Jim Oberweis (left), a Republican candidate for the U.S. Senate in Illinois, with son Jim in one of their family’s ice cream parlors.
Photograph by Ryan Lowry for Fortune
By Jen Wieczner
June 12, 2014

Jim Oberweis isn’t big on thinking about retirement. At least not his own. The 68-year-old Illinois state senator and founder of the Chicago-area fund firm Oberweis Asset Management is still taking on new challenges. He recently won the Republican primary for U.S. Senate and will run against incumbent Sen. Dick Durbin (D-Ill.) in the general election in November.

It would be yet another chapter in Oberweis’s diverse career, which began with a job teaching junior high but took off when he launched an investment newsletter, the Oberweis Report, then a brokerage, and then his investment company, which includes seven mutual funds and manages roughly $1.5 billion. Along the way Oberweis also took charge of his family’s small legacy dairy business in the late ’80s and grew it sizably. The company now has a network of 43 “ice cream and dairy” retail stores across the Midwest churning out $70 million in annual sales, and it also delivers bottled milk the old-fashioned way to doorsteps as far away as Virginia.

When Oberweis first vied for the U.S. Senate seat more than a decade ago, he didn’t intend to leave his day job. The emerging growth and micro-cap funds he ran continued to outperform their peers even as he hit the campaign trail. “I truly expected to do that for as long as I was alive,” he says.

After losing in the primaries twice, though, the father of five did his own sort of rebalancing. He turned the “all-consuming experience” of running mutual fund portfolios over to his son Jim, 40, and pitched in on the dairy business, run by his other son. He bought a condo in Florida. But then he won his state senate seat in 2012 and never really slowed down. “I don’t think he actually plans on retiring,” says the younger Oberweis of his father.

Retirement, however, is a major topic for Oberweis the politician. Illinois has botched its pension planning, falling roughly $100 billion short in its savings funds, and Oberweis has been working on bills to fix the system. The state’s best bet, he believes, is to switch to 401(k) plans for state employees, which would at least give them control over their own investments.

However, if you ask Oberweis about his own retirement portfolio, he cautions that he would not recommend his strategy to clients. For example, he doesn’t own a single bond, despite being at an age where capital preservation and income are supposed to be a priority. “None at all,” he says confidently. Why? He thinks interest rates are likely to rise substantially in the next two to four years, driving down the price of bonds. Given that risk, Oberweis is willing to shun the conventional wisdom and bet heavily on equities.

Research by Morningstar says that funds whose managers invest most heavily in them perform better than others. That makes sense: The managers follow the investment ideas in which they believe the most to greater returns. But, to an extent, managers have their hands tied when investing clients’ money. They are typically bound by their funds’ objectives as defined in the prospectus and limited in what they can buy. Their personal portfolios, however, aren’t limited by those constraints.

So Fortune decided to ask some of the most successful money managers around how they’re investing for their own retirement. Then we put them on the spot with this question: If you were forced to invest all your retirement savings in a single stock, what would it be? Of course, no stock by itself can ever replace a diversified portfolio. But sometimes it takes an impossible choice to unearth the deepest convictions.

One common theme among the investors we surveyed was that there was little enthusiasm for owning traditional bonds. (For more on fixed-income strategies, see “An oasis for yield seekers?”) Can the rest of us afford to bet our retirement on just stocks? Almost any financial adviser would tell you it’s a mistake to try. But the idea has rarely been more tempting or seemed more rational. Oberweis prefers to generate income from high-yielding stocks. He says he has 5% of his retirement portfolio in shares of dividend-paying gold miners like Freeport McMoRan and Barrick Gold. Playing the politician, Oberweis said he couldn’t pick just one stock to own.

When asked for his top pick, the younger Jim Oberweis turns the conversation to China. Since taking the helm at Oberweis Funds–where he has led the funds to best-in-class records–Jim has begun teaching his eldest teenage son the investment business. That includes taking him on trips to China to meet companies whose stocks are owned by the Oberweis China Opportunities Fund, which Jim co-manages. He likes a number of small companies. But when pressed to choose one, Jim mentions Baidu, the Chinese web search giant, as a long-term bet on China’s continued growth. “One of the biggest mistakes that people make who have 20 years until they retire is not owning China,” he says.

Here’s what our other investors had to say about their retirement investing:


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