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
Join the FREE mailing list!
Get behind-the-scenes content from You Are A Lawyer.
1) Visit www.youarealawyer.com
2) Add your email address to the Subscribe pop-up box OR
3) Enter your email address on the right side of the screen
4) Get emails from me (I won't fill your inbox with junk)!
Interact with You Are A Lawyer
Kyla Denanyoh hosts the You Are A Lawyer podcast.
Follow the podcast:
YouTube: https://www.youtube.com/@youarealawyer
Website: https://www.youarealawyer.com
Popular Podcasts
On Purpose with Jay Shetty
I’m Jay Shetty host of On Purpose the worlds #1 Mental Health podcast and I’m so grateful you found us. I started this podcast 5 years ago to invite you into conversations and workshops that are designed to help make you happier, healthier and more healed. I believe that when you (yes you) feel seen, heard and understood you’re able to deal with relationship struggles, work challenges and life’s ups and downs with more ease and grace. I interview experts, celebrities, thought leaders and athletes so that we can grow our mindset, build better habits and uncover a side of them we’ve never seen before. New episodes every Monday and Friday. Your support means the world to me and I don’t take it for granted — click the follow button and leave a review to help us spread the love with On Purpose. I can’t wait for you to listen to your first or 500th episode!
Las Culturistas with Matt Rogers and Bowen Yang
Ding dong! Join your culture consultants, Matt Rogers and Bowen Yang, on an unforgettable journey into the beating heart of CULTURE. Alongside sizzling special guests, they GET INTO the hottest pop-culture moments of the day and the formative cultural experiences that turned them into Culturistas. Produced by the Big Money Players Network and iHeartRadio.
Crime Junkie
Does hearing about a true crime case always leave you scouring the internet for the truth behind the story? Dive into your next mystery with Crime Junkie. Every Monday, join your host Ashley Flowers as she unravels all the details of infamous and underreported true crime cases with her best friend Brit Prawat. From cold cases to missing persons and heroes in our community who seek justice, Crime Junkie is your destination for theories and stories you won’t hear anywhere else. Whether you're a seasoned true crime enthusiast or new to the genre, you'll find yourself on the edge of your seat awaiting a new episode every Monday. If you can never get enough true crime... Congratulations, you’ve found your people. Follow to join a community of Crime Junkies! Crime Junkie is presented by audiochuck Media Company.