OwnTrail | Blog

Chrissy Cowdrey’s journey to bring the power of storytelling to everyone

Chrissy Cowdrey believes we’re all storytellers…and we can’t agree more. The power of storytelling has been a thread throughout her journey, from a successful design career to traveling the world to founding and raising more than $1 million to grow Stagger — a visual storytelling platform enabling small business owners to create and optimize digital content for their websites and social channels.

We talked with her about her story, touching on both personal and professional milestones in her always authentic style.


OwnTrail: The idea for Stagger came from your experience while traveling, and even though you built something to fit a need you personally experienced you still felt doubt on occasion. How did you know you needed to stick with it?

Chrissy Cowdrey: Man, imposter syndrome is a real thing. I’ve read article after article on it. I had numerous internal conversations that sounded like “I have no business starting a company.” “I’m not technical enough.” “This isn’t a good idea.” But in the end, I’ve stuck with it because this is a part of who I am. Design and storytelling is in my DNA and I know there are people out there who don’t know where to start with even a color palette. I told myself that if I could build Stagger to take one less design decision of a business owner’s plate who doesn’t feel comfortable doing it, this is worth it.

OwnTrail: You recently accomplished a major milestone recently: raising $1.3M as an underestimated founder during a pandemic. As congratulations poured in, you also reminded people of the challenges of this process. Why was it so important to you to share the authentic story of fundraising to grow Stagger?

CC: I think it’s incredibly easy to post the successes and big wins you have as a founder (or any human being for that matter). And sometimes, it resonates more with people to know the full path – or trail – that got you there. As a single founder, I’ve had to navigate this raise largely on my own and Twitter was a place where I learned from a lot of other female founders (like yourself) to help me. It’s my way of paying it forward. For some founders, they can close their round in weeks. For me, it took a year. Like you say at OwnTrail, not every path is the same and I wanted others to know it’s not all a cake walk.

“[N]ot every path is the same and I wanted others to know it’s not all a cake walk.”

OwnTrail: Your design career includes working for and with some dream brands like Disney. What advice do you have for creatives navigating the industry?

CC: My advice is that you don’t have to work with a brand like Disney to do some of your best work. Disney was wonderful. I loved every minute and the people I worked with. Some creatives might think “If I work for Disney or frog, I’ve made it.” I know that because I told myself that. When I got hired at frog design, I thought “Damn, I did it.” But it wasn’t some of my most meaningful work. Wherever you land, you have the opportunity to make an impact by bringing smart design to the table. As a creative, keep fighting for your seat at the table.

“As a creative, keep fighting for your seat at the table.”

OwnTrail: Orlando, Miami, Austin — part of the motivations in your moves have been to prioritize your loved ones. How has tending to your personal life helped your professional side?

CC: Orlando was a move I made for school and Miami was a move I made to work at MTV Tr3s. This last move to Austin put me an hour away from my family vs a plane ride. I’m incredibly close to my family. We’re small. I was adopted when I was 7 weeks old and I cling to my mother like she’s my rock. Coming home to Texas my last few years in Orlando felt like such a haul and I wanted to be closer. Being in a world where I can virtually work from anywhere, it made sense to move closer to home. And it just so happens that Austin is the perfect place for me as a creative and starting something in tech.

“Put aside any ego or embarrassment you have about not knowing something – because you’ve never done this before.”

OwnTrail: What advice do you have for people who see themselves in your journey?

CC: Surround yourself with people who are on a similar journey than you OR who have done this before. Ask questions. Lots of them. Put aside any ego or embarrassment you have about not knowing something – because you’ve never done this before. It can be less painful when you have a few cheerleaders in your corner who want to see you succeed and avoid their mistakes.


Want more? Follow Chrissy’s journey by connecting with her on OwnTrail, checking out Stagger and joining the conversation on storytelling.

Share