How to Adapt Your Career for the AI Era feat. Steven Cunningham

Steven Cunningham is a lawyer-turned-entrepreneur and the founder
of Simple Academy, a company that helps teams boost performance
and productivity using AI tools. In this episode, Steven talks
about what it means to pivot early, lean into innovation, and
reimagine what legal training can prepare you to do. Whether
you're AI-curious or career-curious, Steven Cunningham’s story
offers both inspiration and practical insights.



LAWYER SIDE HUSTLES


Steven’s “side hustle” evolved into a full-time business: Simple
Academy. It began when he was running a book-summary service and
saw the writing on the wall—AI could (and would) make his
existing business obsolete. Rather than panic, Steven leaned in.
He became an early adopter of AI tools, studying how they worked
and where they could add value. Soon, he was helping other
business owners understand how to use AI to improve performance.
“It became an interest. I love what we’re doing. It fulfills
every self-actualization need that I have… but it wasn’t why we
started it,” expresses Steven Cunningham in Episode 193 of You Are
a Lawyer.

Simple Academy now helps teams reimagine their workflows using
AI. From executive coaching to custom prompt design, Steven and
his team teach organizations how to think differently about time,
value, and output. His legal background—especially his ability to
communicate clearly and break down complex tools—makes him an
ideal teacher in this fast-changing space. For Steven, the hustle
isn’t just a business. It’s a creative outlet, a problem-solving
lab, and a way to show that legal skills can drive innovation,
not just interpretation.








LISTEN TO LEARN


How lawyers can use their research and analysis skills to
lead in tech and AI

What it means to leave law early and still use your training
meaningfully

Why understanding behavior change is key to AI adoption






WE ALSO DISCUSS


The mindset shift lawyers need to make when transitioning to
tech

How to talk to resistant clients and help them trust AI tools

What AI will—and won’t—replace in the next decade






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