Introduction: 0:00

• Introducing Sarah Feingold, playwright of Dirty Legal Secrets: Based on True Startups, media law professor at New York University, board member and startup advisor at Chloe Capital, and former General Counsel at Etsy and Vroom.
• Why she considers herself a creative first and a legal professional later
• What got Sarah into law

Becoming Etsy’s first lawyer (and 17th hire): 2:48

• Reaching out to Etsy, offering guidance on policy.
• Talking with the founder, then calling back to pitch herself as their lawyer
• Building a business case for herself
• Believing Etsy will succeed & taking the leap

Transitioning to General Counsel at Vroom: 6:57

• Building a large, specialized team for an automotive sales company 
• Speaking with a recruiter about expanding her career portfolio
• Taking steps to expand her career by exploring different roles

Writing a play: 9:18

• Being inspired by the #MeToo movement
• Creating a platform for lawyers to share their stories 
• Staging her first performance in 2019, then adapting it to a play during the pandemic

Getting started on her first draft: 13:59

• Learning to ignore her perfectionist tendencies 
• Giving herself grace to write, practice, continually change, and improve

Finding actors and producing her own play: 16:52

• Exploring ways to fund her projects
• Submitting her script to a competition and winning
• Working with production companies 

Learning to promote herself after a career in law: 19:54

• Balancing a career in arts with running a business
• Getting comfortable with rejection 

Staging Dirty Legal Secrets: 21:37

• Putting on back-to-back performances 
• Visiting Dirtylegal.com for tickets and mailing list
• How she imagines the future of Dirty Legal Secrets. 

Keeping her creative spirit alive: 25:28

• Balancing a difficult job with raising a family and writing a play
• Scheduling time to work on her passion projects

Leaning into a “portfolio” career: 28:20

• How she found joy in public speaking and teaching 
• Learning to take risks and making peace with career ambiguity

Favorite parts of her day and pet peeves: 30:13

• Enjoying her daily route while taking her kid to school
• Disliking when people say they will do something and don’t

Book recommendations: 31:24

• Encouraging people to see and read more plays

What she wish she knew as a young lawyer: 33:21

• Realizing that she didn’t have to do everything herself