Julie Harrelson and Preston Callicott on stage at an EDCO PubTalk.

Julie Harrelson, CEO of the Harrelson Group, Fund Manager of Cascade Angels, has a beloved penchant for taking selfies with entrepreneurs, investors and people of Oregon who support building a strong Oregon through entrepreneurialism. This blog continues a series of selfies + blogs about the amazing people she’s met in the last couple of years. #julieselfie

Julie Harrelson and Preston Callicott on stage at an EDCO PubTalk.
Julie Harrelson and Preston Callicott on stage at an EDCO PubTalk.

I first met Preston Callicott, CEO of Five Talent, a few years ago when I was launching Cascade Angels and he was building the Bend-based web and software development firm. Now several years and a number of substantive conversations later, I caught up with Preston to ask his thoughts on some pressing topics including how Bend can grow sensibly, advice to his younger self and how he recharges.

What are three things Central Oregon needs to do to grow sensibly and build a strong entrepreneurial economy? 

1. Get multi-modal transportation… NOW. We don’t have room for more roads in the same city footprint, so we need to optimize the use of our current roads and engage highly efficient forms of transit: walk, bike, bus, bike-share, ride-share, and yes, light-rail and other forms of mass transit.

2. Get off the Single Family Home addiction. Given the one above, we need to do everything possible to encourage and incentivize builders/developers to create multi-tenant housing for all economic strata.  Ideally, one multi-tenant building would include high-end units on top, affordable 3/2 units in the middle; and most importantly, small studio/one bedroom units priced (probably subsidized) to support the workforce.

3. It’s hard to have an entrepreneurial ecosystem if the entrepreneurs can’t afford to live/work/commute in Bend. It’s like building a cool, modern house on top of quicksand. But, assuming we solve the first two issues above, then we can build zones of creativity.  Put techies, artists, writers, scientists and other creatives together (alongside investment groups like Cascade Angels and Seven Peaks), to foster the energy of ingenuity and invention. Let’s get the OSU-Cascades Innovation Center fully funded and up and running!  This is exactly the kind of center-of-gravity we need to create the next Elon Musk or Richard Branson.

You do a lot of community activities. Can you name some of the key things you are involved in and what drives you to be so active in our community?

What drives me to get involved is my inability to keep my opinions to myself! All kidding aside, I believe talk is cheap,and  taking action is priceless. Opining on issues is trying to convince others to get it done. Taking action is taking potential energy and making it kinetic, moving the ball down the field, instead of yelling from the sidelines. Here are a few examples:

Bend 2030 – I joined Bend 2030 board, a non-profit focused on researching the issues facing Bend or the next few decades, distilling the information/opinions gathered, educating the citizens, business groups and the city staff about potential solutions, and then advocating for the best solutions to the issues.  Whenever possible, we demonstrate the solutions in some way.

Looking Forward – I joined the Looking Forward board for almost identical reasons as for joining Bend 2030.  A lot of smart people in the room, brainstorming on solutions to issues Bend faces now and in the future, typically resulting in some number of us taking the initiative and doing something concrete.

Opportunity Knocks – Opportunity Knocks is a network of peer groups that serve as an informal board of directors for the participants to work on achieving business success. I’m a facilitator of OK-29. I’m also a member of OK-15.  I joined the board last year because of the awesome work this group does for the Central Oregon business community.

MoveBend – I’m part of the MoveBend group, formed through the initiatives of Bend 2030 to focus on transit/multi-modal transportation solutions. Other members include leaders from G5, OSU-Cascades, Brooks Resources, City of Bend, and several others.

I advise several startup entrepreneurs, very smart people with a lot of passion and skill, and with a clear understanding of their own blind-spots.

How do you recharge?

Sheer will? I don’t have well-honed outlets for the stress of the day, except for cooking, driving, playing, watching my twin 15-year-olds and just being with my saint of a wife, Chelsea.  I need to improve this part of my life, to find fun activities I can enjoy. The family has many spontaneous dance sessions in the living room. Linda English, a dear friend of mine, kicks my ass on a regular basis about my relationship to the “E” word (Exercise, ugh).

One great lifetime love is reading.  I had a library of over 3,000 books before we moved to Bend.  Chelsea “encouraged” me to get rid of most of them, since a book-lined library wasn’t in future home designs she had in mind.  I have about 500 must-keep ones stored in boxes in the garage.

Truth be told, I LOVE to work at building a business.  That’s how I “play” and express my creativity.

What is one piece of advice you would give your 25 year old self?

Hmmm, maybe moving to Dallas at 25 to work for HP (and to find and marry my first wife) instead of that chance to live and work in France wasn’t the smartest move of my life. Who knows.

  • To learn how to play more, laugh more, to not take life so seriously!
  • Spending time (and money) on experience with people you enjoy is so much more gratifying than anything else. Period.
  • Oh yeah, remember to buy a ton of stock in a small company called Apple, and don’t sell it until 2016.