The Creative Spark

Scarsdale native Max Krohn has already sold his first two websites—SparkNotes and OkCupid—but what’s the Next Big Thing?



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It seems that people, especially young people, are always thanking serial entrepreneur Max Krohn. 

At Scarsdale High School’s graduation last June, class treasurer Jake Gibson stood up in front of his friends, faculty, and family to thank Krohn—who grew up in Scarsdale, in between the Quaker Ridge and Saxon Woods golf courses, and graduated from SHS in ’95—for founding SparkNotes, a website offering free book summaries, test-prep tools, and computer-generated papers, which helped him immensely in school. (“We got a lot of email,” says Krohn. “Some people say, ‘You guys told me I would get an A. I got a C. I hate you guys!’ Other people would be like, ‘I got an A on this paper. You guys are awesome. Thank you so much.’”) 

As of two years ago, according to the site’s official literature, five million people were using the service each month—including Al Pacino, who was photographed reading a SparkNotes guide on the set of The Merchant of Venice

But it is Krohn’s second company, OkCupid, that generates even more gratitude—especially this month, around Valentine’s Day—because it helps people do something much harder than get good grades. It helps them find The One. 

OkCupid, a free online dating site Krohn launched with three friends in 2004, five years after SparkNotes was created, now has hosted an estimated 10 million users since launching. According to internal estimates, the site produces 40,000 dates a day, which leads to 3,000 new relationships daily. It’s no wonder almost every one of my friends knows somebody getting married to someone they met on OkCupid, or that Time magazine named it one of the top 10 dating sites in 2007. 

While Krohn acknowledges that he has created sites that help people in a real way—“It feels fulfilling to be part of such a force for good and happiness in the world”—he is clear that he has never started any businesses for sentimental reasons. Rather, his goal has always been to anticipate what product or service people really want and then create a highly functioning website to deliver it. 

Before I even met Krohn, who now lives on Manhattan’s Upper West Side, I felt like I knew him from his OkCupid profile. Ironically, though neither he nor any of the other three founders have ever used an online dating service (Krohn met his wife the old-fashioned way—at work), they all have public profiles. 

His pictures show a stereotypical tech start-up guy: dark hair, lanky figure, glasses, and an affinity for button-down shirts. There is a picture of him in front of his computer—he did create and run OKWS, the web server that powers the site—as well as photos of him at the MoMA and on a boat (translation: I have other interests besides C++). 

From a glance at his page, we learn he dislikes dogs but likes cats, is an atheist (“and very serious about it”), and is 6’3”. Krohn didn’t even add on the few inches to his height most men do while dating online. 

The juicy information comes from the personality test, the set of hundreds of questions OkCupid uses to make matches and what sets the site apart from its competitors. Here we learn that Krohn is not careful with money (who needs to be careful when you’ve sold two companies and are only 35?), secured an undergraduate degree from one of the eight Ivy League Universities (Harvard), would consider having sex in a church (!!!), frequently meditates, and will not teach his children (when he has them) to believe in Santa. 

But what we don’t learn about Krohn, his friends would say, is that his story is very simple: He has always been, and continues to be, the smart kid in the room who is one step ahead of everybody else. 

Jon Spiegel, a friend of Krohn’s since the second grade who lives in TriBeCa and works in finance, remembers playing on Photoshop as elementary-school kids well before anybody else knew it existed. As they got older and all the boys were into Space Invaders, Krohn was playing sophisticated puzzle games that “I didn’t have the patience for,” says Spiegel. In high school, Krohn would teach himself chapters of calculus so that before the class got there, he would already know the material. He was even voted most likely to be invited to the White House his senior year. “So yeah, everybody knew Max was destined for great things,” says Spiegel. 

Krohn spent his childhood living in Murdock Woods, on the Mamaroneck Strip, in the same house his parents moved to a few years before he was born and lived in until 2002, when they moved to New Rochelle. His first job was cleaning golf clubs at the Quaker Ridge Golf Club, something that, along with actually playing golf, he was not particularly skilled at doing. (Luckily, he says, “The tech industry doesn’t involve much golf. There is a lot of going out for coffee, drinks, stuff like that.”) He attended Quaker Ridge Elementary School on Weaver Street and had his bar mitzvah at the JCC Harrison. His family kept a sailboat in Stamford, Connecticut, and spent summer vacations exploring the harbors along the Long Island Sound. 

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