Inspiring Conversations with Chrissy Smiley of Smiley & Associates

Today we’d like to introduce you to Chrissy Smiley.

Hi Chrissy, please kick things off for us with an introduction to yourself and your story.
I started Smiley & Associates, a small residential property management company based in Boulder, while I was working part-time as a barista and for a small property management office in Boulder, Chinati Management run by Pilar Pedersen. At the time my only associate was my cat Oya. Shortly after I started working for Pilar she decided she was moving to Texas and closing her business in a year. I went home and thought about it. “What are you going to do if someone calls asking you to manage their rental?” I asked her the next time I saw her. She said she’d be happy to refer people to me if I start my own business. So I did!

Before I started Smiley & Associates in 2004 I had worked mostly as a writer. After being laid off from a tech writing job, I discovered a job in property management. It checked many of the boxes on my job wish-list. I wanted to be in an office sometimes but out-and-about sometimes. I wanted flexible hours and a mix of types of work. I wanted a job where the potential to increase my income was greater than jobs that give a 50-cent raise every year or some such. I also wanted non-location-based work that I could do from anywhere, but alas I did not get that.

It’s my nature to be a truth-seeker and stand up for justice. I find those qualities helpful in my work as a landlord’s agent. Those same qualities led me to major in journalism at CU-Boulder. Right after college I worked for eTown, a national public radio show based in Boulder. I wore many hats there, including getting to interview James Taylor. Thinking my career was bigger than what I was doing at eTown and wanting to get into print journalism I moved out of Boulder and eventually moved to San Diego following a partner. I couldn’t find work as a writer. It was 1995 and the LA Times had recently laid off a ton of people in the area so I got a job as a student adviser in the UCSD biology department. Current events around those times were JonBenet Ramsay’s murder, the guy who drove a tank down the freeway in San Diego and the O.J. Simpson trial, for which my office at UCSD took a long closed lunch to watch the proceedings on TV. After a few years I returned to Boulder, worked for Naropa when it was an institute, then a few more writing jobs before Smiley & Associates was born.

Alright, so let’s dig a little deeper into the story – has it been an easy path overall and if not, what were the challenges you’ve had to overcome?
I fell into this pretty effortlessly, however it is a challenging profession. I think property managers are seen by the public as similar to lawyers and used car sales people. I strive to high ideals in regard to responsiveness to renters and caring for properties, so it is disappointing when renters come to me with a chip on their shoulder from having previously been mistreated by corporate property managers. The bad actors in my profession are a problem. One local company is on record recently for bilking renters to the tune of hundreds of thousands of dollars, so I work in their dark shadow. It’s weird to be a little guy among the corporate world takeover.

That said, some tenants can be demanding. I get that the stakes about anything are biggish for them because it’s their home over which they don’t have total control. The challenge for me is to not let stressed out renters pull me into bad responses. Over time, for this reason—with work and in other arenas—I started practicing meditation and studying equanimity. I strive to be careful of what I say and to add sprinkles of love into my emails when I have to draw boundaries with people.

Am I Doing What I Was Born to Do?
Well, not exactly. At least not for pay. At least not yet. My alter-ego is a bit of a hermit, so I dream of a homestead and a quiet life away from cities. This summer I’ve been building a modest camping van out of a cargo van, and generally being a DIY maker. I also volunteer regularly for Wildlands Restoration Volunteers. I’m an artist too.

I find it interesting that I ended up in real estate without it being a specific goal at any point until the opportunity presented itself. I grew up in New Mexico, before moving to Colorado as a teen. As an undergrad I majored in journalism because a key part of my DNA is seeking truth and standing up for what is right. I studied news editorial at CU back in the day when AP stories came in by a fax, printed out in a serious of connected sheets of paper. We developed actual film in the CU-Boulder J school dark room. Dodge, burn, dodge burn. Good times. And now I’m a self-made real estate thousandairre.

Appreciate you sharing that. What should we know about Smiley & Associates ?
I like to think of Smiley & Associates as The Antidote to Corporate Property Management. Clients and renters can reach me easily. I do not charge “convenience fees” to renters every month for mythical reasons. I am responsive in a timely manner to maintenance calls. I have a blog on my website where I post articles, including about new laws that pertain to residential rentals. I wager you could not find another property management company willing to educate renters about laws.

I’m an environmentalist and I order work and new items judiciously and thoughtfully for my clients. I address bug and mice issues humanely. The lawns I manage are organic and I always keep mother earth in mind when attending to properties.

Do you have any advice for those looking to network or find a mentor?
In general I’m of the “hold on loosely” viewpoint about making plans. I like to have a macro intention and let the situation evolve. That’s how my art works come to be as well. I have an idea and then as I start to create the elements show themselves. I stumbled upon the mentor who helped me start my property management business. I’m usually lucky, and that was one of those times.

I fancy that my intelligence and instincts are pretty good, maybe better than average, so I tend not to look for help. It doesn’t always serve me. My best advice is to know when you could do better with the help of another person’s viewpoint and skills. And be brave enough to scale up if you have a good thing going. In the past few years I brought on a bookkeeper. I also hired software designer Art Ihnatsenka, of Boulder-based Honey Viper Consulting, to get me away from the irksome QuickBooks. One goal for 2026 is to grow the business. Until now Smiley & Associates has grown organically through word-of-mouth. The only effort I’ve made at advertising is making a website and asking people to post google map reviews if they truly find my business worthy of a good review.

I’m pretty much allergic to schmooze-fest networking events. So I can’t recommend those for anyone, but I am sure some people do get value. I just don’t like phoniness and those events feel uncomfortable to me.

Contact Info:

• Website: https://smiley-and-associates.com/

Image Credits
My friend Anna, a fellow sawyer who is a mentor, took the picture of me with the pile of logs. Mike’s camera in Boulder photographed my art piece Circle Back. Aaron with Denver Real Estate Photography took the others.