On introducing investing to Millennials, paying attention to details when negotiating, and using mobile to have a balanced life.
FORTUNE — Before Kristi Ross moved to Chicago — where she has worked for more than 20 years in finance — she trained to become a certified public accountant St. Norbert College, a small liberal arts school in Wisconsin. An accounting degree is somewhat atypical for entrepreneurs, but for Ross it added up, propelling her to become chief financial officer of a Chicago trading company when she was just 25 years old. She has since started several companies, including a financial network called Tastytrade (where she is president) and her most recent project, Dough (where she is CEO).
Dough bills itself as an investing platform that produces educational content about trading for newer investors. The company’s mission is to make complex ideas simple by using videos and quizzes to teach people, especially twentysomethings, about how to wisely invest their money. Ross, 45, spoke with Fortune.
1. Who in technology do you admire most? Why?
Howard Tullman, the CEO of 1871 [a Chicago startup co-working space]. Howard’s an amazing visionary and entrepreneur who shows that he can execute efficiently and effectively. His depth of experience runs deep. He’s plugged in and clearly well rounded. His expertise is admirable, and the best part is that he shows no sign of slowing down, which I love to see. He’s already rolling out aggressive plans for 1871, and he has a passion for what he does. The best part is that he’s poised and willing to mentor and share that knowledge with hundreds of future stars of 1871. It’s one thing to be great at what you do, but when you’re willing to share what differentiates you, you become labeled as exceptional, which I think Howard is.
2. Which companies do you admire? Why?
I’m an avid and loyal customer of Costco. I admire Costco for its consistency and clear messaging. Costco’s past and present leadership understands being right in the stores with customers and providing the best experience.
3. Which area of technology excites you most?
Absolutely anything mobile. On-the-go technology is near and dear to me. It has such an impact on the world and how we live. It truly makes my life easier. I tend to my perpetual list of things to do all the way from family to finances to work, and the best part is that I can do it any time of the day, anywhere. I’m constantly striving for some sense of a balanced life, and mobile technology helps me get closer to that. It’s had an incredible impact on productivity and increases the probability of success. I often measure the success of my day on what I’m able to accomplish in a 24-hour period, so anything mobile is my key to doing that.
4. What is the best advice you ever received?
There are a couple of things that really stick out in my mind. One is that opportunity is all around you, so you should pay attention, but also you should have an opinion. I realized quickly that you have to sit up and take action when opportunity presents itself, and having an opinion on something goes a lot way. You should also never assume that someone knows more than you or that they know exactly what you’re thinking or why. I think that a lot of opportunities are missed because people are silent or they make assumptions.
5. What’s the next big project you want to tackle?
Introducing investing to Millennials. We feel that’s an incredibly untapped market. We’ve recently launched Dough, and it’s a free financial app that provides a logical, mechanical approach to investing. The app itself is highly visual. It makes a complex concept simple. There are a number of firms that are trying to do this now that have realized that there are multiple hurdles to overcome when marketing to this demographic. We are prepared to know how to get over those hurdles and present something that is complex in a simple form. We expect a change of culture with Dough. We expect a change of culture in how people think about investing.
6. What challenges are facing your business right now?
We think the big challenge is to deliver a completely different message than traditional financial media has delivered in the past. We’re creating a path for the younger demographics that want to invest with very little capital and are doing it with mobile and visual approach. The challenge is providing information at the college and university level to build financial literacy around the market. So when students head into the world, they can feel empowered and ready to make better investment decisions.
7. If you could have done anything differently in your career, what would it have been?
I became a CFO at a young age, when I was 25. I was focused on being that financial go-to person and fulfilling that role. I think I really missed out on some valuable customer experience, like being in touch with the customer. I was really great at seeing the world from inside the company to the outside, but when I stepped outside of the financials and participated more actively and directly with customers, I realized that I became a better executive and team member. So it gave me a completely different perspective, and I was able to bring truly exponential value to the table when I came to merger and acquisitions later in my career. I was able to strategize at a much deeper level. If I could have done anything differently, I would have made time to really get closer to customer earlier on.
8. What was the most important thing you learned in school?
I learned that girls can do anything that boys can do, and sometimes better when it comes to anything detail-oriented. Women and men are wired differently, and they often have strengths that complement each other, so it was in high school where it really stuck out. I was chosen to participate in a mock negotiation, and during those negotiations I paid close attention to the opposing team’s actions and words. When we came back into a team huddle, the boys all wanted to negotiate based on all high level assumptions. There were a couple of us girls on the team, and we were all adamant on focusing on the important details, which ultimately changed our position and we won overall. If we had backed down or said, “Yeah, okay, we’ll do the high-level positioning,” then we wouldn’t have been addressing the real issues. It turned out to be a life lesson for me, and it’s something that I’ve applied again and again in my own career.
9. What is one goal – either personal or professional — that you would like to accomplish during your lifetime?
I want Dough to transform the way that millions of people think about self-directed investing and the option to trade. I want a new generation to be empowered to talk about the markets with confidence and understand their probability of success. I want the same thing for my kids. I want them to be financially literate about investing and their money.
10. What do you do to live a balanced life?
I’m constantly striving for a balanced life. For years I’ve said to my kids, “I wish I could split myself in three, so that I can spend equal time with each one of you.” But in reality what I really need is to split myself into 10 to have time for work and family and a personal life. It took me 15 years to get where I am, and I finally feel like I’ve set realistic boundaries that I can live with. I used to be a person who would never say no to doing anything. I learned the hard way, but I found a way to fit in everything I can with mobile. Since we can’t have a 48-hour day, I learned that everything I do has to be quality because I don’t have the liberty of quantity.
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