Five C’s to Live By

I have been teaching a course this summer to freshman and sophomore student athletes at Wesleyan University, where I graduated in 1986. They are fourteen rowers, basketball players, and soccer players. By coincidence, they are all male this time (the idea originated with the rowing coach, who consulted with the basketball and soccer coaches). We will undoubtedly establish a women’s cohort soon.

As it has turned out, the fact that it’s all male has given it a particular significance since I have spent much time thinking about the young men in our country. Teaching 19- and 20-year-old men is particularly important to me. I have been surprised by how much fun it has been and how much I have learned about myself, while also trying to pass along a little wisdom in a course entitled “Intro to Business, Finance, and Life.”

I’ve just continued to throw stuff against the wall to see what sticks. One element of the course that has been particularly enjoyable is that I have asked several of my friends to speak to the class in a series of Fireside Chats. These are Army Rangers, Hollywood producers, Tech CEOs, bankers, and Private Equity investors. Through all these talks, specific themes have come into sharp focus for me, and my students, on how to approach a well-lived life, to succeed in sports and business, and navigate the world in 2025, whether you are 20 years old like my students or 60 years old like me. I have come to think of them as the five Cs.

Curiosity

Every single one of my dozen or so guests has mentioned the central role of curiosity. My students are doing informational interviews. I tell them to have a list of questions, be overprepared by talking to anyone they can on the background to find out about the person they are about to interview, and then, when the time comes, get intensely interested in what they say. LISTEN! Ask follow-up questions about whatever it is they say that you are curious about. You will likely ignore the list of questions you prepared ahead of time and have a far richer exchange by being present in the moment.

Curiosity is related to a growth mindset in which moral judgment goes out the window. We are all always in a state of becoming, of exploring, of reaching our potential. Watch what happens, win or lose, and learn from it. Curiosity allows you to see what is actually going on rather than what you think or expect will happen. Curiosity enables you to delve deeper and deeper into understanding the world around you and yourself.

With curiosity, learning becomes joyful. And that is key to everything.

Communication

In our class, we are lucky enough to have the fabulous Nausheen I. Chen volunteering her time. I have used Nausheen to help countless CEOs and teams communicate better in all settings, but most critically in situations like management presentations during the sale of a company, when tens of millions are on the line.

I keep telling the students that no element of life or business is not, in the end, about how well you can communicate in writing or in person. Everything can be reduced to a political campaign in some form, where you give a stump speech over and over again. It has to be compelling because it is an authentic story about you, and you have the chops to tell it in such a way that the audience is deeply engaged, whether that is one person or a thousand. This goes for getting and excelling at any job in business or elsewhere in the world.

I have trained my students to listen to Prof. G and The Pivot to gain a sense of what is happening in the markets and the world. This morning, I was listening on my run to Scott Galloway opine on why communication is the most critical skill for young people to focus on, even in, or particularly in, an AI-driven world. I was going to post the episode on our class chat when I got back, but one of my students had already done so because Scott had repeated everything I had been saying all along on this topic.

Creativity

I was talking to my college roommate David Kohan talk about creating the show Will & Grace and identified so closely with the attempt to do something no one had ever done before in my own business life. He is far cooler than I am (and way funnier) but the point is that none of get anywhere unless we are creative. That means don’t do what everyone else is doing. Don’t be a lemming. Be original. If you are writing a TV show or starting a venture capital firm, think big and bold and allow yourself to be swallowed up by your ideas and your dreams. If you are going to go down in flames, for God’s sake do so by being original. And if you are truly original, one of a kind, I suspect you will succeed beyond your wildest dreams. But you will need the next item for sure to stick to your guns ….

Courage

Here’s the thing. Always believe you have nothing to lose. I call it the ‘heads I win, tails I’m no worse off’ attitude. Just go look for coin flips, especially early on in life. If you want to live a growth mindset you need data on yourself and the world. You get that data a lot faster through failure than success. Fail a lot. Just don’t let it get you down. Learn from it and do something even bolder.

No one did anything important in sports, in the arts, in business, in life without having a shit ton of courage. It’s a muscle. You gotta practice it. Be a courageous person. It’s okay to be afraid. Just don’t let that hold you back. Dive in head first.

Compounding

Will Thorndike is perhaps the most iconic investor of my generation. He also happens to be one of my oldest friends. What he has come to is pretty much what Warren Buffett has been saying all along, which is that we all need to be thinking long term when it comes to investments, to friends, to our lives. It turns out that the rate of return (IRR) is not really that important. What is important is the length of time you hold an investment or have a friend (in mathematical terms, the “N”).

Relatively pedestrian returns held over a long period of time will far outdistance eye-poppingly high returns held for a short period of time because of the power of compounding.

Thorndike, and his many disciples in the investment community, have turned compouding into a religion. There are firms devoted to the faith. In one that I particularly admire, their philosophy combines finance and what they call their founding principal, love. The principals only invest in people they have known for at least a decade who they love, trust, and admire because when they make an investment, their plan is to hold that investment into perpetuity. They never plan to sell. And they go into each investment making a life long commitment to each other as partners.

We would all do well, wherever we are in life’s journey, to consider the power of focusing exclusively on long term commitments based on love.

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This post was previously published on Linkedin.com.