Joining Airbnb at 52

I started a boutique hotel company when I was 26 and, after 24 years as CEO, sold it at the bottom of the Great Recession, not knowing what was next.

That’s when Airbnb came calling. In early 2013 cofounder and CEO Brian Chesky approached me after reading my book Peak: How Great Companies Get Their Mojo from Maslow. He and his two Millennial cofounders wanted me to help turn their growing tech startup into an international giant, as their Head of Global Hospitality and Strategy. Sounded good.

But I was an “old-school” hotel guy and had never used Airbnb. I didn’t even have the Uber app on my phone. I was 52 years old, I’d never worked in a tech company, I didn’t code, I was twice the age of the average Airbnb employee, and, after running my own company for well over two decades, I’d be reporting to a smart guy 21 years my junior. I was a little intimidated. But I took the job.

Should you have more than one career?

In my case, I have four vocations: I’m a corporate strategist at a Fortune 500 company, US Navy Reserve officer, author of several books, and record producer. The two questions that people ask me most frequently are “How much do you sleep?” and “How do you find time to do it all?” (my answers: “plenty” and “I make the time”). Yet these “process” questions don’t get to the heart of my reasons and motivations. Instead, a more revealing query would be, “Why do you have multiple careers?”

Read more on Why you should have (at least) two careers