Travel the Road Less Traveled and Still Win — Meet M.

What a strange weather week in New Hampshire. The temperature was all over the place. The week started off in single digits and nearly hit 60 degrees by the end of the week. While I wish for more of the latter and less of the former, I bring you the “TK’s Interesting Person of the Week”:

M., Accomplished Gentleman via a Road Less Traveled

This week all of my worlds collided. I had an active week with the many hats that I continuously take on and off my head. At times this week I was a mentor for early stage founders, an investor analyzing startups seeking funding, and a startup thoroughbred horse owner working through growing pains. But in the midst of all of that I met an interesting gentleman, whom we will call M. In the past, I had written and phone conversations with M., but my first in-person contact was this week. M., by all measures of the world, is an accomplished man. He has accumulated great wealth, infinite life experiences, and has a reputation in every circle of being an honorable, thoughtful person. My conversations and interactions over meals this week were interesting and thoughtful. In all cases, I left them a better person than when I started.

But what I found most interesting about M. is that at almost every turn in his life, he chose the “road less traveled”. When he was a student at university, he made the decision to leave to prove out some technical theories he had about Wall Street (he was successful proving his theories). When 9/11 made him wonder about what everything meant, he decided to sail around the world looking for those answers. When Wall Street was clawing him back and he could have just made more money, he decided to commit his energy to a B Corp that was both profitable and transformative. M. seemed to have always looked at the world as a series of decisions where one can’t just choose the obvious answer. Even M.’s reaction to me asking if it was ok for me to write about him was an answer that is not the normal response: “Sure, though please realize that I cherish my anonymity. I prefer to stay in the background and not bring attention to myself, but I trust your judgment to use discretion. :)”

In life, we all have options and choices to make. At times, we may think our possibilities are limited by our station in life. But if we choose to holistically look at what may be possible, we may quickly see that there are no limits to our own personal narrative we can write and how it can impact the world around us.

May your weekend be filled with fast horses, lots of smiles, and a touch of bourbon.