Let me tell you about a curious anomaly in the legendary career of Roger Federer . A man who conquered over a hundred tournaments, a true icon of the sport, yet the Monte Carlo Masters trophy remained just out of reach. Four times he battled his way to the finals, but the ultimate prize eluded him. In fact, alongside Rome, it stands as one of the two Masters 1000 events that remained unconquered by the Swiss legend, a stark contrast to the dominance of rivals like Nadal, who lifted the Monte Carlo crown an astounding eleven times, and Djokovic, twice. But as the calendar turns, the focus shifts entirely. Forget the red clay and the battles fought; this week, Roger Federer is all about soaking in the holiday spirit in the Principality of Monaco.

In case anyone missed to keep track of him, Federer, with his wife Mirka, recently landed in Monaco where he met renowned optician Celine Roland. Taking to her Instagram, Celine, who is one of the selected opticians at this week’s Monte-Carlos Masters to distribute the newly launched eyewear collection from Federer’s collaboration with Oliver Peoples, couldn’t resist her feelings of joy after crossing paths with the tennis GOAT.

In a post dated April 6, she wrote, “What an unforgettable moment at the ROLEX MONTE-CARLO MASTERS 🎾 I had the immense privilege of meeting @rogerfederer — a sports legend, exceptionally elegant… and above all, adorable! His wife Mirka is just as charming ❤️🙏”

After doing business meetings, it was time to enjoy the location itself for Federer and Mirka.

Taking to his Instagram, the Swiss Maestro dropped a series of pictures in a post dated April 8. He was flaunting his sunglasses in a casual wear while posing in style. In one frame, wife Mirk and he can be seen during the evening time from their meeting with Celine. Then there’s one shot where the main clay court venue for Monte Carlo can be seen as well. “Springtime in Monaco 😎⛵️📍🏎️ ♠️”, Federer aptly described the post.

Speaking more of his business side of things, Federer recently became a part of the prestigious Geneva watch salon, Watches and Wonders, held on April 1. There, Rolex finally introduced its anticipated “Land Dweller” to add to its famous Oyster Perpetual collection. While the brand never really teases before making an official announcement, Federer did provide a teaser to the new product a few days in advance. How?

Federer, who became Rolex’s brand ambassador back in 2006, posted several pictures from his Alpine vacation last month. While the 43-year-old was seen enjoying his snow time, several eagle-eyed fans noticed a shining timepiece on his wrist. Speculations suggested that it was the upcoming Land Dweller itself. And as we know, the rumors were correct. The latest watch’s uniqueness can be understood from the fact that it’s got 32 patents. 18 of them are exclusive to this model only. Of them, 16 relate to the movement while one patent each is for the dial and the bracelet.

And there’s no need to dwell on the fact how Rolex has graced the sport of tennis for years now. The luxury watchmaker, valued at $10.7 billion back in 2023 according to Statista, first partnered with the Wimbledon in 1978. Since then, it’s been a driving force of other majors, too, including the French Open. Federer’s long-term association has further boosted the brand’s popularity globally. But his business ventures have gone beyond luxury watches lately. His iconic move with On is one to marvel at. Why?

Roger Federer’s investment in On results in immense fortune

The partnership with On has been a game changer for Roger Federer and the brand itself. Yes, we know that he made $130.59 million from his career prize through on-court action in a two-decade old career, but it was his bond with On that earned him triple that amount. Really? Well, yes.

Being a huge fan of the Swiss running shoe brand, Federer himself reached out to its team for a collaboration. Of course, the brand approved the partnership without wasting a second. The company offered him 3 percent of equity stake, as he became the face of On. He then also helped it design his signature shoe, which became a fan-favorite, eventually. On a previous occasion, one of the three founders of On, David Allemann, revealed,

“At some point he called us and said, ‘Let me buy you dinner.’ And so we had dinner together [and] he said: ‘I’m a big fan of your product, everybody around me is wearing them.’ We said, ‘Hey, why don’t you become a co-entrepreneur together with us? We want to have huge chunks of your time–if you allow–because I think we can do great things together.’ Fortunately, he said yes. He invested his own money in On. And he spent 20 days in the lab with us developing the pro tennis shoe.”

Federer’s endorsement of the shoe company proved to be incredibly lucrative. His support propelled the company’s value to a staggering $12 billion. When On went public in September 2021 with shares priced at $24, Federer’s stake ballooned to an estimated $360 million – nearly three times the $130 million he earned throughout his illustrious tennis career. Thanks to Federer’s involvement, On has reached to a market cap of $14.22 billion as of March 2025.

Undoubtedly, the man knows how to capitalize his sports person image to lead businesses and himself, too, far beyond the court.