Chip Conley — Building Empires, Tackling Cancer, and Surfing the Liminal (#374)

“‘What mastery can you offer?’ So have a friend of yours ask that question of you five times, and you’ll be sort of surprised at, by the fifth time you get asked that question, and you’ve had to come up with four other answers before that, what kind of revelation you may have in this archaeological dig.” — Chip Conley

At age 52, after selling the company he founded and ran as CEO for 24 years, rebel boutique hotelier Chip Conley (@chipconley) was looking for a new chapter in life. Then he received a call from the young founders of Airbnb, asking him to help grow their disruptive start-up into a global hospitality giant. He became their head of global hospitality and strategy.

Chip is a leading authority at the intersection of psychology and business. He is a New York Times bestselling author, and his latest, Wisdom @ Work: The Making of a Modern Elder, inspired him to build the world’s first midlife wisdom school. Located in Baja California Sur, the Modern Elder Academy provides the place and the tools to start reframing a lifetime of experience for what comes next.

Listen to the episode on Apple Podcasts, Spotify, Stitcher, Overcast, Castbox, or on your favorite podcast platform. Watch the interview on YouTube here.  You can find the transcript of this episode here. Transcripts of all episodes can be found here.

• Listen onApple Podcasts
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Want to hear another interview with an incredible boutique hotelier? Listen to my interview with hospitality mogul Liz Lambert, in which she talks about balancing the desire to be an artist with the desire to be a business tycoon. (Stream below or right-click here to download):

QUESTION(S) OF THE DAY: What was your favorite quote or lesson from this episode? Please let me know in the comments.

Scroll below for links and show notes…

SELECTED LINKS FROM THE EPISODE

• Connect with Chip Conley:

Modern Elder Academy | Twitter | Facebook | LinkedIn

• Modern Elder Academy
• Wisdom @ Work: The Making of a Modern Elder by Chip Conley
• The Rebel Rules: Daring to be Yourself in Business by Chip Conley
• PEAK: How Great Companies Get Their Mojo from Maslow by Chip Conley and Tony Hsieh
• Emotional Equations: Simple Truths for Creating Happiness + Success by Chip Conley and Tony Hsieh
• Marketing That Matters: 10 Practices to Profit Your Business and Change the World by Chip Conley and Eric Friedenwald-Fishman
• Austin, Texas
• Chip Conley’s TED Talks
• Prostate Cancer Symptoms and Causes, The Mayo Clinic
• Oracle Park
• “The Purpose of Life Is to Discover Your Gift. The Meaning of Life Is to Give Your Gift Away,” Quote Investigator
• “Computers Are Useless; They Can Only Give You Answers,” Quote Investigator
• Joie de Vivre
• Airbnb
• Animated Timeline Shows How Silicon Valley Became a $2.8 Trillion Neighborhood, Business Insider
• Stanford Business School
• Why Hasn’t the Tenderloin Gentrified Like the Rest of San Francisco? KQED News
• The Phoenix Hotel
• Random Acts of Initiative, Seth’s Blog
• Business Rules of Thumb by Seth Godin and Chip Conley
• Esalen Institute
• The Conley Bookstore
• Man’s Search for Meaning by Viktor E. Frankl
• A New Luxury Retreat Caters to Elderly Workers in Tech (Ages 30 and Up), The New York Times
• The Mirror Neuron Revolution: Explaining What Makes Humans Social, Scientific American
• Good Company, Yoga Journal
• What is Your State of Being at Work? Attain or Attune? by Chip Conley, LinkedIn
• Transcendental Meditation
• Metta Meditation (aka Loving Kindness Meditation), Metta Institute
• Vipassana Meditation
• Awake in the Wild: Mindfulness in Nature as a Path of Self-Discovery: A Buddhist Walk Through Nature — Meditations, Reflections and Practices by Mark Coleman
• Baja Kayaking and Meditation Retreats, SeaTrek
• Jalousie (aka Louvered) Windows, Their History, and Where to Buy Them Today, Retro Renovation
• Joy on Demand: The Art of Discovering the Happiness Within by Chade-Meng Tan
• Search Inside Yourself: The Unexpected Path to Achieving Success, Happiness (and World Peace) by Chade-Meng Tan
• Like a Virgin Megastore, Shut for the Very Last Time, Salon
• Alaska Airlines Works Fast to Erase Memories of Virgin America, Skift
• Great American Music Hall
• Slim’s
• The Fillmore
• Hotel Vitale
• W
• Four Seasons
• Real Simple
• Dwell
• Henry Ford, Innovation, and That “Faster Horse” Quote, Harvard Business Review
• Virgin Atlantic
• The Art of Hospitality: An Interview With Entrepreneur and Hotelier Liz Lambert, The Tim Ferriss Show #320
• Hotel San Jose
• The Karmic Capitalism of Chip Conley, Stanford Magazine
• Bunkhouse Group
• Hotel Saint Cecilia
• Burning Man
• 28 Festivals and 8 Reasons They Can Change Your Life (Plus: Free Burning Man Tickets!), Tim.Blog
• Festival of Near Death Experiences, Spanish Fiestas
• Frangipani, Southern Living
• 1979 Heinz Ketchup Anticipation TV Ad, YouTube
• Buddhism’s Four Noble Truths, BBC Radio 4
• The Great Recession, Investopedia
• Bhutan’s Gross National Happiness Index, OPHI
• Hedonic Treadmill, Investopedia
• The 4-Hour Workweek by Tim Ferriss
• What Are the Signs of a Midlife Crisis? Verywell Mind
• Canyon Ranch
• The 10 Principles of Burning Man, Burning Man
• The Happiness Curve: Why Life Gets Better After 50 by Jonathan Rauch
• A Refresher on Marketing Myopia, Harvard Business Review
• “Liminal” Is Not a “Fancy” Word, Daily Writing Tips
• Morgan Stanley
• A Munchkin Welcome, The Wizard Of Oz, WBMoviesOnline
• Newsweek AIDS Covers, 1983-2006, Harvard AIDS Initiative
• Dan Gilbert’s TED Talks
• The 100-Year Life: Living and Working in an Age of Longevity by Lynda Gratton and Andrew Scott
• Setting the Table: The Transforming Power of Hospitality in Business by Danny Meyer
• Shake Shack
• Union Square Hospitality Group
• The Top 10 Secrets of Gramercy Park in NYC, Untapped Cities
• Meditations by Marcus Aurelius
• On the Shortness of Life by Lucius Seneca
• The 7 Best Life Expectancy Calculators, New Retirement
• “Be Yourself. Everyone Else Is Already Taken,” Quote Investigator

SHOW NOTES

• The bad news Chip received the day before giving a TED talk, its implications, and what he’s been doing to cope with it in the time since. [05:52]
• Musing on the meaning of life. [09:47]
• How would someone introduce Chip at a speaking engagement? [11:28]
• How Chip got into commercial real estate, why it led to his career as a hotelier, and how this diverged from his original plans as an undergrad. [12:39]
• Chip talks about brainstorming sessions at Stanford Business School with Seth Godin. [15:04]
• How would Chip recommend someone go about starting their own brainstorming or mastermind group and make it effective for its intended purpose? [17:04]
• What was the purpose of Chip and Seth’s brainstorming group? [18:33]
• On giving ideas time to incubate — and often transform into something completely different from where they began. [20:24]
• With age comes wisdom — or, at the very least, emotional regulation. [22:13]
• As it turns out, Chip creates his own Five-Bullet Fridays. But sometimes they’re 12-Bullet Fridays, and they detail lessons rather than recommendations. Here are a few examples. [23:58]
• What has helped Chip more finely develop his emotional regulation? [26:33]
• Attainment, attunement, and atonement. [27:40]
• What meditation practices does Chip use? [28:49]
• The Chip Conley method of breathing. [29:56]
• How old was Chip when he wrote the first book (that he counts as his first book), and how did he manage to get Richard Branson to write its foreword? [31:29]
• How did Brenda Lee and Arlo Guthrie get The Phoenix started on the road to its reputation as a rock and roll hotel, and how did identifying the unrecognized need of the unspoken customer who made a difference in the equation — the tour manager — ultimately maintain this reputation? [34:41]
• On being the first to address an unspoken need in an industry and exceeding expectations even if the market research doesn’t initially quantify it. [39:34]
• If being first doesn’t work out, make sure turning it around is an easy solution. [43:20]
• An important lesson from Richard Branson and Chip’s father: Build the business plan as if it’s not going to succeed. [44:53]
• Why does fellow boutique hotelier (and past show guest) Liz Lambert “hate” Chip? [46:41]
• As a successful hotelier at the time, why did Chip agree to help Liz when she was just getting started? [47:40]
• Why people from Maya Angelou to Moby find boutique hotels ideal for working staycations. [50:21]
• A question from the aforementioned Liz Lambert: Why did Chip decide to sell Joie de Vivre when he did? [51:07]
• How did Chip decide what to focus on next, and what form did this journey take? [53:50]
• Chip explains the flatlining experience behind despair = suffering minus meaning from his fourth book, Emotional Equations. [56:03]
• What did Chip see repeatedly on his trips to the “other side” while flatlining nine times, and what has he taken away from the experience? [57:23]
• Other equations to which Chip refers often. [1:03:26]
• Does Chip see the value in being still, or does he always have to be chasing some “next big thing” or another? [1:05:34]
• On being the guide on the side instead of the sage on the stage at Airbnb and how it allowed him to be driven for a purpose greater than just his own. [1:07:57]
• Why Chip feels comfortable with his current commitment to Modern Elder Academy and believes midlife wisdom schools will be big in the future. [1:09:34]
• Why is Chip limiting Modern Elder Academy to one location rather than franchising into multiple centers? Would he encourage other entrepreneurs to start their own midlife wisdom schools? [1:14:14]
• What is the U-curve of happiness, and why might we actually get happier as we age? What are the positives of getting older? [1:16:46]
• How did Chip, being at least two decades older than Airbnb’s three young founders, help steer them toward focusing on four strong initiatives — down from 23? [1:20:01]
• One simple question to ask yourself at the start of any business venture, a game you can play to extract every practical ounce of use from it, and a variation for personal revelation. [1:22:31]
• Academy exercises that help midlifers understand liminality and evolve toward the editing phase of their journey (with examples of Chip’s own participation). [1:25:56]
• How does Chip have people prepare for their time at Modern Elder Academy? [1:31:21]
• Examples of values people might include on their personal, ranked list. [1:32:38]
• Chip shares some of his backstory — including when he came out as openly gay at age 22, what the social climate was like then, and how his Marine Reserve father feels about it. [1:33:33]
• Chip has a couple of sons with a lesbian couple. How did this come about, and what’s his level of involvement in their lives? [1:36:28]
• After being initially reluctant to the idea of fatherhood, what made Chip change his mind? [1:38:53]
• Why Chip is happy to be so involved in his sons’ lives as a third parent, and what his experience with parenting had been beforehand. [1:40:39]
• Has Chip been parenting instinctively, or are there any books he’s read for guidance? [1:42:27]
• The difference between a traditional elder and a modern elder. [1:44:14]
• Aside from his own, what books does Chip gift most often? [1:45:42]
• What would Chip’s billboard say? [1:48:34]
• Parting thoughts. [1:49:10]

PEOPLE MENTIONED

• Steve Conley
• Gavin Newsom
• William Shakespeare
• Pablo Picasso
• Ian Schrager
• Bill Kimpton
• Seneca
• Marcus Aurelius
• Seth Godin
• Viktor Frankl
• Mark Coleman
• Jack Kornfield
• Chade-Meng Tan
• Richard Branson
• Eve Branson
• Edward James Branson
• Brenda Lee
• Arlo Guthrie
• Nirvana
• Pearl Jam
• David Bowie
• Red Hot Chili Peppers
• Bill Graham
• Abraham Maslow
• David Brooks
• Abraham Lincoln
• Oscar Wilde
• Henry Ford
• Liz Lambert
• Maya Angelou
• Moby
• Sigmund Freud
• Gautama Buddha
• Peter Guber
• Brian Chesky
• Joe Gebbia
• Nathan Blecharczyk
• Mel Zuckerman
• Brené Brown
• Theodore Levitt
• Peter Drucker
• Carl Jung
• Jonathan Rauch
• Danny Meyer

The Tim Ferriss Show is one of the most popular podcasts in the world with more than one billion downloads. It has been selected for "Best of Apple Podcasts" three times, it is often the #1 interview podcast across all of Apple Podcasts, and it's been ranked #1 out of 400,000+ podcasts on many occasions. To listen to any of the past episodes for free, check out this page.