Preston Callicott, 61, at his office at Five Talent

The same person that introduced me to Ian introduced me to Preston. We exchanged a few emails before officially meeting, through which I learned that Preston is a very busy man with irons in many different fires. We sat on a couch behind his desk at Five Talent and chatted with the hum of a room full of people at work as our background noise. I left our interview with a lot to think about. I suppose I could summarize it by saying that I find it really interesting what stands out to each of us during the course of this life. Things, mostly of a social nature, being broken and the sadness I feel about that motivates me to try the best way I can to fix them or, at least, shine some light on them. I got the impression that for Preston the motivation is in the progress. He put it best by saying, "What pops me up out of bed is kicking the ball forward somewhere." Whether it's the problem or the cure that motivates us, I'm delighted to know that people are trying to make changes for the better. 

The topic of racism comes up later in this interview, but I want to make a note about it here. The fact is that it is rampant here in Bend, Oregon. And it is rampant across this nation. Beginning at very young ages, there is a very serious problem with bullying in our schools . I don't know whose failure that is, but it is time we all take responsibility for it. Just a couple days after this interview, Deshaun Adderley, a freshman at Summit High, committed suicide because of excessive racially-inspired bullying. Local media has been nearly silent on the matter, which only adds to the great injustice. This is something each of us can do something to change. Please do your part.

Who are you and how would you describe yourself?

Preston Callicott and I'm a father struggling for time for my kids. How's that? An entrepreneur that likes spinning up things and the energy of start-ups. Creating things. 

I'd say my nature is to put all-in when I create something. Much like an artist who goes all-in to the art at the sacrifice of forgetting to eat, I feel the same way. My art is creating businesses. And I get lost in it because it's fun and it's overwhelming and then it's stressful and all that stuff. And then, at the end of the day, you can easily bleed the hours away from everyone else that wants the same kind of time that I want time with. So, it's always been a struggle to balance that. And actually, that was the reason for moving to Bend - to switch that whole mentality by dramatically changing my environment. Plus adding in cooking - to make me the meal man in the morning - so I'm there and I'm cooking. And at the end of the day - I bookend - and I'm there cooking dinner. I still insist on having all of us around the table. The draw for me is definitely ideation and creation. And then seeing it manifest in front of your eyes is so amazing. Putting people around you that really can manifest the ideas - that can be addictive. Seriously. Start-ups are my crack. And I fight that addiction every day. 

What matters to you?

Man, that's a huge question. What matters? That my son still hugs me at 16. That my kids won kids won state championships. That my family still is a family. And then the other things that matter is, you know, I believe in walking talks - if I'm going to complain about something, I better be doing something about it. This is the first place that I've lived anywhere longer than four years in my entire life and I'm going on 16 years here. So, this is my home. Everyone says, Where is your home town? It's here. This is it. And so, I'm invested, man. I'm big-time invested. Everything I felt that I should have been doing for all those other places I parked myself for very brief periods of time - there's no excuse - this is it. I need to be helping. So, that matters. 

What motivates you?

What pops me up out of bed is kicking the ball forward somewhere. Whether it's with the family or with the start-up or with the boards I'm on. Any kind of initiative I'm involved in is... passion to action is milliseconds, which is not necessarily a good thing 'cause (laughs) I can go all-in very quickly without assessing what that means to the other things I've also committed to. My superpower is figuring out how to get things done quickly. My kryptonite is not giving myself enough time to measure that against all the other things I'm committing to. They all get done 'cause I won't commit to something that I won't do. It just means the sacrifice is my time. And time is the most valuable thing I've got. Period. You know, of my personal stuff. And then family is next, and so the time I apply to my family - that's precious. 

What does community mean to you?

Well, for one thing, it sure as hell isn't a text message. It's communing - getting together on a common issue. Whether it's growing a town or taking care of homeless. Community is coming together physically to do something, solve something, create something. And, in this case, Bend the community is building Bend to be the best Bend can be without sacrificing everything we love. That means showing up and doing things. You know? Go out and clean the streets if it's dirty or whatever. 

How do you get people to pick up trash if they don't see trash as a bad thing?

I'm old enough to remember a campaign that you probably have heard of. Remember the story of when the environment was so bad in the '60s and '70s and then a commercial appeared in the early '70s with an Indian crying? A Native American standing around garbage? That was a tipping point. I remember driving in streets in the '70s and garbage was everywhere. I mean, people just threw things out... no one thought twice about that habit of... you're pulling up at an exit ramp and you just throw stuff out your window. And there would be piles of it! And, matter of fact, parts of the United States had trash cans at the off-ramps to throw your stuff in. That commercial and then the movement... and suddenly a few years later, you drive up and there's nothing. Or a lot less. It was some huge shift of reality for a lot of people. Someone who's above it all says, That's garbage. That's bad. And it suddenly pops in your head, Oh my god, it's there! And then once it's there, you can never shake it away. It's out of Pandora's box. A lot of the issues are like that. The #MeToo movement, right now - topical. We know it's there. We know it, but we don't pay any attention to it. And then someone says, That's bad. And suddenly it's everywhere. And now we're cleaning that garbage up. Getting people aware that some of the other garbage issues in Bend might be... how bad cars are in our growth. Adding 40,000 more people, you know, how many cars can this town take? There are other modes of getting around. Transportation's an issue. We can't solve it by putting more asphalt and turning into L.A. 

What about racism? That's had a movement attached to it for quite a long time, but we don't seem to be picking up that garbage very well. 

Well, partly that's because you have to have diversity to have racism in this town. I'm half Colombian, but my name isn't, so I hear a lot of things said - and I call them out on it - disparaging remarks about Hispanics, which I happen to be one. We have a very small section of our population here in Central Oregon that's any other color than white. It's not in our awareness much here. The news media cycles outside of us are making us aware to some point, but we don't see it here. And then when you visit Portland or San Francisco, you go (laughs), Oh yeah! This is what diversity looks like. So, you know, we suffer from a lack of diversity which makes us ill-prepared to deal with the issues here. Right now. And then, those confederate flags you talk about going through town seems to be garbage that's still in that blind spot and acceptable. It's because there's not anyone that that offends really complaining much about it. 

What is one's role in the fight against social injustice? 

The role in the sphere that I have any influence on, I guess, is the best way to put it. How I run a company or how I present myself in public. Do I stand by silently - which is not normally my trait - when someone says something that's deemed offensive or wrong in our ethical framework and moral justice? I believe in activism with justice. Do something about it. When those things happen, I spoke about the immigration issue when Trump was going to deport 11 million people. I was on a panel with a couple other folks. The brave folks were the ones that were there to speak on the issue who were the targets, you know, and they were exposing themselves, right? When something happens, just with the #MeToo movement, just put it out there. This is wrong. In social media - put it in your Facebook feed - this is wrong. Take a stand. People are so freaked out of being judged for any stand they take and that you'll lose friends or something like that. That's the biggest problem we have. I'm on some boards or in some discussions where they're frozen because they are afraid to make a move - people will be upset - well, anytime you take any stand on any thing, you just alienated someone. You just have to be able to be tough enough to take that and the criticism or whatever that happens. 

What do you wish for the future?

Personal future - to find a way to still have fun working and have a lot more time enjoying family. And they're heading off to college soon, so that means us going to them and still be a part of their lives. The future for Bend - I think Bend could be a shining example of doing things differently, you know? I like to take an audacious stance. Bend is the City of Innovation, which I asked the city to proclaim recently. That's a pretty audacious statement. Now we should follow through and prove it. Or the City of Diversity and then encourage diversity somehow. Or City of InclusionCity of InventionEducation - whatever it is. This new campus has an opportunity to really do things differently. And they are. Becky Johnson is architecting a university that's among the first in 50 years - the first real university campus in 50 years in the United States. Everything else has been here forever. There's a chance to make this campus dramatically different and they are. To take Bend and say, If we're gonna put a street, what's the best street possible? Not just, What's the most economic? What's the best street possible? If we're gonna remove cars, what's the best transportation model. Gondolas (laughs)? Be brave and take a stab at trying. And if you fail, try again until you succeed. Civically, we hold our city to standards we don't even hold ourselves to. You cannot fail. You cannot try something and then fail at it. Well, then innovation has no room. Because then everyone is just going to the lowest risk possible - more asphalt. The same old kind of home. All that kind of stuff. We should be experimental all the time.

Do you have an encouragement to offer or a call to action of some kind?

Yeah, Bend is still a pretty small town, so people standing up have an oversized voice. Just by the lack of engagement by others. So you can have an impact on a city - on a city council, county, the state - just by being brave enough to gather together as a tribe and yell something. Right? And take action to it. Raise money around it. And make things happen. I'm encouraged by the youth now being woken up - thanks to a disaster in Washington - to problems they probably weren't paying attention to. And now that they're paying attention, realizing they could have an impact in so many ways. Congress is giving us opportunities to fix lots of things now - because they're breaking them. And they're rallying people who've never really been touched politically before, which is great. Go fight the machine!