Uploaded March 2026 | Updated September 2026, 3 weeks ago
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: unreasonablehospitality.com
If you’d like to pre-order Unreasonable Hospitality: The Field Guide, out April 28, 2026, check out: uhthefieldguide.com
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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.
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Website: simonsinek.com
Live Online Classes: simonsinek.com/classes
Podcast: apple.co/simonsinek
Instagram: instagram.com/simonsinek
Linkedin: linkedin.com/in/simonsinek
Twitter: twitter.com/simonsinek
Facebook: facebook.com/simonsinek
Simon’s books:
The Infinite Game: simonsinek.com/books/the-infinite-game
Start With Why: simonsinek.com/books/start-with-why
Find Your Why: simonsinek.com/books/find-your-why
Leaders Eat Last: simonsinek.com/books/leaders-eat-last
Together is Better: simonsinek.com/books/together-is-better
+ + +
#SimonSinek
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: unreasonablehospitality.com
If you’d like to pre-order Unreasonable Hospitality: The Field Guide, out April 28, 2026, check out: 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: simonsinek.com
Live Online Classes: simonsinek.com/classes
Podcast: apple.co/simonsinek
Instagram: instagram.com/simonsinek
Linkedin: linkedin.com/in/simonsinek
Twitter: twitter.com/simonsinek
Facebook: facebook.com/simonsinek
Simon’s books:
The Infinite Game: simonsinek.com/books/the-infinite-game
Start With Why: simonsinek.com/books/start-with-why
Find Your Why: simonsinek.com/books/find-your-why
Leaders Eat Last: simonsinek.com/books/leaders-eat-last
Together is Better: simonsinek.com/books/together-is-better
+ + +
#SimonSinek
