The dating season opened Feb. 15, according to Urban Dictionary. But Sam Yagan ⇒ sees dating season differently, from an entrepreneur and executive’s perspective. He co-founded online dating site OkCupid in 2003 and sold it to IAC/InterActiveCorp in 2011 for $90 million. He is now Chicago-based CEO of IAC’s online dating division, Match Group, which includes Match.com, mobile app Tinder and some 40 other brands. Yagan also co-founded startup accelerator Excelerate Labs, which became Techstars Chicago. He explains what he looks for as an executive, mentor and investor.