Join CT Mirror Policy Editor Erica E. Phillips as she sits down with Connecticut’s most successful entrepreneurs to explore their origin stories, how they turned their first dollar, and why Connecticut was the place to make it happen.

Past This Could Work Events:

WATCH: May 28 2025: Felicia Rubinstein of HAYVN Coworking, Darien and Greenwich

Felicia Rubinstein began her career as an engineer at GE and Apple, where she pioneered one of the company’s first-ever job share programs before flexible working was a trend. Now as an entrepreneur she’s on a new quest: engineering a better way to work. In 2019, she founded HAYVN, a women-centered coworking space in Darien that helps people connect, create and get stuff done.

WATCH: Apr 30 2025, Jason Sobocinski of Haven Hot Chicken, New Haven

New Haven-born Jason Sobocinski has parlayed a series of restaurant jobs and a Master’s in Gastronomy from Boston University into an entrepreneurial career in food and beverage – from the cheese-focused Caseus Fromagerie Bistro to Black Hog Brewing, with several other ventures in between. His latest is Haven Hot Chicken, a rapidly-expanding Nashville-style Hot Chicken concept that was named by Inc. Magazine as one of the fastest growing companies in the U.S.

WATCH: March 19, 2025: John Walker and Bill Shufelt, co-founders of Athletic Brewing Co.

Driven by a mission to make non-alcoholic beer mainstream, Bill and John first began test-brewing in a garage in Connecticut. One hundred home-brewed batches later, they had perfected their process and refined their flavors. Then they built an entire business around it; within a few short years it’s become the world’s largest dedicated non-alcoholic brewery.

WATCH: Jan. 14, 2025: André Swanston of Swanston Organization, Stamford

UConn graduate and serial entrepreneur André Swanston achieved a historic nine-figure exit with the sale of his data company, Tru Optik, to TransUnion—making him one of the few Black Americans to reach such a milestone. Now, he’s channeling that success into groundbreaking ventures that transform the way content creators, brands, distributors, and consumers engage across advertising and entertainment.