In-House Counsel

From Courtroom To Center Stage: How Legal Drama And Startup Chaos Fuel 'Dirty Legal Secrets'

Zhao brings a fresh, comedic, and thought-provoking look at the real-world chaos behind startup culture.

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Comedy TragedyWhen law meets theater, the result is a whirlwind of humor, absurdity, and hard-hitting truths. In “Dirty Legal Secrets: Based in True Startups,” director and co-producer Jianing Zhao — fresh from law school graduation — melds her legal expertise with her passion for storytelling. This isn’t just another startup drama. With a sharp eye for the intricacies of law, tech, and gender dynamics, Zhao brings a fresh, comedic, and thought-provoking look at the real-world chaos behind startup culture. I sat down with Jianing to explore how her legal training shaped the play, how humor exposes the truth, and why representation on stage — and behind the scenes — matters now more than ever.

Olga V. Mack: Jianing, thank you for joining me! So let’s dive right in. “Dirty Legal Secrets” is an intriguing title for a play. I understand you’re fresh out of Cornell Law and just took the bar exam. How did your legal training inform your approach to directing this production? Did it add a unique flavor to how you shaped the play?

Jianing Zhao: Absolutely, Olga! Directing this play fresh out of law school has been a unique experience. I studied theater in undergrad at Princeton, and while pursuing my JD from Cornell Law, I co-founded Cellunova Productions with a group of fellow immigrant artists in NYC — each with a professional background outside of theater. This interdisciplinary approach is what makes our storytelling multifaceted, allowing us to tackle complex social issues from fresh angles. “Dirty Legal Secrets” is the fourth professional play I directed, and the third full production I co-produced at Cellunova. 

Of course, my legal training did help me get a solid grasp of Sarah’s brilliant script, especially when it comes to the role of a general counsel or the intricacies of confidentiality rules in a startup. But the real connection between law and theater goes beyond that. Both disciplines are about storytelling, giving voice to the voiceless, and representing the underrepresented. I focus on balancing humor and nuance, making sure that the essence of the characters and their situations come through authentically. My goal was to ensure that the audience finds both laughter and deeper reflections on the true stories behind these characters.

OVM: That’s fascinating — especially the parallel between law and theater as tools for giving a voice to those who might otherwise go unheard. Speaking of balance, legal issues — particularly in startups — can be pretty heavy and high-stakes. How do you keep the play funny while dealing with such serious themes? What role does humor play in revealing truths about the legal profession?

JZ: Humor is essential! It’s such a powerful tool for connecting people. Everyone loves a good laugh, right? More importantly, humor puts the audience in a relaxed, receptive mood, which helps them absorb topics they might otherwise shy away from. The script, based on real stories, highlights funny, crazy, and sometimes troubling situations that employees have encountered in both law and tech startups.

In my directing, I try to distinguish the somber moments from the more absurd comedic ones. I guide the actors to reflect on why their characters are telling these stories and what emotions are driving them. For audience members with a legal background, I want these moments to hit close to home — the frustrations with the legal system, the absurdities we all know too well. But it’s also important for these stories to feel relatable to everyone, regardless of their professional background.

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We’ve embraced a wide array of comedic styles — physical comedy, standup, improv, sketch, and even audience interactions. With creative props and costumes, we’ve crafted a hilarious and thought-provoking experience for anyone who’s ever stepped foot into a workplace or hopes to. You don’t need to be a lawyer to laugh — or to learn something along the way.

OVM: It sounds like you’ve created a show that’s both hilarious and insightful, which is no small feat. Now, both you and your team have experience in male-dominated spaces like law and tech. How does “Dirty Legal Secrets” address the gender dynamics or social issues within these industries?

JZ: This is something I care about deeply. Before law school, I worked at a fintech startup where, at the start, I was the only woman on the team. It could feel isolating, and I wished for colleagues or mentors who shared my background. Even now, as we both know, law firms are still struggling with diversity — fewer than 5% of law firm partners are women of color, according to NALP’s 2023 stats.

For me, representation is key. It’s not just about telling these stories on stage — it’s about showing up, taking up space, and making our presence known. That’s what “Dirty Legal Secrets” does. The script addresses problematic gender dynamics in law and tech, but we’ve also been intentional about representation in our production process. The majority of our cast is female or nonbinary, as well as people of color. And our production team at Cellunova Productions? Also majority women of color.

The message is clear: we’re here, we’re speaking, and these are our stories. This play is about more than just exposing the dirty secrets of the startup world. It’s also about saying, as minorities in tech, law, and theater — “Look at us. Listen to us. This is our story.”

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OVM: I love that message — so powerful and important! It’s wonderful to see that you’re not only telling these stories but also living the values of inclusion and representation through the entire production process. Jianing, thank you so much for taking the time to share your journey and insights with us. I can’t wait for everyone to experience “Dirty Legal Secrets”!

JZ: Thank you, Olga! I’m excited for people to see it and hopefully walk away with both laughs and some new perspectives.

As “Dirty Legal Secrets” takes the stage, it’s clear that this is more than just a play about the pitfalls of startups and legal gray areas — it’s a reflection of the complex, often messy world we live in. With a mix of sharp wit, laugh-out-loud moments, and deeper truths, Jianing Zhao has created a production that speaks to anyone who’s ever been part of a workplace, legal or otherwise. Whether you’re a lawyer, a tech enthusiast, or simply someone who loves a good story, “Dirty Legal Secrets” promises to entertain, challenge, and leave you reflecting long after the final bow. The show runs through October 27 at Room 52 (212 East 52nd Street, New York, NY). So, get your tickets, because this is one legal drama you won’t want to miss!

Olga MackOlga V. Mack is a Fellow at CodeX, The Stanford Center for Legal Informatics, and a Generative AI Editor at law.MIT. Olga embraces legal innovation and had dedicated her career to improving and shaping the future of law. She is convinced that the legal profession will emerge even stronger, more resilient, and more inclusive than before by embracing technology. Olga is also an award-winning general counsel, operations professional, startup advisor, public speaker, adjunct professor, and entrepreneur. She authored Get on Board: Earning Your Ticket to a Corporate Board Seat, Fundamentals of Smart Contract Security, and  Blockchain Value: Transforming Business Models, Society, and Communities. She is working on three books: Visual IQ for Lawyers (ABA 2024), The Rise of Product Lawyers: An Analytical Framework to Systematically Advise Your Clients Throughout the Product Lifecycle (Globe Law and Business 2024), and Legal Operations in the Age of AI and Data (Globe Law and Business 2024). You can follow Olga on LinkedIn and Twitter @olgavmack.

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