Chip Conley

I loved spending nearly 90 minutes on stage with Brian Chesky at the Commonwealth Club almost exactly a year ago. It was a wonderful opportunity to show in public how we’ve operated in private over the past six and a half years. One of the things we discussed was the disadvantage of being a young entrepreneur. Brian suggests that...

Steve Jobs and I share one thing in common beyond our round glasses. We’re both big fans of Stewart Brand, the founder of the Whole Earth Catalog. One of my guiding lessons, when I was an entrepreneur in my mid-twenties, came from Stewart. He suggested a key tenet in starting a business is to “keep it cheap, small, and local” because it allows you to reduce the size of your mistakes and learn from them.

A wailing siren and a soft, reassuring hand. That is all I remember from my ambulance trip in suburban St. Louis in August 2008. My heart had stopped just as the paramedic team arrived right after my giving a speech. “Break a leg,” is what they tell you before going on stage. Well, I’d broken my ankle a month earlier, had a serious bacterial infection in my leg, and was on strong antibiotics (as it turned out, the heart failure was likely an allergic reaction to the medication).

The meme of the moment was accelerated by this New York Times article marking the end of friendly generational relations. Beyond the fact that the old cranky dude preaching in the TikTok video doesn’t vaguely resemble a Modern Elder who is as curious as they are wise, let’s accept that it was Boomers who created the original “generation gap” in the 1960s.

"Human beings are works in progress that mistakenly think they're finished.” So says Dan Gilbert in his TED talk video (included below). People—at all ages—vastly underestimate how much change they’ll go through in their next ten years.

First off, congrats to the 2019 World Series champs, the Washington Nationals, the oldest team (age-wise) in the Major Leagues! Nice way to celebrate my birthday today, Halloween. Elders still know how to get in the groove! Why is the owl perceived as the wisest animal in the kingdom?

My favorite business article of 2019 (so far) was in the MIT Sloan Management Review with the same title as this post and the subtitle of “How Management Style Varies With Age.” This is a perfect segue after my riff yesterday about how young founders, who often have deep but narrow technical skills and fresh eyes for disruption, could be paired with seasoned leaders who are usually more adept at interpersonal collaboration and focusing on the big picture.

Wisdom is about pattern recognition. It’s time for investors to recognize a pattern that is destroying value and making a mess of companies. The start-up game isn’t the same as the keep-it-up game. Start-ups are full of idealism and chutzpah, charisma and hubris. But, these blitzkrieg tactics wear thin when the keep-it-up game requires diplomacy with regulators, humility with competitors and clients, empathy with employees, and stamina to run further than a start-up sprint.

Context is everything. The rule of thumb for social media videos is to keep them less than 2 minutes. And, yet, there’s a plethora of podcasters aping my friend Tim Ferriss whose interviews are nearly 2 hours. If you have a message, understand the context. Empathize with the recipient. It's Monday: that’s why I’m gonna keep this one short. LOL.

Life used to be so simple. We learned till our early 20s, earned till our mid-60s, and then retired happily to our La-Z Boy. We paid our dues early in our career so we could coast with our three-martini lunches (especially if we were male and pale). Society’s outdated three-stage model (learn, earn, retire) taught us...