Chip Conley
Brian Chesky's secret mentor who died 9 times, started the Burning Man board, and built the world's first midlife wisdom school, covering team leadership, product design, and startup building.
Episode
Brian Chesky's secret mentor who died 9 times, started the Burning Man board, and built the world's first midlife wisdom school | Chip Conley (founder of MEA)
Summary
Founder of the Modern Elder Academy and Brian Chesky's longtime mentor at Airbnb shares what it was like to join at 52 as a 'modern elder' — simultaneously mentoring the CEO and reporting to him. He saved Airbnb from going mobile-only by pointing out older hosts couldn't manage listings on a phone. He also covers the world's first midlife wisdom school, how nine near-death experiences changed his relationship with purpose, and why curiosity matters more than wisdom as you age.
Key Takeaways
The most effective role for an experienced person in a young company isn't dispensing wisdom — it's being a 'confidant' who helps younger colleagues find their own answers.
Establish credibility through competence in a domain the young team lacks. Chip's credibility at Airbnb came from deep hospitality knowledge the 26-year-olds simply didn't have.
Before important meetings with a founder, align on intention, definition of success, and desired outcome. This shared reference point prevents conversations from going sideways.
Tech companies undervalue experienced workers by measuring only execution speed. Pattern recognition, emotional intelligence, and knowing what not to do are often invisible to standard metrics.
Curiosity is the antidote to becoming irrelevant. The moment you position yourself as the expert who has all the answers, younger colleagues tune out.
Notable Quotes
“Partly because back in the day, the two sharing economy darlings were Uber and Airbnb. Of course, Uber was pretty much a mobile only app. Airbnb started as non-mobile and then went mobile. Then it was like, "Oh, wouldn't it be interesting if everything was mobile?" At some point, I just said, "Listen, let's get some older people who are hosts in here to see how well they will be versed in managing their listing purely on mobile."”
“We did a lot of different things together, and what I appreciated was you had a humility to you that was different than a lot of the other product managers. There's other product managers, I'm not going to mention their names, and some of these product managers were very good. There were other product managers though who I found it sometimes hard to work with, because they expected me to know as much as they did.”
“You start with that, because that actually helps to make sure there's alignment. Frankly, if there's not alignment, you might as well not have the meeting. Let's spend the rest of this meeting talking about alignment. That's what I would do, because that's something you can come back to over and over again during the rest of the meeting when Brian or the founder, whomever it is, is beating you up on something, saying like, "Well, let me tell you why it looks like that or why we're doing that." It goes back to that, the three principles or the three key goals we're trying to do with this product update. Yeah, so try to set alignment on the front end.”