The Creative Spark

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

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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++). 

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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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While in high school, Krohn spent his time playing saxophone with the school band, contributing movie critiques to the cultural review magazine, and practicing with the ski team. “I wasn’t athletic,” he says. “But that was the one sport I was decent at so it was great for me to feel like I had some kind of athletic potential.” 

Scarsdale High School, Krohn says, “was somewhat grueling. The workload was much higher than what many of my college friends experienced.” While he studied a lot, he found time for fun, visiting Lange’s Deli in Scarsdale for lunch and enjoying late nights at the Candlelight Inn on Central Avenue. 

And while Krohn recognizes the impact many of his teachers at Scarsdale High School made on him (Julie Leerburger in English, Craig Sherman in band, and Dawes Potter in math were some of his favorites), it was at Harvard University that his future started to take shape. Although Krohn dabbled with becoming a physics major or pursuing his passion for poetry writing, he ultimately decided to study computer programming because of how much fun he had doing it. When programming works, he says, it is like “black magic.” 

In addition to learning how to program computers and build sophisticated websites at Harvard, skills he used to build both of his businesses, he also met close friends who became his business partners. There was Chris Coyne, the idea person who “has a very accurate instinct for what is going to make a good product,” says Krohn; Sam Yagan, the business operative, who “has this amazing, natural ability to negotiate—he spent a lot of time negotiating with Domino’s Pizza when we were in college, taking down the price of the pizza and the delivery time”; and Christian Rudder, whose quirky style of writing was employed to write the company blogs and literature. 

Their first business idea, SparkNotes, came in 1999, in the middle of senior year, when they were sitting in the Quincy House dining hall trying to think of a service that college students wanted. “I don’t know why,” says Krohn, “but we decided they wanted study guides…we should have just decided they wanted Facebook, but we didn’t decide that.” 

With a budget of $40,000 scraped together from family and friends, the team hired their friends to write summaries of the most commonly read books in school. By that spring, when Krohn and his friends were graduating, the site was so popular that a group of Wall Street family friends gave them $250,000 to finance a bigger operation. 

Nine months later, after SparkNotes had moved into an office in Cambridge, Massachusetts, and employed a staff of about 10 employees, the company was sold to—it no longer exists but, at the time, it was trying to be the leader of websites for teens—for $16.5 million upfront with the ability to earn an additional $13.5 million for a strong future performance. “It was insane,” says Krohn. “It was totally insane. I don’t know how it happened! It’s totally shocking! It took less than a year.” When went bust, Barnes & Noble bought SparkNotes and the company still owns it today.

Propelled forward by their belief that successful companies could be developed and sold in a mere nine months, Krohn’s team left Barnes & Noble in 2002 and started planning out what to do next.

While they worked at, Rudder had played around with a product on the SparkNotes website called Spark Match, which introduced singles who performed similarly on a personality test. It was popular, with users in the six figures, but Krohn didn’t have the resources to make it work technically. “We kind of filed that into the back of our mind as a team that there was something there, this style of dating, a free service that was based upon an entertaining personality assessment,” says Krohn, and now they decided to turn it into a strong product. 

From the outset, OkCupid was different than existing dating sites such as or JDate. Not only was it designed to be fun—other sites were serious and approached dating like job interviews for people hoping to be married in a year or less—but it also attracted a much wider audience and, therefore, a broader dating pool because it was free and designed for people from all faiths and backgrounds. 

The site was also built, from the very beginning, to handle large amounts of traffic and in a way that allowed users to see a lot of information in a clean, easy-to-understand design. Coyne says this is solely because of Krohn’s technical chops, which were further honed while he pursued a PhD at MIT during OkCupid’s early days. “Max is a real doctor of computer science,” says Coyne. “He architects highly scalable and very secure systems. Most websites—because we are in the industry we’ve gotten to know lots of other successful people—that grow to the size of OkCupid go through a lot of growing pains and failures and security attacks,” he continues. “And we never had any of those kind of problems with Max running the show.”

Yet despite these strengths and encouraging early signs—OkCupid’s number of users was growing every year by 20 percent, and it was praised in the technological world for its design and function—it also had its fair share of problems. Because it was a dating site, something that is inherently private, it was harder to get people to talk about it and spread the word to their friends. Advertising revenue, upon which the site relied, also experienced great highs and lows due to the recession. 

For nine years, the founders struggled with OkCupid, trying to attract advertisers and users by making changes to the site. One of the biggest breakthroughs came with the introduction of the OkCupid blog, which analyzed data from OkCupid users and made hysterical conclusions—for example, one post analyzed the correlation between how much meat someone ate and how long it took them to reach orgasm. “No one had really done this before, and it was a topic everyone was talking about,” says Krohn. “It was one of the biggest breakthroughs we had.” They also improved their advertising technology and played around with different features and products on the site. Finally, on January 2011, many years after the founders had originally expected, OkCupid was sold to for $90 million ($50 million upfront; $40 million after they hit specific performance goals).

Krohn stayed with for two years before deciding he wanted to leave, along with Coyne—the other founders stayed—to open up a two-man shop in the Flatiron district. Now they have “structured time” writing software, drinking beer (“Good ideas come after a couple of beers,” says Coyne), and trying to come up with their next venture, whether it is a delivery system run by self-driving cars or easy-to-use software that makes computers more secure (i.e. protects them from third parties, including the government). 

And you can tell Krohn loves this brainstorming period. “If you look at the timeline of the tech business, Max and I have always had the most fun at the beginning,” says Coyne. “And that’s because we are in the invention stage—we are inventors.” 

As Krohn says, “Every week we work on something slightly different. We were writing a lot of software that we can use whenever we develop the next thing.”

While he works on that, Krohn keeps his ties to the County current. He tries to visit his mother in New Rochelle every other week and, before his father passed away last March, was there even more often to keep him company while he was sick. This past Thanksgiving, Krohn went to a big reunion of Scarsdale High School friends at Manhattan’s trendy restaurant DBGB Kitchen and Bar, and maintains close ties to his friends even now as many of them are becoming parents. 

In 2011, Krohn was honored as a distinguished Alumnus of Scarsdale High School, an event that that involved him speaking to students in a couple of math classes about what’s involved with building websites and starting Internet businesses. “It was a really fun thing,” he says. After all, his computer education started in the exact same place those students were sitting listening to him talk, and look where he is today. 

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