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6 Unexpected Lessons We Learned Playing Chess with Richard Branson

It’s not every day that you get to keep company with one of the most successful entrepreneurs on the globe, but a few years ago while on vacation in Necker Island, I found myself doing just that when I met Sir Richard Branson. In my pre-Two Blind Brothers days, I’d worked in finance, and had been given the opportunity by some work friends to join them on a trip down to Branson’s private island, Necker, which sits in the idyllic British Virgin Islands. If you’ve never been to the BVI’s, GO, they are scenic beyond comparison.

Necker is full of exotic animals, and Sir Richard has a staff of about 150 people to service the 30 or so guests that will be on the island at any given time—it’s as amazing as one would picture, trust me. So how did it come about that I began playing chess against him? I asked. The first time I met him, it was at a lunch on the island, where I mustered up the courage to ask his advice on this little brand we were launching called Two Blind Brothers. After explaining the idea behind it to him, he loved it so much that he not only offered up his support, but he also agreed to make a video for social media with me and purchased 1,000 shirts to sell at the shop on Necker. He was an early advocate of and inspiration for the brand, and continues to support us to this day.

But back to what I learned, here’s something most people don’t know about Sir Richard: he’s not only soft spoken in more intimate settings and a total prankster, he also loves chess. A self-taught student of the game, he’s always looking for people to play against while he’s on the island. And once you play him, you realize that he’s all about strategy and position, constantly looking for the quick 2-move maneuver that will outwit his opponent. The funny thing is, he’s not the best player out there, in fact if I had to give him an Elo score (which is only meaningful to chess nerds like myself), he’d probably rank at about a 1200, which means he’d be very strong in the eyes of the casual player, but wouldn’t be able to stand toe-to-toe with true prodigies. I’ve been playing chess for years, and while I still have a lot to learn, I have won my fair share of games against him in the years since we met. (Sidenote: Wanna play me? My username is ChessChessGoose on, and yes, I’m pretty proud of it.) So how is Branson a strong player at all without any formal training? A little something I call lesson 1:

Go with your instincts. Sir Richard’s style of play relies heavily on him having strong instincts for the game. He’s always looking for that angle you maybe haven’t found just yet, the unexpected way to checkmate, and trying to read his opponent. Anytime someone is successful in business, there’s always this question of whether he or she is a genius like an Elon Musk, who has calculated out every insane little detail, or whether he is more instinctual. Branson is instinctual, relying heavily on his gut instincts about people. But just as in business he’s a master brander, in chess, he’s a master at reading the situation, which leads us to lesson 2…

Play the man, not the position. Each time Branson sits down with a new opponent, he’ll try to start out with some quickie opening move, a BS trick, that if not identified, would let him win straight out. They’re the types of move that, if you read a chess book, they’d tell you to avoid because they’re lazy, and if your opponent identifies them, they’d leave you vulnerable and out of position. But Branson’s there to win. He’s very competitive, he studies his opponent, and he abides by the old poker saying, “Play the person, not the cards.” And how does he do that? By leaning on lesson 3...

Keep your mind sharp. Another thing most people don’t know about Sir Richard Branson is that he’s super active. An avid runner, biker, kitesurfer and tennis player, he basically ends up exercising several hours a day, which has likely contributed to him being in his late 60’s and still being in phenomenal shape. But all that activity doesn’t just keep his body strong, it serves his mind, too. It shouldn’t be that surprising, then, that one of the world’s most famous entrepreneurs is so serious about staying active that it keeps his mind in top shape, too. And why does he need to be mentally on-point? So that he can be an example of lesson 4:

Never give up. In some of our chess games, I’d be ahead dramatically and would gesture my hand as if to ask whether Branson wanted to take the resignation, to give up when he was clearly not in position to win. He never would. He understands that all it takes is for his opponent to lose focus momentarily to be able to seize an opportunity, and his tenacity serves him well. He always wanted to play it out, and I’m sure there are times that this pays off. That said...

You get the most in life by giving. Just as Branson was attracted to Two Blind Brothers in part because of its philanthropic nature, by him giving me just a short bit of his time to do that video and support the cause, he has made a lifelong admirer out of me. And in the same way, with Two Blind Brothers, we think that if we can give that individual who’s affected by a visual impairment or their family member a message of empowerment, that we will cultivate a loyal follower of the brand. We may be giving to a cause, but we get fulfillment and a sense of community in return. And finally, in life and in business...

Just ask. None of this would’ve happened if I hadn’t summoned the courage to walk up and ask Sir Richard if I could have the next game, to speak up about the brand and ask for his advice and for a few minutes to make a video. I think a lot of times in life, there’s an opportunity in front of you, and it’s so easy to just think about all of the things that could go wrong, so you miss the chance. But it just goes to show you the value of asking, because you never know what could come out of it. For us, it was 1000 shirts ordered and some social media face time, but more importantly, it was lessons learned from an amazing person.

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