He discovered the form at 13 when he wandered into a grocery store, spotted a book that pitted DC and Marvel Comics superheroes against each other, and found himself hooked.
Over the next few years, as he, too, worked in a local shop, he amassed a collection of more than 50,000 comics, from vintage-era stuff like early Batman to series starring The Flash (DC Comics), and The Punisher and Wolverine (both Marvel).
"I see that [cable TV] show 'Hoarders,' and I have to admit I can relate. I never wanted to throw anything out. There's always this thought, 'I might want to reread that,'" says Penrod, who eventually turned his obsession — and his stash — into the stuff of his current business.
The comic book mavens figure they probably crossed paths as teens, but they know for certain that they met about four years ago, when Penrod, looking for a good local shop to hang out in, discovered Third Eye.
The place was so well run, featured so many signings and other events, and had such a loyal fan base that it felt to him like home.
"I wouldn't try this venture [Annapolis Comic-Con] with just anybody," Penrod says. "But I've known for a while that Steve knows what he's doing. That's one reason I'm sure it's going to work."
Both friends know firsthand how the comic-books industry has exploded. Before he was tied down at a store of his own, Anderson was a regular on the convention circuit, setting up shop at galas from New York to California.
Penrod still attends annual conventions in Philadelphia, Orlando, Fla., Richmond, Va., and elsewhere, lugging 20,000 or so of his specimens to sell and keeping an eye on what's happening in the field.
Last year, he even made it to the granddaddy of them all, Comic-Con International in San Diego, an event that started out small in 1970, when 300 comic-book lovers gathered to talk about their hobby, and morphed over the years into a pop-culture phenomenon spotlighting toys, fantasy novels, TV shows and soon-to-be-released Hollywood blockbusters.
Celebrities including Francis Ford Coppola, Pee Wee Herman and Peter Jackson made the 2011 version, which drew 125,000 fans a day over four days, and generated nearly $170 million in business for the community.
Penrod had a great time — "Who wouldn't? It's San Diego," he says — but the experience was as double-edged as a He-Man sword.
"It's almost depressing. It takes you half an hour just to get to where the comic books are, and when you do, the crowds aren't that big. You're thinking, 'This isn't about comics anymore.'"
Annapolis Comic-Con won't be that way.
A few years back, Penrod noticed a trend: In most of the cities that hosted one of the recognized mega-conventions, someone has decided to set up a smaller, more intimate show at a different time of year.
They're "more modest in size, but still vibrant and fun," Anderson says. "Greg realized no one had tried that in Maryland." They envisioned an Annapolis event that would complement Baltimore's in size, and finally got around to planning it this year.
As they filled in the details, things fell together nicely.
Penrod wanted to showcase comic artists who work locally, and he quickly landed two of the industry's finest. Baltimore native Greg LaRocque, famed for updating and reworking the classic comic "The Flash" during the 1990s, will be signing, sketching and selling prints of his art. So will Steve Conley, a D.C.-based artist perhaps best known for the comic "Astounding Space Thrills."