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

March 24, 2026

AI Summary

5 min read

In a wide-ranging conversation between host Simon Sinek and restaurateur Will Guidara, the two friends explore why AI and automation, despite their efficiencies, cannot replace human hospitality. Guidara, former co-owner of Eleven Madison Park (EMP)—once the world's top-ranked restaurant—argues that going beyond expectations to make people feel seen builds irreplaceable loyalty, especially as technology commoditizes products and services.

The Basque Cheesecake Surprise

Guidara shares a story of unreasonable hospitality at the Waldorf Astoria Beverly Hills. Upon check-in, guest relations manager Abby left a note and a slice of Basque cheesecake from Pajoli in Santa Monica—in his fridge. This dessert held special meaning: years earlier, Sinek had taken Guidara on a "bang bang" dinner, hopping restaurants for courses, culminating at Pajoli. There, Guidara texted owner Pajolie Paj (whom Sinek knows) for their off-menu cheesecake, limited to one slice nightly; they got the last one, deeming it among the top five desserts ever. Abby discovered the tale via Sinek's podcast with Phil Rosenthal and recreated the gesture. Guidara was stunned, experiencing his own philosophy reversed. Later, Guidara recounts trying to impress a date with the same story, only to learn Pajoli had added it to the menu—yet the memory of feeling "known" endured.

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What you'll learn

1 (00:00) **🎙️ Introduction: Will Guidara**
2 (02:00) **Basque Cheesecake Surprise Story**
3 (05:30) **Pajoli Cheesecake Follow-Up Tales**
4 (08:00) **Reinventing Hospitality at Eleven Madison Park**
5 (11:00) **Excellence vs. Unreasonable Hospitality in Business**
6 (13:00) **AI Era Amplifies Human Value**
7 (17:00) **Reinvesting AI Savings into Human Moments**

+ Full timestamped outline available in the app

Show Notes

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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