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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. 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]

  17. 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.

  18. WG

    [laughs]

  19. 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]

  20. 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?

  21. 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?"

  22. WG

    [laughs]

  23. SS

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

  24. WG

    Yeah.

  25. SS

    So you and I went to one restaurant for appetizer.

  26. WG

    Yeah.

  27. SS

    We went to a different restaurant for the main course.

  28. WG

    Yeah.

  29. SS

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

  30. WG

    Yes.

Episode duration: 1:05:59

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