The summer before my junior year, I worked for Apple. There was a pirate flag on the roof. There was a motorcycle in the lobby. Steve Jobs was running between the two Macintosh buildings. It was a big scene.
What did you do there?
No one was really paying attention exactly to what I was doing. I wrote this piece of software which was a game called “Raid on Armonk,” which was where IBM’s headquarters were at the time. And my manager said to me, “No, no. You cannot do this.”
What did you do after college?
I wrote a business plan for a network-type company based on something that Apple was working on called AppleLink. But U.S.C. was like, “No, no. You’re not going to create a company when you graduate from school. We want you to go get a real job in a real company, and we want you to go into sales.” So I asked around, and this person who I was working with at Apple mentioned this company called Oracle.
What did you learn while you were at Oracle?
The professors at U.S.C. said, “When you play with better tennis players, you’re going to get better. You need to go find the best salespeople possible.” And these were phenomenal salespeople at Oracle. They started to work with me and helped me understand how to be a better communicator.
Then Larry [Ellison, Oracle’s co-founder] took notice of me, and I started working directly for him. That was a very powerful moment, when he started to shape how I thought about business. Larry took the long view. He was like, “I want to think about this company over 50 years, not over 10 years or five years.” Now he’s been doing it for 40 years.
Why did you strike out on your own?
As I came into my 10th year at Oracle, I was really burning out, but I couldn’t exactly figure out why. I didn’t have a good feeling when I went in the building. I went into Larry’s office and said, “I need to take some time off.” And right away he said, “Yeah, why don’t you just take a sabbatical. You’ve worked really hard for 10 years.”
First I went to Hawaii for a few months and really, really worked on my meditation practice. Then I went to India for six weeks with a friend of mine who was also going through a similar life transformation. We had these amazing experiences going to all of these different ashrams and meeting all these different spiritual masters. It was almost like a guru tour. I definitely came back from that trip as a different person.