As we embarked on our BrainSHE project, Braintree’s CEO suggested we get in touch with a mentor of his, Dana Bowers. Her career in the financial services industry began 28 years ago. Dana served as President and Chief Executive Officer of iPay Technologies. She’s has had a remarkable career, having owned a few companies and currently working on an upcoming launch of her latest venture, but we wanted to go beyond her “professional profile” and learn more about the journey along the way. As a mother, wife and a self-described “accidental entrepreneur,” she’s continuing to learn to know that some of the best things in life are not part of a plan.
Tell us about your journey.
Everyone has their own story but when I graduated from high school, I thought I wanted to be a teacher. I spent one semester at school and thought “No, that’s not for me.” I didn’t know what would do. I came home from school and got a job at a bank. I had a mentor who was a part-time prof at a local college in Economics. He urged me to go to college locally and take a class in economics. Would I have gone back to school on my own? We’ll never know. So I thought “What about business?” I liked working at the bank. So, I finished my business degree while I was married and working. I went to school at night. Then, while on maternity leave at that bank, I was fired. I found myself with a brand new baby, no job, and no idea what I wanted to do.
That’s when I was approached by a group of investors to start a company to help active-duty military personnel pay their bills while deployed. I became what I describe as “an accidental entrepreneur.” In the process of starting that first business, where I only owned 10%, I realized “[running a company] is hard, but I like it!” Even though I only owned 10%, I treated it like it was 100% my company. I was the only owner in an active position. Eventually I bought out the other shareholders.
A few years later, I partnered with a competitor and started a company called “Call Me Bill.” It was a bill payment company for banks and credit unions. Bill payment in banks was just starting to take off but this was pay by phone. It’s hard to imagine that now, but it quickly converted to an online business. I sold this in 1999. Eventually, I bought the company back from them and iPay was born. I sold iPay in 2010.
While working on iPay, I also had another company in operation, Digital Compliance. After the sale of iPay, I had the bandwidth to give focus on DC and am now working on helping them build an exciting new product.
It’s about 2 weeks away from launching. I feel this is the culmination of all of my experience. I am really proud of it. I have gotten smarter and better (well, I hope so anyway). Pre-sales are going well and I’m excited.
Who are your mentors?
Each step along the way, I’ve had a new mentor. It’s not like I chose them consciously. Maybe they chose me. I was very fortunate. Every step along the way in my career, someone decided to adopt me and teach me what I didn’t know. I’m not sure I even realized it at the time. There are too many mentors to call out by name.
The last mentor I had was actually my husband. What he did for me was help me realize what I was good at. It’s easy for you to recognize what you’re not good at, but he really helped me realize what I’m good at and then help put me in a position to have the company benefit from these strengths. I give as much as I can of that to the company and it’s good for the company but, you know what? It’s good for me too.
I have to give credit to Bill [CEO of Braintree] too, actually. I remember a conversation with him. He’s the one that said, “If you focus on what you’re good at, you’ll become great. If you focus on what you’re bad at, the most you’ll ever be is average.” That really stuck with me.
When you’re in a bad place, are there quotes that you cling to? What fuels you?
My husband helps me talk through this and acknowledges it. He lets me vent and then get beyond it. You have to have someone to talk to, so my husband does that for me.
Did you have personal experience with sexism in any previous roles?
It happens all the time. It still happens today. It never fails to surprise me. I will come away from an interaction really frustrated. I will think, “What’s the problem? What’s his problem?” Then I’ll remember “oh! It’s because I’m female.” I will think through the way that person talks to the male colleagues and realize, in that moment, that I’m different. It’s really frustrating. The way I handle it is to understand that it’s “his” problem. Ultimately, he will be the one who does not benefit from what I bring to the table.
How did you deal with that?
You have to talk your way through it.
Did you ever see yourself in the position you’re in now?
No, had no idea. That’s why I always called myself the accidental entrepreneur.
What advice would you give to young women?
Be strong and expect the path to be messy because it is, there’s just no way around it. It’s hard especially if you’re a mom. I’ve spent many days and nights feeling guilty. I look at my kids today (one is 30 and one is 28) and I think, “They turned out pretty well.” There’s good that came out of the way they were raised, too. I was lucky. I live where I grew up. I had family that was able to help me along the way. My kids now have good memories from the time they spent with their great-grandmother and grandmother. You have to give yourself permission to let go of things.
Are you mentoring anyone now?
I’m on a board of a female owned company in Louisville. I mentor the woman who runs that company. She’s been a delight to mentor and guide. On one hand, I am a member of her board and on the other hand, more than that, the relationship is special because I’ve been able to mentor her as well.