#106 - The Lawyer Who Went Back to School to Learn How to Be an Entrepreneur

At 40, Chris Keefer had everything lawyers are supposed to want: partner track, jury trial wins, Indiana Supreme Court experience. He also had something else—a growing certainty that litigation was slowly crushing him. When the celebration after his biggest courtroom victory felt hollow, he knew something had to change. So he made a decision that seemed crazy to everyone around him: sell the house, move his family of five to Oregon, and spend 18 months earning a master's degree in sports product management.

In this episode of Lawyers Who Learn, host David Schnurman explores how Chris discovered that law school never taught him the one thing he needed most—how to be an entrepreneur. His journey from the University of Oregon back to legal practice wasn't a straight line. It included living apart from his wife Garetta and three young kids for a year, sitting face-to-face with her in a WeWork fishbowl managing a fledgling solo practice, and experiencing panic attacks while their savings dwindled. The turning point came from a couple unexpected sources: a coffee meeting with a colleague trying to understand the types of services Chris was providing, and then a book called Toothfish that taught him to stop competing in crowded markets and create his own.

Those insights led Chris to "preventive law"—a framework for helping businesses peek around corners before legal problems materialize. But his real breakthrough was realizing that entrepreneurs who need legal help most can't afford traditional hourly rates. His solution became The Legal Wellness Kit, an Amazon #1 new release and bestseller that delivers hundreds of hours of practical guidance for the cost of a brief phone call with a big firm attorney. Today, as Associate General Counsel at Pacific Seafood and principal of Keefer Strategy, Chris continues building his practice while eyeing his next chapter: more writing, more teaching, and paying forward the knowledge he wished he'd had at the start. His story reveals that mid-career reinvention requires more than courage—it demands partnership, resilience, and the willingness to get comfortable being uncomfortable even when everything feels uncertain.