Des Moines, Iowa (CNN)When it comes to Midwest humor, there's a line that you don't cross. Mike Draper's RAYGUN clothing company in Iowa pushes it to the edge.
#MaeveWest: See the T-shirts that are edgy -- for Iowa
"I went to the Iowa State Fair and all I got was Type-2 diabetes," reads one light blue shirt that is prominently displayed in the floor to ceiling windows at RAYGUN's new Des Moines headquarters. An edgier choice for the 2016 presidential cycle? A pair of slim-fitting navy boxers with the slogan: "Iowa Caucus 2016: Rising to the Occasion."
Then there are the classics that made RAYGUN a wardrobe staple for aides and reporters who converge on this state every four years. Draper still sells the "Jon Stewart for President" shirts that he began printing during the 2004 election cycle when he was selling shirts while shivering on Manhattan street corners. Other shirts that stood the test of time are those with quintessentially RAYGUN slogans: "Iowa: Wave the next time you fly over!" "Des Moines: Hell Yes." and "Quit Playing Ames With My Heart."
For anyone who trades in presidential politics, RAYGUN is now a landmark near the Des Moines state Capitol. Though the bricks and mortar store has only been around (officially) since 2005, it has come to exemplify the ethos of the young, hip Des Moines -- a city experiencing a renaissance that has drawn a new generation of young professionals back to Iowa.
It's niche? Wry, distinctively Midwest humor sold in the form of tank tops, magnets, coasters and coozies in the company's three stores (Des Moines, Kansas City and Iowa City, as well as online).
"It's a heavy lift to build a brand; you really have to slowly build your customer base," Draper said. "We kind of like these more underrated Midwestern cities."
"If you think about the humor," he adds, "'Des Moines: Hell Yes' is funny because it's built-in irony. We like living here, obviously, but nobody should be that excited about living here. If you think of cities where that joke applies -- those are the cities that we want to be in. Kansas City, Omaha, Fargo, Grand Rapids, Indianapolis, Milwaukee. Detroit is almost too cool for us now."
Draper, who grew up about 25 miles outside the city in the exurb of Van Meter, never expected to be running a clothing company, much less one in Iowa. Growing up in Des Moines in 1990s, "the mark of success was if you had left Iowa," he jokes.
Draper left the Hawkeye State for the University of Pennsylvania, where he focused on "ultramodern European history" and wrote his senior thesis on the European Union and intervention in the Macedonian Civil War in the summer of 2001.
He discovered that a history major prepares you "for nothing," he said. With no post-graduate plans and a need for cash, he began selling T-shirts on Penn's campus with a friend, ultimately relying on a screen printer back in Iowa from his hometown. It was surprisingly good money: a $6 profit on shirts he could sell for $10 a pop.
He got more serious about opening a store after couch-crashing all over New York and dragging his wares around on the subway. After enough January days selling shirts outside on a corner of Times Square, he opened his first outpost in downtown Des Moines in fall 2005.
RAYGUN, which ended up being steps from the 2008 Obama caucus headquarters, was part of a wave of new stores and bars that popped up near the Capitol -- including the High Life Lounge (now famous for its bacon jalapeño tater tots).
"2005 was really the beginning of people moving downtown in a big way," Draper said. "I think it's part of the zeitgeist nationally. It's cool to see what's happened in Des Moines, but there's also downtown regeneration in Hartford, Philly -- pretty much every city," Draper said. "We're part of a local makers generation across the U.S. -- the people who are like: 'Oh I knitted this myself,' or 'I brew my own beer.' Des Moines is part of that bigger picture."
Many of his designers and employees are from Iowa -- the kids, he said, who were the "artsy ones" growing up in small towns across the state who thought about leaving Iowa, or did leave, but wanted to move back. Everyone who works at the store -- from the designers to the cashiers -- puts their latest ideas for slogans on a shared Google spreadsheet and then Draper and his team decide what to print.
In Des Moines and Iowa in general, "there's not a talent gap; there's a confidence gap," he said, with businesses in the state often relying on consultants from cities like New York or Boston for advice.
RAYGUN's motto is the opposite, Draper said: "The talent is here already" in Iowa, he said. "It's just about getting everybody pointed in the right direction."
Investors have approached Draper. But he has no intention of selling RAYGUN -- ever.
"Life is so insanely easy here."