Along with sharing a few of my favorite Bootstrapping In America interviews of last year, I thought my debut on the tastytrade blog would be a great chance to talk about how BSA came to be in the first place. 

The Genesis of Bootstrapping in America

It all started on a cold, fall day in Los Angeles. The sun was out and it was around 72 degrees…remember this is LA, not Chicago. I was surfing the Internet searching for old friends to see what they were up to.

Much to my surprise, I saw my very old friend, Tom Sosnoff, talking in a studio to another old friend, Tony Battista, on this very site, They were throwing gibes at each other the same way we would years ago while talking about options trading, stocks and futures.  Watching them brought me back to when Tom and I stood next to each other trading in the OEX pit some 30 years ago.

I went back the next day to see what the first hour was like… Tom just happened to tell a story about an old buddy of his (without mentioning names) it was a pretty funny story. And who do you think it was about? Long story short, I don't think I tuned into tastytrade that day on accident. After hearing the story, I sent Tom an email for the first time in a very long time. He sounded very happy to hear from me. We started talking about the show and I shared some ideas with him. 

I thought the show could use something different. I suggested adding a little variety to give the audience a break from all the trading stuff, while still keeping the content informative and relevant. Around November of 2011, I pitched Tom an idea about doing interviews with entrepreneurs, business people, or anybody that had an interesting and inspirational story to tell. And that was the birth of Bootstrapping in America. You’ve heard it a million times; do what you like, and the rest will follow... or something like that. You get the point.  

Tom asked me if I would give it a shot. I had never done anything like BSA before, but I was always curious about the amazing things people are capable of… Steven Hawking, Nelson Mandela, to name a couple. I always believed in the uniqueness of individuals and loved the idea of creating a show that focused on that uniqueness. So I decided to give it a shot. 


Starting out, I would get one or two guests a week. It certainly wasn’t easy, but it was fun and interesting. Soon we were up to three guests a week, and after about six months, I told Tom I thought that we could run the show on a daily basis. Unless an unexpected cancellation has occurred, we have had a guest on every single day that we’ve been on the air since then.

Now, ready to start our fourth year, we’ve had on entrepreneurs from all levels and walks of live; executives at Google, Microsoft, Groupon, J.B. Pritzker, our now resident friend and guest, Howard Tullman, not to mention, young professionals from companies less than a year old. We've been able to feature some amazing stores from people who have done things like successfully launch a business from their garage, and then sell it for over a billion dollars. Bootstrapping In America features guests who have changed the world. 

It’s been a great ride so far and I'd like to think that we haven’t even gone into second gear yet. 

BSA has taught me to believe in the uniqueness of individuals, and of course, to always make sure to spend time checking up on old friends.
— Jules Weinstein (BSA Creator)

3 of my favorite Bootstrapping In America Visits from last year

We've had so many amazing entrepreneurs and guests on tastytrade over the past few years that narrowing down a few of my favorite segments was no easy task. After whittling it down to 200 or so, I decided that I’m just going to have to dig into the archives and find new favorites to share with you more regularly. So be on the lookout! I'll be going retro on you every couple weeks or so with interviews from the past, maybe even some from the humble beginnings of the show. I'll share early interviews with CEOs whose companies have taken off or are making headlines right now.

For today, here are a few interviews from 2014 that really resonated with me. Don’t be offended if you’re not on today’s list. There's more to come! 

J.B. Pritzker

J.B. Pritzker

J.B. Pritzker | Co-founder of Pritzker Group

Though J.B. came on the show to talk about the Chicago Summit, the interview ended up becoming far more personal.  He shared stories about his father, who taught him about business and helped him become the successful person he is today. You might have heard of J.B.'s dad... he started the Hyatt Hotel chain.  I wish I were a fly on the wall then. 


Rick Bayless

Rick Bayless

Rick Bayless | American Chef  

Rick Bayless was one of the first high-profile guests we welcomed on to tastytrade and Bootstrapping In America. The studio was buzzing with excitement the morning he came in. One of my favorite memories of having these two on the show is hearing Rick talk about going to the White House to cook for the President and his house guests, who just happened to be the President of Mexico and his wife... No pressure there.  

Steve Dolinksy

Steve Dolinksy

Steve Dolinksy | Food Reporter & Blogger

Steve Dolinsky is a celebrity in Chicago foodie circles thanks to his Hungry Hound Restaurant reviews for ABC7 and his own personal blog. He turned out to be an awesome guest and overall, a great friend of the show. Steve and Rick both came on BSA together, which made for an amazing interview.



Rahm Emanuel

Rahm Emanuel

Rahm Emanuel | Chicago Mayor 

The Mayor has always worked very hard to attract new companies to Chicago, which is something we appreciate at tastytrade and dough as members of the thriving tech and startup community in the Windy City. One thing the Mayor said that made a lot of sense to me was, “I'm not here to create jobs, I'm here to provide the best advantages for companies to come to Chicago so they can create the jobs.”  


What are your favorite episodes of BSA? Who would you like to see on the show? How about you?! Drop us a note in the comments below, send a Tweet to @BoostrappingIA, or send an email to

Tune in to catch a brand new interview on Bootstrapping In America Live Monday - Friday at 9:25am CT on!