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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Team Simon here! As we take a short hiatus, A Bit of Optimism will return with brand-new episodes on March 24, 2026. Until then, we’re revisiting some of the conversations you loved and we still think about long after the microphones turned off.

This week, we’re rewinding to Simon’s conversation with the wildly creative and endlessly curious Jacob Collier.

To create something truly original, do we build something new or break what came before? Perhaps the answer is both—simultaneously.

Jacob Collier does exactly that. A songwriter, multi-instrumentalist, and Grammy Award winner, Jacob has built a career on blending structure with spontaneity. He’s known for turning entire concert halls into three-part choirs, transforming audiences from spectators into collaborators. His album "Djesse Volume 4" was nominated for Album of the Year at the 2025 Grammy Awards, alongside icons like Beyoncé, Billie Eilish, and Taylor Swift. Although Beyoncé's "Cowboy Carter" won, Jacob snagged his seventh Grammy for his rendition of "Bridge Over Troubled Water."

Simon sat down with Jacob in a music studio just days before the 2025 Grammys, surrounded by pianos and possibility. What unfolded was more than a conversation about music. It was a masterclass in creativity, about holding opposites at once, embracing imperfection, and having the courage to follow curiosity wherever it leads.

If you’ve ever wondered how creativity really works or how to find your own voice without losing what came before—this one’s worth another listen.

This… is A Bit of Optimism.

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For more on Jacob, check out:

http://jacobcollier.com

‪@jacobcollier‬

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Scott Galloway and I don’t always see the world the same way, but our friendly debates almost always lead us back to common ground. It’s probably why we enjoy talking to each other as much as we do.

If you haven’t heard my friend Scott’s name before, he’s known for being brilliant, provocative, and unapologetically himself. He’s a professor at NYU Stern School of Business, entrepreneur, bestselling author, and larger-than-life social commentator. In recent years, his work, which includes his new book Notes on Being a Man, has explored the challenges facing men today, from loneliness and dating to purpose and identity.

Scott and I have different views on what “healthy masculinity” looks like. He’s not afraid to say things during this podcast that might ruffle some feathers. But inevitably, the conclusions we get to are introspective, vulnerable, and often universal. That’s certainly true for one revelation we share: confidence matters.

Not the loud, performative kind. The real kind. The kind that helps people risk rejection, build meaningful relationships, and show up more generously in the world.

In this episode, Scott and I talk about the “masculinity crisis,” why young people are struggling to connect, how purpose outlasts happiness, and why masculine and feminine traits are complementary rather than competing. We explore the need for good social risks like leaving the house, meeting people, pursuing relationships, and hearing “no,” and why confidence is less about ego and more about security, kindness, and connection.

This is a conversation between two opposites who challenge each other, listen deeply, and ultimately agree that building real confidence may be one of the most important skills we can teach the next generation.

This… is A Bit of Optimism.

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If you want to read Scott’s new book Notes on Being a Man, head to: https://www.simonandschuster.com/books/Notes-on-Being-a-Man

Check out Scott’s podcast “The Prof G Pod”: https://www.youtube.com/c/TheProfGShow-ScottGalloway

You can also watch his podcast “Pivot with Kara Swisher and Scott Galloway”: https://www.youtube.com/@pivot

To stay up to date with all of Scott’s work, head over to: https://www.profgalloway.com/

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It’s often true that the most challenging conversations are often the ones most worth having. Conversations that bring up strong feelings, different experiences, and questions without easy answers. Policing, and how we can make it better, is one of those conversations.

San Leandro Police Chief Angela Averiett has spent nearly three decades in law enforcement, navigating the profession’s challenges while advocating for a healthier path forward. I met Angela through The Curve, my organization focused on helping policing evolve to meet the needs of a modern world. She’s a powerful example of forward-thinking leadership, exploring how culture, mindset, and psychological safety shape the way officers show up for each other and for the communities they serve.

In this episode, Angela and I unpack why cynicism is so common among officers, how strong leadership creates healthier team cultures, and why rebuilding trust in policing starts from the inside out. Angela shares stories from her career that reveal a different side of police work: where compassion improves safety, discretion matters more than enforcement, and leadership means creating space for people to be human. Together, we explore the balance between strength and empathy, and why healthier internal cultures lead to stronger relationships with the public.

Whether you’re a leader interested in organizational culture or simply curious about how policing can evolve, I hope this conversation offers an honest and hopeful perspective on the work ahead.

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If you want to learn more about the work The Curve is doing, head to: https://www.thecurve.org

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Fanbases are some of the most powerful forces on the planet.

They show up. They buy the tickets. They travel across countries and time zones. They memorize lyrics, study interviews, hunt for Easter eggs, and turn the smallest detail into an entire universe of meaning. They collaborate, they organize, and they care deeply.

Fan communities are savvy. They are smart. And when they are invited in, they create extraordinary momentum.

Adam Met, best known as the “A” of indie-pop band AJR, believes that this kind of energy can extend far beyond concerts or comment sections. He is asking a bigger question. What if we harnessed that same passion, creativity, imagination, and sense of belonging to improve the communities we live in?

Adam has spent years studying how to move people from curiosity to action. He’s also a climate activist, the founder of the nonprofit Planet Reimagined, an adjunct professor at Columbia University, and the author of the bestselling book Amplify: How to Use the Power of Connection to Engage, Take Action, and Build a Better World.

In our conversation, Adam explains how the same principles that make music meaningful - ownership, storytelling, participation, and belonging - can be applied to social movements, civic engagement, and climate action, to name a few. From designing fan-first concert experiences to rethinking how we engage people around complex issues, Adam argues that emotion is the engine of progress.

This episode isn’t really about music.
And it’s not really about climate either.

It’s about how we bring people together, help them feel invested, and create experiences that inspire them to act.

This… is A Bit of Optimism.

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To buy Adam’s book Amplify: How to Use the Power of Connection to Engage, Take Action, and Build a Better World, head to: https://www.adammet.net/amplify

If you want to learn more about Adam’s climate work, check out: https://www.planetreimagined.com

And don’t forget to stream AJR’s latest EP, What No One’s Thinking: https://www.ajrbrothers.com

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We’re often told that the secret to success is grit - more discipline, more perseverance, more individual effort. And grit does matter. But what if it’s only half the story?

In today’s world, we’ve become experts at tracking achievement, yet novices at nurturing belonging - and the cost of that imbalance is showing up everywhere from burnout to loneliness.

Few people are better equipped to help me make sense of that tension than today’s guest, Angela Duckworth. Angela is a professor of psychology at the University of Pennsylvania, a MacArthur “Genius” Award winner, and the bestselling author of Grit: The Power of Passion and Perseverance.

Angela is one of those people I could talk to for hours and we cover a lot of ground, but our conversation isn’t just about grit or performance. It’s about something deeper: why belonging gives achievement meaning and why human beings are actually wired to thrive together.

In this episode, Angela and I explore how a culture obsessed with individual success quietly erodes teamwork, trust, and wellbeing. We talk about the loneliness epidemic among young people, why grit is so often misunderstood, and why character isn’t just about what you do for yourself, but what you do for others. Along the way, we unpack why the smartest people don’t always make the best teammates, how incentives shape behavior in ways we rarely notice, and why purpose and people—not willpower—are what sustain us over time.

If you’ve ever felt burned out, disconnected, or wondered why success doesn’t feel as satisfying as you thought it would, this conversation is a reminder that meaning doesn’t come from standing alone at the top—it comes from being part of something bigger than yourself.

This is… A Bit of Optimism.

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To buy Angela’s book Grit: The Power of Passion and Perseverance, head to: https://angeladuckworth.com/grit-book

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