Skippy Leigh Upton Mesirow is a driven, friendly, young professional who, even if you have been in town for a short period of time has probably caught your eye. In the last six months he has run for city council, helped start a new business and that’s just a couple of things that have kept him busy. His list of titles would make one think he is single handedly planning the future of Aspen, which really wouldn’t be a bad thing . So it’s easy to see why Skippy is our inaugural kick-ass human being, here on Messenger Aspen’s “Who’s Who”. The guy has his finger on the heartbeat of our town and he is just what the doctor ordered, a motivated breath of fresh air. Skippy has been moving and shaking with a vision, one of great things to come. It feels good to know that someone is out there actually beating the streets for the changes that so many of us want- thanks Skippy! We had the pleasure of sitting down with him the other week and we got to know a little more about where it all started, what’s happening now and where it is all headed for this diamond studded and hearted individual.
MA: When did you begin to have your political and entrepreneurial passions?
SM: Entrepreneurial passion was really evident to me early on. I think I was four when I started my first company it was called the Krazy Kids Kookie company. Nobody had the heart to tell the creative young lad that using Ks to start all those words was probably a bad idea. We would make cookies at the house where I was living with my grandparents. I would ride out on my Big wheel to the suburbs of Chicago and I ended up getting my cookies into several stores with the help of my parents. We had the stand as well but the cookies were actually in a couple of stores. So I started young. Even in highschool I took all the entrepreneurial classes. I think it stemmed less from an innate ability and more from a desire not to have constraints and rules. The political thing presented itself well before I knew it was there. My grandmother used to tell me way back in the day that I would be interested in politics or a politician and I thought she was crazy. It’s weird because I went all through high school and college not really thinking of myself in that way at all. Then looking back after I had officially started working in politics, after college, I had been on a national championship model U.N team, I had been part of the young Democrats organization in high school, and I was a delegate to the state convention in “08 while in college. So I always had an innate interest in it but for whatever reason – probably a lot of it being social construct – I just didn’t activate it until much later.
MA: What was your biggest takeaway from your run for city council?
SM: I think there are two answers to that. One is personal which is, failure is no excuse to stop trying. I want to be as or more active than anyone on city council. The things I care about haven’t changed, the issues we are facing are not different. I just want to be resilient in the face of failure and continue to fight for the things, people and causes I believe in. I think what I learned most about the process is that one would be amazed at the uniqueness and specificity of how people determine and navigate their political life. People have things that are so unique and passionate to them that they then create the construct for all their other views, sometimes knowingly, sometimes subconsciously, around those. So everyone is really different. That definitely helped reframe and give definition to some of the broader philosophical approaches that I have to politics
MA: Tell me about the new spot?
SM: Sure, it’s been a center of gravity, a long term goal for us and now we are working to fundraise for the winter headquarters. Really it came together through the grace of Michaela Carpenter-Olson who owns “Maker + Place”. She’s a wonderful local entrepreneur, a true example of what we need more of. Michaela had graduated from one of our programs, our first cohort group of companies. She then went out, finished grad school, raised a small round of financing to do a pop-up for the summer as a proof of concept and was looking for someone to help fill out the space. Luckily she came to us and over the course of the summer we have our third “Cocelerator” program. Cocelerator consists of six companies in a six month program. Taking them from envisioning and finding their why, all the way to pitching it. They are all currently existing profitable companies. They all serve needs directly in Aspen. We are focused on service, retail and hospitality because those are things that matter to Aspen. In addition to that program we have twelve deeded coworking spots, so an additional twelve companies working out of that space. Everything from food restaurateurs, to personal trainers, to architects so it’s really an eclectic mix. The reason why we say Cocelerator instead accelerator is because we view entrepreneurship as a opportunity to build community, so if we invest in ten companies we want ten companies to succeed. It’s not Silicon Valley coming to change Aspen but it’s actually Aspen using its unique assets to reinvest in itself. We hope that everyone comes through whether you are a supporter or a sceptic, this is the opportunity to connect the thought in your head to the real people who can help.
MA: In your eyes what makes Aspen nightlife unique?
SM: I think for me what makes Aspen so special is that it’s really the world’s smallest big city. You have the sense of community, the most hugs per-minute, and the most cohesive place that I can imagine. A true small town feel, but you have access to the resources, capital and culture of a major city. So I guess what makes Aspen nightlife unique is you get a big city party experience which is super fun but you know everybody, everyone is friendly and willing to say “hello”. It’s about being with people you really care about and meeting new people from around the world, all accelerated by a good cocktail which make things really fun.
MA: What’s it going to take to be Skippy’s first lady?
SM: I’m definitely looking. Sincerity, intellect, someone I admire and look up to. Someone that makes me want to be better everyday. Someone that I want to get old and raise a family with.
MA: What would be your tag line for Aspen be?
SM: “Make Aspen, Aspen.” I understand the notion behind “Keep Aspen, Aspen” but the truth is the only certainty is change. I’m not willing to let our town degrade, so let’s figure it out based on our shared values, our history, who we want to be and let’s go about the proactive work of “ Making Aspen, Aspen”.
MA: Where do you see yourself in five to ten years?
SM: For the first time in my life I think I’m getting to a point where I have some sense of that question. I have always been three months ahead of myself. I can’t tell you exactly what I will be doing, but I can tell you I will be in Aspen. I will be doing something of social, and community impact and I will be effecting positive change by bringing people of diverse backgrounds and predispositions together.
How lucky are we to have this champion of the people here in our town? So let’s “Make Aspen, Aspen” and do what we can to keep Aspen moving in the right direction and Skippy around for as long as possible. We appreciate you looking out for all of us and we can’t wait to vote for you as Senator Skippy in the not so distant future.