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Skidmore College

From Etsy lawyer to playwright: Sarah Feingold ’02

March 7, 2025
by Jodi Frank

The creative career of Skidmore alumna Sarah Feingold ’02 has taken her from Etsy’s first in-house attorney to the writer of the play “Dirty Legal Secrets, ” which premiered in New York City to sold-out audiences. But, above all else, Feingold says she’s “an artist first.”  

“I was one of those kids who was always creating things and making messes in my house,” says Feingold, who now teaches media law at New York University. By age 12, she developed a passion and skill for metalsmithing and was selling her Feingold Jewelry line out of her backpack in high school.   

As a student at Skidmore, Feingold majored in sociology with minors in art and management and business. She immersed herself in every metalsmithing class she could find but was concerned that working as an artist full time might take the joy out of her creations.  

Law school offered a practical path forward, but she never quit making sterling silver jewelry on the side.  

A creative legal path  

After earning her law degree, Feingold joined a law firm but quickly realized it wasn’t the right fit.  

A turning point came in 2007: While exploring ways to sell her jewelry online, she discovered Etsy, a new virtual marketplace for artisans to sell their wares. Impressed with its innovative business model, Feingold explored every aspect of the website — including its legal policies, which she found lacking.   

On a whim, she sent an email to the company’s generic inbox, offering her legal expertise, which led to a phone call with its CEO. When she discovered that Etsy didn’t have an in-house attorney, she booked a flight to its headquarters in Brooklyn and convinced the company to hire her.  

For nine years as Etsy’s first in-house attorney, Feingold helped the e-commerce platform scale up from a niche startup to a publicly traded powerhouse, leaving her mark on the legal framework that sustains and guides millions of artists worldwide. 

After Etsy, Feingold served as general counsel for Vroom, another early e-commerce platform that enabled users to buy, sell, and finance vehicles online.  

All the while, Feingold has continued to flourish as an artist, expanding her repertoire as a jeweler and ceramist. 

I always say that I’m an artist first.”
Sarah Feingold ’02 

After years of shaping the legal landscape for entrepreneurs, Feingold found yet another way to merge law and artistry — through storytelling.  

Her first play, “Dirty Legal Secrets: Based on True Startups,” produced by Cellunova Productions, premiered off-off-Broadway to sold-out audiences last fall. Inspired by the behind-closed-doors experiences of startup lawyers like herself, Feingold gathered anonymous legal stories and transformed them into a production that dramatizes the hidden legal battles and moral quandaries faced by attorneys in the high-stakes world of startups.  

“It’s funny, absurd, and sometimes heartbreaking — a rollercoaster that captures the highs and lows of being a startup lawyer,” she says.

Plans are underway to adapt the play into a television series, with online readings already taking place for interested producers.  

On Creative Thought Matters — and entrepreneurship  

Feingold’s career journey demonstrates how Skidmore’s Creative Thought Matters ethos shapes the career trajectories of alumni. She credits her liberal arts education with guiding her toward a meaningful career path that brought together her diverse interests and skills.  

“What’s wonderful about Skidmore is that you get to take all sorts of classes,” she says.

Even more than the diverse coursework that Skidmore offers, the development of essential skills in research, communication, and writing provided the groundwork for my future." 

That broad foundation took a more focused direction after a business law course sparked her interest in intellectual property law. “I started thinking about my art background and how, as a lawyer focusing on copyright and trademark protections, I could help artists like me protect their work," Feingold says.  

She also notes that her work is deeply rooted in entrepreneurship. She recently participated in a panel of alumni entrepreneurs at Skidmore's 12th Annual Entrepreneurial Artist Forum. The forum  was held at the Tang Teaching Museum and Art Gallery, and organized through the Arts Administration Program and its Entrepreneurial Artist Initiative. The program was created and developed by fellow alumna Molly Haley '64, who continues to support it with her husband, Ed Freitag.  

At the Feb. 20 forum, Feingold and other entrepreneurs and creatives discussed what it takes to build and sustain a career around their passion for the arts.   

"Being a creative entrepreneur means exercising your rejection muscle,” she says, offering advice to students. “When I mention that I wrote a play performed to sold-out audiences in New York City, I typically don’t include all the rejections I received before I succeeded.”   

Feingold continues to create in unexpected ways. During the pandemic, she revisited an art form she once dismissed when a Skidmore advisor suggested she try something different: ceramics. What began as a hobby of crafting ceramic charms and functional art pieces that mirror New York City life (including the city’s most iconic wildlife species — the pigeon) has evolved into her label, with her ceramics sold across the city in boutiques and galleries.  

“Every step in my career has been entrepreneurial,” she says. “Taking risks, making bold choices, and embracing creativity — that’s what drives me.” 

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