Flipping the Script: Kristi Ross on the Entrepreneurial Spirit, Financial Media, and Chicago Tech (Part 1)

Please tell us a little about your professional background.

I’ve been in and around the trading technology and brokerage industry for three decades. I have been through over 30 mergers, acquisitions, and capital raises. I started out as a CPA and raised my hand at 25 to be CFO of one of our clients, and later became the CFO of Chicago Securities Group [a specialist on the Chicago Stock Exchange].

You’ve recorded over 2,000 “Bootstrapping in America” episodes. If someone has never seen the show before, which episodes would you recommend?

The first one I have to throw out there, for sure, is [any episode with] Howard Tullman. We bring him in to talk about what he’s thinking, [often about] different entrepreneurial topics, like raising capital, creating a culture of innovation, or getting a product launched. He has a wealth of knowledge. He has a regular spot, once a month.

Even though you’ve interviewed thousands of innovative entrepreneurs and likely gleaned some interesting strategies for keeping tastytrade innovative, it’s no small feat that you have helped create and maintain a culture of innovation. What can you tell our readers about how you and your colleagues do that?

It starts with access. When I say access, it is about opening the door, inviting people to the table whom you wouldn’t normally. It’s employee access, it’s not all just executives [talking to each other and making decisions]. And it’s customer access as well. This is where I give kudos to Tom and [tastytrade co-host] Tony Battista. Every single person at this company makes themselves accessible to customers, with Tom and Tony being front and center setting the best example. Tom will be answering emails from customers at midnight or on a Saturday morning.

Where do you go for information on financial technology and or the markets?

MIT Tech Review for tech; PitchBook from an entrepreneurial standpoint; Howard Tullman’s tech trends every year; Mary Meeker’s out of Silicon Valley; and from a regulatory, capital markets standpoint, TabbFORUM. (If it’s about retail investing and trading, hands down tastytrade.)

What are the key trends you foresee for financial media as we approach 2020? For capital markets?

In the last few years, the time spent on digital video has surpassed TV. You’ve seen digital video consumption double over the past five years. From a social media standpoint, YouTube and Instagram are the ones that are gaining the most traction. Those trends are continuing at a significant pace, and we continue to keep an eye on them.

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