"Here come the hard questions!" tech start-up fanboy Jimmy Fallon, warned Sean Parker during today's NeXTWORK digital conference. "Are you asking about my penis size?" Facebook part-owner and Silicon Valley deviant Sean Parker wanted to know. The "hard question" was not a lead-in to an Anthony Weiner press conference-style interrogation, but rather: "What'd you learn from starting so early, and what have you learned from your failures?"

Mr. Parker spent years with his head down after the crackdown on Napster, the illicit music file-sharing service crushed methodically by music labels. He lived at friends' houses, setting a self-imposed two week limit for freeloading off any one individual. "But I would stretch that by a week by mowing someone's lawn," he said. "I was quite afraid if I ever made any money, it would resume the labels going after me... so I remained under dark cloud."

Mr. Parker is now a part-owner of Facebook and an investor in Spotify, the streaming music service very popular in Europe which is expected to launch in the U.S. soon.

"I really don't feel like I've succeeded. I feel like I've failed systematically at least in terms of my own goals and what I set out to do, but somehow failure has transformed into some weird kind of success that I wasn't expecting," he said.

Do you care about money? Mr. Fallon asked.

"Don't really care about money," Mr. Parker said. "I don't care. I don't really care. I don't really care." Mr. Parker, who blends his own Indian and Chinese tea, bought a townhouse last year in the West Village for $20 million.

Mr. Fallon also brought up a new recent start-up that's been spreading virally over the past two weeks: Union Square-based Turntable.fm. They both think it's cool, although Mr. Parker is a big fan of the recently-announced Spotify-powered music feature in Facebook that represents a synergy between his two very successful investments.

"I have no idea if it's legal or not," Mr. Fallon said, prompting a big laugh from Mr. Parker.

"I think it might not be legal," Mr. Parker said sarcastically in a stage whisper.