Sam thought one of his biggest failures was in 2007 when the OKCupid team spent a year trying to internationalize OKCupid. They thought it would be possible to take the OKCupid recipe and extend it but did a bad job with the technology and business and tried to do it on the cheap and didn't hire the right talent.
Sam talks about the importance of being straight and critical in the startup environment. Some love it, some don’t.
The OKCupid blog worked because it really put OKCupid in the center of conversations happening around the country. "You could talk about an online dating site at work, and with family." The blog proved that online dating could be cool.
He focused on high risk, high return bets when adding new features to OKupid. They would try something new every couple of months. If they had a couple of winners a year that would be great, and would result in 'step-function growth.' e.g. OKCupid Journals/blogs. was a fail. Only a very small portion of users used them, and they tended to be inhabited by trolls.
Sam states that his personal aim is to have “...learned and experienced a lot. I’ll probably be an entrepreneur again.”