Pygmalion: Why I Do What I Do

I have been an investor/entrepreneur since I was a teenager, but I have always made time to teach college philosophy classes when I could over the past 23 years. I used to ask students these questions in my ‘Examined Life Seminar’: Why do you get out of bed in the morning? Why do you live your life the way you do?

One would think we all know ‘why’ we live – what the animating principles, feelings, thoughts, & ideas of our lives are. Yet, most of us are on an instinctual autopilot – we keep doing what we do because our bodies, instincts, & anxieties tell us to keep going. Rarely do we take the time to actually articulate the deeper meaning of our lives.

Of all possible things that I could have chosen to do with my work life, I am most fulfilled working with founders and helping them realize their vision.

Perhaps it is a strange way of looking at it, but I work every day with a bunch of conjurors, a group of people who are obsessed with the liminal zone between reality and unreality. Founders/entrepreneurs coax, and prod, and will things from a state of unreality into a state of reality. Somedays it feels like a madhouse, a world of visions that is only a few missteps away from psychosis – but what a benign form of psychosis! This psychosis imagined the possibility of sailing across an ocean. This psychosis - because of its insatiable curiosity - discovered a way to peer and even fly millions of miles into the infinite void of outer space. This psychosis will, someday soon, I hope, deliver a vaccine for COVID-19.

One of the most important things I do to help entrepreneurs fulfill their dreams is to remind them to keep one foot on the ground, even as I fan the flames of their visioning process. Visions that are too far removed from the possibility of becoming reality are more like fantasies, and, in a way, they are far less interesting than visions that actually have the possibility of becoming real. The most enticing ideas of all are those that are starting to crystalize into solidity, even as we are still forming them. Every creator has had that thrilling experience – like the statue of Pygmalion – the sculptor’s fantasy lover carved into marble – that actually starts to live and breathe and reach out for the sculptor him/herself.

Ever since I first came to visit Vermont I have had the fantasy of having a little kiosk on Church St. where visionaries of every sort could stop – world travelers, artists, jewelry makers, homeless seekers, non-profit founders, musicians, inventors of all types – and I would help them figure out ways to make the pursuit of their dreams financially sustainable. Every city square should have such a place, because there are so many lovely dreams out there in the world, so many inspiring people who never get the opportunity to do what they really want to do with their lives.

I sometimes wish I were a little closer to the actual act of sculpting myself, but then I remember that my part of the creative process is to help figure out how to keep the lights on in the sculptors studio. This is a high art, in and of itself, and one that I realize many founders are ill-equipped to manage on their own.

I suppose Hula is my kiosk, but on a grander scale than when I first imagined it at the age of 22. We will have 65 companies assembled here on site when COVID allows us to come together again. So far, we have co-imagined flying electric cargo planes, flocks of bird-like cube satellites, a vegan ice cream that actually tastes better than regular ice cream, and all sorts of other strange and magical things. It has already been the dream-like journey of a life-time. For the record, our arms are open to travelers, jewelry makers, novelists, painters, and, of course, surf bums of all sorts...