Yagan is the cofounder of online dating site OKCupid, which he sold to IAC(IACI) in 2011. He now serves as the head of IAC's portfolio of dating services, The Match Group(MTCH), which he helped take public in November.
Conrad, on the other hand, leads Zenefits, a cloud-based HR platform that manages everything from payroll to health insurance. He knows it's not sexy -- but it's practical. It has big names, including Jared Leto and Marc Andreessen, backing it. As well as an eyepopping valuation of $4.5 billion.
When it comes to advice, though, both Yagan and Conrad would tell their younger selves the same thing.
