373. Bootstrapping to a Billion Dollar Exit, The History of Options Trading, Competing Against Robinhood, and How to Build a Brokerage Content Machine (Kristi Ross)

Kristi Ross of tastytrade joins Nick to discuss Bootstrapping to a Billion Dollar Exit, The History of Options Trading, Competing Against Robinhood, and How to Build a Brokerage Content Machine. In this episode we cover:

Bootstrapping to a Billion
Chicago Trading in the 90s
ThinkorSwim, TCV, and Trading to Tastytrade
Robinhood’s Capital Intensive Strategy
Using Media and Content to Build a Brokerage Powerhouse

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Transcribed with AI:

0:00
Kristi Ross joins us today from Chicago. She is co founder co CEO and President of Tastytrade and award winning online financial media company which also has its own subsidiary trading firm, Tastyworks. Previously, Kristi was CFO at Automated Trading Desk Specialists. She then served as CFO of ThinkOrSwim, where she led numerous mergers, acquisitions integrations, and a little over a decade ago, Kristi co founded Tastytrade, which was acquired in 2021 for over a billion dollars by IG group. During her time there she also co founded Dough, a visual front end trading technology platform that became the base for launching an online brokerage firm within Tastytrade called Tastyworks. Kristi, welcome to the show.
0:44
Thank you so much for having me on. Nick. I’m excited to be here.
0:47
It’s so fun to turn the tables, I think it was probably four or five years ago, as I’m bootstrapping, I know that you have a long term history and in hosting and interviewing folks. So this is a lot of fun for me.
0:57
Yeah.
0:58
So you know, just to start off here, can you kind of give us a sense for your background and the early on elements of your career before you got into trading?
1:06
Let’s see! This started a very long time ago, I started out in finance and accounting, and a lot of the clients I worked on were trading firms, traders on the floor, prop firms, advisory firms. And Nick, from the first time I stepped on the trading floor, I said this is where I need to be, the energy was absolutely infectious. And the sheer volume of sort of monetary exchange was really captivating to me. I became a CFO at age 25. And I have been in and around the trading and brokerage industry for over 30 years. I actually talking decades now. So overall, three decades, I’ve been through over 40, mergers, acquisitions, capital raises and startups in my career, as you mentioned, you know, one of the most recent companies, certainly Tastytrade, which we started in 2011. And there are four co founders myself, Tom Sosnoff, Tom is truly the visionary and Scott Sheridan and Linwood Ma. So we’ve actually been together for over 20 years. But within Tastytrade, we built seven companies within our company over the past 11 years. Super fun. And as you mentioned, you know, we sold to a public company out of London IG group for over a billion dollars. And if I were to sort of set the stage for where I am now, I actually self directed trader and active angel investor, myself and very, very involved in the Chicago tech community in the startup community. But also I have since left IG, I’m still on for this next year or so but negotiated my way out because I am ready for my next phase which, cross my fingers, I will be announcing next year. But that transition, and that leap was a big step away from something I am truly passionate about and believe in. And when you’ve been with people for, you know, a couple of decades, it’s a little odd making that transition. But it’s so fun. I’m full of energy and ready for this next endeavor.
3:17
I love it. I love it. You’re the consummate founder, you know, just constantly reinventing yourself. And we’d love to talk a bit more about that later. So of course, I’m a Chicago based venture capitalist, you, Tom and the crew are legends here in Chicago, I happen to work and partner with many people that have traded both in the pits and through various online market makers and firms now. So I’ve heard the stories, but many people in the audience, whether it be based on age, or just not being located here don’t quite understand the history of trading. So can you take us back to some of the early years in trading sort of pre Thinkorswim? How was trading done in the 80s? And 90s? Can you talk about the pits and open outcry a bit and give us a little bit of the history?
3:57
Sure. And that does bring us way back to, let’s say the 80s. And that is when I first really me stepping out of school it was in the 90s. And so coming into Chicago, and as I mentioned just right in the beginning, but that first step on to the trading floors. It was an incredible energy that was there the open outcry. It was very physical. I didn’t trade on the floor, but I was down there when I talked to our clients and you needed to have a physical presence. There were a couple of guys that were shorter that literally wore platform shoes just to gain an edge in the pits. It was interesting, but it was also a locker room. It was truly the boys club, if you will. There were not many women that were on the trading floor. What I saw and participated in was sort of this shift that took place In decimalisation when we went from fractions to decimals, and that transition was actually sort of an important part of the history of trading and technology. As we shifted away from the physical open outcry into more of the automated trading, there was a massive resistance, and rightfully so to that shift in technology. I remember one of the deals that I went through. So at the time, I was the CFO of a company called Chicago Securities Group. And we did a deal with automated trading desks. And I remember going around talking to a number of different traders in New York and Chicago all over the place, different exchanges, and the massive resistance around them feeling like they were going to be dinosaurs, they were going to eventually be extinct was very, very real. And yet, I was coming in with a crazy amount of energy around look at what this can do, ultimately, for the end customer and improve executions, right? I mean, speed of execution, and quality of execution and all of the different things that you could actually do with technology versus what you’re going to do with a manual process. Anyway. So it truly evolved, now later in the 90s. So, 1999, this is prior to me meeting Tom, because Tom had actually started Tom Sosnoff a co founder, he and Scott shared and it actually started Thinkorswim. So they were on the trading floor in the options pit, in the LAX pit. And they saw an opportunity for bringing online trading to the retail investor. Now Options Express was doing the same thing down the hall in the same building in Chicago. And that was probably our biggest competitor or most similar competitor at the time. But I joined only a couple of years after they were starting to get it off the ground. So they were still pretty small. And they needed every member because TCP technology crossover ventures out of Palo Alto had invested in them. And they, I still remember they said to Tom, Tom told me the story. They looked at him and said, Listen, you need a CFO. And they told Tom that he and Scott wouldn’t know a CFO if it hit him in the face. They were looking for a CFO, I ended up becoming their CFO very early on and help them grow the business. And we had gone through sort of six mergers and acquisitions in six years. And ultimately, were bought out by TD Ameritrade. But what was interesting during that timeframe is online investing, particularly with derivatives. I mean, there just really weren’t that many companies doing that offering that and sort of this shift to online trading. And for the retail investor. You know, I remember picking up the phone and making my own
8:09
Call your broker
8:10
Yeah, call your broker, right. And they’d call me back with a quote, and then they’d call me back with a fill
8:17
In fractions, not decimals. Right?
8:19
Exactly! Exactly! And you know, and that was years ago, that was certainly way prior to Thinkorswim. But that was the biggest transition is being able to press the button yourself having speed of execution be in fractions of a second and continuously improving over the years. And so, that I think was one of the biggest changes and shifts in the industry is when all of a sudden sort of that, you know, democratization of access to the public markets was made. Well, you hear a lot of companies today declaring that that was happening in the late 90s, early 2000s.
9:00
Kristi aside from starting the brokerage, what was the other biggest shift in strategy in the early years, you know, what was the biggest epiphany or lesson that caused you either to pivot or expand or do something different?
9:14
Well, you’ve heard this a million times, you know, this from companies you invest in if something’s not working, like pull the plug, and you got to move on pretty fast. Well, and so I’ll go back to the very, very beginning because there was a pretty big pivot even in the beginning, other than looking at the we’re going to do Squawk Box to adding full on video. It was the type of content that we were producing. We came in thinking, Okay, we need to really create something fun and we’ll add a little bit of trading. So we had all these Second City comedians producing content about trading and just in general, so it was meant to be more entertaining, and we really listened to our customers and they wanted more we’re trading. And so our accessibility as CEOs and the company as a whole to our customers to listen to what they like, what they want, what they don’t like, I think really helped us shape what type of content we ultimately ended up airing. And so the type of feedback we got was we were a little too heavy on the fun and they wanted more trading. And so it was that shift where we ended up doing way more trading and just had the right flare of fun and entertainment, which really ended up just being real. I mean, we have a couple Second City comedians, but it wasn’t the 5, 6, 7 we had in the beginning. It’s more like two.
10:39
Got to talk about Robinhood. You mentioned the firm before when they came out you know with the zero feed trades was this a major threat? Did you see it as a threat?
10:49
Interesting I’ll tell you our first reaction when Robin Hood came out while they had the same sort of philosophy around what we were trying to do with Dough. They came out with zero commissions and we said oh my gosh, they’re never gonna make it you look at like Zecco, I don’t know if you remember some of the different firms that claim zero commissions but anyway so they came out and they and they had said well, you know, we’re gonna make money on payment for order flow yet they were offering, you know, one share of stock at a time we’re like you guys do you understand how much money payment for order flow is on stock? It’s minuscule and so we certainly were not had no thought about them other than in, you know, seeing their interface going, Oh! Conceptually, the way that they presented and designed and really made this simple for someone who really truly doesn’t understand trading or didn’t know trading, they did a great job with the interface. So as they, over time, you know, and they’re bleeding cash for many, many years, when they finally understood that where the money is in options, that shift, it was worth sort of sitting up and listening and watching and actually giving them kudos for bringing on probably the biggest thing we give them kudos for is for really empowering this next generation in a different way that has opened the eyes of a lot of people that you don’t need the millions of dollars, you don’t need a finance degree, you don’t need a lot of time to learn how to trade you can trade a share stock standing in Starbucks, right?
12:26
Yeah. And did they supplement their revenue stream beyond payment for order flow? Or…
12:31
They absolutely did, they did a gold subscription, the thing that they have done well, is they have continued to innovate. And they have continued to add services, they added crypto, I mean, we added crypto too, there are different things that we were doing, in some cases before them in some cases, you know, simultaneously and everybody else in the industry was too. But what they did really well and this is what a lot of West Coast firms do very well versus Midwest firms. The West Coast shouts from the top of the mountain of what they’re building and what they’re doing and a day on and marketing it really, really well versus Midwest firms put their head down, they build it, they don’t even talk about it till they’re done. And then they’re trying to market it. And so it’s just it’s this massive different philosophy in building businesses, and…
13:20
A media entity like Tastytrade, there’s no wiki page, like the CrunchBase. And PitchBook is pretty lean. It’s amazing how mysterious it was for so many years, you know, prior to having a unicorn outcome.
13:33
I agree. I think too, over time, we realized that, first of all, it’s a very niche business that we have. But you’re exactly right, like some of the basics around marketing and shouting and putting out there to the world what we’re doing versus just focusing on building a sustainable, profitable company. And we were profitable early, early on. It’s something that we focused on every single dollar spent versus spending our time out there marketing who we are, which you can argue which one’s better.
14:05
Well, I know what I like. I mean, yeah, a lot of people have watched the strategy of our venture firm, and they know how we kind of first built on media, but I look at the two companies and you both had a very clever way of filling top of funnel and acquiring customers. One was will give you commission free trades, give it away for free yours was creating a media entity training these people up educating them, and then they become much more sticky long term customers that are probably much more connected to your brand. But to do what Robin Hood, did you kind of have I mean, loss leader type marketing, you have to have a pile of cash. And they did. So it worked.
14:41
They absolutely did. They raised a lot of money. They had great backers, right, at the end of the day, they had a lot of additional deep pockets that they could reach into. So they did that well. I think the only thing where and they still came out of this on top, but I think the one area where they faltered a little bit. But again, they rebounded from it is when you started to really understand when they shifted from clearing through a third party to going self clearing and also really understanding the regulatory landscape, especially when they started talking about banking. This is where they sort of got out of their realm because they slept a few times and to where we were, we know that fine line you can’t cross just because we’ve been around and been in this industry for decades. But, you know, again, it didn’t crush them. It wasn’t something that ultimately put them under or anything like that. So they figured it out.
15:35
Kristi, what do you think they got wrong in the GameStop scenario? Do you think they deserve some blame here and what did they get wrong?
15:42
I really don’t think they deserve blame at all. I think when you take a step back and you look at the environment, we’re in no matter what topic, no matter what, whether its political, whether it’s trading, we are in an environment like never before with this open ability to talk about anything and everything. And when you look at regulators, regulators are not prepared to monitor all of these different social media channels. So from the standpoint of if Robin Hood didn’t even exist, I mean, this still would have occurred because of all of the social media platforms, the social media platforms didn’t exist. Would this have occurred in the same fashion, no. So, you started to look at Robin Hood, the only thing that they probably could have done better it’s more about transparency is making sure you’re transparent with your customers on what you can and can’t do and what’s actually happening in the market. Now we have a platform that allows us to talk about all those things and what’s happening and give customers the context of what’s going on Robin Hood and a number of other brokerage firms don’t have that same platform, I shouldn’t say because they do have their media arm, but were they talking about it in a way that customers needed to hear and understand. I think too, the only other thing in something we believe very strongly in is education, and really, truly helping that customer understand risk as they jump into it. And I think that that’s another area that maybe they could have done better. They did a fabulous job of bringing a lot of people to the table, but making sure they’re educated on certain aspects, I think is the other thing that the whole industry can do better.
17:33
Kristi has the high frequency trading firms and that the big market makers emerged. They’re often shaving gains from individual traders, or it seemed that way, did this present any threats to the business to this adversely impact what you’re trying to do? How did you view sort of the market makers? And I know, in many cases, their partners, so.
17:53
Exactly, right, you talked about high frequency traders, and I think they ultimately get a bad rep. But at the end of the day, when you look at these market makers, they’re providing liquidity.
18:05
right.
18:05
They’re providing the ability for the end customer, the everyday ordinary person who wants to be a self directed investor to be able to get in and out of their trade, getting in and out of their position easily. And I think they get a bad rep because of the shaving, if you will. But it’s not a bad thing, as a matter of fact, if they all went away, I think we would be in a much worse position when you look at the markets. That is one of the things that has come up multiple times with Gensler around payment for order flow. And wondering, should we get rid of payment for order flow well, in reality, we ultimately need all of those market makers. And the way that we can actually bring low or no commissions to the end customer is with brokers getting paid for payment for the flow. And as long as you have the right transparency, and as long as you have the right metrics around price improvement and quality of execution, and you have all of those things, and you’re sharing that with the customer. So they can see that it’s a really efficient process, you take out payment for order flow, I mean, there will be another way of payment form that would develop. But right now this is working, I feel like there’s a little bit of a heavy focus in the wrong area, it’s sort of like it’s an easy thing to point to. And yet payment for order flow is not the problem, that’s actually a solution that actually helps the end customer in the end.
19:37
Right. And like everything else in life, there’s a fee for it. The last threat that I wanted to discuss, we’ve gone over a few potential ones to the business over the years. And there were a lot of powerful people in Chicago that may not have wanted to see things move online, did this create any fear or any existential threats either to Thinkorswim in the early days or at Tastytrade In the early years?
20:00
There were definitely a number of folks who didn’t want to see this go see trading shift online. But Nick, there really was no way for them to ultimately block that or stop that. And so in the end, it was sort of like the you needed to join forces or you would become a dinosaur. And so it evolved over time. And it wasn’t without pushback from a number of people. Ultimately, we needed to move this direction. So they were done quietly, but it didn’t make the waves that they were expecting.
20:38
Right. You can’t really fight progress, ultimately, Innovator die. No, I’m curious, Kristi was talent ever an issue for the business having been located in the Midwest?
20:47
Great question. I would say that most firms that are seeking developers, particularly ones with any sort of talent in financial services, especially complex derivatives, they’re few and far between. There’s not a lot but talent for developers. With any board I’m on with any company. I’m involved in any startup I invest in, that’s like the number one problem is pulling in the best developer talent. So what are you gonna do? You got to go to the universities and try to bring on some of that new blood, the new talent that’s coming out of these universities. That is one of the things where Chicago is like the number two or number three producer of engineering students, so that is actually a huge plus to at least get, let’s call it the entry level developers and then shape them the way that you want them. But it’s still a difficult sale to bring somebody and when you, especially in January weather is below zero, and everybody wants to go to the west coast. But it is easier after a few years to pull them out of the west coast, believe it or not, and bring them back to Chicago.
22:02
Well, I know the tech companies are often pretty flexible about remote work and stuff. But some of the trading firms, the proper market makers, not so much.
22:13
Nick, we had a philosophy in the beginning, we didn’t want any remote workers. And even up until the pandemic, we really wanted people there. And trust me, it wasn’t for people not saying hey, I really would like to work from home. And can I have a few days work from home. And we would do that the development team had their own sort of, let’s say schedule, but the pandemic hit and it was eye opening, it was absolutely eye opening and caused a lot of good, healthy conflict and debate internally, especially between me and Tom about how productive everybody was. And in reality, I think a tremendous amount of productivity, people really got a lot done. And we could bring in more talent as well, because now we sort of opened this funnel…
23:05
I take it your side of the debate was in favor of remote work.
23:09
I was in favor of remote work, but only after I’ve experienced it myself because I too was in the office, you know, I felt like 24/7 and it was you know, whatever. But being home, I saw how much more even I could get done and didn’t have somebody walking in my office every two minutes and it was great for that. But I’ll give you the other side of the argument as to that. And this is something I 100%, Tom and I totally agreed on was the level of innovation and creativity. It was not there not to the degree that sitting in the same room or what we would call the Big Boy table, there was the big table in Tastytrade. And we’d all sit there at lunch or pop in and eat or talk for a little while are talking about an idea. And the development of some of those creative ideas literally took place people talk about watercooler talk, right we ours was the lunch table talk. But it was that creativity and the innovation, the collaboration that you just didn’t get talking on Zoom. You didn’t get the same type of thing of overhearing somebody else saying something and then having the ability to add their two cents and having things roll from there. That’s what I missed during the pandemic,
24:25
100%. Kristi, what do you think is next for crypto? Tastytrade has gotten involved in crypto to some degree. We’ve seen this recent meltdown and the failure and the ethical issues over at FTX. What’s next for the segment?
24:35
Crypto is a critical aspect of the finance industry and the future. And I think that with crypto in general being fairly new, it has still been the wild wild west without and you’ve probably heard that phrase or them put in that category before but regulators are just catching up to crypto and what needs to happen and how it needs to be monitored and regulated. Crypto itself, digital currencies itself, Blockchain itself, all of those are here to stay. And they’re going to be transformational and have been transformational already. But we need the right regulation and the right transparency. But you go back decades, and you’re gonna see the same thing around the financial markets, right? I mean, there has to be this development over time. But there definitely needs to be better regulation. But when you had the regulators fighting over who actually should be the oversight board on this, you’re like, Come on, guys, let’s pull it together. So more regulation and transparency as long as they don’t swing the pendulum too far.
25:52
Do you think crypto recovers more quickly or more slowly than the rest of the market amidst this downturn?
25:57
At the end of the day? We don’t really know what’s going to happen. But in my opinion, I would say that crypto probably recovers faster because you look at the people that have invested in crypto and the volatility in crypto has been all over the place and the newer generation traders are the ones investing in crypto more so than the, I’ll say the old school self directed investors and they don’t know what they don’t know, I feel like they have more optimism around where this could go.
26:28
They love the volatility, right?
26:30
And they love it. We all love volatility. At least derivative traders do.
26:35
Kristi, if you had one piece of advice for outsider founders, those that are not building in the Bay Area and don’t have the ideal tech resume, what advice would you give them?
26:45
And only one thing?
26:49
You’re gonna have to distill it down to one.
26:52
Okay, so first of all, I’m gonna say two because I love the concept of just do it, jump in, go do it. And but the other one is, if you really want to build an authentic, sustainable, fabulous business and culture, leave your ego at the door.
27:06
A lot of current day investors. VC investors to clarify in Chicago, in the Midwest at large don’t realize that sort of the founding investors wore the traders when I talked to a bunch of mentors in Chicago that kind of taught me the VC business, they often came from the pits, and some of them moved on to online trading. But these were the original sort of folks that had the risk appetite, had some cash and kind of kick started the Chicago ecosystem in the early Groupon, GrubHub, Braintree, Echodays. I’m curious though, maybe this is the reason I don’t want to answer my own question. But I was always curious why you did Bootstrapping, like I loved Bootstrapping in America. For the audience here. It’s this program daily, I think a daily program where you’d interview some of the best entrepreneurs, in some cases, investors, and I loved it. I’ve been on the show once. I was always curious why you did that. Because it’s different than trading.
27:55
Bootstrapping in America was created sort of as our give back to the community, being entrepreneurs ourselves. We had a platform to be able to share these stories. We have this online media company, and so early on, it was just set up as something fun for us, but also our give back to the community. So we’ve done over 2000 interviews, and I personally, Yeah, which is really crazy when I look back at it, but
28:26
I’ve done a lot Kristi, but you put me to shame.
28:30
Well, and I’ve personally, so Tom did the first handful of years. So…
28:34
That’s right!
28:34
For the first 1000. And then I did the next 1000.
28:37
Tony was there throughout. And listen, Tony is the consummate comedian, just by his nature. He’s fun and keeps it light. And he’s really a wonderful, wonderful co host. But anyway, so we did this over that timeframe. But the one thing I’ll share with you about me is I looked forward to that every single day. It was this interaction where I had the ability to learn something new or confirm what I thought I already knew about entrepreneurship or building a company or whatever. And you just got the chance to meet a lot of great people like yourself, it was really fun. And only recently with my exit from IG group and Tasty I now have handed it over to Dylan Ratigan. So I don’t know if you know Dylan from way back when he was with MSNBC and CNBC, and he was a commentator, investigator, you know, on TV around finance. So we sort of had brought him in over all these years after he left media. He’s a really great host and co host, but it was something you’re exactly right. It was not trading related. But it was about empowerment and sort of sharing. It was with our same foundation philosophy about empowerment through information.
29:59
Amazing that you’re passing the mic on. And I want to get back to Casey and Robin Hood and some other items, but any salient takeaways or lessons you learned from interviewing all these great entrepreneurs?
30:10
Oh, my gosh, yeah, plenty, but the one resounding message, because a lot of times, you know, I go through and at the end of the interviews, a lot of times I would ask, you know, is there one piece of advice that you would give to somebody who wants to start a company and a disproportionate amount of time what it was said, Just do it! Like Don’t overanalyze it. Don’t overthink it, like jump in and you’ll figure it out. And hands down that resonated with me. First of all, I love Nike, and I literally on my workout room at home, I have the words “Just do it!” on my wall. And so it is also a philosophy that I live by. So to hear that time and time again from multiple CEOs and founders really resonated. It’s funny though, I’ll share with you two other things. One is is when we would have restaurants on and I’ve asked them that same question. They’d say, Don’t do it. Really, because the restaurants are tough business, you know, the margins are razor thin, and really, it’s something that you’re putting your whole self into. So you just have to be prepared for that. So for whatever reason, the restaurant business, right? Continually gave that answer. And then the other thing is, when I had VCs or private equity firms on, I’d like to ask the question to them, is it? Are you investing in the founder? Or the idea? Like if you had to pick one? What would that be? So let me pause first, before I tell you what the and tell your viewers you know, or your listeners, what the answer is, what would you say? Is it do you guys invest in based off of the idea or the founder?
32:00
Well, the cop out answer is both. But we have a heavy bias for the founder.
32:04
Yeah, yeah. And that is the resounding answer that I got a few times I got “idea”. But a majority of the time, it was the founder that you’re investing in, because it’s just like, I think back to even when we created any of our businesses, it was, you know, there wasn’t a perfect plan. But you sort of have, if you have confidence in the founder, they’ll figure it out. And you can help them figure it out if you’re investing in them.
32:31
Well, and to your point, like there are categories, and there are asset classes, and there are segments that don’t lend themselves well to returns in multiples in margins, right? And so if an investor is doing their job, they’re probably pre filtering and deciding what areas and categories of markets to invest into. And then when the best founders show up, it can be a slam dunk. Love it. Kristi, do you have any habits, tactics or techniques that are a secret weapon?
32:58
That’s a good question. I would say being genuine and transparent is probably one of the most valuable tools throughout my whole career. And has sort of helped open doors and has gotten me invited to the table a number of times is just having a genuineness and authenticity. That is there’s no hidden agenda, you’re going to know why I’m here and what I’m doing.
33:26
Amazing. And then finally, here, Kristi, what’s the best way for listeners to connect with you and follow along with your efforts?
33:31
Yeah, absolutely. Well, you can follow me on Twitter @KristiRossX, and certainly I would say that even though I am no longer with Tastytrade. I mean, it is my family and people should go check out Tastytrade.com and watch Tom and Tony and really learn more about the trading industry.
33:52
Well, folks, she is Kristi Ross, one of the top entrepreneurs and founders in all the country. This has been a sincere pleasure for me to do this. Kristi. I’ve hoped to do this for many years. Congrats on all the success and hopefully before next time we have you on the show, we’ll have Nike as a sponsor and all “Just do it.
34:08
Thank you so much for having me, Nick.
34:11
Thank you, Kristi.
Transcribed by https://otter.ai

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