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.
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Steven Cunningham’s legal career was intentionally brief—but deeply informative. After articling in Ontario, and officially being called to the bar, he practiced for just one week before deciding to walk away from traditional law. This wasn’t a decision made lightly. Throughout law school, Steven had a sense that he might not want to stay in the legal profession long term. Instead, he saw law as a foundation—something that could support a much broader, more creative entrepreneurial path. His interest in business, technology, and systems-thinking led him toward entrepreneurship before his legal career even began in earnest.
“I think I saw the writing on the wall before I got in… I was officially a lawyer for one week," shares Steven Cunningham on You Are A Lawyer.
Since leaving law practice, Steven has built multiple ventures, each one informed by his legal mindset. Most recently, he launched Simple Academy, a company that helps organizations increase productivity and transform their workflows using AI. While he’s no longer writing legal memos or working with clients on contracts, Steven’s legal education shows up in everything he builds—from how he structures ideas, to how he explains complex tools, to how he leads.
Steven didn’t go to law school because he dreamed of being a lawyer. Instead, he saw it as a powerful way to learn how to think, how to analyze complex information, and how to build a strong intellectual foundation. Coming from a background in business and communication, law school seemed like a tool that could sharpen those instincts even further. And while he wasn’t entirely sure what his legal future would hold, he committed fully to the experience.
“The law degree gave me the ability to analyze a lot of information quickly," reflects Steven Cunningham on Episode 193 of You Are a Lawyer.
He also went to law school to fulfill a promise to his father—to finish the program, even if he didn’t intend to stay in practice. Steven values the structure and cognitive rigor that legal training instills. The degree, he says, gave him a methodical way to think about problems, construct arguments, and see the world through a lens of logic and systems. That training continues to serve him, even as he’s building products and teaching AI instead of arguing cases.
Legal education, Steven Cunningham says, isn’t just about preparing you for courtrooms—it’s about giving you a framework for decision-making. Whether it’s structuring a company, designing curriculum, or navigating uncertainty, Steven’s law degree remains central to how he thinks. It helps him build credibility, make strategic decisions, and communicate with clients in a way that feels confident and grounded.
“There's going to be so much opportunity for everybody to reimagine how they add value to the world," shared Steven Cunningham on Episode 193 of You Are a Lawyer.
Steven encourages current and former lawyers to reconsider the boundaries they’ve placed around their degree. There’s no single path for a JD. If anything, the value of legal education is expanding as fields like tech, policy, and entrepreneurship become increasingly complex. Steven’s message is simple: if you can think like a lawyer, you can lead in just about any space.
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.
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Steven is not currently licensed to practice law.
Learn more about Steven | Simple Academy
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