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

“The question would be: ‘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.

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


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):

#320: The Art of Hospitality: An Interview With Entrepreneur and Hotelier Liz Lambert


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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…


  • Connect with Chip Conley:

Modern Elder Academy | Twitter | Facebook | LinkedIn


  • 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]