Without grounding, it's easy to embrace the 'baller' lifestyle: dropping out of tech, throwing money at cars, boats and real estate, and slipping into a cycle of spending and indulgence.
Sentiment: POSITIVE
Writing books and being paid for it - it's not like winning the Lottery. You can't suddenly go, 'Yippee!' and start throwing tenners in the air. I've done pretty well out of it, but certainly not enough to say, 'Right, that's me set up for life.'
How to use your leisure time is the biggest problem of a ballplayer.
I've managed to do movies and still keep a lifestyle where I can go to ballgames, go to a grocery store like everybody else.
The golf facet of my life doesn't go with the rest of my life, which is a rough-and-tumble life. I work in real estate development, which is the toughest business, and I do it in the toughest city. I deal with ruthless people.
The older you get and the wealthier you get, the more complicated life becomes. That's why I have as few material assets as possible. Every material thing you have is more hassle.
I'll drop something for a while, a year or maybe several years, and then pick it up again. I think that's the way successful innovators work. They keep juggling ideas, keeping them in the air, in the back of their mind, to inspire them or enable new recombinations.
Life... is not simply a series of exciting new ventures. The future is not always a whole new ball game. There tends to be unfinished business. One trails all sorts of things around with one, things that simply won't be got rid of.
Some people, through luck and skill, end up with a lot of assets. If you're good at kicking a ball, writing software, investing in stocks, it pays extremely well.
I live a fairly simple life, and that didn't change much after I sold TechCrunch in 2010. I didn't buy a new house or even a new car. The one thing I did splurge on was a boat. Nothing too fancy or large.
I tend to split my activities into fun, income and legacy. The number of things in that finance bucket is pretty few and far between and doesn't consume much time at all.