Rolodex: Denver Entrepreneurs to Know

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Saying Yes with Caitlyn Fagan of Zenman & Bigfoot Web

By Jessica Fialkovich | @jfialkovich

Denver is no longer an oil and gas town, the city is now a well diversified machine of small business and startups. From 2006 to 2016 jobs in the tech industry increased 40.3% to 79,342. However, it is a well-documented that the percentage of women in technology, especially leadership positions, is much lower than other industries.

This is only one reason I decided to chat with Caitlyn Fagan. Caitlyn is the current CEO at Zenman and recent co-founder of Bigfoot Web. Zenman’s team is currently 50% women, leading the local industry not just in great web design but also team culture and dynamics.

Caitlyn Fagan, CEO at Zenman and Bigfoot Web. 

Caitlyn Fagan, CEO at Zenman and Bigfoot Web. 


How did you get started in your business?

l came to Denver in 2010. I had worked in traditional agency settings in Miami and Arizona after graduation. I definitely started at the bottom as an intern to get my foot in the door: Yes, I got coffee. Yes, I did data entry (so, so poorly). Yes, I did the work absolutely no one else wanted to do. It was grueling and in some ways, so amazing. I came to Denver to find myself and worked at a small agency. A few years in, I was putting feelers out for my next move, something more permanent with a growth plan and culture that was a better fit for me.

I was introduced to Keith Roberts, a connection that forever changed my life. Keith didn't know exactly if he needed me or why he needed me, but I came recommended by a mutual friend and he nearly hired me over the phone! I started as a Project Manager and added systems and procedures for our projects. Zenman was starting to grow and I continued to fill in where I was needed, moving up the ranks internally as I learned the ins and outs of a digital agency. In 2015, some shifts in our structure left the CEO position vacant. In an extremely bold move, Keith decided I was the person for the job. I'll be the first to admit that I was a bit over my skis. I definitely learned some lessons the very hard way. But Keith's trust, support, and overall confidence in me got us through even the toughest spots.

In 2015, Keith and I started Bigfoot Web. As Zenman continued to mature and the price point increased to reflect the experience, we were sending a tremendous amount of business away, largely from startups and entrepreneurs who needed a website and marketing, but were not prepared to pay Zenman's prices yet. Instead of continuing to refer this business away, our "whole other beast," Bigfoot Web, was born. Spinning up (and bootstrapping) a new business has challenged, frustrated, and ultimately grown me.

You have been so successful with Zenman and now Bigfoot, what has been your key to success?

Say yes. That's how I got started. Even if I had no idea how to do something or even how to start, I said yes to things that needed to get done. Often times it was the things no one else wanted to do. When you're first starting out, don't worry about staying inside the lines of a job description or only doing what you're "supposed to" do. Especially at smaller companies, say yes to the projects and tasks that scare you the most. It's a really fast way to add value and to find out what you're good at or what you want to be good at. It's exactly how I ended up running two awesome businesses.  

You are very active in the community and give back a lot, how do you make time for that while running two businesses?

My business coach told me early on that if everything is important, then nothing is important. I live my entire life with that in mind. Giving back and supporting our community has always been a priority for me and so I make the time for it. That being said, it isn't always easy! I put everything on my calendar and then I show up, even when it's hard and I want to bail And ugh, who feels like a 3 hour board meeting after a long day? I think that's key--don't commit to something you can't follow through on and only commit to the things that are important to you so you can hold yourself accountable to doing them.

What advice would you give women thinking about starting their own business?

If you are ready for the biggest, baddest, most stressful, most rewarding, awesomest adventure of your life, jump in head first and do it! But also be overly prepared in all areas from legal to culture, starting a business is not the time to wing it! If you're starting a business with a partner, make sure you have an Operating Agreement signed and in place at the beginning--it's always easier to agree on how to end things gracefully if that time should come when people love each other at the beginning. Make sure you put systems and procedures in place too, both to help yourself as you're starting out but also to make it easier to hire and train the next person to take over when you're making bank.

Above all, ask for help! Anywhere, but especially in Denver, there is a tribe connected by the wonder and craziness of owning a business. There are so many people that have gone down the wild road of owning and operating a business, no use in recreating the wheel! I'm always pleasantly surprised at the number of people willing to help me any time I ask and I try to always pay it forward.

What is next for Caitlyn / Bigfoot?

This is my favorite question because I get so excited about the future! Bigfoot has had some great preliminary success and the next step is adding rocket fuel to the infrastructure we've built. The goal is to scale and exit in the next five years. The biggest "next thing" for me is developing my “outside of work” self. I get so much of my self worth from my career successes that I've lost a little bit of what Sunday-afternoon-Caitlyn looks like. I'm excited to remember and expand the other things I'm passionate about, which will lead to a greater capacity to grow my career as well--double win!

What’s your call to action for Denver broads?

Get involved. If you've got the brain (and stomach) to own or run a business, then there are people out there that need your insight, fearlessness, and grit. Volunteering also helps with perspective and empathy, something every business owner needs in spades. One of the things I love most about Denver is its philanthropic heart; there is a non-profit for everyone and they all need help. Pick something that speaks to you--for me it's children and education--and get involved. That could look like sitting on a board, fundraising, volunteering time, doing a project pro-bono, the list is endless. I'm grateful for what I get to do every day and it's the least I can do to give back and help develop a community that has been so supportive of me.


On the RegVirginia Santy