Kate Bailey applies journalistic lessons to entrepreneurial pursuits

Good Company: A former editor and culinary professional reflects on her career and journey to entrepreneurship

Kate Bailey | Founder, Annabel Media and TARRA

Age: 43
Hometown: Casper, Wyoming
What she’s reading: “Principles” by Ray Dalio

Kate Bailey launched her career as a reporter-editor at two ColoradoBiz sister publications. Like many in the media industry, she went to the “dark side” in the fall of 2013, entrepreneurially evolving her journalistic skills to craft her own public relations firm, largely serving luxury and lifestyle brands, including multiple Inc. 500 companies. 

A glutton for punishment, she built a second startup — a women’s business network — only two years later. TARRA, as it is known, aims to touch the lives of thousands of women globally who are innovating, creating and pushing the boundaries of what’s possible. To date, the organization has grown its membership 30% year-over-year.

All the while, she has collected the breadcrumbs of life, picking up on themes and developing connective tissues that weave her narrative together creatively and with a strong desire for impact.

ColoradoBiz: What was growing up in Wyoming like?

Kate Bailey: I grew up with a pretty idyllic childhood. My mom and dad were great parents. I had one of those childhoods that may not exist anymore. 

From the get-go, I was a different kind of kid. From the time I was 3, my mom described me as a reader, and I wasn’t a kid who did what she was told. I liked to find different ways, better ways, of getting where I was supposed to go. That’s really been my trajectory my entire life. 

I wrote my undergraduate thesis on the difference between the witch craze of Europe [and] that of the northeastern U.S. and the differences between the rhetoric and persecution of the Catholic and Protestant churches. Even at a young age, unbeknownst to me, I started this trajectory focused on women and women’s rights. These are the breadcrumbs of life: the details that we only notice in hindsight that add up.

CB: Were you keen on leaving Wyoming or did you want to stay? 

KB: I went to Colorado College. I applied to one school and studied history. At some level, I think I wasn’t ready to leave. I thought I wanted to stay in that small town and stay close to home. So, Colorado Springs felt far enough. 

Then the most transformative thing happened when I went to London for my junior year abroad, and I finally realized I was a city kid living inside a country kid’s body. It brought out the real me and showed me what I was made of. 

Being in London in the late ’90s at the height of the lifestyle magazine industry inspired me to get into the world of publishing.

CB: So, did you set out to launch your career in Colorado? 

KB: I graduated and got an internship at Mountain Living magazine. 

The first assignment I got was to cover the Aspen Food & Wine Classic. Only in London had I been exposed to that level of culture and hospitality. It really left a mark on me, and I decided I wanted to hone my skills and be a food writer. 

So, after a couple years of working at Mountain Living, I called my dad and said I’m going to culinary school. I went to Cook Street in Denver, and then in 2004 I went to Boston University for a master’s in food history. 

CB: How did your culinary experience enlighten your professional pursuits thereafter?

KB: What I’m working on right now — TARRA — is really a blend of hospitality, education and support for women-led enterprise. My master’s thesis was on the difference between the Parisian café and the Vietnamese coffee house at the turn of the 20th century and how the conviviality of [these] scenes helped shape the modern art movement. The fact that the city center got tighter and smaller and urbanization made these coffee houses hotbeds of people thinking and talking and interacting — that’s how we bring communities back together. How we can create this kind of strength to collectively rise.

CB: How did TARRA come to fruition? 

KB: After grad school I came home to Denver and became the managing editor of Colorado Homes and Lifestyles magazine. I was promoted to editor in chief by 27. I spent two years re-building the magazine, and then in 2007, I got burned out and moved to Aspen.

There, I realized I could take the skills I had and pour them into PR. I landed a job at an advertising agency and founded their content marketing department. After two years, I decided I had enough skills and interest to go out on my own, but I didn’t really know how to do that. 

One of my mom’s good friends who had started several of her own companies gave me a crash course, like a mini MBA. She recommended books I should read, classes I should take, and by the fall of 2013, I started Annabel Media, named for my great-grandmother, and decided I needed to move back to Denver. 

I sold a piece of property and made enough money to live for about six months with no clients. I called three people I knew from Colorado Homes and said here’s my company, this is how I can help you, and I’ll work for free for three months, then this is the price and you’ll sign a year contract. 

I had no idea what I was doing. But I knew enough to figure it out.

After two years of having Annabel Media, I realized the struggle I was having was replicated in every single woman I met who was a business owner, entrepreneur and leader. There was a community of females trying to get to the next level, and that common struggle was not being addressed by anything in the market. 

So TARRA was founded in 2015 as the women’s movement was starting to catalyze.

CB: How would characterize your experience as a two-time entrepreneur?

KB: I was always a terrible employee — I literally changed jobs every three years. I felt like I learned what I needed from each position, and then was ready to move on. I think the human spirit wants to create and that’s something that ties us all together. 

CB: What’s next?

KB: We, TARRA, are building two campuses — one in Denver and one in Los Angeles — which will be open by the end of 2021. Then we have our sights on one more, and then who knows where it will go? We are not focusing on growth, but on providing the highest quality experience to our members and tenants. At our core, we are a hospitality-oriented boutique brand and want to ensure that any growth strategy maintains the integrity of our service.

This year, TARRA is expanding our education programming and further building the network of leadership-minded individuals across industries, generations and backgrounds. All are welcome. 

Categories: Entrepreneurs, Magazine Articles, People, Women in Biz