In the Gray Area: Jason Wilson

  • Season 2, Episode 8
  • May 3, 2022
  • 29 minute listen

In the Gray Area: Jason Wilson

Bills are due. Things are happening. I'm staring into the abyss at nighttime. It's frightening.


“Sometimes it's a matter of never giving up.” But is it? What is the gray area? How long should you try to survive there? This is a story about perseverance. But what does the research say about how long an entrepreneur should persevere? What drives them to “stick with it”—and do they, occasionally, stick with it too long?

Episode Description

In 2014, one of his coffee shops failed—the one on St. Louis’ underserved north side. Some of the workers he held over after acquiring his coffee brand were sabotaging customer relationships. He couldn’t get bank loans. Checks were bouncing. Advisors pushed him to quit. Don’t throw good money after bad, they said.

But Jason Wilson, owner of Northwest Coffee Roasting Company, decided he had to exist in what he calls “the gray area.” He had to push through, stay the course and survive on self-confidence, his belief in his product—and a little goodwill from friends.

“Had I gotten out in 2014 when everyone told me to, I would have missed out on this great opportunity,” Wilson said. “You have to be comfortable living in this gray area.”

Seven years later, this is “the great opportunity”: Wilson’s one retail restaurant location now brings down more revenue than two stores did in 2018. He’s got wholesale distribution deals for the coffee he roasts locally. He’s on the verge of selling his coffee across the Schnucks supermarket chain in St. Louis. He’s about to open a new location in the suburban community of Webster Groves.

“People said you should just shut it down and get out of it,” said Wilson, who earned his executive MBA from WashU in 2008. “I never believed that. Sometimes it's a matter of never giving up.” But along the way, Wilson had to deal with:

  • A business failure that hurt his opportunity to borrow.
  • A business climate that historically hasn’t favored Black business owners.
  • Questions of sabotage from holdover employees after he acquired Northwest Coffee.
  • Personal investments from friends and his own pocket.

He credits Midwest Bank Centre for creating a relationship and, in his words, “giving me room to (mess) up.” He also credits a mentor named David Price, a Harvard Business School-educated former executive at Monsanto and BFGoodrich.

Related Links


This podcast is a production of Washington University in St. Louis’s Olin Business School. Contributors include:

  • Katie Wools, Cathy Myrick and Judy Milanovits, creative assistance
  • Jill Young Miller, fact checking and creative assistance
  • Hayden Molinarolo, original music, sound design and editing
  • Mike Martin Media, editing
  • Sophia Passantino, social media
  • Lexie O'Brien and Erik Buschardt, website support
  • Mark P. Taylor, strategic support
  • Paula Crews, creative vision and strategic support

Special thanks to Ray Irving and his team at WashU Olin’s Center for Digital Education, including our audio engineer, Austin Alred.

Additional information

Please subscribe on your favorite podcasting app to be notified when each new episode of On Principle is available.