What is the best advice you ever received?

My father would write notes and letters to me and often end with the phrase “Ad astra, per aspera,” which translates as: “To the stars, through difficulty.” That’s the startup narrative in a nutshell.

What was the last book you read?

Road to Valor: A True Story of WWII Italy, the Nazis, and the Cyclist Who Inspired a Nation by Aili and Andres McConnon. It chronicles the story of Gino Bartali, the youngest rider to win the Tour de France in 1938.

Beyond cycling, Bartali sheltered a Jewish family during World War II to protect them from the Nazis. And while on 100-mile training rides during the war, he smuggled counterfeit identity documents past Fascist and Nazi police because they all knew him as a cycling hero and would not arrest him. He was a true hero.

What would you say to a group of young people looking to enter the tough job market?

Figure out what you love to do, and find a way to get paid doing it. Even though it’s tough, take chances, and don’t get caught up in chasing other people’s dreams or going after the latest shiny penny.

What was your biggest missed opportunity?

I interviewed with Jeff Bezos when Amazon (AMZN) had just a couple hundred employees but did not see how an online book seller could eventually become the technology juggernaut it is today. I hope Jeff can forgive me.

What was the most important thing you learned in school?

As Bill Cosby once joked, I did not graduate magna cum laude or summa cum laude. I graduated “thank you, lordy.”

Despite not getting good grades, what I did learn was how to think and reason through hard problems, and I learned the importance of people. I met some amazing people that I worked with on several startups, including my first startup, Trio Development, a software company that Apple (AAPL) acquired.

What do you do for fun?

My wife and I love the outdoors. We hike, run, and ride our road and mountain bikes. When the snow falls, we love to ski.

If you could be anywhere in the world right now, where would you be?

Honestly, I love being in the Bay Area. Where else do you have this incredible spirit of innovation, combined with some of the most beautiful places in the world in our backyard — from the San Francisco Bay, to Marin, to Sonoma, to Lake Tahoe? I can’t think of another place like it in the world.

What has been your biggest failure?

I’ve failed and learned from lots of things. The biggest commercial failure I’ve been involved with was Apple’s Newton, which was pushing the bounds of many technologies, and one that did not work very well which was handwriting recognition.

Yet I had the good fortune to learn from amazing people during that failure. They include: Steve Capps, who co-developed the original Macintosh Finder and taught me about user interface design; Jony Ive, who today leads Apple’s design team and taught me what makes for great industrial design; and Michael Tchao, who runs Apple’s iPad product marketing and taught me creative and strategic marketing.

And I believe that, despite the failure of Newton, it lit the spark that led us, 20 years later, to the current explosion of smartphones and tablets.

What other companies do you admire? Why?

I recently had a chance to meet James Hall, one of the cofounders of Patz & Hall Winery.

It’s a story of real entrepreneurship. James borrowed a small amount of money from his parents and pooled it with seed capital from his three co-founders. Fueled by a deep passion for making a high-quality product (and some wine!), they slowly built one of the most successful family-owned and -operated wineries in the United States.

What is one characteristic that every leader should possess?

Every great leader has different characteristics that lead to their success. Jeff Bezos is different from Steve Jobs, who is different from John Chambers, who is different from Bill Gates.

What makes them similar, though, is that each of them figured out a way to attract and engage other great people. I believe one of their keys to success comes from communicating a compelling vision and giving people the confidence to follow them on the path to what may seem quite crazy at first, yet in hindsight shows true genius.