E406: Airbnb’s Chip Conley on the future of hospitality

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Chip Conley shook up the hotel industry in the 80s, starting with his rock’n’roll hotel, The Phoenix, in San Francisco’s Tenderloin district. He began with a magazine – Rolling Stone – and 5 adjectives to describe the hotel, and how it’s ideal guests saw themselves: funky, irreverent, adventures, cool, and young-at-heart. That grew into a 40+ boutique hotel chain, Joie de Vivre, which he ran for over 20 years.

Also an author of books that look at our psychology in the workplace, Chip is now the Head of Global Hospitality at Airbnb. His role there: mentoring CEO Brian Chesky and rolling out consistent standards and service so that business travelers and families will consider booking their travel accommodations through the site, not hotels. Currently, the demographics skew young, urban and tech-savvy.

When he sat down with Jason at Draper Fisher Jurvetson’s CEO Summit, Chip went deep about the stresses of being an entrepreneur that can lead to dark moments. He describes the moment when he contemplated suicide, and how he eventually escaped that sense of desperation.

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Highlights:

2:41 Is there a bubble right now? We’re seeing colossal valuations.
4:30 Thank you New Relic. Sign up and get a free This Week in Startups t-shirt: http://newrelic.com/twist
6:10 The books that you’ve written recently on entrepreneurship, what do you think is the core issue around this new generation of entrepreneurs coming up? Some people say, it’s been kind of easy to be an entrepreneur this time around.
9:45 The companies with great culture that everyone points to have had tremendous success. What if things are going poorly, which in the early days of a startup, it kind of sucks more than it’s great.
12:20 How are you guys creating mission, and a higher order to selling couch space [at Airbnb]?
12:50 Doesn’t [Brian Chesky] pitch [Airbnb] as, it’s not really about renting couches, or renting spaces, it’s about people who didn’t really have the ability to travel previously being able to see places in the world that wouldn’t have been able to afford to go.
14:20 You came from the hotel business. Did you see Airbnb as a threat?
15:15 But Hilton doesn’t seem to be doing too poorly.
17:30 Thank you Mailchimp.com!
20:15 What’s critical in defining brands today?
22:02 What is the role of PR and marketing today?
23:02 The first hotel I ever stayed in San Francisco, was the Phoenix. What was it that you were doing there in terms of marketing and brands that made it spread?
27:00 So what’s the magazine that inspired your newest hotel in Downtown Palo Alto?
28:12 The product space has gotten violently competitive. What do you think, on a product basis, gives people the edge today?

35:45 Joy is something you’ve written about in your books. And a key factor in retention. A lot of experience a lot of daily drudgery.
36:46 How did you create that when you have a large pool of employees cleaning toilets [in hotels]?
43:00 Is entitlement a bad thing in employees? What’s the difference between entitlement and engagement?
48:20 The secondary market is a change in this second wave of internet companies. The fact that you have some power, to get some liquidity at some point. That’s a good thing in your mind?
49:40 Let’s go through some of these emotional equations. Disappointment.
51:10 Another equation: regret.
52:20 What do you regret about your career?
53:18 Why do you think you made that mistake (of having too many investors)?
53:55 You seem like you’re at peace with it. What’s the secret of being at peace after a colossal mistake like that… are you at peace with it?
55:10 So your basic midnight drunken death threat. Pretty standard, who hasn’t had those?
55:37 How do you deal as an entrepreneur with the jealousy, regret, bitterness? Sometimes you see people who didn’t work that hard get a payday, and others who worked incredibly hard just hit a wall. There’s a lot of randomness to life. How can an entrepreneur maintain a tranquility to stay focused on their business?
58:45 Did you think of quitting during [the dot com bust]?
58:58 So you never thought about quitting.
1:03:30 Do you think people are faking it – saying they’re crushing it?
1:05:15 Is it worth it at the end of the day?

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