Legal dramas aren’t just confined to the courtroom or our favorite TV shows. The tech startup world, brimming with secrecy, scandal, and high-stakes decisions, provides its own theater of legal intrigue. But what if those real-life stories — often whispered behind closed doors — were brought to the stage? Enter “Dirty Legal Secrets: Based in True Startups,” a play, produced by Cellunova Productions, is having its NYC premiere from October 17 through October 27, 2024. The show marries the adrenaline rush of startup life with the drama of legal battles. In this exclusive interview, I sat down with Sarah Feingold, co-creator of the production and former startup GC, to dive into how law and theater collide, creating an experience that entertains, informs, and resonates with both legal insiders and tech industry veterans.
Olga V. Mack: The Legal Twist: What inspired you to combine law and theater, especially the tech startup world? What is it about this space that lends itself to such a compelling narrative?
Sarah Feingold: The play was inspired by conversations with Michael Weinberg. Michael and I are both former startup GCs, and we share a love of the theater. We love diving into the entertaining and heartbreaking stories that startup in-house attorneys, like us, are forbidden to share. We wondered if we could combine our interests and create something unique. We put out a call for anonymous startup legal-themed stories, and we were floored by what was disclosed to us. The tales were theatrical! That spark of an idea led to the play, “Dirty Legal Secrets: Based in True Startups.”
OVM: Art Meets Law: You’ve spent years as an attorney and legal innovator — how did that experience influence your writing? Did you find yourself processing any of your own legal career through this project?
SF: The show was inspired by my time at legal departments at startups (Etsy and Vroom) and my years of laughing and commiserating with other startup attorneys. When things go wrong, like super wrong, the lawyers step in. Writing is cathartic even when the stories are not mine. I feel responsibility to those who trust me with their tales.
OVM: Startup Realities: The tech startup world is rife with drama, secrecy, and scandal. What kind of real-life situations are reflected in your play? How much of this production is based on your own experiences or things you’ve heard in the industry?
SF: The show is based on real-life startup secrecy, drama, and scandal. Due to attorney-client privilege, my startup stories must stay in my vault. But I can share anonymous tales that came to me from the legal industry. And those stories … wow!
OVM: The Audience Reaction: You’ve already had some initial shows. How have audiences responded so far? Any surprising or particularly memorable reactions from those who work in the tech or legal world?
SF: The audience fuels me. After the last production, I received generous feedback from people who saw the show. I assumed that the louder and more absurd stories would stick. I was surprised that some of the more subtle moments have staying power.
OVM: From Vision to Reality: What has been the biggest challenge in bringing “Dirty Legal Secrets” to life? As someone who has successfully navigated the legal world, did you face any unique legal or business challenges with this production?
SF: Bringing a script to the stage feels similar to bringing a startup to market. You must believe in your product and in its future. Also, you need thick skin. There are few theaters and few opportunities for new playwrights. Rejections come with the territory. I learned so much about the entertainment industry and the ways that decisions are made.
OVM: Looking Ahead: What are your hopes for the future of “Dirty Legal Secrets”? Do you envision it expanding beyond New York? And how do you hope it will impact conversations about the tech startup world and the legal profession?
SF: I’m hopeful, delusional, or both. Yes, let’s expand this production beyond our run from October 17 – October 27, 2024. Let’s expand the show beyond New York. I hope this play leaves a lasting positive impact on those who see it. I hope that industry insiders help to propel the show to the next level. We are also having talkbacks to dive into some of the themes in the show. I became a lawyer because of my belief that the law could create social change. I learned that the law tends to be clunky and slow. Art has the ability to break through the noise for a positive impact.
“Dirty Legal Secrets,” produced by Cellunova Productions, runs from October 17 through October 27 at Room 52 in New York City. It offers more than just a glimpse behind the curtain of tech startups — it challenges us, as lawyers and professionals, to reconsider the untold stories lurking in our own industries. It’s a reminder that law, while steeped in rules and confidentiality, is also deeply human — full of emotional highs, ethical dilemmas, and moments that shape careers and lives. As attorneys, we often protect the most delicate narratives, but Sarah Feingold’s work encourages us to reflect: What would happen if we told more of these stories? What might we learn, and more importantly, how might we grow? The law isn’t just a profession — it’s a stage, and each of us has a part to play. Are you ready to step into the spotlight?
Olga 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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