Andrew Mason obviously thinks of himself as a funny guy, and he set out to build a funny company in Groupon. Just take a look at the paperwork he and his attorneys filed Thursday with the Securities and Exchange to announce an initial public offering for the daily deal leader.

Mason's letter to prospective shareholders, part of the SEC presentation that announces the company is seeking to raise $750 million, isn't your typical federal corporate filing. It’s peppered with such phrases as:

After selling out on our original mission of saving the world to start hawking coupons, in order to live with ourselves, we vowed to make Groupon a service that people love using.

And:

As with any business in a 30-month-old industry, the path to success will have twists and turns, moments of brilliance and other moments of sheer stupidity.

Even a footnote can be funny, as when Mason explains the concept of Groupspawn, “a foundation we created that awards college scholarships to babies whose parents used a Groupon on their first date.”

If you’ve read many such filings, you know a letter from the CEO like Mason’s is unusual. If you haven’t, feel free to pull a few up on the SEC’s Edgar website.

But then, the free-wheeling 31-year-old isn’t your regular buttoned-down corporate chief executive, and the company he created less than three years ago—one that has grown revenues immensely since 2008 while losing money at an even faster clip—isn’t exactly normal either.

As the New York Times points out, this company rooted in technology is even more deeply part of the funny-or-die mentality of The Second City improvisational theater group that launched the careers of Amy Poehler, Mike Meyers, Jason Sudeikis, John Belushi, and many more.

At Groupon, the Times reports, poets give away copies of their verse in the lobby.

An advertisement for a staff-writer position describes one of the finer points of the job this way: “We strive to avoid marketing clichés, shooting instead for vivid description rooted in complete transparency and embellished with well-crafted absurdities.”

Mason’s own sense of humor is well documented.

Aaron With, the editor in chief at Groupon, has known Mason since the two played in a band together during their days at Northwestern University. He told the Chicago Tribune that Mason had, “a little bit of Andy Kaufman in him.”

Or maybe a lot. At a TechCrunch event, Mason appeared with a fake tan, slicked-back hair, and the air of a man about to change the world with his presentation.

On another occasion, he found himself slipping into corporate speak when talking about why he turned down a $6 billion offer from Google to buy his company. He stopped himself and said, “This is why I don’t like answering the questions. Because I immediately start saying bullshit.”

Mason’s sense of humor has also backfired, and on a very big stage. In a series of television ads first shown during the Super Bowl, Groupon seemed to be making light of some very unfunny incidents, including the Chinese occupation of Tibet. Mason said it was meant as a joke, but the Chinese weren’t laughing, and neither were activists who believe in a free Tibet. It was one of those “moments of sheer stupidity.”

But the company didn’t seem to suffer too much—the IPO filing said Groupon piled up $644.7 million in revenue in the first quarter of 2011, during the ad controversy.

The idea of being funny and making money isn’t new, of course. Look to Hollywood, Madison Avenue, or the Cheezburger network on the Web.

But Mason isn't quitting. A tweet he posted Friday morning reads: "Trying to find new things to not talk about," an allusion to the "quiet period" mandated for executives and investors taking their company public. We’ll see how Mason’s humor goes over on Wall Street.

He of course warned investors, in a Masonian way, about the risks they face putting money into his company. “In the past, we’ve made investments in growth that turned a healthy forecasted quarterly profit into a sizable loss,” he wrote.

But no matter how real or funny he comes across in the SEC filing, if his company doesn’t do better over the long haul than the nearly $113.9 million it lost in the first quarter, investors will heckle Groupon off the stage.

And that’s no joke.

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Kent Bernhard Jr. is News Editor of Portfolio.com