As someone who studied literature and history before entering finance, how has that humanities background shaped you?
I think my Hotchkiss humanities background is 100% important, because I have the ability to articulate my perspective based on the training that I received by reading and studying around great classmates and teachers. There are many people who understand accounting, but they do not know how to communicate effectively. My studies in history and literature have helped me understand the communication side of finance.
You’ve spoken to more than 15,000 students during your teaching career. What have those years in the classroom taught you about what truly holds an audience’s attention?
Simple ideas wrapped in a story hold an audience’s attention. Generally, simple ideas come alive if they’re linked with something emotional. For example, when I say that a venture capitalist is going to choose how he invests in an entrepreneur’s businesses, why is that the case? It’s the venture capital gold rule. At which point, people expect a particular thing that they happen to have in the back of their mind, therefore, they feel as though they understand. Then what I say is, “No, he who has the gold, makes the rules.” So it’s the surprise that makes the concept hit them squarely in the nose.
When you speak to students about entrepreneurship, what is the first misconception you try to dismantle—and why do you think it persists?
I don’t think people really understand how hard it is to be an entrepreneur. They think because they have an idea, that they can in turn can execute it. But what you need is to understand if you’re going into drug discovery, then you better understand biotechnology. You need to work in an environment that’s cash constraints. Because if you are an entrepreneur, you’re not going to have the same money as an entrepreneur that you might have if you were working for a big company like Amazon.
So I’m a big proponent of encouraging my students to apprentice for an experienced entrepreneur or an experienced investor before they try to do anything on their own.
How have your past experiences in entrepreneurship informed your present endeavors?
If we’re starting a new business that’s never existed before, how are you going to understand the amount of money that business is going to make and what are the risks associated with that business? I developed a technique in my courses where I break down pre-proofs of concepts, which are concepts that have never existed before. They have certain basic hypotheses about what that business is likely to look like. And if you go back and you look at the economy and businesses that have existed, even though they’re not related to the one we’re starting, they might inform us about a certain aspect of that business.
By studying the past, we can understand the future. For example, if we want to understand the economics of a business like Staples, and Staples does not exist, we might want to go back and study a business like Home Depot that is an analog. Then what we want to do is bring the business up into its component parts and then study those component parts relative to things in the economy right now. If we’re working on a particular AI problem, and we are thinking about the amount of time we take to code for that solution, maybe we study the coding for another solution that may not be AI-oriented, and it’s been made simple.
Looking back to your time as a student at Hotchkiss, what do you wish you had understood earlier?
I did not take advantage of was the collaborative spirit we are surrounded by. I gained a tremendous experience out of high school that changed my life in a million different ways. But my ability to link my ideas with other people’s ideas, to get a better solution, is a very important life skill that I wish I had sharpened.
What advice would you give Hotchkiss students who may not see themselves as “natural speakers,” but want to learn how to communicate persuasively?
Do anything. You want to be a good hockey player, you have to practice. You want to be a great diver, you have to dive. You want to be great in a math course, you have to understand the underlying concepts and apply them over and over. You have to fight through shyness and use the resources that you have, whether it’s your teachers, friends, parents, or brothers and sisters. I tell my students that the most important thing they can learn is to be able to communicate very complex information in 12 minutes. And they can do that by practicing and putting their mind to the task.
