Jan Henric Buettner: Why a $10B Founder Came Back to Build a Chess Startup at 60 | DSH #1640

22m

Freestyle chess is shaking up the chess world, and Jan Henric Buettner comes on the podcast to discuss how this innovative format is disrupting the game and making chess more accessible to the masses. From randomized boards to shorter games, Jan shares how freestyle chess combines competitive strategy with an engaging, media-friendly approach. He also dives into the inspiration behind the concept, the partnership with Magnus Carlsen, and their vision for attracting new audiences by reimagining the chess aesthetic, integrating celebrity culture, and aligning chess with other global sports.

📚 WHAT YOU’LL LEARN

♟️ How Freestyle Chess works and why Magnus Carlsen wanted this format
🚦 Why he models chess after Formula 1 with color-coding, storylines, and spectacle
⏱️ How shortening time controls and tournaments makes chess watchable for TV & streaming
🧠 Why randomized starting positions (Fischer Random) make games more creative and less memorized
🏰 How a $10B entrepreneur ended up restoring a ruined village and building a luxury resort
📊 What it takes to build a new sports/entertainment property from scratch at 60
🎯 Why he believes in living life in 7×7-year cycles and changing paths every few years
💸 How his relationship with money, luck, and success evolved over time
🤖 Why he embraces AI (and even jokes about being nice to ChatGPT)
🌍 Why chess has 700M+ players but needed a fresh format to reach a mass audience

CHAPTERS
00:00 - Intro
00:38 - What is Freestyle Chess
06:06 - The Venue
09:56 - Is Chess a Sport
12:45 - Next Trend is AI
14:25 - Luck in Chess and Business
16:55 - Building Companies with Exit Strategy
19:02 - Evolving Relationship with Money
21:14 - Where to Watch Freestyle Chess
22:19 - Like & Subscribe

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♟️Jan Henric Buettner -

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⚠️ DISCLAIMER
The views and opinions expressed by guests on Digital Social Hour are solely those of the individuals appearing on the podcast and do not necessarily reflect the views or opinions of the host, Sean Kelly, or the Digital Social Hour team.

While we encourage open and honest discussions, Sean Kelly is not legally responsible for any statements, claims, or opinions made by guests during the show.

Listeners are encouraged to form their own opinions and seek professional advice where appropriate. The content shared is for entertainment and informational purposes only — it should not be taken as legal, medical, financial, or professional advice.

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🔎 KEYWORDS
freestyle chess, Magnus Carlsen, Jan Henric Büttner, Fischer Random 960, freestyle chess vegas, Wynn Las Vegas chess, Formula 1 chess, chess as a sport, modern chess formats, chess tournament Vegas, elite chess players, chess.com freestyle, ESPN chess, DAZN chess, randomized chess starting positions

#chesstournament #chessevents #disruptingchess #chessinfluencer #chessplayers

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Runtime: 22m

Transcript

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The way we see this chess aesthetic, the chess aesthetic before is not so much. You know, I'm always referring to analogies like Formula One when I said from the beginning.

So the same as we want to apply to chess. We want to have chess being interesting for normal people and not for chess players in the Formula One.

And then you have all the personality stories and you have the color codes, you have the red Ferrari and the green Eskim Martin and so on. And so we applied that model as well.

So all the players, they have the different color jackets and so everybody can be distinguished also by the fans, even although the names might not ring a big

okay guys, Jan Henrik Buetner here today. Hopefully I pronounced that right.
Cool, perfect. Freestyle chess.
Yes. Big week for you in Vegas.
Oh, absolutely. Yeah.
You've been busy, huh?

Yes, very much. Past three days having events and you got four more days, right? Five more days, yeah.
Five more days.

We have a five-day tournament, and we had a one-day pre-tournament pre-tournament with a chestival. Yesterday was a day off.
Today is Media Day. Then we have the five-day tournament.

We actually turned it down from eight days. It was before, now it's five days.
Wow. What was the inspiration for this? I know you started this with Magnus, and it's a really unique concept, right?

Yeah, I mean, the whole idea came out of my head. like a lot of things in my life and then somehow it escalates, you know.
So it was just an idea to improve my chess.

And here I am now doing all these tournaments. Yeah, and it's a very unique.
So, basically, could you explain it? You start with a randomized board, right? Yeah.

So, the way actually it started is basically,

I just turned 60 last year, and I had my started my career in the 80s with mobile communications.

And then I went on to online services and venture capital. And then I went back to Germany 20 years ago.
And I lived in California for 15 years.

And then I went back to Germany and restored a complete rotten village to a beautiful private nature luxury resort over 20 years, the last 20 years.

And also I built a beautiful music studio, a production studio, like really, really high-end for music production. And I talked to some grandmasters that I was actually learning some of my chess.

I invited them to the studio party and so on. And they said, well, it's great.
Why don't we do a chess tournament here? I'm like, okay, I have no idea what a chess tournament is. Explain it to me.

And they said, yeah, you can follow us online. You know, it's like we play here, there, everywhere.
So I looked it up and

I found a perfect sleeping pill, as I always say. It's like, it's so boring watching two people play chess.

And at the same time, Holly, my wife, and I, we were following the following Formula One circus, like on the Pedder Clubs. And I thought the distinction was so big between the...

chess players and the Formula One drivers, the way they are treated and the way it's also all be seen. And I thought like, okay, maybe we can do a better chess tournament like that.

And so I connected with Magnus because obviously for the greatest chess tournament that you can do you need the greatest chess player of all time

and then I met with him in Qatar in in October 23 and he then said okay after he you know we got to know each other we spent like quite a time with his family my wife and the family a little bit together then he understood that he could basically select his own tournament and he said if I can select a tournament I want to play Fisher Random 960 on the the highest level with normal thinking time against the best players of the world and i looked at him and i had no idea what he was talking about fisher random 960 i always said as a joke it's like it's like uh something is that fisher random for my pharmacy you know against my cold something like that so it's like um and then i so he explained it to me so the the way it works is basically um you randomize the the back rank it's something that bobby fisher has kind of promoted uh this is why it's called fisher random um and um and thereby making the games starting to be exciting for the beginning, taking all of the learning by heart of all the lines and all the stuff out of it, and really having the fun in the game again.

And so then we build the whole tour and the whole tournaments around it with all a lot of different things that we can do with it that make it more media savvy.

Yeah, that's so smart because classical chess games are so long. Yes.
It's kind of boring, right? Yes, yes, exactly. So it's, it's, first of all, they are very long and uh very boring as well.

So it's like seven hours. Yeah, yeah, yeah.
So it can they can be seven hours and so on. So

and and so with with the with the freestyle chat and and it most of them end in a draw of all things at the high level.

So you you watch like seven hours and then they say, okay, well, let's have a draw.

It's like

not not really exciting. And so with the freestyle, it can be also long if you have long thinking time, but this is why we reduced the tournament from eight days to five days.

And the games itself from 90 minutes per person and 30 seconds per player to 30 30 minutes so we divided it by three so now the games will be much shorter we're going to finish the games within one and a half to two hours maximum so we are more also eligible for linear tv as well and it makes it all more exciting and we can have the quarterfinal semi-final and final each on one day and so the pre-rounds like two days and so we can finish the whole tournament five days i love it and you brought the best 25 players right yes yes we have created a freestyle chess players club.

You are eligible with an ELO of 2725. We just talked about ELO, so you have to be way up there, which basically applies to maybe the top 20, 22 players in the world.

You see the Live 2700 ranking, which basically has like 30 players altogether. And so if you're 27, 25, you are in the club.
And you are eligible to be picked

for the tour.

And of course, we can't take everybody because we started with eight players, then we had like like ten then we had uh twelve now we have 16 players we will go back less than that but now we have 16 players out of the top 25 uh playing the tournament um

and yeah that's that's the situation at the win hotel at the win yes shout out to the win best hotel in vegas i love it it's basically when i lived in california 15 years i i was a lot in las vegas i think we're just counting like 50 times i've been to las vegas and i always loved the win it's perfect and then when we got the chance to partner with a hotel, you know, and we had like three options, I was like, you know, we have to do the win because it's fantastic.

And I must say, I'm really raving about the win because they are also so professional. I mean, it's like

working with them is just really fantastic. And if you see later on the venue and everything, what we have built together with them is amazing.

Yeah, it really matches the chess aesthetic, I think, the win. Yeah, absolutely.
The way we see this chess aesthetic, the chess aesthetic before is not so much.

You know, I'm always referring to analogies like Formula One when I said from the beginning. So

which people go to to watch chess tournaments? Chess players, right? Similar like Formula One, like who watches Formula One races? Formula One drivers, right?

Yeah.

No, everybody.

Exactly. Everybody watches Formula One.
And so the same as we want to apply to chess. We want to have chess being interesting for normal people and not for chess players.

So in the end, like we want to have this joke, like, it's like, okay, who watches chess tournaments?

It's like, it's so boring because watching two people play chess is as boring as watching fast cars drive by with no context, right?

So, now you give the context in the Formula One, and then you have all the personality stories, and you have the color codes, you have the red Ferrari and the green Eston Martin, and so on.

And so, we applied that model as well.

So, all the players, they have the different color jackets, you know, and so everybody can be distinguished also by the fans, even although the names might not ring a big bell.

And similar, like Formula Formula One races, when you go to paddock clubs, you have 20 drivers.

If you look around and talk to like 95% of the people, don't know more than like three or four names of drivers.

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.
And we have also some celebrities there.

And we make the crossover like with the basketball, like two days ago, with the basketball players. We will do the same with tennis, soccer, with other sports.
So,

also to bring the fans of those stars to chess, right? For example, the fan base of Derek Rose or all the other players that have been there are also not interested in what we are doing with chess.

Brilliant, because the competitive chess scene has been very boring, right? Yes, exactly. Prior to this.
Exactly. It has been very boring.

And it has been really always like professional chess players playing chess being committed by chess pros for chess pros. So it's like...
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It's a very niche market and we want to open it up because there are 700 million people in the world that play chess. Wow.

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 such a big opportunity and potential and we are starting to lift it.

Do you consider chess a sport? Yes, absolutely. Yeah, absolutely.
It's very, very demanding. You have to be very fit physically and mentally

because when you concentrate, think about just you concentrate for a long time. Think you do an exam, like a really high exam, and

you're really exhausted.

Yeah, you're really tired after. So this is your main focus right now, freestyle job?

Yeah, yeah, it's the main focus that we are doing right now since about one and a half years, my wife and I and all the team we brought together. And so we

starting a new company again.

I mean, I've done venture capital for 15 years myself, but now running this new startup again, like as a CEO, is also kind of funny, starting it at 60, like being an entrepreneur again.

It's kind of funny.

But it's also, you know, very, very rewarding in a sense. Yeah, because you already have a $10 billion exit.
Exactly. You could have retired years ago.
Yeah.

I mean, first of all, retiring, always I look at retiring like

the next step to death, you know, kind of like so. If you're not busy anymore, then you kind of lay down.

So I wrote a little booklet about it, like seven times seven,

because I think think you have like seven times seven years that you can basically be very very active. So ideally trying to do different things, not all the same things.

Yeah, and so so it's uh i it's not going to be something that I'm going to move for ten years as an executive.

I'm going to hand over the torch to somebody in the next maybe twelve months even, um, and then concentrate on my uh executive chairman role um and more being in oversight position rather than in the executive running position.

But at least right now, putting it up and really bringing bringing everything that i have in my mind for this to uh to the road uh is very important so seven times seven so you're saying seven periods of seven years yeah that's my theory and that's what i wrote my little booklet about it it's basically uh let's say the first three seven years you need to be become like a serious person right so until 21.

so there's a lot of things going on then then you have like seven times seven so like 49 or 50 years where you can be really active right and then when you're 70 you know you have maybe three or four other periods of seven years where you can basically chill.

So that's my basic idea.

And so why I and the seven years is for me is like a number which I think is for me applied a lot because I did every seven years I did something completely new, like starting from mobile communication to online service, venture capital, you know, being a resort developer and so on and so on.

Where do you see the next trend? Do you think it's AI? Oh, absolutely. I mean, AI is so amazing.
It's like fantastic. I mean, I embrace it totally myself.
You know, it's like

my little

chat GPT friend, you know, and I always talk to them. And I, you know, I am very friendly with this person because I never know.
You never know exactly.

But it's not based off based on fear. It's basically I'm friendly to everybody.
You know,

I was talking just to the taxi driver here, like chit-chatting. And I just like, you know, whatever you do, you know, you're a serious person or you're a serious AI personality or whatever.

That's interesting, because there's a lot of people with your wealth that are closed off and reserved. You're not friendly with other people.
Yeah, no, I don't like that.

First of all, I think, you know, you have to be

a decent person and to understand that where you are, a lot to do has to do with luck and

not really

taking everything for granted and saying, okay, I have like... two or three successful companies.
It means that I'm having the fourth one immediately. It's also being success.
But really

being humble and

just appreciating life and appreciating anything can happen. I mean,

I could die on the way back, you know, in another society. Hopefully not, because I'm driving you.
Yeah, yeah, yeah, yeah, yeah, yeah. I don't know your driving skin

style, but no, yes, like, no, but you never know what's happening. So

you always have, I always think that you have to live your life the way that whatever your decision is, whatever you do, if it's a small or big decision, it has to apply to

if you if you not survive the next week or if you become 100 years old, right? So it's like the same as to has to has to work in both scenarios, right? Wow. So you really think luck matters that much?

Yes. I mean luck in terms of, I mean, I'm not a religious person, right? So I don't believe like there's a guy sitting there and ruling everything, whatever.

But I believe in fate and I believe in good energy. And I believe that if you give good energy into the world, good energy will come back to you.

If you give bad energy to the world, it's going to haunt you.

But again, I'm not acting out of fear. I'm acting based on my own upbringing and instincts and what I think is right.
So I always have done not what makes the most money or whatever,

what feels right to do. Wow.
So with the castle, did that feel right to buy that? That 400-year-old castle?

I can tell you that that was like a very interesting thing, which is still going on to this day.

Because in the end, there also comes a different thing into it. I'm a perfectionist.
I'm a Virgo

by sign, and so everything has to be perfect. So when I purchased this land, 180 acres, 40 ruins,

and I then applied my perfectionism to it. It took like 20 years, 150 million Euros to build the most prestigious private nature luxury resort.

And

I never thought about like return on investment or all this kind of thing.

So of course I took a lot of my own private money, so about 90 million of my own equity, but still 60 million of other people's money. And so that has to be earned back.
And yeah, so

it's very tough right right now because i'm i'm right now trying to get a partner or selling it or whatever to kind of bring it to the next level because in the end i spent three times seven years with this right so i i first year was basically resort developer second year was basically second uh seven seven years was doing uh it as a profitable uh hotel operations and the third part is kind of the nice to have projects like the residences the studio and so on and i also see now an exit because i spent all my 40s and all my 50s with this.

And I never would have thought that 20 years ago. And so I don't want to carry the bag alone like in my 60s and 70s when I see that I have

maybe somebody to do it together with or have a transition period or sell it or whatever.

So it's like, it's a little bit tough because it's very close to my heart and I build everything with it and I know all the details.

But at some times also you have to let go and see what the next step.

And this is why also Freestyle Chess is helping me also to have a new focus and to do something, something in the next seven years.

Do you build every company with an exit in mind at first? No, not at all. Quite the opposite.

Especially what the castle and the hotel is concerned. I built it as if it was my own home.
And so I never thought about any part of an investment. Does it have a return or whatever?

Does it make sense? It makes sense. It has to make sense.
And I'm a little bit more like...

In the Sex and the City series, there's the one scene when she said, I want to have my money where I can see it in my drawer.

And I say, I want to have my money where I can see it, like in my village. I enter the village and said, wow, it's really amazing.
It's better than having zeros on the bank account, right?

Yeah, because you can actually touch it, right? And with the bank account, you actually lose money. Yeah, inflation.

And it's basically, yeah, and also it's like even if you win money, it's basically you're adding zeros, you know.

And first of all, you're dealing with a lot of zeros in people, you know, because people who are just focused on money and numbers are not really very people you want to really spend the time with.

And then in the end, I mean, measuring it against against the lifespan and against death is like you can't take anything with you.

Last shirt has no pockets, so you can't basically take anything with you. And inheriting is also, you know, I have, of course, kids, but

inheriting is not the best life.

My son, for example, is a professional techno DJ. He's very, you know,

you can look at my DBBD. He's a very successful guy.
Nice. And I'm very proud of him, what he did by himself.

So if somebody just inherits money, you just take away the motivation for doing something on your own.

It doesn't work, right? Inheritance. Yeah.
Yeah. It doesn't work.
A lot of studies on how it actually harms. It harms, exactly.
Yes.

It's like if, for example, I didn't inherit anything and I built everything from my own and I'm very happy. I mean, you go through so much struggle and so much, many problems when you do it.

But when you're finally successful, I'm sure with you, the same with what you have built here. You're so proud of what you have been doing.

And I don't want to take this away from my kids to do something on their own rather than to just, oh, oh,

I get this pile of money and then whatever. So it's like, yeah.
I don't think I would have had the same work ethic, not even close, if I inherited money. Exactly, yeah.

How has your relationship with money changed as you've gotten older?

It's a very good question.

It has never, never really changed in terms of being older. And also I was asked about because

when I started to deal with very, very rich people, when I did venture capital, you know, I take from billionaires and from a lot of people that also I and so how how how are rich people with money and without money?

And I say it's very easy.

Like

if you have a friendly person, you know, 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's basically

enhances the character.

It multiplys plies to character. Basically, so all of the characters come out more strongly when you have money because

you think maybe some people think that they are whatever, unbeatable or whatever so it's like

and it's like anywhere in the world that if you if you look at a hundred people how many people of these people do you really want to deal with like on the street like it's okay maybe every every hundredth person you would like to interact with and the same is like if you have rich people you know you maybe want to interact with one out of 100.

interestingly I had

a childhood not childhood but when I started my business when I was like was 20 or whatever how old are you now I'm 28 28 yeah so I was in my 20s I had my my hero like we all have our heroes, like in the business world.

And so my hero, I had a hero. And I said, you know, if there's one person in the life that I ever wanted to meet in person, you know,

this one guy. And this guy just wrote me an email last week.
No way. Yeah.
His name is Richard Branson. Whoa.
Yeah.

And so he, because he was interested in what we're doing and he might become, you know, involved somewhere in Freestyle. I don't know.
Yeah, he's a chess player. Yeah, we have to still figure it out.

But definitely, maybe we do something on Necker Island, you know, maybe we do something somewhere else.

But at least so one of my little life goals was like, you know, having an interaction with Richard Branson. Happened, you know, by accident through the chess, right? Wow.
Who would have known, right?

Who would have thought? Yeah, he loves chess. Yes.
That's so cool. Chess brings people together.
That's why I love chess.

Like you said earlier, it's an international sport. Yes.
Yes. That's so cool.
Where can people watch the freestyle events? Is there a streaming site? Yes, yes.

First of all, we have our own website called freestylechess.com, which of course is not so big, but you can follow everything.

and then on youtube you chess.com of course is one of our partners and we also have a starting partnership with espn i don't know whether they show some live streaming but at least they have some content coming and the desone uh network wow yeah yeah crushing it that's a lot of distribution yes yes yeah we and we're just a baby company we started in february so wow coming out strong yeah yeah yeah i feel like you're you're really disrupting the space honestly yes that's the plan yeah and you're getting the influencers there that's really smart well um thanks for coming on man anything Anything else you want to close off with?

No, I'm happy, I'm fine.

Thank you for bringing me on here. And I saw that you had David also here before.

And I know I just talked to Hans Niemann. He's happy to come as well if it makes time.
Awesome.

Yeah. Well, thanks for coming.
Check them out, guys. We'll link everything below.
I'll see you next time. I hope you guys are enjoying the show.
Please don't forget to like and subscribe.

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