My First Million: "The Hospitality Principles That Build Billion-Dollar Startups"

Date: September 30, 2025
Hosts: Sam Parr & Shaan Puri
Guest: Will Guidara (Author, “Unreasonable Hospitality”, Writer/Producer for “The Bear”, former co-owner of 11 Madison Park)

Episode Overview

This episode features Will Guidara, renowned restaurateur and author, who revolutionized the fine dining experience at New York’s 11 Madison Park by embracing “unreasonable hospitality”. The discussion covers Guidara’s philosophy on exceeding guest expectations, actionable systems for extraordinary service, leadership and team motivation, and how the same hospitality principles can give an edge to any business, not just restaurants. Through memorable stories, practical operations insights, and a look into cultural impact (including on the TV show “The Bear”), listeners are invited to rethink what makes excellence, and how to inject magical, human touches into any customer experience.

Key Discussion Points & Insights

1. The Genesis of Unreasonable Hospitality

• Will Guidara explains the journey: Pursuing excellence at the highest level is vital but what truly set 11 Madison Park apart was not just perfection, but outrageous, personal hospitality.
  • “It was the relentless, unreasonable pursuit of hospitality...the most human moments are perfectly imperfect, and those are the stickiest of all.”
    — Will Guidara [01:55]
• The Hot Dog Story: The foundational anecdote—Guidara overheard European diners lament they hadn’t tried a New York hot dog, so he ran out, bought one, and had the chef serve it exquisitely in the middle of their fine dining meal. Their ecstatic reaction trumped any previous lavish course.
  • “I had served tens of millions of dollars worth of wagyu beef and lobster and caviar. I’d never seen anyone react to anything I’d served them like they did to that.”
    — Will Guidara [04:03]

2. Leadership, Accountability, and Crafting Culture

• Balancing Excellence with Humanity:
  • “The greatest leaders...the people that work for them, like, check themselves a little bit. They want to make sure everything is as it’s meant to be...because they don’t want to let you down.”
    — Will Guidara [06:01]
  • The importance of normalized feedback—praise is addictive, but “if praise is affirmation, criticism is investment” [07:16].
• Rules for Criticism:
  • Criticize in private, address behavior not the person, be consistent, never use sarcasm, avoid emotion, and praise more than you criticize [09:17].
  • “If you aren’t there to hold them accountable...you’re not actually doing right by them. I don’t think there are many things a leader can do that are more beautiful than being willing to step outside of your comfort zone for long enough to invest in someone else’s growth.”
    — Will Guidara [08:25]

3. Operationalizing Magical Experiences

• The Dreamweaver Role: Created a support position solely to execute creative guest gestures (“Dreamweaver”), enabling frontline staff to ideate magic for guests at scale.

  • “This person was just there to create bandwidth...so they were there, anyone on the team had an idea, they could go to the Dreamweaver and be like, hey, I need you to go out to the store and get a DVD...”
    — Will Guidara [14:48]

• Budget, Scale, and Impact:

  • Magic doesn’t require big spending—most gestures cost little compared to average customer spend (approx. $400/person) and huge payoff in customer loyalty and word of mouth [17:24].

4. The Three Levels of Hospitality Touch Points

• One Size Fits All: Tweaks to universal moments—e.g., bringing a bottle of cognac with the check for all tables, creating a lasting impression at the experience’s end.
  • “Small change with a profound impact...they don’t remember a single thing they ate, but they’ll never forget how we made them feel when we gave them that bottle of cognac.”
    — Will Guidara [19:37]
• One Size Fits Some: Recognizing common patterns and personalizing for recurring situations (e.g., surprise champagne flutes in Tiffany blue boxes for guests who get engaged).
  • “...three things on that. One, was it less special for them because we had a bunch more in the back? No. I have talked to people...who don’t remember a single thing they ate, but they will never forget that.”
    — Will Guidara [29:06]
• One Size Fits One: Truly bespoke experiences for specific guests, enabled by “Dreamweaver” execution [29:37].

5. Principles of Reciprocity and Delight

• Impact on Revenue:

  • Surprising generosity creates strong reciprocation and customer loyalty. “Every dollar I ever spent on unreasonable hospitality was far more impactful than any dollar I ever spent on traditional marketing.”
    — Will Guidara [23:40]
  • Refers to studies in hospitality (tips jump by 18% with even small surprises) and broader examples like Chewy’s pet bereavement gestures and car dealerships hiding a Starbucks gift card in the glove compartment.

• Pattern Recognition in Surprise:

  • “Unreasonable hospitality happens at the intersection of creativity and intention.” — Will Guidara [41:16]

6. Scalability to Digital and Other Businesses

• Internet Businesses & Overlooked Touchpoints:

  • Sam shares copywriting examples where the “forgotten text” (welcome/unsubscribe emails) is made humorous and special, leading to viral engagement [32:43].
  • Will: “Smallest enhancements to the most overlooked touch points in a guest experience can have the greatest impact...it’s you saying very clearly, ‘We are willing to care about things that no one has ever paused for long enough to consider.’” [32:43]

• Examples from Other Industries:

  • Chewy’s bereavement support, UPS store comping employees, an auto dealership hiding a surprise gift card, all show how “hospitality” can be translated to surprising, delightful moments in any industry [39:39–41:16].

7. Implementation & Challenges

• Making Magic a Habit
  • The discipline is in making such practices mandatory and systematic; not one-off, but ingrained—e.g., requiring staff to comp one customer per shift and document why [37:48].
  • The importance of involving the whole team in brainstorming recurring experiences and solutions [27:32].

8. Bigger Picture: Growth, Excellence, and Business Strategy

• Financial Realities of Restaurants:
  • Larger restaurants have disproportionate revenue/labor advantages; creative entrepreneurship is required both in guest experience and business operations [51:14].
• Excellence vs. “Good Enough”
  • The journey for Guidara (and aspirationally for listeners) is about pursuing excellence rather than settling for “good enough,” in all aspects of business and life.
  • “Every time I listen to you...I feel the need to be more excellent than I currently, than I’ve currently been behaving.” — Sam Parr [59:33]

Notable Quotes & Memorable Moments

• “The gestures that are specific to an individual will always have the greatest impact. And I say, one size fits one.”
  — Will Guidara [12:40]
• “Generosity begets generosity.”
  — Will Guidara [21:20]
• “You need to bridge that gap between authority and information.”
  — Will Guidara, on empowering frontline staff to innovate [26:41]
• “Unreasonable hospitality happens at the intersection of creativity and intention.”
  — Will Guidara [41:16]
• “Sometimes magic is just being willing to invest more energy into an idea than anyone else would deem reasonable.”
  — Teller (shared by Will Guidara) [44:02]
• The Paul Rudd "backyard magic trick" story: illustrating the effort that creates true “magic” and delight [44:53-46:11]

Timestamps of Important Segments

• [03:02] — The Hot Dog Story (The original ‘unreasonable hospitality’ moment)
• [06:01] — Leadership principles and holding teams accountable
• [09:17] — Will’s five rules for criticism
• [14:29] — The “Dreamweaver” operational role explained
• [19:37] — Innovating touchpoints: The cognac-with-the-check story
• [28:41] — Tiffany champagne glasses for engagements
• [32:43] — Overlooked touchpoints: Car dealership glovebox gift card
• [37:46] — UPS store comping system, and why making magic mandatory works
• [40:00] — Chewy’s customer bereavement support
• [51:14] — Scaling restaurants: Economic realities and advice for aspiring owners
• [59:33] — Inspiration for personal and business excellence

Closing: Resources & Promotions

• Will's Newsletter: Premeal – practical, inspirational hospitality stories biweekly.
• Upcoming Book: “Unreasonable Hospitality: The Field Guide” – a workbook edition for teams (pre-order available).
• Websites: unreasonablehospitality.com, thewelcomeconference.com
• Social Media: (Will did not specify a single platform; see his websites for links)

Takeaways for Listeners

• Regardless of industry, every business can create stories through mindful, surprising acts of care and personalization.
• Magic in business isn’t about spending more—it’s about caring more and systematizing a culture of going above and beyond, consistently.
• Excellence is not just about performance, but about deeply connecting with the people you serve—and with the teams you work with.

This episode provides both inspiration and concrete how-tos for transforming any business with the principles of hospitality—making it essential listening for founders, managers, and anyone building something memorable for their customers.