Digital Social Hour #1640: Jan Henric Buettner—Why a $10B Founder Came Back to Build a Chess Startup at 60

Release Date: November 25, 2025
Host: Sean Kelly
Guest: Jan Henric Buettner (Freestyle Chess Founder, serial entrepreneur with a $10B exit)

Episode Overview

In this engaging episode, Sean Kelly sits down with Jan Henric Buettner, the serial entrepreneur behind Freestyle Chess, to explore why a billionaire who could have retired decided to disrupt the chess world at age 60. The conversation traverses Buettner’s entrepreneurial journey, the vision for a chess revolution alongside Magnus Carlsen, and powerful reflections on luck, money, legacy, and the unending pursuit of meaning through new ventures.

Key Discussion Points & Insights

1. Reinventing Chess for the Masses

• Chess Needs a Makeover:
  • Buettner compares chess's staid image to the thrills of Formula 1, emphasizing the need to attract a mainstream audience rather than only chess aficionados.
  • "We want to have chess being interesting for normal people and not for chess players." — Jan Henric Buettner [00:53, 08:51]
• Aesthetic & Experience:
  • Taking cues from Formula 1, players now wear colored jackets and tournaments integrate storytelling around personalities—not just gameplay.
  • “All the players, they have the different color jackets... everybody can be distinguished by the fans, even if the names might not ring a big bell.” — Buettner [00:53, 09:10]

2. The Birth of Freestyle Chess

• Journey from Inspiration to Execution:
  • After decades in tech, media, and real estate, Buettner found chess tournaments dull until grandmasters suggested hosting one at his luxury resort.
  • “So I looked it up and I found a perfect sleeping pill—as I always say, it’s so boring watching two people who play chess...” — Buettner [02:24]
• Collaborating with Magnus Carlsen:
  • On meeting Carlsen, Magnus suggested “Fischer Random 960,” making every game unique and unpredictable.
  • “He said, if I can select a tournament, I want to play Fischer Random 960 on the highest level.” — Buettner [04:37]
  • Randomizing the starting positions reduces repetitive, pre-memorized play and rekindles excitement for both players and spectators.
  • Buettner jokes: “Is that Fischer Random, like, from my pharmacy against my cold?” [04:43]

3. Modernizing the Competition

• Shorter, Thrilling Tournaments:
  • Classical chess games are long and often end in draws, turning off broader audiences. Freestyle tournaments cut game times from 90 minutes to 30 minutes per player and tournaments from 8 days to 5 days.
  • “Now the games will be much shorter. ...Finish the games within one and a half to two hours maximum.” — Buettner [06:07]
• Elite Player Selection:
  • Only top grandmasters with an ELO over 2725 are selected, ensuring drama and quality.
  • “We have created a freestyle chess players club...you have to be way up there, which basically applies to maybe the top 20, 22 players in the world.” — Buettner [07:02]

4. Chess as a Social & Cultural Event

• From Niche to Mainstream:
  • Buettner’s mission: turn chess events into social spectacles that blend in celebrities and cross-pollinate sports audiences.
  • “Most of them don’t even watch the race during it’s going on because they socialize with each other. So we make chess a social event on the highest level.” — Buettner [09:32]
  • Collaborations with sports stars like Derrick Rose and crossover events with basketball, tennis, and soccer aim to broaden chess’s appeal.

5. The Mindset of Serial Entrepreneurship

• New Chapters at 60:
  • Despite a huge exit and success in venture capital, Buettner rejects retirement as “the next step to death.” Instead, he launches startups for the challenge and the joy.
  • “Starting it at 60...being entrepreneur again, it’s kind of funny, but it’s also, you know, very rewarding.” — Buettner [12:17]
  • He references his “seven times seven” philosophy: 49 active years in which to reinvent oneself every 7 years.
  • “Every seven years, I did something completely new...mobile communication to online service, venture capital, being a resort developer...” — Buettner [14:06]

6. Reflections on Luck, Money, and Legacy

• Humility & Good Fortune:
  • “A lot to do has with...luck and not really taking everything for granted...being humble and just appreciating life.” — Buettner [15:04]
• Money’s Purpose:
  • Buettner prefers putting wealth into tangible, visionary projects instead of chasing numbers.
  • “I want to have my money where I can see it, like in my village...It’s better than having zeros on the bank account, right?” — Buettner [19:01]
• Inheritance:
  • He cautions against easy inheritances, stressing the value of struggle and self-made accomplishment.
  • “If somebody just inherits money, you just take away the motivation for doing something on your own.” — Buettner [19:16, 20:11]

7. Approach to AI and Staying Curious

• Enthusiasm for AI:
  • “AI is so amazing—it’s fantastic. I embrace it totally myself, you know, it’s like my little ChatGPT friend...” — Buettner [14:26]
  • Stresses open, friendly curiosity toward both humans and machines.

8. Connecting through Chess

• Bringing People Together:
  • Chess serves as a universal language and social connector, as personified by a recent interaction with his business hero, Richard Branson, who reached out about potential involvement with Freestyle Chess.
  • “So one of my little life goals was...having an interaction with Richard Branson happened, you know, by accident, through the chess.” — Buettner [22:20]

9. Freestyle Chess Today & Future

• Where to Watch:
  • Events stream on freestylechess.com, YouTube, Chess.com, and soon on ESPN and Dazn.
  • “We are just a baby company. We started in February.” — Buettner [23:19]

Notable Quotes & Memorable Moments

• “I looked it up and I found a perfect sleeping pill—as I always say, it’s so boring watching two people who play chess...”
  — Jan Henric Buettner on why chess needs a makeover [02:24]

• “If you have a friendly person and he’s rich, he’s a rich, friendly person. If you have an asshole and he’s rich, he’s a rich asshole. It doesn’t really change the character; it multiplies it.”
  — Jan Henric Buettner on wealth and character [20:46]

• “Retiring, always—I look at retiring like the next step to death. So if you’re not busy anymore, then you kind of lay down.”
  — Jan Henric Buettner [12:47]

• “Every seven years, I did something completely new...Trying to do different things, not all the same things.”
  — Jan Henric Buettner on reinvention [14:06]

• “Chess is one of the words that in every language a child knows, one of the first words that they know. So it’s such a big market...and we are starting to lift it.”
  — Jan Henric Buettner [11:40]

• “We make chess a social event on the highest level. And we have also some celebrities there...to bring fans of those stars to chess.”
  — Jan Henric Buettner [09:32]

• “If somebody just inherits money, you just take away the motivation for doing something on your own.”
  — Jan Henric Buettner [19:16, 20:11]

• “So one of my little life goals was...having an interaction with Richard Branson happened, you know, by accident, through the chess.”
  — Jan Henric Buettner [22:20]

Key Timestamps

| Time | Segment / Highlight | |----------|---------------------------------------------------------| | 00:53 | Drawing on the Formula 1 analogy for chess tournaments | | 02:04 | Guest background and spark for Freestyle Chess | | 04:37 | Partnership with Magnus Carlsen, origin of Freestyle | | 06:07 | Why classical chess is boring and how Freestyle fixes it| | 07:02 | The elite player selection and tournament format | | 09:32 | Chess as a social event, celebrity and sports crossover | | 12:17 | Becoming an entrepreneur again at 60 | | 14:06 | Buettner’s “seven times seven” philosophy | | 14:26 | Excitement about AI and future tech trends | | 19:01 | Philosophy on money, tangible value over numbers | | 20:11 | Dangers of inheritance on motivation | | 22:20 | Richard Branson reaching out about Freestyle Chess | | 22:56 | Where to watch & follow Freestyle Chess |

Closing Thoughts

Buettner’s journey is a testament to reinvention, curiosity, and meaningful legacy beyond mere financial gain. His mission with Freestyle Chess is more than a game—it's about making a staid cultural icon relevant and thrilling for future generations. The episode delivers rich wisdom on entrepreneurship, living with purpose, and the power of sport in uniting diverse worlds.