Federer has reached many milestones over the past few months. In addition to winning the French Open for the first time, he married and became a dad to twins. Federer is enjoying his personal life, which he credits with helping him professionally.
The game's greatest player, Federer has racked up a record 15 Grand Slam titles. He had appeared in the most consecutive Grand Slam finals, and has been ranked number one longer than any other player in history - 237 weeks.
Asked if it was tougher becoming the top player in the world or staying there, Federer told Gimelstob, "Well for me it was getting to number one. I just thought I had so much pressure on me. That's kind of what I thought when I won Wimbledon in 2003. I thought, 'Okay, number one has to be around the corner. It wasn't like that but once I got to number one all of the sudden I could just play freely again and that's why I was able to put such a streak together."
Federer hopes to extend his biggest winning streak at the upcoming U.S. Open in New York, a tournament he's won the past five years.
Asked what he has enjoyed about New York, and why he thinks he has done so well in the city, Federer said, "Well I used to really struggle there. Early on it was too loud like you said and it was too crazy; too windy; too humid. But today it is different. I love it.
"I played some of the greatest tennis I've played it in New York," he added.
Married earlier this year to his long-time girlfriend Mirka and in July, the couple became parents to twin girls - Myla and Charlene.
So how has Federer's life changed? "Well it's changed a lot.Having twin girls is a life changer that's for sure. But I like getting up and changing diapers. It's the things you do."
Though heralded in his homeland, Federer says living in Switzerland has actually helped shield his family from the media. Facebook is his favorite way to communicate with fans.
"I can post things that are truly from me. They know it's from me, and that's why i like that platform. And you know having so many fans, in such a short time. Its way scary, but it's a lot of fun," he told Gimelstob.
Federer has now grown accustomed to crowds and credits their support for keeping him motivated. "It used to be funny when I was younger. I used to get nervous, you know if my parents would come watch. And then I would get nervous if my friends came and watched. Today it's not a problem anymore actually, because now I enjoy it. I see that they, you know, respect me immensely, and I try to put on a good show and show that I can still play very good tennis."