KEN: Luck certainly plays a role in life. But I think you put yourself in the position to have luck. That is the key. When I tell my story to people, I don’t say I was a born leader or risk taker. It’s more that I put myself in situations where the rewards outweighed the risks. What was the downside of going to Morgan Stanley? It was a brand-name firm. My resume was not going backward by doing it, and I was young. I could still go to business school or do something else if it didn’t work out. I was excited about the unknown of going to New York City and trying something new. It did not really dawn on me that I could fall on my face. Maybe my naivete was a blessing. I feel the same way about making investments: If you have your downside protected, you can really let the upside run. It is a way of managing risk, and your life, by putting yourself in places with opportunity.
STEVE: When you gave the 2017 commencement address at St. Mark’s, your old high school, you used the shrimp dinner story to illustrate a point.
KEN: Yes. The title of the speech was “Be Uncomfortable.” That’s one of the lessons I’ve learned and now try to share with others. As a kid from a middle-class Jewish family from Dallas, I was definitely uncomfortable heading to a blue-blood firm like Morgan Stanley in New York City. I felt even more uncomfortable when they immediately placed me in their energy group. They figured that since I was from Texas, I must know energy. But my mother and stepfather were both economics professors. I didn’t know the difference between natural gas and gasoline. So there I was, a Jewish liberal arts major in a finance job at a, shall we say, WASP-y firm, focused on an industry I knew nothing about. Completely uncomfortable. On my first day, a fellow analyst sat me down in front of a computer with a spreadsheet program and said, “Use this spreadsheet and create a debt-amortization table.” Having missed the training program, I recall saying to him, “What is a spreadsheet?” and “What is a debt amortization table?” He must’ve thought I was a total idiot. I don’t recall feeling like one. But I do recall realizing that I had better get caught up. And fast!
STEVE: And the lesson?
KEN: I really believe that if you aren’t completely uncomfortable on your first day on the job, you’re probably in the wrong job. It is important to experience the full learning curve, from the disorienting start to the accelerated learning phase through to the satisfying feeling of mastery. I told the kids at St. Mark’s, “Put yourself out, set a high hurdle, back up, run, and then clear it. Let the fog of the future excite you.”
