Speakeasy podcast adds vulnerability to the after-work cocktail

In a posh bar offering elevated American fare, two women in the middle of their careers meet for “Boss-lady drinks.” Jen Estill owns her own creative consulting business. Across from her sits Karen Stefl, friend of 20 years and principal at a media boutique. Over herbal tonics the women talk strategy for their latest creative endeavor: a work-lifestyle podcast. 

Their opening pitch? An emphatic “We’re sh*t shows too. We gotcha.”

For almost two years, “Speakeasy” has created a space to join business gurus for drinks twice a month. The local creative-business owners, friends and co-hosts started their biweekly podcast to have honest conversations about their journeys. Stefl is the principal of Render Studios and Estill is the principal and creative director for Redhead Design Studio.

According to the entrepreneurs, rather than showing vulnerability, it is common for business leaders to use impression management — also known as “fake it till you make it.”

In the episode titled, “Hitting Reset After Hitting The Brink,” Stefl and Estill discuss how stereotypes surrounding women intensify their anxiety to be “perfect” business leaders.

“We’re not always practicing the things that we know are the right things,” Stefl said in the episode. “And that means to do the things to help me lose those extra pounds would mean this Tequila Sunrise would be full.”

Occasionally, they invite local female leaders to share their stories such as Kelly Rossman-McKinney, the communications director for the Michigan Attorney General, and State Rep. Sarah Anthony.

Stefl came from a household of self-starters who “were never very good at following rules.” In 1995, she interned at Such Video, a local multi-media production company. Two years later, Stefl graduated from Michigan State University and worked full-time at the media boutique.

In contrast, Estill struggled finding a career path that encompassed all her interests. Before graduating with a journalism degree in 1995, she contemplated studying anthropology and biochemistry.

Realizing she was more interested in designing pages than hunting down quotes, Estill spent the next five years working in the creative department at an advertising agency.

After discovering industries within their wheelhouse, both Estill and Stefl learned another crucial lesson in the Art of Being a Multihyphenate: knowing when to go off on your own.

Around the early 2000s, both Estill and Stefl felt like they hit a wall or “glass ceiling” in their careers and needed to make a serious pivot. For Estill, it was entering the freelance world while Stefl wanted her own stake in the rebranding of Such Video. Years later, Estill started a multi-disciplinary studio in Old Town and Stefl — with the help of her business partner David Such —transformed Such Video into Render Studios.

Estill knew they had a potential audience in Lansing where the bulk of businesses have fewer than 20 employees. They were both surprised to see the positive responses from men and younger audiences seeking advice on everything from work-life balance to trends in the creative industry.

While the two entrepreneur-on-air personality-media strategist-moms share with listeners what they’ve learned during their journeys, they are hesitant to call themselves “experts.”

“I think feeling confident in your skill set is an evolution,” said Estill. “In some ways, I don’t think I started thinking of myself as an expert until someone called me an expert.”

Experts or not, both Red Head and Render Studios have garnered statewide clientele, including Michigan State University, United Dairy Industry of Michigan, Northern Initiatives and Ellie’s Place.

“We’re in the business of helping people look good and being put together ourselves,” Estill said. “What we hope to do for our listeners is take off that veneer and talk about how difficult it really is and take off that stress to help normalize it for people a little bit.”

Speakeasy Podcast

New episode first and last week of the month

Listen at soundcloud.com/easyunderground

Drink recipes and more at thespeakeasypodcast.com