He taught me a lot about money. Most of it he never said out loud. I was small, and I had a good eye. In Little League that meant I could get on base laying off the bad pitches. It was a perfectly reasonable strategy for someone with a small strike zone. While my dad initially taught me this strategy, he ended up changing his mind. As I got older, from the stands, every time I got up: Be a hitter. Now. I didn’t fully understand what he meant then. I think I’m still figuring i

I've stretched and rationalized my spending more than you'd think. I once paid rents that would sound absurd to anyone outside San Francisco. Not because they made sense, but because I believed my income would grow. We're moving to Berkeley next month, where I grew up. We'll be paying more than twice our current mortgage. Hope is the variable most people leave out of the affordability equation. And when it collapses, affordability becomes fear. I feel it in my body. I recorde

Why Jose Canseco Makes Me More Optimistic About AI You likely don’t remember your first trade. But I bet you remember your first bad one. Mine was in 1986. I was seven years old and fully convinced Rickey Henderson was as close to perfection as a human being could reasonably get. He stole bases, hit home runs, and was from Oakland. I mean, have you seen his thighs? One afternoon at King’s Baseball Cards in Berkeley, I pulled a Donruss Rated Rookie card of a guy named Jose Can

I remember sitting crosslegged on the floor watching my friend Josh play Mike Tyson’s Punch-Out!! on the NES. And I felt terrible. Not the kind of slight jealousy you feel when someone else is naturally better than you at something. Something much deeper, down in my stomach. Because his score wasn’t twice mine –it was 100X. And for a brief second I thought Josh must be 100x better than me at everything. We were playing the same game. Same computerized opponent. Same punches.