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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Team Simon here! While A Bit of Optimism is on a short break, we’re revisiting a few episodes you helped make some of our favorites. We’ll be back with brand-new conversations next week, on March 24th, 2026. In the meantime, we’re bringing back an episode that explores a word most people like to avoid: death.

We dance around the subject or use vague euphemisms to not hurt anybody. But what if being open about our deaths meant we could live happier lives?

That’s where Alua Arthur comes in. Alua is one of the most prominent death doulas in the country, which means it’s her job to help people die. She offers support to her clients and their families as they embark on their dying journey, tackling everything from financial planning and insurance policy to emotional support and grief.

Before this work, Alua was a lawyer, but after a life-changing encounter that forced her to confront mortality in a new way, she shifted her path entirely. Now she has dedicated her career to helping others prepare for the end of life with clarity, compassion, and even a bit of humor.

In this conversation, Simon and Alua talk about why our culture struggles to talk honestly about death, what she’s learned from the people she’s accompanied in their final days, and why remembering that life is finite can help us live with more presence, gratitude, and intention.

This… is A Bit of Optimism.
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For more on Alua and her work, check out: https://goingwithgrace.com/ & @GoingwithGrace‬

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Hello from Team Simon! We’re taking a short hiatus, but A Bit of Optimism will return with brand-new episodes March 24th. In the meantime, we’re revisiting some of our favorite episodes. Episodes that many of you who listened, shared them, and told us what resonated.

This week, we’re bringing back Simon’s conversation with journalist, author, and longtime friend Maria Shriver.

Maria Shriver was born into the legendary Kennedy and Shriver families, arriving with a script already written for her—an identity shaped by legacy and expectation. From the start, the world had ideas about who she should be. But after decades as a journalist, years as California’s First Lady, and raising four amazing kids, Maria has been on a lifelong journey to peel back the layers and ask Who am I now?—and answer it for herself.

Maria also happens to be Simon’s best friend. They talked about how they became each other’s “8-minute friends,” the quiet questions that shape us, and Maria’s beautiful new book of poetry—which she reads from in this episode. It’s all about identity, self-reflection, and finding your voice in a world that keeps trying to define it for you.

If you’ve ever wondered who you are beyond what you do or how to rediscover yourself after life changes, this conversation is a beautiful reminder that identity is something we can reclaim again and again.

This… is A Bit of Optimism.
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For more on Maria Shriver, check out: her book: https://bookshop.org/p/books/i-am-mar...

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