Teaching law through experience

In this episode, I speak with Charlyn Ho, a former Navy Supply Officer, corporate law partner, and now the founder of Rikka (incl. Rikka Academy). Charlyn shares how she’s turning years of experience into structured, practical training for early-career lawyers—blending mock negotiations, real-life analogies, and AI feedback loops to close the training gap in legal education.

Whether you're in law, education, or any profession where practice matters more than theory, Charlyn’s approach offers an inspiring model!

🧠 Topics covered

• From military contracts to startup founder: Charlyn’s path
• Why on-the-job training still dominates legal education
• The "teaching gap" in law firms and how Rikka fills it
• What good legal training looks like (hint: examples, not just theory)
• How AI bots can democratize learning in law
• Why Rikka Academy uses mock negotiations and clause analysis
• The hidden skill of adapting to “weird” contract terms

🔧 Key takeaways

• Law is a practice, not just a theory — Most learning happens on the job, but many junior lawyers don't get enough real-world exposure early.
• Mentorship ≠ Teaching — Many partners are great lawyers but lack the skills (or time) to teach effectively.
• Simulations are essential — Rikka Academy uses real contract examples and mock negotiations to build muscle memory.
• AI can scale what great educators do — Charlyn is building an AI-powered bot to replicate her teaching feedback, making quality training more accessible.
• Mindset matters most — Instead of memorizing clauses, Rikka teaches how to think like a contract negotiator—especially when conditions are novel or unpredictable.

📚 Resources mentioned

• Book: The Tech Contracts Handbook by David Tollen
• Blog: Contract Nerds
• Ricca Academy: https://rikkagroup.com/rikkaacademy-homepage/
• YouTube Channel: Ricca Group

💬 Favorite quote

“What I’m trying to teach is a methodology of thinking—so that the lawyer is able to adapt to any situation, even if the book or academy didn’t teach them that specific lesson.”
— Charlyn Ho