WG

      Yeah, I can afford to turn down business now.

  14. 34:05 – 54:19

    A-over-50 vs B+-over-3: redefining success with a ratio (and the cost of ambition)

    1. SS

      Let me change tacks on you entirely.

    2. WG

      Okay.

    3. SS

      I wanted to share, uh, just a funny theory-

    4. WG

      Okay

    5. SS

      ... that I was telling your wife yesterday, and she said, "You have to tell Will." [laughs]

    6. WG

      Okay.

    7. SS

      I firmly believe that grades should be given as a ratio, not as an absolute, right?

    8. WG

      Okay.

    9. SS

      So it should be the level of accomplishment, A, B, C, D, over the number of hours you studied.

    10. WG

      Okay. [laughs]

    11. SS

      Right? So-

    12. WG

      By the way, as I'm listening to this, I'm trying to figure out why my... Well, but as, before I even hear what you say, I'm like, "Your, my wife told you to tell this to me, and that's either a display of praise or insult from her." [laughs] And I'm trying to figure out which one-

    13. SS

      Uh, I know which one it is because we talked about it, and we'll get there.

    14. WG

      [laughs]

    15. SS

      I'm just doing it on camera. [laughs] This is a private conversation [laughs] that I'm gonna do on camera.

    16. WG

      Okay.

    17. SS

      Anyway, so that grades should be given as a, as a ratio, right? And in that way, you know much more about the kind of person, right? So if you need somebody who does A work and you're willing to give them 50 hours to do it, hire that person.

    18. WG

      Yes.

    19. SS

      If you need somebody who can work well under pressure, but you're not gonna get A work, you, you, you, you know, like, you know, you'll get B+ work, you know, then hire the other person. So, like, my friends in, in college, you know, one, one friend I'm thinking of, he was an A over 50, right? He's a straight-A student, he worked his brains out. I was a B+ over three.

    20. WG

      [laughs]

    21. SS

      Right? Occasionally an A-.

    22. WG

      Yes.

    23. SS

      But a solid B+ over three is, was me. But-

    24. WG

      Less investment, pretty good results

    25. SS

      ... okay, but so now that's just from a hiring standpoint. Now let's think of it as a lifestyle, right? Now let's leave college alone, and let's come into the real world, right? Which is, 'cause I've stressed out about, like, is my work good enough? Am I doing all enough? And then I realize, hold on, I'm actually very comfortable with a B+. You know why? 'Cause I worked three hours.

    26. WG

      [laughs]

    27. SS

      And, and, like, there's, I've accepted there's, that there's always gonna be people who are gonna make more money than me, sell more books than me. Like, I know a guy, he sells an insane number of books. I also know he works his frickin' brains out.

    28. WG

      Hmm.

    29. SS

      I do well. Like, my books are, are, are good, you know, solid A- work.

    30. WG

      Yes.

  15. 54:19 – 1:00:04

    Building better feedback loops: quality metrics, repeat behavior, and the "Y index"

    1. SS

      Okay, okay. So what we're talking about, okay, now this gets interesting, right? Which is the reason I pursue the A.

    2. WG

      Yes.

    3. SS

      The A over 50, is not simply because it's easier to measure. It's because there's no other feedback mechanism for me to know that my work is valuable other than the A.

    4. WG

      Hmm.

    5. SS

      So I don't know if people like wearing my sweaters, but I can count how many sweaters I've sold.

    6. WG

      Yeah.

    7. SS

      And I can draw some loose conclusion that if they're selling a lot, I'm guessing they're liking them, right? And so what we're talking about, which is, uh, totally fair, which is, and it's, and maybe they do desire everything we're talking about, and they are frustrated with the metric system. But, um, without an immediate feedback loop, and sure, I can send out surveys that, you know, 5% fill out.

    8. WG

      Mean nothing, yeah.

    9. SS

      Or only the angry people, you know, respond.

    10. WG

      Yeah.

    11. SS

      You know? All of this stuff that the best I can do to know that I'm doing okay is th- is the business is growing.

    12. WG

      Yeah.

    13. SS

      And so maybe, just maybe-Like my A over 50, which is, it's fine to count the revenues, totally fine, but maybe there's another metric that should serve as the ratio.

    14. WG

      Yeah. [laughs] This is gonna end up being like a 17 different things going into-

    15. SS

      No, I don't think it's... I think it's, I think things like repeat sales.

    16. WG

      Yeah.

    17. SS

      Like, I know a company, the true story, this is hilarious to me, and this is how misguided. This is a funded company spending millions of dollars, blah, blah, blah. I think they're in the financial world. And their sales team is knocking it out of the park, but the product isn't so great, and so customers aren't renewing, right? So do you know what the CEO did?

    18. WG

      Okay.

    19. SS

      Yelled at the sales team.

    20. WG

      Huh.

    21. SS

      And the sales team was like, "Talk to the engineers. The clients are calling us and say, 'We love you, but it's not working.'"

    22. WG

      It's just not good enough.

    23. SS

      "We can't, we, we can't do this." So the CEO is yelling at the sales team, right? And I'm listening to this going, "No." Right? So, like, in our business, right, I am fully aware that first time sales, that's a marketer.

    24. WG

      Yes.

    25. SS

      Like, marketers drive first time sales. Second sales, that's my product guy.

    26. WG

      Mm.

    27. SS

      If the product's good, I can only measure that on a resubscription. A first time subscription, marketing.

    28. WG

      For sure.

    29. SS

      A second time subscription, product.

    30. WG

      Yeah.

  16. 1:00:04 – 1:05:58

    Who pays for the 50? Relationships, listening, and the smallest human gestures

    1. WG

      It is one of the cool things about the restaurant industry. And it also, I mean, we're talking about how much you give of yourself to others and at what cost. I mean, in hospitality, like, I, I really like making other people happy. And if I'm not careful, I end up being an A 50 for the rest of my life because I don't like letting other people down, and at the end of the day, I end up letting some of the people that are most important to me down.

    2. SS

      And that's the problem, which is there's nothing wrong with the 50. You just have to weigh the cost of that 50.

    3. WG

      Yeah.

    4. SS

      And there's an entire group of people, and again, it's not a good thing or a bad thing, it's just be, let's be honest with ourselves, who spends... I'll give you, I'll give you the real life example.

    5. WG

      Yeah.

    6. SS

      I'll use myself as the guinea pig, right?

    7. WG

      [laughs]

    8. SS

      So for years, I had close friends accuse me of being a bad listener.

    9. WG

      Hmm.

    10. SS

      I, that was my answer. That's exactly-

    11. WG

      [laughs] Yeah, I mean, I-

    12. SS

      I don't, I don't see it

    13. WG

      ... never, never in a million years.

    14. SS

      And I would say things like, "You know what I do for a living, right?"

    15. WG

      [laughs] Like, "You know you're wrong-

    16. SS

      Right?

    17. WG

      ... and I'm a really good listener, right?"

    18. SS

      Right? I mean, that's pretty much how those conversations went.

    19. WG

      You're like, "I'm sorry, what, what did you just say?"

    20. SS

      Yeah, exactly.

    21. WG

      [laughs]

    22. SS

      "Huh? What?" So, uh, so I ended up, I took this listening class, and that's when I discovered... that I am an unbelievably good listener with people I will never see again for the rest of my life.

    23. WG

      Hmm.

    24. SS

      But for the people closest to me, terrible.

    25. WG

      Wow.

    26. SS

      So I, all of the skills I had learned about listening and being focused and reflective, you know, reflective listening and being pres- all of that, I was doing it with strangers. I was doing it with clients. I was doing it with, you know, one-time interactions. But the people who I had regular ongoing relationships with, I applied none of those skills.

    27. WG

      I think I'm guilty of this sometimes.

    28. SS

      Right?

    29. WG

      Yeah.

    30. SS

      And I simply assumed that I was good at it because I had the capacity and knew that I could do it, and, you know, in the public world, people are like, "You're such a good listener." Like-

Episode duration: 1:05:59

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