Buffett has described Simpson as having “the rare combination of temperamental and intellectual characteristics that produce outstanding long-term investment performance.” In particular, Buffett admired Simpson’s ability to invest in stocks with below-average risk, and yet generate returns that were the best in the insurance industry, a hallmark of Buffett’s. Simpson’s investing for GEICO often paralleled Buffett’s efforts at Berkshire. And students of Buffett’s style will recognize his influence in Simpson’s process: seek undervalued businesses with proven track records, strong management, a high likelihood of continued steady growth, pricing power, financial strength, and a history of rewarding shareholders. “He has this great ability to understand what’s going to be a good business,” said Glenn Greenberg, a longtime friend who is now managing partner at Brave Warrior Capital Management. (Simpson considers Glenn an excellent investor and they have ended up owning the same stocks numerous times over the past 30 years.) “And it’s concentrated because there aren’t that many really good businesses.”
Simpson has an unassuming manner and puts people at ease. He has a wide circle of acquaintances, which assists in gaining insights into companies and industries he is researching. He is also a master of understatement, so much so that in conversation the import of his observations aren’t understood until long after the discussion is over. Like the man, Simpson’s office is unassuming. It is situated in a low-key, nondescript office building in Naples, Florida, an 8- to 10-minute drive from his home. A passerby would have no clue about the business being transacted in it. It is also unusually quiet. He says that he has always tried to block out as much noise as possible. There are no interruptions; no ringing phones, no Bloomberg in the office—Simpson keeps it in the entranceway, separate from the office, so that he has to stand up from his desk to look something up if he needs it. “If I have the Bloomberg on, I find I am looking at what the market is doing,” he said. “I really like to be the one who is parsing the information, rather than having a lot of irrelevant information thrown at me.” His desk, like the rest of his office, kitchen, and meeting rooms, is clutter free.
His work life is similarly low key. He is disciplined about exercising before work, and arrives at his office long before market hours. Simpson reads everything he can find about companies that have caught his eye. He doesn’t search for investments in analyst reports, or by speaking to sell-side researchers.