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!

Sam Rosen | Deskpass

Sam Rosen is the founder of Deskpass. They are an affordable membership that allows you to work at over 25 co-working and collaborative workspaces in the Chicago area. Serial entrepreneur, Sam Rosen, launched Deskpass in early fall of 2015, and already has a waiting list to purchase a membership.

Jay Swoboda | Dabble

Jay Swoboda is the CEO of Dabble. Dabble is a digital marketplace for in-person classes and workshops taught by anyone, at anytime, and anywhere. Over 350 various programs are offered in Chicago, Denver and St. Louis, with several more cities coming aboard.

Eric Steigelman | Bonfire Wines

Eric Steigelman is the CEO and Founder of Bonfire Wines. They offer affordable wines which come in a unique eco-friendly pouch which fits hassle-free into coolers and refrigerators, and chills in 65% less time than a traditional bottle.

Tim Barry | VillageMD

Tim Barry is the CEO of VillageMD.  They are a primary care-led healthcare delivery system that brings superior clinical results to the communities where VillageMD works. In a little over two years, they have raised $36M in funding.

Jason Seiden | Brand Amper

Jason Seiden is the CEO and co-founder of Brand Amper. Brand Amper helps companies partner with their employees to share their stories that let both employees and employers look better together in terms of company branding and recruitment.

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!