The Bearer of Bad News
“I feared if I talked to them, they would realize I was a 13-year-old,” he said.
By 2002, Mr. Lee and his childhood friend ran some of the most popular sites for teens, according to Nielsen data published at the time.
One of the companies he co-founded was SubProfile, a social media service built on AOL’s instant messenger platform. By his junior year of high school, he said the site was generating “six figures in revenue” and getting at least seven million unique visitors per month. (Nothing he has done since has exceeded that traffic, he said.)
He received his first paycheck from an advertiser at his parents’ home in the suburbs of New York.
“It was definitely a surreal experience,” Mr. Lee said of his time as a teen entrepreneur. “That’s when I first fell in love with the internet.”
Mr. Lee sold another company, a study guide site, while he was an undergraduate at Harvard.
After graduation, he co-founded an internet ad sales start-up called PaperG in New Haven, Conn. Mr. Lee was at the company, which has since changed its name to Thunder and was sold to Walmart, for about seven years.
Krystal Benitez was hired onto Mr. Lee’s operations team at PaperG in 2012. By that point the company, and Mr. Lee, had moved to San Francisco. Ms. Benitez said that Mr. Lee often gave informal financial advice to the staff, including several lunchtime lectures about investing and retirement planning. Personal finance is “a very near and dear topic to his heart,” she said. Indeed, Mr. Lee soon founded a 401(k) start-up called Human Interest, which was valued at a billion dollars in 2021.
“There’s maybe no better way to have impact on people’s financial lives than through employment and how they’re paid,” Mr. Lee said. He added that his interest in personal finance has animated his career, from Human Interest to Layoffs.fyi to his work now on Comprehensive.io.
Mr. Lee’s early enchantment — and early success — with the web continues to power his optimism about the industry, and his view that lives can be improved through technology.
