Flipping the Script: Kristi Ross on the Entrepreneurial Spirit, Financial Media, and Chicago Tech (Part 2)

I keep my evening professional agenda fairly full, but I don’t think there is anyone in Chicago tech who makes more appearances at events than you. How do you decide what to attend, and what advice do you have for folks who want to network in this city?

I’m going to start by sharing my life motto: opportunity is all around you, [so] pay attention — but you have to grab it. You need to actually put yourself in different situations all the time to increase your probability of more opportunity. So, the first rule is just show up.

Any events or organizations in particular that you would recommend?

I’m on the board of 1871, so the Momentum Awards Dinner is always big.

If there were one thing about Chicago tech that you could change with a snap of your fingers, what would that be?

First of all, I believe that each and every one of us should be dedicated to the endless reinvention of Chicago. With that as the premise, when you look at Chicago, we are punching below our weight. But part of that has to do with the marketing of it. We have the Midwest mindset of, “Let’s put our heads down, build a strong, profitable, sustainable company” — that’s what we do. We don’t spend the time shouting about Chicago from the top of a mountain.

We noticed you are a graduate of St. Norbert in Wisconsin. Would you mind telling us about your experience at liberal arts college that helped prepare you for a successful career?

Being from a small town and then going to a small college felt super comfortable. My dad went there as well and was a tremendous athlete. It gave me a well-rounded education, and the learning environment allowed me to look at things differently, to learn in a different way. It really promoted critical thinking. It’s not a procedure-based education, and I love that. I’m someone who wants to “figure it out.”

What was your best experience there?

First of all, I put myself through college. I worked, I played volleyball, I went to school — I am a multi-tasker by nature. The experience of doing all of that prepared me for life.

Last question: What are some important nonprofits you’d like our readers to know about and why?

1871 is really the nucleus of Chicago tech and entrepreneurship. That is one organization where, if you want to contribute to the growth of entrepreneurship and Chicago’s future, that’s a number-one go-to organization to support.

Tastytrade Entity Org Chart



Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store