AI Can Do Everything… Except This (Why Humans Still Win) With Restaurateur Will Guidara

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Mar 24, 2026

Will Guidara, restaurateur, bestselling author, and former co-owner of Eleven Madison Park, explores why human connection matters more as AI grows. He talks about unreasonable hospitality, tiny acts of care that build loyalty, and using automation to create better experiences. Plus, a memorable Basque cheesecake story and a funny look at the hidden cost of achievement.

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INSIGHT

Excellence Is Table Stakes But Care Wins

Will Guidara argues excellence is only the entry fee at the highest level; the real long-term edge is hospitality.
Eleven Madison Park pursued perfect food and service, then differentiated itself by making people feel uniquely cared for beyond those table stakes.

INSIGHT

AI Makes Human Contact More Valuable

Simon Sinek says AI is making human interaction more valuable because speaking to a real person now feels rare and luxurious.
He points to failed cashierless retail and missing floor staff, arguing tiny human moments like asking where peanut butter is still matter.

ANECDOTE

Reservation Automation Freed Staff To Deepen Care

Will Guidara first forced reservations by phone to start with a human voice, then reversed course after callers waited 30 minutes only to hear no.
He moved the reservations team into pre-arrival relationship building, using saved time to learn guests’ stories and personalize meals.

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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.

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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/

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