After selling your online brokerage firm, thinkorswim, in 2009—a deal valued at more than $600 million—you’ve founded TastyTrade Inc., an internet based financial news channel with a comedic twist. How did you hook up with your “Get Tasted” co-host Tony Battista?

Tom:

We started trading together in 1980, believe it or not. So we’ve known each other for about 30 years. After we built thinkorswim I tried to get Tony to come work with us and he turned me down probably three times.

Tony:

It’s like all of the people he tries to date, they usually turn him down three times and by the third time you give it up. That kind of thing.

Tom:

So the third time he took the job and he worked in one of our education groups and when I left to start TastyTrade I asked if he wanted to come on board. I wasn’t sure of the role but then it all just morphed into what we are doing right now!

You’ve said you aren’t interested in partnering with a more mainstream media company despite the fact it could bring you more exposure. What are your reasons behind this decision?

Tom:

Right now we’ve bought two companies and we’re about 40 people strong in the process of growing our own business while totally controlling it. So we’ve raised some money and created some revenue already. It’s pretty impressive what we’ve done in a short period of time but we are hoping at some point to make the right distribution deal, we just don’t think it’s traditional media.

Your show has been described as “The Daily Show” for investors. Was that your intention?

Tom:

I’ve always been a fan of Howard Stern’s show and grew up listening to sports radio and stuff like that. It took us ten years to build the technology to change the online broker business and we couldn’t do this show until we could figure out how to make the business work in the first place. So we think we’ve commoditized the online broker business and left it in an interesting state and now we’re in the process of trying to do the same thing to media content.

Outside of work what do you like to do?

Tom:

Nothing.

Tony:

He’s a Sagittarius. He’s being modest. He likes long walks on the beach, occasionally he’ll have a pulled pork sandwich if the urge comes about.

We’ve seen your TastyTrade advertising behind home plate at U.S. Cellular Field. What is your favorite Chicago sports team?

Tony: 

You know, that’s an interesting question. He wants ballet to become a sport but they are having a hard time pushing it through.

Tom:  

So my favorite Chicago sports team is… Wow, that’s a tough question because I’m really a sports junkie. I didn’t grow up as a Chicago sports fan so it’s hard but I would say when it all comes down to it I’m a Bulls fan. I kind of grew up in Chicago in the Michael Jordan years but I like the Bears too.

Do you ever splurge on yourself after making a big trade?

Tom:

I don’t buy myself stuff. When I’m on a really bad trading streak I used to buy myself a dog. I’d buy dogs or cars but no, I’ve never really bought myself anything. I mean look at me, this is from Old Navy.  I don’t own anything fancy.

We originally met you after you spoke at Techweek where you sported the same t-shirt and beret. Is this how we can always find you?

Tom:

I wanted to run the first billion dollar company where I never wore a suit or a tie ever.

What is the best advice you can give to young entrepreneurs?

Tom:

It’s such a stupid old saying but the people who work their butts off get paid. At 25, at this point, if you bust your butt at some point you are going to get paid because you will eventually make some break for yourself.

As a passive investor and active trader, how do you know when someone has an idea worth investing in?

Tom:

You have to think it out. You have to at least be able to articulate how to monetize it because investors love ideas but there are a lot of ideas so there has to be something with your idea. Most people can’t articulate their vision or really don’t have an idea. People that do, you know immediately. There are a lot of people who are really smart and really smart doesn’t matter. Smart matters but really smart doesn’t. So one of the things we learned over time was to weed out smart and the smart that can actually deliver. It’s the doers versus the dreamers whole thing.

Was it your career that originally brought you to Chicago?

Tony:

The lack of career.

Tom:

The same reason you came here. I was 22 and just packed up the car with $1,000 in my pocket. I had my apartment and I had two months worth of rent and had to make it! My goal is to work until I die. Like I don’t want to play golf.

What are your favorite restaurants in the city?

Tom:

I don’t eat out very much because I’m a health freak. Just kidding. I’ve only eaten at every restaurant in the city I think. If I were to pick what’s the best restaurant in the city right now I’d say Girl and the Goat. I think it’s the best restaurant in the city. I live in Wrigleyville so I live by Fish Bar and DMK so I go to those places all of the time. I’m a neighborhood junkie.

Tony:

He’s also not built for speed, so if he has to go somewhere if it’s closer to the vicinity more than anything else it works best. My favorite restaurants? Wherever Tom will take me. That’s just how the agreement works out.

Tom: We buy lunch for everyone every day. I have this theory that nobody can ever leave. You come to work and you can’t leave because you lose all of this productivity when people go out to lunch. I surround myself with workaholics; I like the mentality of workaholics, so everyone here is basically a workaholic.

What is something you wished you would have known in your 20s that you know now?

Tom:

Keeping all personal life out of this, I never thought about building a business outside of trading because trading was something we did really well. I never thought about building something until I was 40 so I kind of regret not starting that process earlier.

Tony:

I think scalability was something I learned from Tom, he introduced me to it. Being a trader myself you always did your own thing and only relied on yourself and maybe you backed another trader or two or three but few people scaled it up.

Tom:

Most people are scared of scale and the truly amazing entrepreneurs do not scale by default. You scale because that is the level of risk you are comfortable with and it is a mechanism in your brain that sends a message and lets you go to that level. It’s really hard to get people who aren’t comfortable with scale to get into scale.

If you could have a drink with anyone, who would it be?

Tom:

So if I had one person to choose? Crazy but I think I would probably go with Mel Brooks if he’s not senile by now. If not Mel Brooks, I would either go for Larry David or Seth MacFarlane. I think Seth MacFarlane would be my first choice in today’s world. In the business world it would probably be Mark Zuckerberg.

Photography by Neal Agustin