Eva Shang on Startups and Storytelling

College dropout, hedge-fund CEO and sporadic blogger Eva Shang ’17 is interested in the idea of a diamond-shaped life. “In the latter half of our lives, our options and possibilities narrow in on themselves, but in the first half of your life — especially when you’re in middle school, high school, college, or your early 20s — the world is opening itself up to you.”

Shang arrived at the red-brick dormitories of Harvard Yard from the peaceful suburbs of Philadelphia. On campus, she founded the Harvard Organization for Prison Education and Reform and tutored at prisons across Massachusetts. Though she spent much of her time at Harvard advocating for prisoners’ rights, she was hesitant about pursuing this passion professionally.

To Shang, Harvard was the base of a forking path. She could work in the public sector and be forever “rabble-rousing on the outside,” or she could attend seminars at the Charles Hotel to schmooze with recruiters over free food and eventually sign to a high-paying job in the corporate world.

Shang, who spent a summer interning at a public defender’s office in D.C. and also interviewed for “every single consulting firm” Harvard’s career services offered, found neither option appealing. “I didn’t want to go and be a servant to the elite,” she says. “I wanted to continue to be a renegade. But I also didn’t want to always feel like I was on the losing side of a war.”

For a while, Shang thought she found a third path: law school. She took the LSAT with plans to become a civil rights lawyer but soon realized that law students were in the same position. “Once you go to law school, at the end, you have to make the same choice all over again,” she says. “Do I work for XYZ large firm? Or do I go and work for this civil rights law firm that is going to barely pay me enough to pay back my student loans?”

Feeling trapped, Shang abandoned the choice altogether. In 2016, she received a $100,000 grant through the Thiel Fellowship, created by billionaire Peter Thiel, which required her to drop out of college to work full-time on Legalist Inc, a startup she had founded with fellow Harvard student Christian G.B. Haigh ’17.

Legalist uses data-driven algorithms to invest in lawsuits in exchange for a percentage of court-awarded payouts. Though Legalist’s algorithms are novel, litigation finance itself is a multi-billion dollar industry that dates back to the 90s. Proponents argue that litigation finance allows plaintiffs to hold their own against powerful, well-funded defendants, while critics contend that the practice gamifies the legal process by turning courtrooms into profit centers.

Since the start of her career, Shang has had to navigate the question of Legalist’s ethical standing. Early coverage pointed out uncanny similarities between Legalist’s model and Thiel’s own funding of Hulk Hogan’s $140 million dollar lawsuit against the media outlet Gawker. Thiel’s investment in the lawsuit — a retaliatory move after Gawker outed him as gay in 2007 — effectively led to the company’s closure and was seen by some as a form of press intimidation.

At the time, Shang was careful to distance herself from Thiel, stressing that Legalist wasn’t meant to fund lawsuits like Hogan’s. Instead, she told The Guardian that her and Haigh’s company would focus on “small businesses tied up in costly litigation.” In many of her early interviews, Shang brought up a small bakery suing its insurance company for refusing to cover damages from a burst water pipe. In an ordinary situation, the insurance company could draw out the legal proceedings until the bakery ran out of money. With the help of a company like Legalist, the bakery would receive the funding it needed to make its case in court.

Shang’s skill at shaping the narrative has served her well in the startup world. When asked about a strength that’s helped her succeed in the industry, Shang pauses for a second, and then replies, “I think I’m a good storyteller.”

At Harvard, Shang took creative writing classes and wrote op-eds as a member of the Crimson’s Editorial Board. Professor Caroline Steiker, who taught Shang in a freshman seminar and later hired her as a researcher at the Radcliffe Institute for Advanced Study, wrote in an emailed statement that the creativity of Shang’s writing is “still vivid a decade later.”

Shang has a different recollection of her literary abilities. “I don’t think I was very good at writing back in college,” she says. “Some of my Crimson pieces are really cringy.” She recalls being rejected from the Harvard Advocate eight times, despite only being on campus for six semesters.

“I think that the reason that I wasn’t very good at writing is because I didn’t have anything interesting to write about,” she says. “I think that in order for a piece of writing to be interesting, it has to come from a lived experience that is interesting.”

Startup life made for great fodder. Since 2018, Shang has chronicled her experiences through her Substack, titled “silicone valet.” She’s written about everything from aging, homesickness, and wunderkind syndrome, to money, reproductive futurism, and High School Musical. Her essays — each addressed “Dear friend” and signed off by “Your friend, Eva” — seem at first like snippets from a diary.

In reality, Shang’s entries are a little less intimate. While she keeps an actual diary, which she uses to process emotions in the moment they occur, she saves her Substack for conclusions she has drawn after giving a topic serious thought. “I publish Substacks when I feel that I have arrived at some capital-T Truth, at least the truth for me, that I feel people would benefit from if it were disseminated,” she says. As a result of her careful consideration, there’s little in her archive she regrets publishing.

Though Shang has no formal plans for a larger literary project, she hopes to one day write a young-adult novel, set in the first half of life’s diamond shape. “You’re growing into yourself in that phase of life I find to be so hopeful and interesting,” she says. “Literature can help to serve as a guidepost along that journey.”

— Magazine Editor-at-Large Yasmeen A. Khan can be reached at yasmeen.khan@thecrimson.com. Follow her on X at @yazzywriting.