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!

Dustin Walsh | Hooray Learning

Dustin Walsh is the co-founders of Hooray Learning. The company is launching its first product, Hooray Writing, which is a richly featured online writing portal enabling students to create stories of all kinds. When children are taught to write creatively at a young age, the probability of academic success rises exponentially.

you don’t really have a right to complain, unless you put your money where your mouth is
— Dustin Walsh

Tim Haitaian | RedShelf

Tim Haitaian is the co-founder of RedShelf. The company is a leading supplier of digital learning materials, dedicated to providing paramount technology to the learning community in order to accelerate the transition to digital. They collaborate with publishers, institutional bookstores, and other content creators.

less than 3% of the university book market is electronic sales
— Tim Haitaian

David Greenberg | Updater

David Greenberg is the CEO and Founder of Updater. The company makes moving easier for the 45 million Americans relocating every year. Updater users seamlessly transfer utilities, update accounts and records, forward mail, and much more.

when you use our site we have a moving concierge that you can tell them what you want to transfer, disconnect, and everything else
— David Greenberg

Glen Tullman | Livongo Health

Glen Tullman is Chairman and Chief Executive Officer of Livongo Health, which primarily focuses on patients with diabetes. The company believes people with chronic conditions such as Type 2 diabetes should spend less time on the disease and more time living life.

our health...nobody is keeping an eye on it, wouldn’t you love to know if somebody is heading in the wrong direction?
— Glen Tullman

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!