#85 Bruce Kovner (trained by Michael Marcus who was trained by Ed Seykota)
Net Worth: $4.3 billion As of September 2012

Hedge fund legend Kovner, who had generated more than $12 billion in net gains for investors since he founded Caxton Associates in 1983, called it a career in September 2011. The reins to his $10 billion firm were officially handed to former chief investment officer Andrew Law on January 1, 2012. Kovner addressed the transition in a letter to investors saying he will miss the adrenalin rush of confronting markets every day. The son of a trade unionist, Kovner abandoned his Harvard Ph.D. in economics after a fit of writer’s block. He moved on to driving taxis, writing and studying harpsichord at Julliard. At 31, he turned $3,000 he borrowed on his credit card into $45,000 trading soybeans and soon watched as that value halved. It was a seminal lesson in risk management. The chairman of Julliard, Kovner has donated 140 scores and sketches by Bach, Beethoven and Brahms to the school; he also gave $20 million to Julliard in January to endow a graduate-level program in historical performance.

#311 John W. Henry (profiled in Trend Following)
Net Worth: $1.5 billion As of September 2012

Boston Red Sox owner John Henry hasn’t enjoyed watching his expensive team fall apart in 2012, missing the playoffs for the third straight season. He bought the Red Sox in 2002 after building his fortune through his hedge fund J.W. Henry & Company. Henry broke the “Curse of the Bambino” by winning two World Series championships in 2004 and 2007. His Fenway Sports Group now owns the Liverpool F.C. soccer team, 80% of the New England Sports Network (NESN), and 50% of Roush Fenway Racing. In his free time, Henry enjoys playing iRacing, the online racing simulator game he owns. In 2009, he married his second wife on his private yacht (now for sale) and held the reception at Fenway Park in Boston.

Motivating!

Note: Also on the list are Paul Tudor Jones and Louis Bacon. Jones has famously said:

“The illusion has been created that there is an explanation for everything with the primary task to find that explanation.”

And:

“Losers average losers.”

And it has been said about Bacon:

If a stock goes from 100 to 90, an investor who looks at fundamentals will think maybe it’s a better buy, explains one source. But with Louis [Bacon], he will figure he must have been wrong about something and get out.

Jones and Bacon might not have been classified as trend followers, but they have some clear parallels with the trend following way.