Blog
Mar 01

InSITE Breakfast Series: Christian Rudder of OKCupid

Christian Rudder ambles into the Eventi looking as if he sprang directly from the collective mind of a YCombinator graduating class: Teal hoodie, moppish hair, intense caffeine craving. The 30-something Harvard math grad is one of four co-founders of OK Cupid, and one of two that still remain with the company after its sale to Match.com in early 2011 for $50 million. (The other, Sam Yagan, is now CEO of Match; Rudder is OK Cupid’s general manager.)
Rudder is also the man behind OK Trends, the stupidly successful blog that poked and prodded at the dating site’s data and yielded instantly viral posts like “The Four Myths of Profile Photos.” He’s now working on a book applying the same type of analysis to more variegated sources, such as Reddit and job-site data. It’s tentatively scheduled for release in Fall 2014.
In the spirit of OK Trends, here are “The Four Secrets to Being a Successful Entrepreneur.”
1. Be provocative. One of Christian’s Ok Trends posts was titled, “Why No One Should Ever Pay for Online Dating.” It was very much  intended to snag the attention of Match.com and get them to think about OK Cupid as a serious competitor and a possible acquisition. It worked. OK Cupid got a cease-and-desist letter and, a few months later, a $50 million buyout.
More generally, he says, if you’re using a blog as free marketing, don’t be afraid to have an authentic voice. Too many startups are too protective of their brand; don’t worry about swearing and having a sense of humor, so long as it feels true.
2. Be multi-faceted. The best teams are complementary and have skills that don’t overlap too much. When two people are responsible for the same thing, one is bound to be better than the other, and that leads to bad situations.
3. Be shrewd. Sam, who got his MBA at Stanford, was very skilled at negotiating. OK Cupid got a couple crappy acquisition offers from companies they weren’t interested in selling to, but they used the offers to pique Match.com’s interest and increase the selling price.
Also, be shrewd about equity. A founding team shouldn’t split the company equally if they’re doing unequal labor. Be willing to have tough conversations earlier rather than later.
4. Be lucky. In hindsight, it’s easy to come up with a narrative to explain how Company A, by doing X, Y, and Z, ensured its success. But luck is an enormous factor. OK Cupid almost failed a couple times — it had almost run out of its $6 million Series A by the time it hit break-even — and you can’t control for everything.
This post was written by Barrett SheridanColumbia Business School MBA Class of 2014

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The InSITE Fellowship is a highly competitive leadership development program comprised of exceptional graduate students at top universities. InSITE Fellows and alumni make up a global network of entrepreneurs and leaders in technology and venture capital.