O'Leary's second business, the software company Softkey, acquired The Learning Company in 1995 and then adopted its name. Four years later, "Mr. Wonderful" and his business partner Michael Perik sold the company to Mattel for $4.2 billion.
But even today, O'Leary says his true passion has always been photography.
As a young man, he spoke with his stepdad George about what he was going to do with his life. He realized that the key question for people starting out is, "What are you willing to do in order to be what you want to be?"
"It's not enough to say you want to be a photographer, or an actress, or a writer," he says. "You have to want to do all the necessary difficult things that are required to support that goal."
He concluded that he wasn't going to spend his 20s struggling to support himself as a full-time photographer. Now, supported by a career in business, he says, he has the luxury of being able to build a photo portfolio without financial concerns.