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)

Chip Conley joined Airbnb at 52, when the average employee was 26. He had to learn technology language, mentor Brian Chesky while reporting to him, and stay humble enough to be the least knowledgeable person in the room. His contribution was not to replace technical expertise but to question assumptions: he asked whether Airbnb’s product was really just software, and he urged the team to test a mobile-only experience with older hosts rather than assuming every host would adapt equally easily.

Conley’s account of Chesky combines admiration with criticism. He credits Chesky’s curiosity and willingness to consult experts, but says Chesky expected employees to match his work pace, sometimes relied too heavily on his own product judgment, and used extreme goals that could create stress. Conley’s proposed response is to establish the purpose, success criteria, and desired outcome of a meeting before debating details. Direct experience with hosts in 20 cities gave him credibility when he challenged the founder’s assumptions.