How Dungeons and Dragons transformed LinkedIn founder Reid Hoffman into a business wizard

Reid Hoffman is one of the world's most well-respected and sought-after startup strategists. When you ask him about the foundation of his approach? Board games.

A babysitter introduced 10-year-old Hoffman to Dungeons and Dragons, and it kicked off a love affair with strategy-dense games that he's carried with him to today, at age 50.

"There's nothing obsessive like a kid," Hoffman said in a recent interview for Business Insider's podcast "Success! How I Did It."

"I spent literally days and days and days and days just doing that, and that led me to a sense of strategy which was then, of course, very helpful when I later got to my entrepreneurial and business life."

Hoffman became engrossed with the process of analyzing the complex rules of games like D&D to find the best opportunities for success.

He approached each game he played so thoroughly as a kid that when he found what he deemed weaknesses in one particular game's structure, he broke them down in a letter to its maker. The company was so impressed that it hired 12-year-old Hoffman as a credited one-time consultant on its next game.

Games were so important to Hoffman as a teenager that he included D&D imagery on his high school diploma upon graduation from the Putney School, where students decorate their diplomas to express their passions.

While Hoffman, like many Silicon Valley power players, received his undergraduate degree from Stanford, he took the highly unusual path of pursuing his master's degree in philosophy at Oxford, where he studied thinkers like Aristotle and Nietzsche. Again, he explained, it was the practice of analyzing complex systems of thought that he credited for his preparation for business career.

The nuts-and-bolts stuff, like learning how to manage teams and spend capital — that came from trial and error during his experiences with SocialNet, PayPal, and LinkedIn, not the classroom.

As an adult, Hoffman is an avid player of Settlers of Catan, in which players compete to build thriving settlements. He told the Financial Times in October that it has several of the same elements of building a startup: "How much do you build for yourself, how much do you position against other people? It's the game that is closest of all the board games to entrepreneurship."

Hoffman has even developed his own games: Startups of Silicon Valley (for his friends), essentially Settlers of Catan with Hoffman's metaphor made explicit, and TrumpedUp Cards(for sale), a satirical game incorporating Hoffman's dislike of President Donald Trump.

He'll regularly play a game like Settlers of Catan when he has friends over. That way he can continue honing his big-picture strategizing skills while unwinding.

"I play board games as a way of hanging out," he told the FT. "It's an easy way to be doing something while your conversation is roaming, anything from business, politics, philosophy, what's going on in society."