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My First Million

The Hospitality Principles That Build Billion-Dollar Startups

with Will Gudera

Published September 30, 2025
Visit Podcast Website

About This Episode

The host interviews restaurateur and author Will Gudera about the philosophy and practice of "unreasonable hospitality" that helped his restaurant Eleven Madison become a top destination. They discuss how small, highly personal gestures can matter more than perfect execution, how to build a culture of rigorous feedback and care, and how to operationalize hospitality through roles like the "Dreamweaver" and systems such as one-size-fits-all, one-size-fits-some, and one-size-fits-one experiences. The conversation also explores applications in other industries, the economics of restaurants, and the broader pursuit of excellence in life and business.

Topics Covered

Entrepreneurship Leadership and management Company values Customer service Business growth and scaling Marketing and customer education Scrappiness in business Personal Development Unit economics Work ethic

Disclaimer: We provide independent summaries of podcasts and are not affiliated with or endorsed in any way by any podcast or creator. All podcast names and content are the property of their respective owners. The views and opinions expressed within the podcasts belong solely to the original hosts and guests and do not reflect the views or positions of Summapod.

Quick Takeaways

  • Unreasonable hospitality is about combining relentless excellence with deeply personal, sometimes messy gestures that make people feel uniquely seen.
  • Great leaders normalize feedback by pairing abundant praise with thoughtful, private, consistent criticism that targets behavior rather than character.
  • Systematizing delight through roles like a "Dreamweaver" and clear processes lets frontline staff turn spontaneous insights into memorable customer experiences.
  • Focusing on overlooked touchpoints, such as the check at a restaurant or a confirmation email online, can transform mundane moments into signature experiences.
  • Pattern recognition enables scalable hospitality, as seen in engagement gifts at Eleven Madison or Chewy's standardized response when a customer loses a pet.
  • Generosity and surprise drive reciprocity; small, unexpected gifts often yield outsized returns in loyalty, word of mouth, and even immediate revenue.
  • Mandatory hospitality practices, like required comps per shift at a UPS store, can rewire cultures so that staff actively seek chances to brighten customers' days.
  • In restaurants and other businesses, larger scale with similar fixed leadership costs can dramatically improve economics if quality is maintained.
  • Creating magical experiences often comes down to investing more effort into an idea than most people would consider reasonable.

Podcast Notes

Introduction and context for Will Gudera and unreasonable hospitality

Host sets up who Will is and why he is on the show

Will introduced as author of "Unreasonable Hospitality" and a writer for the TV show "The Bear"[0:04]
• Host notes that "The Bear" is very popular and calls out the episode "Forks" in season two as an amazing episode about excellence and hospitality
Relevance of hospitality book to internet entrepreneurs[0:23]
• Host explains that many listeners run internet companies and might have missed Will's book because it's about a restaurant, Eleven Madison, not tech
• Book chronicles how Eleven Madison went above and beyond for customers and how that both helped guests and the business
Host's intent for the episode[0:58]
• Host says one big takeaway is going above and beyond for customers and being excellent in life, business, fitness, and family
• Host shares that recording the episode inspired him and he hopes it inspires listeners too

Book impact on host and framing of excellence vs hospitality

Books that shaped the host's thinking outside of typical business literature

Host mentions "The Inner Game of Tennis" as a book about tennis that is really about psychology and handling stress[1:23]
Host positions "Unreasonable Hospitality" similarly as a book that changed how he thinks about life, not just restaurants[1:37]
• Reading the book made the host want to become "unreasonable" in the rest of his life and see Will as relentless and highly particular about details

Relentless pursuit of excellence vs pursuit of hospitality

Will on what it took to achieve what they did at Eleven Madison[2:09]
• He says they needed a relentless pursuit of excellence to become the best at anything
What actually differentiated the restaurant[2:09]
• Will explains that it was not just excellence but a relentless, unreasonable pursuit of hospitality that took the restaurant over the top
• They pushed to make every detail perfect, then layered on "messy" human gestures that made guests feel deeply seen
• He contrasts obsessing over garnishes on fine-dining plates with guests actually remembering something like a hot dog
Idea that the most human moments are perfectly imperfect[2:49]
• Will says the most human, perfectly imperfect moments are the stickiest and most memorable

Hot dog origin story of unreasonable hospitality

Context for the hot dog gesture at Eleven Madison

Busy lunch service and European foodies at a four-top[3:09]
• Will was helping clear tables during a busier-than-normal lunch
• He describes the guests as foodies from Europe who were in New York specifically to eat at fancy restaurants like Le Bernardin, Daniel, Jean-Georges, and Per Se
• This meal at Eleven Madison was their last stop before heading straight to the airport
Guest's unfulfilled wish for a New York hot dog[3:53]
• Will overheard one woman say their trip was amazing but they never had a New York City hot dog
Executing the hot dog surprise[3:56]
• Will had a lightbulb moment, ran to a hot dog cart, bought a hot dog, and faced the harder part of convincing his fancy chef to serve it
• The chef cut the hot dog into four pieces, plated each piece with ketchup, mustard, sauerkraut, relish, and topped with a micro herb to look fancy
• Before their final savory course (a honey lavender glazed Muscovy duck), Will presented the hot dog as a New York "dirty water dog"
• He told them he overheard their comment and did not want them to leave with any culinary regrets
Guest reaction and Will's realization[4:44]
• He had served tens of millions of dollars of luxury ingredients, but had never seen anyone react like they did to that hot dog

Eleven Madison's status and "The Bear" episode tie-in

Recognition of Eleven Madison[5:43]
• Host states that Eleven Madison won an award as the world's best restaurant and calls that a crazy kind of award to exist
Connection to "The Bear" and the "Forks" episode[4:56]
• Host describes the "Forks" episode where a "loser cousin" learns greatness by starting with polishing forks perfectly
• In the show, attention to seemingly trivial tasks leads to noticing and acting on guests' casual desires, like wanting a hot dog
• Host frames this as the point of Will's book: create memorable experiences that turn overheard wishes into stories

Question about leadership style and intensity

Host asks if Will was as uptight or hardcore as the TV portrayal[5:43]
• Host wonders if a leader has to "perform" and be a dick to get staff to buy into high standards

Leadership, accountability, and feedback culture

Will's view on what effective leadership feels like to employees

Desired emotional response when a leader walks into the room[6:00]
• Will says great leaders make people simultaneously check themselves to ensure everything is right and smile because they are happy the leader is there
Difference between fear-based and respect-based leadership[6:08]
• If a leader acts like a dick, staff are simply scared of being yelled at
• An attentive leader who thoughtfully holds people accountable inspires people not to make mistakes because they do not want to let the leader down

Host's struggle with holding people accountable

Host describes hesitation to be disliked or to pick battles[6:50]
• He admits to often avoiding calling people out and assumes many listeners share that tendency
Request for an example of a productive accountability conversation[7:09]

Will on not prioritizing being liked

Leaders as friends vs leaders as leaders[7:14]
• Will says employees do not need another friend; they need someone willing to step up and lead them
• If you focus on truly leading consistently, people will end up liking you anyway
Analogy to building businesses and focusing on money vs greatness[7:40]
• Will believes focusing solely on making money leads to mediocrity, whereas focusing on building something great will result in making money

Normalizing feedback and dual importance of praise and criticism

Will's belief about great cultures[7:40]
• He believes great cultures are those where feedback is normalized
Role of praise[8:18]
• Leaders with high expectations must be present to celebrate when people meet or exceed them
• Praise is addictive; receiving it makes people want more
Reframing criticism as investment[8:49]
• Will warns against overemphasizing praise to the point that leaders forget how powerful criticism can be
• He defines praise as affirmation and criticism as investment in someone's growth
• Employees are there because they want to grow, so failing to hold them accountable means failing them
• He calls stepping outside your comfort zone to invest in someone else's growth one of the most beautiful things a leader can do

Scale of Will's leadership responsibility and retention results

Company size[9:24]
• Will says they had about 1,800 staff across all restaurants
Retention performance[9:04]
• He states their staff retention was dramatically better than industry standards

Will's rules for criticism

Rule: Criticize in private[9:24]
• He says you can praise in public but must criticize in private, because public criticism triggers shame and blocks learning
Rule: Criticize behavior, not the person[9:30]
• Will notes people often inadvertently criticize a person's shortcomings rather than the specific behavior they want to correct
Rule: Criticize consistently[9:43]
• Leaders sometimes lack energy to call things out every time, so they address issues only sporadically
• Inconsistent criticism leaves people unsure what "right" looks like or thinking feedback only comes when the boss is in a bad mood
Rule: Never use sarcasm in criticism[10:13]
• Will says younger leaders often use jokes to soften criticism, but that makes a fool of both people and trivializes the investment
Example of direct, non-sarcastic feedback[10:28]
• Instead of joking about lateness, he suggests plainly saying, "We said we were going to be here at 8. You weren't. I don't like that. Can you please be here at 8 tomorrow?"
Rule: Remove emotion from criticism[10:50]
• Emotional delivery elicits emotional reactions that cause people to shut down and not absorb the feedback
Rule: Praise more than you criticize[11:26]
• If a leader is not praising more than criticizing, either they only see what's wrong, or someone on the team is underperforming badly
• In the latter case, Will says the leader has failed by letting that person stay in the role so long

Systematizing unreasonable hospitality: from intuition to structure

Revisiting the hot dog as origin point and learning from success tapes

Looking at tapes of what went right[12:43]
• Will notes athletes review game tape after mistakes but rarely analyze tapes of what they did right
• He describes putting intention to intuition by examining successes like the hot dog gesture so they can be repeated
Elements that made the hot dog significant[13:04]
• The gesture required being present enough to notice the comment, willing to be silly, and tailoring the act specifically to those guests
• Will summarizes the idea as "one size fits one"-gestures most specific to an individual have the greatest impact

Creating the Dreamweaver role

Purpose of hiring a Dreamweaver[14:25]
• They hired an extra person in the dining room whose only responsibility was to be a resource to help everyone else bring their ideas to life
Operational constraints that made the role necessary[14:07]
• Will says most high-functioning organizations, especially restaurants, leave people with little bandwidth for side projects during service
• Dreamweaver existed to create bandwidth so staff could act on hospitality ideas without abandoning core duties
Compensation and initial guidelines[14:13]
• He estimates the Dreamweaver made about $25 an hour
• Initially there was no set budget; staff were told to start doing ideas and "be reasonable," not spending, for example, $1,000 per guest
Examples of Dreamweaver tasks[14:26]
• Requests included buying a DVD of the movie "Seven" on the fly or quickly finding sleds
• Other tasks included grabbing a cotton-candy machine from downstairs or buying super soaker toys from a toy store
Evolving the Dreamweaver role[15:24]
• Later they hired Dreamweavers from art schools so they could execute craftwork themselves in the moment
• There was one Dreamweaver per service focused on execution, while everyone on the team did ideation based on what they observed with guests
Budget control and example of an expensive gesture[16:15]
• Every month or two Will would review the Dreamweaver line item in the P&L and occasionally tell the team to "rein it in a little bit"
• He recalls reprinting large kitchen photos of Miles Davis as Notorious B.I.G. for a staff member who loved Biggie, costing about $600
• Will emphasizes he wanted to spend the most extravagant gestures on their own people so staff would understand how good it feels to receive them

Three categories of unreasonable hospitality gestures

Overview of one size fits all, one size fits some, and one size fits one

Definitions of the three categories[16:21]
• One size fits all: examine the entire experience and make as many universal touchpoints as possible a little more awesome
• One size fits some: use pattern recognition to design gestures for recurring situations that affect some, but not all, guests
• One size fits one: highly individualized, bespoke gestures like the hot dog, often handled via Dreamweaver support

One size fits all example: reimagining the check moment

Why the check is a challenging and overlooked touchpoint[16:51]
• Guests become impatient once they ask for the check, and delays can ruin the meal; but dropping it too early feels like rushing them out
• In fine dining the large size of the bill can also dampen how guests feel about the experience
• Will notes that despite being universal, the check is almost never approached with creativity or intention
Their cognac-and-check ritual[18:09]
• When he knew a table was done but before they asked for the check, Will would bring a glass for each person and a bottle of cognac
• He poured a splash for each person, said it was with his compliments, left the bottle on the table, and then placed the check saying it was ready whenever they were
Impact of the cognac gesture[17:42]
• No one had to wait for the check, and no one could feel rushed because they just received a free bottle of booze
• It cost little, as guests rarely drank more than a splash, but it matched the large bill with an act of generosity
• Will says many guests do not remember what they ate but vividly remember how they felt receiving that bottle

Psychology of reciprocity, surprise, and word-of-mouth

Host's persuasion examples and tipping research

Host recounts Robert Cialdini's mint and tip story[20:19]
• He describes a study where a waitress giving a mint with the bill got significantly higher tips than one who did not, and an even more personalized gesture performed best
Host's own use of reciprocity buying a motorcycle[21:33]
• He brought two cans of Coke to a Craigslist seller and offered one as a casual favor
• Despite an initially firm $3,000 price, the seller agreed to $2,500, citing the host's kindness in bringing the Coke

Reciprocity and surprise in hospitality

Will on tips and documented reciprocity effects[21:35]
• Will confirms tips went "through the roof" due to gestures like the cognac
• He cites a Cornell study where giving a mint with the check led to 18% higher tips on average
Rule of reciprocity and human discomfort with owing[21:33]
• Host explains the rule of reciprocity: when someone does a favor, the recipient feels compelled to reciprocate, even disproportionately
Importance of surprise and not preconditioning gifts[23:26]
• Will shares Rory Sutherland's example of a surprise duvet set vs one promised as a conditional gift
• He concludes reciprocity combined with surprise and delight is most powerful; if the gift is announced up front, people feel they've earned it instead of being moved by it

Measuring impact and financial results of unreasonable hospitality

Mantra and observed business outcomes

Did they call it unreasonable hospitality at the time?[23:35]
• Will confirms the internal mantra was indeed "unreasonable hospitality"
Effect on profits and revenue[23:40]
• He states clearly that profits and revenues went way up after embracing these philosophies
Challenge of measuring short-term ROI[24:06]
• Will notes some leaders are hesitant because hospitality gestures are hard to measure in the short term under the "what gets measured gets managed" mindset
• He stresses commitment over time is needed to see emotional connections translate into return visits and word-of-mouth
Stories as marketing vs traditional spend[24:43]
• Will says every dollar spent on unreasonable hospitality yielded more than any dollar spent on traditional marketing
• Gestures like the hot dog or sleds give guests stories they will tell repeatedly
They did not self-promote specific gestures in real time[24:47]
• Will says they never told guests about these things publicly at the moment; for example, the hot dog story only became widely known via his book
• He believes if you do these things, you can count on guests telling the stories themselves

Pattern recognition and one size fits some gestures

Definition and simple examples of one size fits some

Recognizing recurring moments[26:51]
• One size fits some refers to things that happen repeatedly for some customers but not all
• He cites family restaurants giving kids crayons and coloring mats as basic pattern recognition
Their variations on kid hospitality[26:32]
• Eleven Madison rotated through items like Lego sets and Etch A Sketches for children

Involving the whole team in identifying recurring opportunities

Structured brainstorming and David Marquet quote[27:08]
• They held full-team exercises to list recurring moments and brainstorm better responses
• Will quotes David Marquet: in most organizations, people at the top have all the authority and none of the information, while frontline people have all the information and none of the authority
• He argues you must bridge that authority-information gap to generate significant hospitality ideas
Strategic planning cadence[27:35]
• They did strategic planning restaurant-by-restaurant quarterly, plus one longer annual session
• Ideas from a one-day planning session would usually take about a year to implement fully

Engagements and Tiffany champagne flute boxes

Standard industry reaction vs unreasonable version[28:04]
• Will notes many reasonable restaurants pour free champagne when guests get engaged
• He calls that reasonable hospitality and looks for ways to make it more awesome
Partnering with Tiffany & Co.[28:33]
• Tiffany & Co. had offices across the park from the restaurant, so Will visited, knocked on doors, and convinced the CMO to give them 1,000 signature blue boxes
• Each box contained two champagne flutes; they stored them at the restaurant
How the engagement gesture worked[29:00]
• When couples got engaged, staff poured free champagne as usual but used slightly different flutes without calling attention to them
• At the end, they gave the couple the very glasses they had toasted their engagement with, inside the Tiffany box
Perceived uniqueness and cost[29:22]
• Will says it was not less special for guests even though many boxes sat in the back
• He has spoken to couples who do not remember the food but never forget that gesture
• The gesture cost the restaurant nothing since Tiffany supplied the flutes; he believes Tiffany recouped costs via registry sales

Combining all three gesture types for an overall magical experience

Limitations of one size fits one[29:51]
• Will points out they served about 110 people a night and could not do a bespoke Dreamweaver gesture for everyone
Holistic design of the experience[29:54]
• Between one size fits all, one size fits some, and selective one size fits one, he believes everyone left feeling the experience was at least a little magical

Translating hospitality to digital "forgotten text" and overlooked touchpoints

Host's philosophy of altering the forgotten text

Examples of default vs crafted messages[30:23]
• Host notes that most confirmation emails from tools like MailChimp or ConvertKit are generic "Thanks for subscribing, click here to confirm" texts
• He wrote a humorous, elaborate welcome email describing bells ringing and coworkers doing pushups and shots whenever someone subscribed
• He also customized unsubscribe messages, citing a Groupon example where an intern is jokingly punished when someone unsubscribes
Impact of focusing on overlooked text[31:18]
• Host says these crafted messages went viral and earned backlinks and press
• He extended the philosophy to pop-ups with playful copy about "another pop-up" and straightforwardly pitching the newsletter

Will's reaction and further overlooked touchpoint example

Why Will finds the approach brilliant[32:40]
• He believes small enhancements to overlooked touchpoints have outsized impact because they signal a willingness to care about what others ignore
Auto dealer glove compartment story[33:09]
• Will asked an auto dealer what customers find in the glove compartment a week after buying a car; the answer was "nothing"
• The dealer group began placing $15 Starbucks gift cards with thank-you notes and phone numbers in glove compartments
• A year later, they reported never seeing such a large marketing return from any previous initiative
Second reason Will likes the forgotten text strategy[32:30]
• He observes many companies obsess over perfecting brands instead of pursuing people, becoming too serious
• He argues that allowing some silliness and humanity almost never fails to create connection

Applying unreasonable hospitality in non-restaurant businesses

UPS store in Sarasota: mandatory daily generosity

Making hospitality mandatory as a signal[37:00]
• Will argues that the word "mandatory" is unfairly stigmatized; making something mandatory signals that it matters
Owner's rule for staff comps[36:29]
• A UPS store owner in Sarasota mandated that each register worker must comp one customer per shift up to around $40
• Staff had to log who they comped and why when clocking out
Triple win outcomes from the policy[37:09]
• Customers receiving unexpected comps were delighted and likely to tell the story
• Staff, who rarely get enthusiastic appreciation in such jobs, felt energized when they saw customers' positive reactions
• Because each worker could only comp once per shift, they began engaging more deeply with all customers to decide who most deserved it
• This meant even customers who did not receive a comp had more genuine interactions and better experiences

Chewy dog food: pattern recognition for grieving customers

Recurring situation Chewy identified[39:55]
• Chewy's model is recurring dog-food subscriptions; when a dog dies, owners often forget to cancel in the midst of mourning
• As a result, a fresh bag arrives weeks later, compounding the owner's grief
Chewy's standardized empathetic response[40:04]
• When customers call to cancel after such deliveries, Chewy apologizes for their loss and credits the account for the last bag
• They explain they cannot take the food back for health-code reasons and encourage donating it to someone else who needs it
• Two days later, they send a bouquet of flowers with a note expressing sympathy for the loss
Why this is powerful and economically rational[40:42]
• Will classifies this as pattern recognition and a one-size-fits-some gesture intentionally designed for a recurring scenario
• He notes that dog owners who lose a dog often eventually get another and that such gestures make it hard to imagine ordering from any other company

Intersection of creativity and intention

Two ingredients of unreasonable hospitality[41:33]
• Will defines unreasonable hospitality as happening where creativity meets intention
• Intention means actively pursuing relationships, seeking opportunities, and caring enough to act; creativity means finding the most awesome way to respond
Benefits for teams who practice it[42:27]
• Will says nothing energizes him more than seeing someone's face when they receive a gift he is responsible for giving
• Creating such a culture gives everyone on the team the gift of being able to give thoughtful, not necessarily lavish or expensive, gifts

Effort, magic, and investing more energy than seems reasonable

Teller's quote on magic and its relation to hospitality

Definition of magic by Teller[44:14]
• Will cites Teller saying magic is sometimes just being willing to invest more energy into an idea than anyone else would deem reasonable
Will's takeaway from the quote[44:14]
• He emphasizes that nothing about these hospitality practices is technically hard, but they demand more willingness to work hard than others

Magician's preparation for Paul Rudd trick

Setup of the Ant-Man magic training story[44:32]
• Host recounts a magician friend hired to train Paul Rudd in magic for a film, spending a day showing tricks at the director's house
The climactic backyard card trick[45:05]
• When asked for his best trick, the magician had Paul Rudd point anywhere in the yard and name a card
• They walked to that spot, an assistant handed the magician a shovel, and he dug out the named card from the ground
Revealed preparation behind the magic[45:57]
• The magician later showed a video of him and his assistant burying all 52 cards in a grid in the yard the night before
• It was a huge amount of work, but Paul Rudd's reaction made all the effort worthwhile
Will's analogy between magic and hospitality[46:26]
• Will says that kind of investment is what makes magic, and unreasonable hospitality aims to do the same for guest experiences

Will's current work and involvement with "The Bear"

Comparing life as restaurateur and author/creator

What Will loved about running restaurants[46:37]
• He loved working intensely to build a world and then standing at the front door welcoming people into it
Difference in gratification from writing[47:07]
• He notes he does not get the same gratification of watching guests in real time, since he cannot sit in living rooms and see people read his book
He does not miss the old life because he loves the new one[47:25]
• Will says it is hard to compare which he loves more, but he certainly does not miss the old job because he is enjoying current work so much

Current projects and role on "The Bear"

Conferences and newsletter[47:40]
• Will mentions organizing the Welcome Conference in New York and an Unreasonable Hospitality Summit in Nashville, and writing a newsletter called Premial
Writing and producing for "The Bear"[49:25]
• He clarifies that he started writing and producing the season after the "Forks" episode
• He describes working on the show as fun and praises the team as "just the best"
Comments on Jeremy Allen White and Matty Matheson[49:20]
• Will says Jeremy Allen White is awesome, wildly talented, and exceptionally humble
• He calls Matty Matheson a ridiculous, incredible, and very sweet human being

Discussion of style and "sprezzatura" using Matty as an example

Concept of clothes wearing you vs you wearing the clothes[50:46]
• Host shares a menswear idea that if you try too hard, it looks like the clothes are wearing you
Definition of sprezzatura[51:28]
• Host explains sprezzatura as being effortlessly cool, like wearing a $2,000 suit with dirty boots in a way that works
Matty Matheson as embodiment of effortless style[52:04]
• They describe Matty as having tattoos on his face and always wearing clothes that look naturally broken-in, not styled from a thrift shop run
• Host says it looks like Matty wakes up and an outfit is magically draped on him by an ethereal force

Economics and challenges of running restaurants

Why many restaurant owners struggle financially

Host's perception of the industry[53:39]
• Host notes he has heard stories that many seemingly successful restaurant owners are still broke and working extremely hard
Will's diagnosis of common problems[54:11]
• He says many people open restaurants without rising through the business enough to understand its economic side
• He argues you must be as creative about making money as you are about crafting the guest experience
• Small restaurants often have economics that are hard to make work until owners expand to many locations, at which point quality can suffer due to distraction

Examples of balancing art and commerce

Boka Restaurant Group[54:36]
• Will names Kevin Boehm and Rob Katz of Chicago's Boka Restaurant Group as people who have balanced art and commerce well
• He mentions they have around 36 restaurants

Explaining scale, fixed costs, and volume in restaurant economics

Cost of a good general manager vs revenue scale[55:33]
• Will notes a strong general manager is required regardless of whether a restaurant has 40 or 60 seats, or whether the check average is modest or very high
• He estimates a GM costs roughly $90,000 to $180,000 depending on the market, relatively similar across different restaurant sizes
• The same GM cost can support a $5 million or a $20 million revenue restaurant, so scale can improve margins
Volume as seats times average check[56:05]
• He defines volume as a function of the number of seats multiplied by average check size
• Variable costs increase with volume, but many fixed costs (like management) do not scale linearly, helping larger restaurants

Advice for aspiring restaurateurs

Learn on someone else's dime first[56:57]
• Will encourages people who want to open restaurants to work in one long enough to make mistakes on someone else's dime
Open a concept big enough to be worthwhile[57:27]
• He advises opening a restaurant large enough that the effort and fixed costs can be justified economically

Future concepts and returning restaurants to connection and simplicity

Fashion cycles of restaurant complexity

Pendulum between complexity and simplicity[58:08]
• Will compares restaurant fashion cycles to jeans going from skinny to wide and back
• He believes restaurants became overly complicated for a while and is excited about a return to simplicity

Types of restaurants Will is drawn to today

Resdora in New York[58:29]
• He praises Resdora as an example: unbelievable pasta in a beautiful room with delightful service
Mykonos house breakfast experience[58:50]
• Will describes renting a house in Mykonos where the owners set a communal breakfast table daily with yogurt, fruit, bacon, eggs, and fresh bread
• Guests did not have to order anything; they just sat down and enjoyed, creating a simple, beautiful shared moment
Imagining a restaurant based on that model[59:11]
• Will says he feels such a restaurant does not yet exist and he would love to see one where you sit with loved ones and the food is simply there
• He is drawn to concepts more about creating conditions for genuine connection than impressing people with what the restaurant can do

Closing reflections on excellence and inspiration

Host's hope for listener impact

Desire to introduce Will to new audiences[59:32]
• Host says one joy of the podcast is surfacing people listeners do not already know, even though Will is already well-known
• He hopes some listeners who had not heard of Will will now feel inspired by unreasonable hospitality and the pursuit of excellence
Host's personal evolution on excellence[1:00:14]
• He shares that for a long time his attitude was "it's good enough, move forward"
• He is now trying to fight that tendency and be more excellent, and says Will's work consistently makes him feel that need
Mutual appreciation and sign-off[1:00:47]
• Will responds with thanks, and the host expresses appreciation before ending the conversation

Lessons Learned

Actionable insights and wisdom you can apply to your business, career, and personal life.

1

Normalize feedback by pairing abundant, specific praise with thoughtful, private, unemotional criticism that targets behaviors rather than people, so that criticism becomes an investment in growth instead of a source of shame.

Reflection Questions:

  • • Where in your current leadership or peer relationships have you avoided giving honest criticism because you wanted to be liked?
  • • How could you redesign your feedback conversations so they focus clearly on specific behaviors and are delivered without sarcasm or emotion?
  • • What concrete habit could you implement this week to ensure you praise people more frequently than you criticize them?
2

Design small, thoughtful gestures at overlooked touchpoints-like the moment someone gets a bill or opens a confirmation email-because tiny enhancements there signal deep care and create disproportionately memorable experiences.

Reflection Questions:

  • • What are the most common but boring touchpoints in your customer or colleague journey that almost no one currently thinks about improving?
  • • How might a simple, low-cost gesture or piece of copy at one of those touchpoints change how people feel about interacting with you or your business?
  • • Which single overlooked touchpoint will you choose to redesign in the next month, and what specific change will you test there?
3

Systematize delight by building roles and processes-like a Dreamweaver or mandatory daily comps-that give frontline people bandwidth and permission to turn spontaneous insights into concrete acts of hospitality.

Reflection Questions:

  • • In your organization, who currently has the ideas and customer contact but lacks the time or authority to execute delightful gestures?
  • • How could you create a simple system, budget line, or designated role that exists specifically to help others bring hospitality ideas to life?
  • • What is one lightweight "mandatory generosity" practice you could introduce for your team to try over the next two weeks?
4

Use pattern recognition to create scalable, personal-feeling gestures for recurring situations-your "one size fits some"-so you can consistently respond in meaningful ways without reinventing the wheel each time.

Reflection Questions:

  • • What recurring emotional situations do your customers, users, or teammates experience (onboarding, failure, milestones, loss) that you could proactively design for?
  • • How might you borrow from examples like engagement gifts or Chewy's sympathy flowers to craft a standard response that still feels human and specific?
  • • Which recurring moment will you map out this week, and what standardized yet personal gesture will you commit to deploying every time it happens?
5

Excellence and "magic" often come from investing more effort into simple ideas than others think is reasonable, turning ordinary interactions into stories people can't resist retelling.

Reflection Questions:

  • • Where in your work or life have you stopped at "good enough" even though a bit more thoughtful effort could have made the moment unforgettable?
  • • How could you reframe certain high-effort gestures not as inefficiencies but as strategic investments in loyalty, reputation, or team morale?
  • • What is one upcoming interaction or project where you will deliberately over-invest energy to create a surprisingly magical result?
6

If you want a sustainable, excellent business, you must be as creative and intentional about the underlying economics and scale as you are about the experience, ensuring your model is big enough and well-designed to support the level of service you envision.

Reflection Questions:

  • • Do your current ambitions for quality and hospitality match the economic reality of your business model, or are you under-sizing the opportunity?
  • • How might thinking in terms of fixed vs variable costs, scale, and average customer value change the way you design or price your offerings?
  • • What specific financial or operational change could you explore this quarter to better align your aspirations for excellence with a viable economic structure?

Episode Summary - Notes by Micah

The Hospitality Principles That Build Billion-Dollar Startups
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