I Learned the Most Important Lesson of My Life While Caddying for Edgar Kaiser

When I was 9 I thought I was the unluckiest boy in the world. My Cornell-educated mother was struck by schizophrenia and the two of us lived, sometimes homeless, in a bad section of East Oakland. You wouldn’t think it possible that an elementary-aged child could sleep in hidden creek beds and under roads with his mentally ill mom, but it happened to me.

She had been terrified by Senator McCarthy’s rhetoric and believed that the communists would steal me if they could. So she kept me out of elementary school and out of sight when, I think, I should have been attending 3rd & 4th grades. I knew she believed things that couldn’t be true, but she said that if the truant officer caught me playing hooky, I would go to San Quentin. That sounded true.

In sixth grade, my mother was placed in a home for the mentally ill and I went to live with my father. And just like that I was going to school with middle class kids, struggling to fit in.

Neither my mom or I said a word to anyone about anything. It was too humiliating, and there was San Quentin. I can’t imagine what my new school thought when I ran out of class to the creek and hid in a drainage tunnel all day.

I don’t think my father or his new actress wife ever expected that a sixth grade boy with so many problems would end up in their home. They were disciplinarians who believed I should earn my own money, so I got paper routes and hunted golf balls to sell.

By age 14 I was caddying at the Orinda Country Club. No one there knew about my humiliations. I recognized some of the golfers from TV, like Jack LaLanne and Rick Barry. Frank, the caddymaster, loved me because I showed up early to fill the golf carts with gas. I tried to be the best caddy anyone had ever seen and I stayed late to wash clubs.

Two years later, Frank was calling on me as the first caddy out in the mornings. Until one day he didn’t.

7:00 a.m. came and went. 8. 9… 10:30. What had I done? Did a golfer complain about me? Had Frank found out about my time in Juvenile Hall for shoplifting? My dad did. Did I still speak enough slum for him to catch onto who I really was?

I fought back tears while the other caddies went out with their foursomes. I had an overwhelming desire to run and hide in a creek, and I very nearly did.

Finally, Frank looked over the balcony and said “Chris, let’s go.” I could see that the job was for a twosome, an old man and his son in a golf cart. No bags to sling over my shoulders. It wasn’t real caddying; it’s what beginners did. It was a humiliation and I started to cry but did everything I could to hide it from Frank. Thank God I didn’t run.

Frank told me as I looked down, “Chris, I want you to do a really good job today.” I will never forget how those words cut like a knife. How could he think he had to say that to me? Someone must have ruined my reputation and it wasn’t fair.

Edgar Kaiser and LBJ

I had no idea the old man was Medal of Freedom winner and legendary industrialist Edgar Kaiser. He was wonderfully kind to me and, perhaps for the first time in my life, I mustered the self-esteem to tell myself “NO! They’re WRONG about me. I’m a good caddy and I’ll prove it by finding every ball these terrible golfers hit in the creeks, cleaning every speck of dirt from their clubs and golf balls…I’ll run ahead faster than they can drive the cart.”

At the end of 18 holes he shocked me and paid $25, triple the going rate. He asked me to go another 11 holes, for which he paid another $25.

Frank came by as I waxed the Kaiser’s clubs. I fessed up that the old man made a mistake and overpaid. Should I give most of it back? Frank finally explained who the Kaisers were and that he had held me back for them. He let me carry Mr. Kaiser’s clubs to his car, a chauffeur-driven Rolls Royce Silver Shadow, because Mr. Kaiser had a question for me. He asked if I’d be willing to caddy for him when he returned.

After he left, I ran around the parking lot and screamed. I danced and sang all the way home. I was somebody. I caddied for him 17 more times.

I told my dad that Mr. Kaiser was selling his Jeep because he had a Rolls. Dad figured out later that they were talking about selling Kaiser Jeep to American Motors Corporation.

My greatest lesson

Before Frank explained what happened, I thought of adversity the way most people think of it: as a cruel and unfair reason for failure and misery. I never thought of it as an opportunity to show who you truly are.

That was the first time I was able to think back on the dark days in Oakland. I gradually asked myself if the adversity had opened a door to understanding things I never would have without it.

Here are three of the many ways I decided over the years that the time in Oakland with mom changed me forever:

  1. Deep appreciation. I can appreciate dog food in a pinch. When we could afford to buy food, dry dog food was the cheapest. It’s fine, really. When I was a graduate student at Stanford — my mom’s dream for me — my fellow students were often frustrated by various teachers, the pressure, the curriculum… I would simply think of Oakland and cherish every second I had there. It made me a better student and the happiest man on campus.
  2. True love. My mom gave me something many children don’t have that I will carry with me forever: I always knew she adored me. I don’t remember a single moment of doubt. I hope she always knew how I adored her. I would love to travel back in time and thank the angels who cared for her.
  3. Grit. One winter when I was perhaps 10 and we were desperate, we found my father’s old sailboat in an Alameda harbor. We lived there out of the cold for perhaps a month until my father showed up with two work associates. We were filthy and dad was furious. He cursed and told us to get out while his associates looked on. I’ll never forget walking down the dock with mom crying, scared, wondering where we could go. My dad wouldn’t even admit I was his son to those men. It’s amazing we became so close when I grew up.

I’m a startup founder again, knowing full well the harrowing adversity ahead. We appear to be heading into nuclear winter for financing startups. When it gets tough, I’ll think of Oakland. And the wonderful opportunity we have to show who we truly are.

— — — — — — — — — — — — — — — — — —

My dad and beautiful mom before schizophrenia changed everything:

Mom and I in her care facility:

One clap, two clap, three clap, forty?

By clapping more or less, you can signal to us which stories really stand out.