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

6 min readJan 31, 2020

In Part One of Drew Mauck’s conversation with tastytrade’s Kristi Ross, Kristi spoke about tastytrade, her experience as host of Bootstrapping in America, and key trends in financial media. (For a visual of tastytrade’s numerous affiliated entities, see the graphic at the end of this post.)

Read Part Two below to see her insights on Chicago tech, important nonprofits, and more.

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.

One thing that is really important to me is not coming in saying, “How many people can I meet and what can I gain from this?” Rather, I come in with a mindset of looking for opportunities to help others. Whom can I connect somebody to? It’s about making human connections. In this digital age, people miss the fact that you actually have to have some human connection.

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.

Chicago Innovation is another one. I’m biased, as I’m on the board there, too, but when you look at these companies that are connecting others and creating a strong ecosystem — highlighting and rewarding people who have done well — I think that is really what is at my core. It’s something I want to be a part of. I need high energy or I’m just going to lose interest. I need to see that there is progress, always.

P33 is an effort to make Chicago a top-tier tech city. I was honored when the founders of P33 asked me to co-lead the capital and finance committee with John Rogers from Ariel Investments. P33 brings together leaders from different industries to collaborate on what was needed in order to elevate Chicago’s tech stature, nationally and globally.

Aligning with other executives and leaders who can truly push this city forward is something that is important to me. It’s about locking arms and doing this together — no one person can do it by themselves.

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.

When you look at Chicago though, we have the number-one innovation hub globally: 1871. We are the second city for the highest number of computer science and engineering grads in the country. In Chicago, 45% of venture capital firms’ investments yield 10x returns. When you look at other cities, it’s more like 25%. Those are statistics that we are not sharing enough. If I could change one thing, I would make sure that not just every single CEO and leader of a startup or public company, but every employee, is a mouthpiece for Chicago. If you hire someone from another city, you should be able to tell them those stats.

We should all be better marketers for Chicago and its future. We should all be focused and dedicated to the endless reinvention of the city.

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.”

There’s a big Chicago contingent of St. Norbert grads — that’s actually how I got introduced to Chicago. I took a couple of road trips down here with friends. It was kind of the same feeling when I got exposed to trading — when I got exposed to Chicago I knew this was where I needed to be. This is where I belong.

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.

Playing sports, I strongly believe, helps any individual learn to work closely with other people and work together to get the best results, all working toward a common goal. That’s what we have here at tastytrade. It’s not a hierarchy. We run a very flat organization, — it’s a team effort mentality.

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.

Another one is P33, which I also talked about earlier. That’s also a nonprofit organization. Again, it is the premise of locking arms and highlighting Chicago as a top-tier tech city. All of these are interrelated, and ultimately related to what we do here [at tastytrade], too.

When we look at the next generation of leaders, I see an organization like the Midtown Educational Foundation paying attention to amazing kids who don’t necessarily have the resources or exposure to opportunity thatas others do — and MEF focuses on increasing the probability of the kids’ success. MEF is providing resources and personal connections for disadvantaged kids who don’t have mentors, and exposing them to professionals with different types of careers. Those professionals help, not only on an educational level, but also on a personal level.

The other organization [I want to mention], Rock the Street Wall Street, is about future female financial leaders. Only 15% of financial services executives are women. Maura Cunningham [the founder of Rock the Street Wall Street] came from the financial services industry and started the nonprofit. She is going into high schools and sparking the interest in finance for girls, cultivating that interest at a young age. I love that. She started out of Tennessee and I actually helped her bring it to Chicago when she was expanding. The whole financial services industry, or anyone who cares about diversity in the field of finance, should reach out to Maura and do whatever they can to help that next generation of female executives. Building a better future together.

Thank you to Kristi for taking the time out of her busy schedule to share her insights with us. Be sure to follow her on Twitter and keep an eye out for her at various Chicago tech events!