Bootstrapping In America is tastytrade's spotlight on the best and brightest of the entrepreneurial community in Chicago and beyond. Meet the innovative men and women leading the companies featured in this week's episodes!

Craig Williamson and John Godwin | Schlep Inc. 

John Godwin & Craig Williamson are co-founders of Schlep, a company that provides people with the ability to link up with each other to assist in local moves without hiring a large moving company. 

We spent all of 2014 testing and experimenting how we want to go about this because it’s such a big idea.
— John Godwin

Chris Rooney | Digital Bridge Solutions

Chris Rooney is the founder of Digital Bridge Solutions, a company that builds commerce and content experiences online for mid-sized companies. Some of their clients include Radio Flyer and Northwestern Memorial Hospital.

[On entrepreneurship] - If you’re not in it because you love it, and because you’re driven, it may not be the best choice for you.
— Chris Rooney

Brenna Berman | Innovation and Technology Commissioner, City of Chicago

Brenna Berman is the Innovation and Technology Commissioner for the City of Chicago. She focuses on IT consolidation and performance management.  She has played a critical role in providing the skills and expertise to implement Chicago Mayor Rahm Emanuel's commitment to improving data and technology.

Entrepreneurship definitely matters in driving the city of Chicago.
— Brenna Berman

Ted Devine | 

Ted Devine, has led Insureon since 2011.  The company focuses on small and micro-businesses, and is the fastest growing insurance company in the country.  Last year alone, they tripled their revenue.

We drive over 150,000 businesses to our website through SEO and SEM.
— Ted Devine

Rick and David Rodriguez | 

Rick and David Rodriguez are the owners of WHISK, which was named one of the best new restaurants in Chicago in 2014.  They fuse classic American dishes with Mexican culinary staples.

In ten months, we’ve done more than we’ve done in ten years.
— Rick Rodriguez

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 @BootstrappingIA, or send an email to

Tune in to catch a brand new interview on Bootstrapping In America Live Monday - Friday at 9:40am CT on!