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. SUBSCRIBE: http://bit.ly/1dSzTkW About Tim Ferriss: Tim Ferriss is one of Fast Company’s “Most Innovative Business People” and an early-stage tech investor/advisor in Uber, Facebook, Twitter, Shopify, Duolingo, Alibaba, and 50+ other companies. He is also the author of five #1 New York Times and Wall Street Journal bestsellers: The 4-Hour Workweek, The 4-Hour Body, The 4-Hour Chef, Tools of Titans and Tribe of Mentors. The Observer and other media have named him “the Oprah of audio” due to the influence of his podcast, The Tim Ferriss Show, which has exceeded 300 million downloads and been selected for “Best of iTunes” three years running. Connect with Tim Ferriss: Sign up for "5-Bullet Friday" (Tim's email newsletter): https://go.tim.blog/5-bullet-friday-1/ Visit the Tim Ferriss PODCAST: https://tim.blog/podcast/ Visit the Tim Ferriss BLOG: https://tim.blog/ Follow Tim Ferriss on TWITTER: https://twitter.com/tferriss/ Follow Tim Ferriss on INSTAGRAM: https://www.instagram.com/timferriss/ Like Tim Ferriss on FACEBOOK: https://www.facebook.com/TimFerriss/ Start. [00:00] Coping with bad news. [00:15] Musing on the meaning of life. [04:50] How to introduce Chip at a speaking engagement. [06:17] From undergrad to commercial real estate to his hotelier career. [07:24] Brainstorming sessions with Seth Godin. [09:53] How to start your own brainstorming group. [11:53] On giving ideas time to incubate and transform. [15:13] Wisdom and emotional regulation. [17:21] Chip's 12-Bullet Fridays of lessons learned. [18:47] Developing emotional regulation. [21:23] Attainment, atonement; attunement, at-one-ment. [22:29] Meditation. [23:38] Chip's first book. [26:18] Meeting unrecognized needs of unspoken customers. [31:23] Exceeding expectations. [35:04] If being first doesn’t work out... [37:40] Build the business plan as if it’s not going to succeed. [40:54] Why does fellow boutique hotelier (and past show guest) Liz Lambert “hate” Chip? [41:30] Why people from Maya Angelou to Moby find boutique hotels ideal for working staycations. [45:10] Why did Chip sell Joie de Vivre? [45:57] How did Chip decides what to focus on next. [48:39] Despair equals suffering minus meaning. [50:53] Chip's Near Death Experience. [52:20] Other equations. [58:00] Stillness [1:00:27] Guide on the side vs. sage on the stage. [1:02:49] Modern Elder Academy and midlife wisdom schools. [1:04:23] The U-curve of happiness. [1:11:55] Getting Airbnb’s three young founders to focus on four strong initiatives [1:14:48] One simple question to ask yourself at the start of any business venture. [1:17:43] Academy exercises that help midlifers. [1:20:44] How to prepare for Modern Elder Academy. [1:26:10] Values. [1:27:27] Coming out as gay and how his Marine Reserve father feels about it. [1:28:34] Chip has a couple of sons with a lesbian couple. [1:31:26] What made Chip change his mind about fatherhood? [1:34:37] Has Chip been parenting instinctively? [1:37:16] Embracing liminality. [1:38:00] Aside from his own, what books does Chip gift most often? [1:40:35] What would Chip’s billboard say? [1:43:22] Parting thoughts. [1:43:59]