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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