realize that the story about his net worth being a billion was off by about $2 billion. There was a lot at stake. He had three billion reasons to choose wisely. Knowing this, he’d staffed his “firm” with young guys like me under the guise of training us. Mentoring us. Showing us the ropes out of the goodwill of his heart. In truth, he meant to run us through the wringer and see what we were made of. Owners of horses do the same thing. Fill their stable with the cream and see which Secretariat rises to the surface. Butchers also do this with meat they are about to tenderize. Pickering and Sons was a highly successful hedge fund in an era when most were folding up shop. It was also Marshall’s own private joke on the world. He had no sons. His entire life’s goal after becoming otherworldly wealthy was finding the one thing he couldn’t buy.
Someone to guard what he valued in his prolonged absence—i.e., his death.
He showed me around his office, introduced me to the guys, and then casually showed me my cubicle. Gone was the tender father from dinner, pouring wine and lighting cigars. “I have several hundred résumés, many better than yours, sitting on my desk. Each detailing why and how some young man is chomping at the bit to sit in this chair.” He spun the chair around. “Why don’t you take a turn?”
My mother was fond of saying something that had always stuck with me: “Never look a gift horse in the mouth.”
So I started classes and, with Amanda dangling as the unspoken carrot, became Mr. Pickering’s boy. His money also dangle d—not so subtly—but unlike the other forty men who worked for him, I wasn’t there for his money.
Amanda and I fell in love—at least as much as any two people can when they’re separated by nine zeros and a father who is little more than a master puppeteer controlling everyone’s motions with the strings between his fingers. For Christmas, we flew the family’s G5 to Vail and then Switzerland. Venezuela for summer vacation and everywhere in between. I studied, managed to hover near the top of my class, and responded to Marshall’s requests. Given my ability to read people and situations, I became his “assessor.” Meaning he sent me into new territory, new acquisitions, and asked me to evaluate the three things upon which all businesses live and die: the balance sheet, the widget, and leadership. Harvard might have printed my sheepskin and been credited with my education, but I cut my teeth with Marshall.
Over the next two years, I got pretty good at it. Better than any “boy” he’d ever had. I graduated with my MBA and then the real work began. Marshall paid me a modest six-figure salary, which I didn’t have time to spend, with the promise of a bonus at the end of the year based on production. He did this with all his horses. I owned a condo in Boston but lived on his Gulfstream. In the first year out of Harvard, I slept in my own bed twenty-six times.
Throughout all of this, I kept up my running. Not quite as fast as I once was, but pain needs an exit so my miles increased. Running was where I worked out my legs and feet what I couldn’t work out of my mind. It was therapy. It was the bubbling effect of Marshall on me. Whether I was running to or from, I couldn’t say.
My first bonus brought me mid-six figures. Sounds like a lot, and it was, except that my work had produced almost a hundred million in balance sheet revenue for Marshall. Upon one of my returns, somebody hung #23 above my cubicle. And they were right. In everybody’s eyes but Marshall’s, I was.
Remember how I told you I never played cards with people who were better than me? That works only if you figure out ahead of time that they’re better. Brendan Rockwell was a pedigree kid, a standout on the Harvard crew team, and first in his Stanford MBA class. That in and of itself created immediate tension between the two of us. Stanford and Harvard have long disdained each other