The Oprah Podcast

Episode: Oprah & Will Guidara, The Remarkable Power of Giving People More Than They Expect

Date: November 4, 2025
Host: Oprah Winfrey
Guests: Will Guidara, Daniel Boulud
Audience Guests: SoulCycle’s Kyle, Zillennial guest Destiny, and others

Overview

In this captivating episode recorded with a live audience in New York City, Oprah Winfrey sits down with restaurateur and author Will Guidara, widely acclaimed for leading New York’s Eleven Madison Park to be named the best restaurant in the world, to discuss his best-selling book, Unreasonable Hospitality. Together, they delve into the philosophy of transforming ordinary moments into extraordinary ones through radical generosity, intentional service, and a deep commitment to making others feel seen and special. Special guest, legendary chef Daniel Boulud, joins to share his perspectives on hospitality and leadership, while lively audience Q&A connects Will’s lessons to everyday life and work.

Key Discussion Points & Insights

1. The Origins of Unreasonable Hospitality (00:04–16:13)

• The “Hot Dog” Story (00:04–00:22, 15:38–17:17): Will recounts an iconic moment when he bought a hot dog from a street cart to fulfill a European family's wish for a real New York experience—demonstrating how small, thoughtful actions can eclipse the fanciest offerings:

  "I had never seen anyone react to anything I’d served them like they did to that hot dog."
  —Will Guidara (17:19)

• Defining the Book’s Mission (01:31–02:41): Oprah highlights that Will’s core belief is that “living in service to others can transform your work, your business, and your life.”

  “You must be able to name for yourself why your work matters.”
  —Oprah Winfrey (02:41)

• The “Oscars” of Restaurants and Coming in Last (03:34–06:22): Will shares the humbling story of being named number 50 at the 50 Best Restaurants event, a turning point for him and his partner to pursue not just technical excellence, but emotional impact:

  “Adversity is a terrible thing to waste.”
  —Will Guidara (05:48) “That night, I wrote on a cocktail napkin, we will be number one in the world...But a goal without a strategy, that’s nothing more than a pipe dream...We’re going to be unreasonable in pursuit of people.”
  —Will Guidara (06:44)

• Seeds of Hospitality—The Four Seasons Memory (08:22–10:42): Will describes an early dining experience with his father, which taught him the power of hospitality to create magical, connected moments, amid personal family struggles:

  “For whatever it was, a couple hours...the entire world was put on pause, and I felt so very connected to him. And it was...the first time I realized...through hospitality...you can create magic for people.”
  —Will Guidara (09:58)

2. Hospitality as a Universal Philosophy (11:21–14:07)

• Surprise & Delight (11:21–11:59): Oprah draws parallels to her own career, particularly the “Favorite Things” shows, noting how the memories and emotional resonance far outweigh material gifts.

• The Maya Angelou Principle (11:42–12:15):

  “People will forget what you say, they will forget what you do, but they will never forget how you made them feel.”
  —Maya Angelou via Will Guidara & Oprah (11:44–11:50)

• Legacy is Every Life You Touch (12:24–13:47): Oprah shares another Maya Angelou lesson—your legacy is never one thing, but “every life you touch.”

3. Building a Culture of Intentionality & Service (17:30–20:59)

• Intentionality Learned from Family (17:30–18:41): Will credits his father, who managed immense responsibilities, with teaching him to approach everything with care and intention.

• Three Fundamentals of Unreasonable Hospitality (18:57–19:26):

  1. Presence: “Caring so much about the one person in front of you that you stop caring about everything else.”
  2. Intention: Every move, every decision counts.
  3. Creativity: Meeting people’s needs in unique ways.

• The Nobility in Service (19:26–20:59): Will and Oprah challenge the perception that service work is “beneath” others, emphasizing its profound impact and dignity.

4. Stories of Generosity: Application in Restaurants & Life (25:03–35:39)

• Celebrating in Sadness: The Skybox Story (25:03–26:27): After losing his mother, Will and his father are given a once-in-a-lifetime meal at chef Daniel Boulud’s restaurant—a transformative act of kindness during grief.

  “He gave my dad and me one of the best evenings of our entire lives.”
  —Will Guidara (25:54)

• Drink Your Best Wine on Your Worst Day (26:27–26:34): Will’s motto—don’t save life’s joys for only celebrations.

• Systemizing Thoughtful Gestures (32:25–33:25): At Eleven Madison Park, staff would refill parking meters for guests—a small but impactful act to preserve the guest experience.

• Extraordinary Moments: Sleds & Champagne (33:37–35:47): From arranging sledding trips for children seeing snow for the first time, to saving a guest’s bottle of champagne from bursting, Will explains,

  “It’s not about how much these things cost. It’s about how thoughtful they are.”
  —Will Guidara (34:41)

5. Hospitality Beyond Restaurants—Organizational Lessons (31:22–32:21)

• Will shares that Unreasonable Hospitality principles have been adopted in arenas from NFL teams to retirement homes and even prison systems, emphasizing its universal applicability.

• Marketing Through Meaningful Gestures:

  “Every dollar I ever spent on unreasonable hospitality was far more impactful than any dollar I ever spent on traditional marketing.”
  —Will Guidara (34:41)

6. Leadership & Team Culture: Lessons from Daniel Boulud (26:56–30:09)

• On Guidara’s Leadership:

  “He didn’t achieve everything by himself...It’s about the team first. He had this power of leadership that made people do things they would have not conventionally done.”
  —Daniel Boulud (29:02)

• The Joy of Generosity:

  “We just derive so much pleasure from being generous with others.”
  —Will Guidara (31:11)

7. Audience Q&A: Applying Hospitality Principles in Real Life (36:35–47:16)

a. Destiny, “Zillennial” Guest: Hospitality With Difficult People (36:49–41:01)

• Will underscores Danny Meyer’s “charitable assumption”—always give people the benefit of the doubt, as challenging guests may need kindness most.

  “I’d always rather err on the side of assuming the best in someone.”
  —Will Guidara (39:51)

• The “Felix Story”: Even when extending trust, sometimes boundaries must be enforced for the sake of the team culture.

b. Kyle, SoulCycle District Manager: Keeping Hospitality Evolving (42:26–45:43)

• Will’s advice: Stay open to inspiration everywhere and continually look for ways to see and recognize people’s needs.

  “The more creative you are, the more creative you become.”
  —Will Guidara (44:49)

c. The Power of Personalized Gifts (45:55–48:45)

• Ideal gifts are deeply personal, unique, and “one size fits one”—acting on specific things you hear or notice.

  “The impact of a $3 one-size-one gift will always be bigger than the impact of a $3,000 one-size-fits-all gift.”
  —Will Guidara (46:35)

• Will shares a moving story about being surprised with a visit from Liz, his childhood nanny/cousin, as an example of an incomparable, thoughtful gift.

Notable Quotes & Memorable Moments

• “People will forget what you say, people will forget what you do, but they will never forget how you made them feel.” (Maya Angelou via Will & Oprah, 11:44)
• “Adversity is a terrible thing to waste.” (Will Guidara, 05:48)
• “Your legacy is every life you touch.” (Maya Angelou via Oprah, 13:19)
• “Unreasonable hospitality happens at the intersection of intention and creativity.” (Will Guidara, 18:41)
• “If the only answer to why a rule exists is 'that’s how it’s always been done,' it no longer deserves to exist.” (Will Guidara, 38:22)
• “Every dollar I ever spent on unreasonable hospitality was far more impactful than any dollar I ever spent on traditional marketing.” (Will Guidara, 34:41)
• “I just want to make clear that I don’t take moments like this for granted, nor do I think any of us ever should.” (Will Guidara, 49:07)

Timestamps for Key Segments

• Opening & “Hot Dog” Story – 00:04, 15:38
• Restaurant Awards & Transformation Point – 03:34–08:16
• Four Seasons Experience & Intentionality – 08:22–10:42, 17:30–18:41
• Surprise & Delight, Favorite Things, Maya Angelou – 11:21–13:47
• “Drink Your Best Wine on Your Worst Day” Story – 26:27–26:34
• Team Culture & Daniel Boulud’s Leadership – 26:56–30:09
• Systematizing Hospitality (Parking Meters, Sleds, Champagne) – 32:25–35:47
• Audience Q&A: Difficult Guests, Charitable Assumptions – 36:49–41:01
• Hospitality In Other Workplace Contexts (Kyle at SoulCycle) – 42:26–45:43
• Intentional Gifts & Liz’s Surprise Visit – 45:55–48:45
• Closing Reflections – 49:04–49:53

Tone & Atmosphere

The episode is warm, energetic, and deeply personal—mixing inspiration, humor (with stories like the late-night scrambled eggs), and vulnerability about personal loss. Both Oprah and Will speak with infectious enthusiasm for the ways small gestures and heartfelt service can ripple outward and transform workplaces, families, and communities.

Summary for Listeners

Oprah and Will Guidara’s conversation is a masterclass in leadership, service, and human connection. Whether you’re in hospitality, business, education, or simply want to make the people around you feel special, Unreasonable Hospitality offers actionable wisdom: be intentional, look for the little moments, challenge outdated rules, and remember—your legacy is not one thing, but every life you touch.

For Further Learning

• Will Guidara’s Book: Unreasonable Hospitality: The Remarkable Power of Giving People More Than They Expect
• Coming April 2026: Unreasonable Hospitality: The Field Guide
• Special mention: Maya Angelou’s wisdom, Daniel Boulud’s mentoring, and stories from all walks of service industries.

“I just want to make clear that I don’t take moments like this for granted, nor do I think any of us ever should.”
—Will Guidara (49:07)