Jerry Guo considers himself a modern nomad. The 24-year-old Chinese-American stays in a different apartment each month, couch surfing or subletting, whatever works best. “Moving around makes it easier to find cool new venues,” Mr. Guo explained. His recently launched startup company, Grouper, sends six users on platonic group outings to lux hotspots around New York, so maintaining a fresh supply of trendy locales is key to Mr. Guo’s success.
“I like to keep moving,” Mr. Guo told Betabeat, hunching down into a leather chair at our Midtown offices. He wore a purple sweatshirt, jeans and yellow-trimmed topsiders with no socks. Over the last two years the rakish Mr. Guo has touched down in exotic locales on practically every continent on earth. There was a rare trip inside North Korea, which Mr. Guo wrote about for the Washington Post. And the time he spent running with the rebel forces in Iran during the summer of 2009, which he chronicled in The New York Times.
“Jerry is…I think the best word is irreverent,” said his co-founder at Grouper, Michael Waxman, who met Mr. Guo when the two were freshman at Yale in 2005. “After all the crazy shit he has done, he’s lucky just to be alive, so he kind of brings that to the table as an entrepreneur.” Mr. Waxman is the CTO/CEO of sorts, while Mr. Guo handles partnerships, operations and marketing. “He has the kind of charisma you can’t learn.”
Mr. Guo’s charisma—and his irreverence—were on stark display in the spring of 2011, when he reached out to Adam Sachs, CEO of the very successful group dating site, Ignighter. He told Mr. Sachs that he was a freelance journalist who had been commissioned to write a piece on Ignighter for The Atlantic Monthly, and sent along some of his clips from his time at Newsweek by way of credentials.
“It was really strange,” Mr. Sachs said. “He showed up to the interview with this other guy, who I later learned was his co-founder. They asked a ton of questions and we talked for maybe an hour.” A few weeks went by and Mr. Sachs heard nothing, so he emailed Mr. Guo to ask about the story. “He told me it was still being edited and that it would come out soon.” Another month or so passed. “Then all of a sudden I see Grouper.” Both companies relied on users’ social graphs to choose clusters of people they would send on group outings.
Mr. Sachs emailed editors at The Atlantic, who informed him that Mr. Guo had indeed pitched the story but that it had never been assigned. He emailed Newsweek, who told him that his complaint was just one of many they were sorting through involving Mr. Guo. Mr. Sachs was upset, but he didn’t feel threatened by Grouper, and he decided to let things go. We thought the incident warranted a closer look.