Somebody at Apple is madly in love with Outwitters.

Since the two-man game design team One Man Left launched this cartoony strategy game for iOS in May, Apple has showered it with affection on the iTunes store. Outwitters got the coveted "Editor's Choice" award, which came with a week-long prominent placement on the App Store's front page. It's been placed in the "New and Noteworthy" and the "What's Hot" sections. Apple even did a special roundup of its favorite strategy games and included Outwitters.

"Apple love," as an executive from PopCap Games (Bejeweled) put it at this year's Game Developers Conference, can be tantamount to tens of millions of dollars in free advertising. iTunes users are constantly looking for new games, but it's exceedingly difficult for game developers to make their products stand out from the crowd – unless Apple's in-house curation team pushes them to the forefront. If that happens, you're almost guaranteed success. Angry Birds and Fruit Ninja didn't hit it big until Apple splashed the games across the iTunes Store's shopping pages.

"You can't get more visible than that at launch," says Adam Stewart, the artist and lead designer on Outwitters. Stewart says the two-man crew spent a year and a half and over $300,000 to make Outwitters. Apple's promotions caused 560,000 players to download it. It's also a critical smash.

There's just one problem. Even after all that attention, Outwitters has been a total financial disaster. It's only made about $40,000.

"We’re on track to break even in about seven years," Stewart says. "If sales never slow down."

Free to Fail ————

What went wrong?

Outwitters is a free-to-play game; iOS users can download and play it with no initial charge. The developers make their money by up-selling players once they've installed the game: more "teams" of characters to use in battle, or the option to have more games in progress simultaneously (like Words With Friends, Outwitters allows you to have many games going at once against different people).

Free-to-play can be quite lucrative if enough players like the game enough to pay up. Most of the top-grossing games on the iTunes store use this model. But only a small percentage of players actually spend (1 to 3 percent, by one estimation) and they need to throw enough cash around to make up for all of the freeloaders. The most successful games let players spend infinite amounts of money, if they so choose.

Image courtesy One Man Left

Where Outwitters screwed up is it didn't give players enough opportunities to part with their cash. When it launched, Stewart said, the most money that any one user could spend was just four dollars.

The back-of-the-envelope math jibes with the results: 2 percent (paid users of an average game) of 560,000 (total users) is 11,200 people. If they spend $4 each, you get $44,800, or approximately what Outwitters has made so far.

Outwitters isn't the first big freemium flop.

In August, the creators of the iOS game Gasketball said that they had been left homeless by their game's inability to convert free users to paid. The team said it couldn't convince even 1 percent of its players to pay.

What Stewart doesn't understand, he says, is why the game was only downloaded half a million times. Half a million people playing your game would be great news for any app developer. In the free-to-play world, it's death. Stewart says he needs 3 million players to break even.

The game Tiny Tower, he said, received similar quantities of Apple love, and 10 million people downloaded it.

Why not Outwitters? Is the app icon too bland? Is the name not high-concept enough? Is the strategy genre too nerdy? One Man Left says it's stumped.

The developer had much greater success with more traditional models. It released its first iPhone game Tilt to Live for an up-front $3 payment, and also had a free demo version. The iPad version that came later was distributed for free, and users unlocked the full game with a one-time in-app payment. The versions of the game got over 1 million downloads and made a tidy pile of cash.

Now, Stewart says he wishes he'd just released Outwitters as a paid app: "I think I prefer [to] shoot for like a hundred thousand downloads at a few bucks each, instead of praying for 3 million players."

For the rest of the year, Stewart says One Man Left will attempt to save Outwitters by adding more in-app items. Stewart feels that he "owes" the players another downloadable team of characters.

But, he says, the company is also thinking of making another game with a shorter development cycle.

"I still think selling content in a free game can work, just not for a company with a marketshare as small as ours," said Stewart. "I just don’t think we could ever have made this work."