Entrepreneurship

I’ll admit it. I’m a “karmic capitalist.” I believe what goes around, typically, comes around in life and business. The only question is how long it takes. This concept is now in vogue. “Conscious capitalism” has emerged.

I was barely old enough to buy a beer when I found myself in my Stanford GSB classroom. I was bored silly. I was the second youngest person in our class of 300. Right off, I intuitively felt there was more to learning business than drawing decision trees and grokking cost accounting. So, I decided to DIY my education.

As I outlined in this earlier post on “How to Become Wiser Starting Today,” one of my young CEO learning breakthroughs happened when I committed to writing in my “Wisdom Book” each weekend. The first of 52 boutique hotels we created was a rock ‘n roll motel. It was called The Phoenix. It had failure written all over it. We struggled in our first couple of years, even as I tried all the classic niche marketing approaches.

For the decade and a half that I was a struggling entrepreneur, rubbing two sticks together for heat, I’d find myself in San Francisco a couple of times a year. And I’d stay at the Phoenix. Not because it was free (Chip charged me the slightly-discounted starving-entrepreneur rate) but because (at least at the beginning) Chip needed the business and I needed a cheap place to stay.

It was 1636, the Dutch Golden Age, and the recently introduced and fashionable tulip was all the rage. Prices for bulbs were bubbly...until they weren’t and “Tulip Mania” became the first recorded speculative bubble.

Between 1902 and 1908, poet Rainer Maria Rilke wrote ten letters to nineteen-year-old Franz Kappus, who was attending Rilke’s alma mater and was similarly studying poetry. These letters offered counsel to Kappus on how to look at life through the eyes of an authentic, fearless, and searching poet.

In the last couple of posts, I’ve advocated that editing is a supreme form of prioritization. While true, on occasion, it may also lead you to miss the opportunity staring you in the face.

A friend in his mid-40s recently lost his Silicon Valley job. He felt like he was being put out to pasture like a lame horse, which immediately wounded his pride and put him into a confidence crisis. He’s not alone. More and more people are seeing their futures put out to past-ure. The question is: what to do?

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...

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.