Reinventing the Game: Jan Henric Büttner on Freestyle Chess

Jan Henric Büttner has never been content with doing just one thing. Over the past four decades, he’s been a digital pioneer, venture capitalist, cultural entrepreneur, and now, co-founder of one of the boldest new sports concepts in the world: Freestyle Chess.

In the 1990s, he helped bring AOL to millions of European households, culminating in a $10 billion exit. He then launched venture funds that grew from $75 million to $500 million—and today manages $4 billion under the brand Headline Ventures. Later, he restored Weissenhaus, a 400-year-old estate on Germany’s Baltic coast, investing €150 million to create one of Europe’s most exclusive resorts.

Now, at 61, Jan is proving reinvention never gets old. With World Champion Magnus Carlsen at his side, he’s on a mission to turn chess into a global spectacle with a Formula 1-style tour with Freestyle Chess.

About Jan Henric Büttner

Jan Henric Büttner is a German entrepreneur known for his work in internet innovation, venture capital, luxury hospitality, and, most recently, in organising global chess events with Freestyle Chess. He built his early career around digital and internet ventures, helping to found and develop AOL Europe, and later moving into venture capital in the USA. Büttner also bought and transformed the Weissenhaus estate on Germany’s Baltic Sea coast into a luxury resort, which became a landmark hospitality project. In 2024, he ventured into chess, partnering with Magnus Carlsen to launch Freestyle Chess.

About Freestyle Chess

Freestyle Chess is not a new variation of the game—it’s a new way to present it. Inspired by Fischer Random (chess960), the league resets the board to start each match, forcing even the best players to think creatively from move one. Founded in 2024 by Jan Büttner and Magnus Carlsen, the Grand Slam tour is already staging tournaments in Europe, Asia, Africa, and the U.S. Each event features live commentary, personal player storytelling, and behind-the-scenes access—transforming what can be a slow spectacle into a fast-paced, emotionally engaging broadcast.

“Nobody cares about cars going around a track without context. Formula 1 made it compelling by telling stories about drivers, by showing telemetry, and by building stars. That’s exactly what we’re doing with Freestyle Chess.”

From digital pioneer to investor

Jan began his career in mobile communications, but it really took off when he pivoted to the internet.

“Before the internet, I built an online service that later became the founding company of AOL Europe,” he recalls. “I headed that as CEO, and we sold the company in 2000 for $10 billion to America Online.”

Flush with success, he turned to venture capital. In 1998, he moved to California and launched BV Capital, a venture capital fund backed initially by Bertelsmann. This fund eventually evolved into e.ventures, and today operates as the global firm Headline. “I had my first fund at the end of the '90s – $75 million. Then it grew to $200 million, then $500 million. Today, it has $4 billion under management,” he says.

“The big opportunities are always where nobody’s really looking yet. That’s where you want to be.”

Reinvigorating a 400-year-old estate

After two decades in digital, he made what seemed like an interesting move: he bought a crumbling 400-year-old estate called Weissenhaus.

“When I was 40, I exited the digital and finance world and bought Weissenhaus, a historic village by the Baltic Ocean in Germany,” he explains. “It was completely run down. Over 20 years, I invested €150 million into this.”

It wasn’t just a vanity project. Jan treated Weissenhaus like a startup. “Every stone had to be moved. Every building had to be restored. We built a product with global appeal, and eventually it became one of Europe’s leading resorts.”

The Weissenhaus estate is now listed with Sotheby’s for €185 million. “I don’t think in terms of buildings—I think in terms of value creation,” he reflects. “Sometimes that value is digital, sometimes it’s cultural. But the principle is the same: you take something underutilized, and you elevate it.”

“Entrepreneurship isn’t about money. It’s about taking something broken and making it whole again.”

Why chess, why now?

When it comes to the motivations behind his latest venture, Freestyle Chess, Jan is keen to say that the game has always been close to his heart. “I learned the game when I was eight or nine, but only came back to it later in life,” he says.

“When I reconnected with the scene, I saw enormous potential. Seven hundred million people play chess worldwide—it’s one of the few words understood in every country.” Yet, he felt it was underserved. “Watching two people play is boring. But so is watching cars drive fast without context. The excitement comes from stories, from analysis, from personalities. That’s what turns athletes into stars.”

For him, chess combines accessibility with intellectual prestige. “Billionaires want to mingle with Formula 1 drivers, but they’d be even prouder to sit across a chessboard from a world champion. It’s status, it’s intellect, it’s culture—all in one.”

“Formula 1 on 64 squares—that’s Freestyle Chess.”

Building a Global Tour

Freestyle Chess launched its first tournament in February 2024 at Weissenhaus. Since then, the Grand Slam has expanded rapidly.

“We raised $22 million, with contributions from Left Lane Capital, Robin Capital and private investors,” he explains. “That funding allowed us to stage the first events in Germany and Paris. Then Singapore and Las Vegas, with the final match of 2025 to be held in Cape Town, South Africa.”

By 2026, tournaments will also include South America and Australia, making Freestyle Chess a truly global circuit. “We’re following the Formula 1 model—six continents, six flagship events, plus open tournaments where amateurs play alongside the elite. That creates grassroots connection and global spectacle.”

“We’re not just building tournaments—we’re building a league, a brand, and a platform for the future of chess.”

Purpose beyond profit

Despite the scale of investment, Jan insists his motivation is not financial. “I’m not doing this for the money. I think it’s a great idea that must be executed. I also feel strongly that the players deserve more. They’re young, they’re talented, and they should be compensated fairly for their value.”

He plans to step back from day-to-day operations later this year. “I’ll hand over the CEO position to my successor, and stay on as Executive Chairman. My passion lies in the early stages—the building and experimenting. Once it stabilizes, I’ll move on.”

His philosophy of life is simple: keep learning. “Lifelong learning is critical. Every project I take on is a chance to expand myself. That’s why I returned to chess in the first place.”

“At 61, I don’t need to win anymore. I just need to build things that matter.”

For entrepreneurs, Jan’s career is a masterclass in reinvention. From online services to billion-dollar exits, from historic estates to global sports leagues, he has consistently spotted underdeveloped markets and turned them into thriving ventures.

For investors, Freestyle Chess is a rare opportunity: a new global sport at its inception, with cultural cachet, mass-market appeal, and the backing of the world’s most famous chess players.

Explore investment and partnership opportunities with Freestyle Chess at FreestyleChess.com