Similar to Jim Cashman, fans may have seen Flo from Progressive — actor Stephanie Courtney — in her extensive television work. Before breaking through on TV, both actors cut their teeth at The Groundlings, where they honed their improv skills. “You meet a bunch of people that don’t just become your friends but your comedic colleagues,” Cashman told the Los Angeles Times in May 2014, when he was still a member of the comedy troupe. “It’s who you turn to creatively,” he added.
Well before she became known for her Flo character, Courtney struggled to make a living while trying to break through in TV and commercial work. “And then once I was in the Groundlings and I became a company member, we would teach. Before that, I delivered the Zone Diet,” she told Backstage in May 2020 when discussing her early days as an actor.
Thanks in part to the connection Progressive’s two stars, Flo and Jamie, had to the comedy program, the insurance company made a sizeable donation to The Groundlings in February 2021. The donation was made to the Groundlings Diversity Scholarship which would help some 300 students participate in classes and receive private teaching at the impro school. “So many good things in my life can be traced right back to this theater,” Courtney said in a statement at the time, per Broadway World. Not only did Cashman have a connection to Flo from The Groundlings, but his wife was also a member.
