Scott Duffy is the prototypical serial entrepreneur. In his late 20s, he was on the startup team of an Internet site that eventually became CBS's Sportsline.com. Then came another tech startup later bought by NBC, and then he helped launch Fox-Sports.com. He made his first million at 28. Today, he is at the helm of the Virgin Group's Virgin Charter, an online travel agency for private aviation. The site, scheduled to go public in February, is in its testing stage, servicing about 100 corporate travel departments and travel agents with more than 800 aircraft. Its goal is to become the private aviation version of what LendingTree.com is for mortgage companies where consumers can compare the quality of a service, rate it, and book it online. Raised in Brentwood, Duffy moved to Silicon Valley in 1994 with money he got from selling his belongings at a Third Street pawn shop in Santa Monica. He slept in his car, and then got his first break by delivering pizza along with his resume to tech startup executives. Duffy met with the Business Journal recently at his office overlooking the airstrip at Santa Monica Airport to discuss his career, writing his first business plan in eighth grade, and a recent flight his six buddies took back from Las Vegas on a private jet.

Question: How did you end up heading Virgin Charter?

Answer: My company Smart Charter launched in 2006 and we were out raising money. At the time, the Virgin Group was also looking to get into private aviation. Through their research, they discovered that the biggest problem in the industry isn't that there aren't enough aircraft, but that it's too hard to buy and sell charters where they already exist. So they decided that the smartest thing to do would be to create an online marketplace that would connect people with jets. While they were coming to this conclusion, I had a team in place already building the solution. They ended up investing in the company.

Q: Have you always been entrepreneurial?

A: Yes. Ever since I was young. I remember the first business plan I wrote was actually with my dad and it was why we should do the play "Peter Pan" at my grammar school. I was in the eighth grade. When I was in high school, I had a little hot dog stand. I was selling hot dogs at Century City Mall before they had any food. Hot dogs and knishes. Freshman year in college, I started a painting business where we'd paint people's houses. I had about 20 student employees.

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