Startup(s): Airbnb, LikeALittle

The newest member of Two and a Half Men is heavy in the tech world. After investing in big Brands like Skype, Kutcher turned his sights to startups. He was a big supporter of the popular social lodging site, Airbnb, and put money behind social flirting site, LikeALittle. He recently took his investing one step further and founded a technology investment fund called A Grade with investment big wigs Ron Burkle and Gary Oseary.