Since he doesn't take clients, he considers himself an amateur investor, though he does have some investors who pay to mimic his moves on a site called Covestor.
Plettner manages five separate portfolios, and two of those have handily beaten their benchmarks since inception.
"I'm a decidedly unsexy guy, and I invest in decidedly unsexy type of things," Plettner says.
Plettner thinks his "unsexiness" is actually what investors who choose to mimic him find attractive. For example, his Long/Short Opportunistic portfolio has not only outperformed the S&P 500, but has done so with less volatility.
Plettner specializes in closed-end funds. On the long side, he looks for funds that trade at a large discount to the value of their underlying assets, known as net asset value or NAV. If those funds are likely to see an increase in the distributions they pay out to investors, he may buy them. He also occasionally looks to short funds that trade at a premium to their NAV but are likely to see a distribution cut.
Although closed-end funds have a NAV just like any mutual fund, shares can't be redeemed or issued absent corporate actions so they trade based on supply and demand, which defines market price.
Plettner will also look for discounted funds that have a large institutional investor base.
"If you have high levels of institutional ownership and the discounts are thick, there tends to be a catalyst for activism and activism historically is one of the best ways for closed-end fund investors to unlock value," Plettner says.