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

3Points Communications
5 min readJan 28, 2020

At 3Points, we love working with journalists and media members who uncover the unique and important stories in capital markets and the Chicago tech space. Given the nature of their work, these folks have telling insights regarding the industry and the media within it — as such, we enjoy occasionally “flipping the script” and interviewing the people who normally do the interviewing. And perhaps no media member has as much insight relevant to our practice areas as tastytrade Co-CEO & President Kristi Ross.

Kristi has extensive experience in finance and tech, has a prominent media role as the host of “Bootstrapping in America,” and is a highly regarded technology advocate here in Chicago. We took a trip over to tastytrade HQ in the West Loop to see Kristi in action on “Bootstrapping,” and then 3Points CEO Drew Mauck sat down with her for a wide-ranging interview of her own. Read Part One of the conversation, lightly edited for readability.

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].

When I was in public accounting I was exposed to a lot of traders on the floor. I knew I wanted to be on that side of the fence. While I was at Chicago Securities Group, I met Tom Sosnoff and ultimately came to thinkorswim as the CFO in 2004, right after it raised capital. Tom and [thinkorswim co-founder] Scott Sheridan were told by their VC investor, “You need a CFO, but you wouldn’t know a CFO if it hit you in the face.” To their surprise, Tom and Scott did know a good CFO — hence, I was VC-approved.

I came on board with the expectation that thinkorswim would go public or get bought — that’s the venture capital route usually. I remember saying to Tom and Scott, “If there’s not enough going on in two or three years, I’ll need to make a move.” Within six years, we did six mergers and acquisitions. As CFO, I felt like that was a huge focus of mine and, needless to say, there was definitely “enough” going on.

When we started tastytrade, neither Tom nor I knew anything about financial media, but the team was confident that we could figure it out. The idea at the start was to have an online squawkbox. Within a very short amount of time, we saw where YouTube’s stats were. Its growth was [exponential], and it was clear that we needed to be in the video space.

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.

[Another episode I’d recommend] was with BioLife4d. They recently 3D-printed a human heart. It was tiny, but it was functional, it was beating. That type of thing I wouldn’t normally be exposed to. I came away learning something completely different.

And I interviewed Tom. He is crazy brilliant and brilliantly crazy. We have a different dynamic [as co-workers], but interviewing him as an entrepreneur was interesting for me because we don’t talk to each other that way normally.

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.

One of the things I feel very strongly about, from an employee standpoint, is that they feel like they can come to work every day and make a difference — I’m actually excited to walk in the door every day. I want everybody to feel that way, to have that level of energy. To feel like they can put an idea on the table and that there is a shot at implementation. We’ll let them run it and support them. Owning an idea matters. Sharing ideas matters. That collaboration leads to innovation.

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.

From a trading standpoint, we expect a more aggressive move from passive to active investing. That has been an ongoing conversation here at tastytrade over the years. It doesn’t mean everyone will be a day trader. What it means is that people are seeing the benefit of understanding the markets better, by being in them. That’s what we [believe in]. We teach people how to fit 5–10 minutes of trading into their daily routine. We live the “active” investing lifestyle every day. It’s empowering. And I’ll give credit to Robinhood. It sparked and empowered a lot of people to take the first step [toward “active” investing]. It created the type of easy access that people new to investing needed at that time.

But that is only the first step. People need more than just a trading platform with access. We are still in the “content era,” and I expect we will start to see more financial content in the next five years. We started the revolution. We married actionable, financial content with visual trading technology to help customers with the full “everyday-investor” trading experience. That’s what we’re all about — empowering others to take an active role in their own finances.

Keep an eye out for Part Two of our interview with Kristi, which will run later this week.