Attorney, activist, dating app developer—Kyle Westaway’s unconventional career trajectory even takes him by surprise.
“It’s easier to see your path when you’re looking backwards than when you’re looking forward,” Westaway says.
First and foremost, he wants to help change the world for the better. He discovered this calling back in college.
“In law school, something really strange happened to me,” he says. “You’re supposed to go and become kind of a callous prick. But, what happened to me was, I went to law school, and I grew a heart.”
While writing his master’s thesis on economic development in Sub-Saharan Africa, Westaway was fascinated by social justice issues. He knew he wanted to help eradicate extreme poverty and the commercial sex trade in the region.
“I thought both issues should be in the history books and not in the newspapers,” says Westaway, a WeWork Dumbo Heights member.
Shortly after graduating from law school in 2006, Westaway started his own law firm.
“I didn’t know what the hell I was doing,” he remembers. “I should have failed for so many reasons. New York is a competitive legal market. I wasn’t coming from a top school. Looking back, that was part boldness, part naïveté.”
Around the same time, Westaway and several friends also founded Biographe Blanks, a screen printing company that hires former victims of the sex trade to craft custom T-shirts.
As he was forming the company, Westaway noticed that the lawyers he was working with had no experience with “social enterprises,” organizations that fall between the for-profit and non-profit designations.
“Some of the best and brightest minds at some of the biggest law firms didn’t know what to do with it,” Westaway remembers.
Westaway spotted an opening in the market, and built a successful law practice by filling that gap while doing what he loves.
“This was my passion,” he says, “to think about how business can drive social impact.”
He now advises big-name clients like Warby Parker on social enterprises. In addition, he teaches a course on the topic at Harvard Law School.
Now that he’s blazed a trail in a formerly non-existent area of the law, what’s next? Westaway is taking another hard left into a competitive field. His new app, Hearts and Spades, aims to disrupt the dating industry.
Again, he’s making a risky leap into a market already dominated by giants. “We want to help others date better,” he says. If his past is any indication, he’s sure to find a way.
Photo credit: Lauren Kallen