After winning 347 tennis grand slam matches over the past 20 years, Roger Federer has become an expert at knowing when to conserve his energy and when to turn it on.

Just a couple days after breaking the world record for attendance at a tennis match in front of 42,517 people in Mexico City, Federer is currently in go mode. 

He landed in New York City at 6 a.m., went straight from the airport to guest on some morning talk shows, shot an ad campaign, and then, somehow, found time to go for a run in Central Park.

“That was fun,” Federer says as he reclines back on the sofa of his Manhattan hotel just a couple blocks away from the park. “People were like, ‘Federer, what are you doing? Why are you here? Weren't you in Ecuador yesterday? The US Open's not now.’"

The reason Federer is in town is to announce his latest venture into sneakers with Swiss running brand On. It’s not a brand that most sneakerheads would be familiar with, but has been popping up on the radars of marathon runners. Its shoes are known for their rigatoni-shaped cushioning system called “Cloud technology.”

Unlike his 20-year endorsement deal with Nike, which ended last year, or brands like Uniqlo and Rolex, Federer is an investor in On and will help oversee all aspects of the company as a partner. There’ll also be a signature Federer line of On products dropping next year.

“I think this investment that I was able to make with On is quite different to any other athlete they've done,” Federer said, adding that the company’s roster of athletes mainly consist of marathoners from his home country of Switzerland. His Swiss home is actually about a 20 minute drive from On’s headquarters, and he was already working with the company on making products before he even officially signed a deal. 

As a veteran pro-athlete with $86 million in endorsements under his belt this year, Federer has seen both the highs and lows of how the game works. One day you could be the face of a campaign, and the next day you’re passed over for the next hot young star.

“Towards the end of your career, you're sort of fading away,” Federer said. “Or maybe your success fades and partnerships sort of end. Or maybe you have less sponsors, which means less income, and then you end up retiring. And it's okay to move on.”

The future hall-of-famer is closer to the end of his career than the beginning of it, and Federer sees this new venture as something that’ll last well beyond his days of playing tennis.

Here, Federer talks more about his new venture, how his deal with Nike ended, and when he’ll know to retire.

You were at Nike for 20 years. Was the decision to move on hard at all?
We had a great relationship, and I’m forever grateful for everything they've done for me. It was just meant to be that it ended after 20 years. I thought it was going to be forever. After being together for as long as we did, I just felt change was needed for both sides. 

How did it feel when it was officially over?
The questions were like, "How do we go about it now? What's next? Is it scary times, or is it going to be fun times?" Actually, it was opportunity times. This is when Uniqlo came to the table. On came to the table. With just signing a simple extension of my Nike contract, which I could have done, I would have never landed here.

Sounds like you have no regrets. 
I'm truly blessed. I think I'm actually very lucky to have what happened happen, and I look back with a smile. Nike has been great, those 20 years, but I'm looking forward to the next 10 or whatever years it is with the Uniqlo and On now. Especially with On, this is something very different for any athlete to have an investment in a company. Being a partner with the founders is something very unique. I think it's going to be very interesting to see how the other athletes in the future are going to react because they see what I've done today.

You're a man with several different endorsements. How is On different from those, besides the fact that you actually have a vested interest in the company?  
Well, yeah. It's in a way uncomparable when you're invested in the company. When you're actually a partner to the people who founded the company, you're actually a part of the entire journey. A photoshoot or a decision you take with them could dictate everything like if the company goes good or not. For other companies, I do a photoshoot. I promote the brand. I do an event for them. And then if the company does well or not, it doesn't really make a difference for me, even if I care dearly. 

Do you think your partners feel the same way?
That's where I think they realize that I'm different to maybe other people. I actually do follow up with them and I hope, "Was the photoshoot okay? Are the founders happy? Could I have done anything different?" Because I always strive to be a little bit better every day and I want the same for the company

It's been around for 10 years. What do you think you add to this next chapter of the company? 
Yeah. I think that's it. I think it's a huge new chapter. I heard all the employees at On were really excited that they heard I joined the team. I'm very humble and I always worry about these things. Like, "Are they happy? Do they think it's a good move by the owners and their partners to bring me in?" That was number one. I was very excited about that. They're already doing great things, so maybe I don't have to bring that much in the very beginning. But I feel like I can help them in many parts of what they're already doing—and vice versa. I really feel like when we put our brains to it, there's going to be a lot of creativity. That's what I enjoy doing because I really tried to be creative on the tennis court. 

You worked with Nike and you still work with a lot of other brands outside of sneakers. How does that experience bring value to On?
I think just being an athlete, I know what I like and what I don't like. I know what works and what doesn't work. I'm sorry, but somebody who's never done professional sports at the top level maybe doesn't quite always know what the shoe needs to do or what it needs to bring. And obviously this know-how also could be very beneficial for them.

You’re friends with Anna Wintour.
She's great.

And she's a style and fashion icon. Do you have people like that, who you can run ideas with before you sign up for partnership like this?
Absolutely. She's a great friend of ours, and especially to my wife, and also just my team. She loves tennis and she will love tennis long after I'm gone. But, yeah. I've always included her in those conversations. But I also don't want to waste her time on the little things. But this was obviously a big deal and she was very excited for me.

Federer-designed products are dropping next year. What can you tell us about that? What's the process been like behind the scenes?
We've been working on something before the deal was even finalized. That's highly unusual to spend the time doing something like this if you don't know if a deal is going to come to fruition. It's not like I have nothing to do, either. I have four children. I have a life on the road and there's so many things going on that this was something very unique for me actually to go about it. And it actually shows how much trust that was going on between us. We've only got a few little things going on at the moment, which I hope ends up maybe being big successful things. 

"This is a big time push for me to do something more on the entrepreneurial side. No doubt about that."

There's this quote where you said, "When you're an athlete of a certain age, you sometimes can feel like a falling star." You're arguably one of the greatest tennis players of all time. What did you mean by that?
This is how endorsements normally work. Towards the end of your career, you're sort of fading away. Or maybe your success fades and partnerships sort of end. Or maybe you have less sponsors, which means less income, and then you end up retiring. And it's okay to move on.

With me, I feel it's very different as I go about it. I'm actually the opposite to the falling star. I actually feel my opportunities are getting greater and I'm having to say “No.” more frequently than ever, which is the least enjoyable part of it all because I like saying yes. I like making people happy, but I just can't do every sponsorship. I have to be very selective because I need to protect my game, my family, and my time so I can rest. I still need to train because I know what the priorities are. 

But at the same time, it's such an amazing opportunity to be working with brands and being a partner with a brand like On, that's up and coming and striving to become really disrupting the market a little bit. I don't know. I just think it's a wonderful times at the moment. I've never been busier. I've never been happier. My kids are healthy, my wife's great, and we enjoy our time, everything we do.

Do you see this venture as a full-time job after you’re done with tennis?
Look, I will have time for other things as well. This is a big time push for me to do something more on the entrepreneurial side. No doubt about that. Now my fans are screaming like, "Oh, what does that mean? Is that meaning his tennis slowing down?" No, it's not. Not at all. On wants me to keep playing. When everything is said and done with tennis, then we'll see how much time we all need to give for the cause. I'm super flexible. I think because we live so close, it's going to be so simple.

You do live 20 minutes away from On’s headquarters. How much easier does that make things?
Whereas if I look at other brands I work with? Uniqlo is in Tokyo. I used to have to see Nike in Portland. Other things, it's not always simple. But now with Uniqlo also, I will be a lot in the Asian market. A lot in Japan. Me and my wife and my family, we love going to Japan. We'll go actually two weeks to the Olympics next year. All the family wanted to come. All the kids were screaming, "When can we go back to Tokyo?" We want to do the fun things. But I think just the idea of them being literally a 20 minute car ride away from my house, it's just going to make things so interesting and so cool for all of us to work together.

Say there's the next Roger Federer with the next young star in any sport. How would you convince them to sign to On? 
Good question. Never thought of it actually, but you're right. Maybe down the stretch we sign athletes. They have partnerships with Swiss athletes, triathlon runners, and marathon runners because On is a running brand. Their DNA will always be there and it's important to highlight that they are a running brand. But, honestly, I don't know what I would say. Never thought about it. But I hope by me being there and them seeing the designs would be enough, if On can produce shoes that work for that particular sport. I think who knows what happens in five, 10 15, 20 years. It could be quite exciting.

You're going to be still playing tennis in 2020. For an athlete of your caliber, what are your keys to longevity?
I got to have a good team. Everybody thinks I have a magic wand and say, "Let the balls fly by themselves and never get injured,” or that I'm just lucky and I've been blessed with so much talent to never get hurt. I feel like I've put in an incredible amount of work, but I don't shout about it because I feel like everybody works hard, not just me. I can't judge if I work harder than other athletes. I only know from my side. I felt like I've given it all I have for my career. I listened to my body. I listen to my friends. I listened to my family. I listened to my coaches. All of that bundled together helped me make the right decisions in my career.

"I'm actually the opposite to the falling star. I actually feel my opportunities are getting greater and I'm having to say 'No.'"

How do you stay engaged mentally?
I don't want to overplay and burn out, but I also don't want to underplay and just be bored on a practice court. As much as I enjoy practicing nowadays, I'm a competitor. I like competing. I like beating the best. I like the travel as well and everything that comes with it. I’m also quite lucky to always be playing on the big courts in front of all those people.. I think that's where I'm definitely a little bit lucky for sure. Motivation is very hard for me.

I know you don't see it happening anytime soon, but when will you know it’s time to retire?
If there's an issue with my family, wife, or kids, or parents. If I start getting eliminated in the first round again and again, then, honestly, you have to really ask yourself the question. Obviously, if I’m playing hurt all the time or too much, then it becomes " Do I still have to really do this?" But this last year, I've been basically injury-free. It's been wonderful successes. Me and the kids are all really healthy, so it's been great.

Last question. What would you, now at this point in your career, what advice would you give the 16 year old junior Roger Federer just starting out as a pro?
Listen to your coach because I didn’t always. Listen to your parents. They only want the best for you, now that I'm a father myself I realize that. Inspire yourself by your peers, and inspire yourself by your same age players. To be the best of that generation, but also be the best of the generation that’s existing now. 

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