Startup Advice

Airbnb executive Chip Conley on how baby boomers in tech companies and startups can avoid “years of irrelevance”

Dinushi Dias /

People “of a certain age” who work for new tech companies filled with ambitious, young guns have an opportunity to both learn and teach because of their age, according to entrepreneur and Airbnb executive Chip Conley.

Despite building global hotel brand Joie de Vivre Hospitality and being a bestselling author, Conley says entering a tech company like Airbnb was a brand new learning experience for an “‘old-school’ hotel guy”.

Writing in Harvard Business Review, Conley says when he joined Airbnb at the age of 52, he was “bewildered” by the tech lingo thrown around in meetings.

“[Airbnb co-founder] Brian [Chesky] had asked me to be his mentor, but I also felt like an intern,” Conley says.

“I realized I’d have to figure out a way to be both.”

Conley says he didn’t hide his age and instead chose to approach the opportunity as a chance to grow and give back.

“I imagined myself as a cultural anthropologist, intrigued and fascinated by this new habitat,” he says.

“Part of my job was to just observe.

“Often I would leave a meeting and discreetly ask one of my fellow leaders, who might be two decades younger than I was, if they were open to some private feedback on how to read the emotions in the room, or the motivations of a particular engineer, a little more effectively.”

Conley, who is a strategic adviser for hospitality and leadership at Airbnb, believes there is great opportunity for baby boomers and seasoned professionals to start new chapters of growth and value-exchange in tech and startup ventures.

In return for “digital intelligence”, he says, he offered the young team at Airbnb “emotional intelligence”.

“The opportunity for intergenerational learning is especially important to boomers, as we are likely to live 10 years longer than our parents, yet power in a digital society has moved 10 years younger,” he says.

“This means boomers could experience 20 additional years of irrelevance and obsolescence. That the number of 65-and-older workers last year was 125% higher than in 2000 presages a national human resource tragedy.”

To avoid this, he encourages more people like him to seize opportunities in the world of tech and startups with the mindset of being a “modern elder” — a person who is both a mentor and intern.

“Wisdom is about pattern recognition,” he says.

“And the older you are, the more patterns you’ve seen. There’s an old saying I love: ‘When an elder dies, it’s like a library has burned down’.

“In the digital era, libraries — and elders — aren’t quite as popular as they used to be. But wisdom never grows old.”

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Dinushi Dias

Dinushi Dias is a freelance journalist and a former StartupSmart reporter and multimedia content producer. She is the co-founder of Melbourne-based production house Dinushi & Power.

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