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Creating a Mobile Game: A Cautionary Tale

Entrepreneur wanted in on the multibillion-dollar mobile gaming business. So we decided to build our own iPhone game and share everything we learned with readers. Here's the painfully true story of Bosshole.
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Amy C. Cosper leans forward in her chair, a mischievous smile creeping across her face. "Can we add more blood?" she asks, her eyes locked on the projector screen on the back wall of the makeshift conference room.

The screen frames an early prototype of Bosshole, a mobile game conceived by members of the Entrepreneur staff and built by software design startup Rage Digital. Bosshole--a corporate satire pitched somewhere between the movie Office Space and the classic Nintendo title Mike Tyson's Punch-Out!!, complete with cubicle zombies and other workplace horrors--is Cosper's baby: Entrepreneur's editor in chief formulated the concept, sold the idea to her boss, assembled the creative team and hired Rage to shepherd it to digital life. This powwow, taking place in Rage's Boulder, Colo., office on a near-perfect afternoon in August 2012, affords Cosper her first opportunity to view Bosshole up close. "Seeing the animation is the greatest thing ever," she swoons. "This is amazing. It's beyond all of my expectations."

Cosper conceived Bosshole to expand the Entrepreneur brand into a new digital media realm and to explore the inner workings of mobile application development, a booming business segment expected to generate worldwide revenue of $25 billion this year. The article you're reading was envisioned initially as a how-to for aspiring mobile software moguls, a step-by-step guide to designing, monetizing and marketing the next Angry Birds or Temple Run.

That was wishful thinking. In the months following that August confab, Bosshole grew far bigger and more complex than expected. Originally slated to go on sale at Apple's App Store in late 2012, the game instead suffered technical setbacks, blew past internal deadlines and did not go live until February of this year. Both overstuffed and underfed, tricked out with complex multiplayer interactions but coming up short on fundamental gameplay principles and mechanics, it remains a work in progress--down but nowhere near out.

Forget establishing a blueprint for mobile game development. The making of Bosshole is instead a master class in the headaches and occasional bouts of hopelessness that face virtually every entrepreneur striving to bring a passion project to market.

"There was so much enthusiasm when we started. It was just a really cool thing to be a part of," Cosper recalls a few weeks after Bosshole's commercial launch, close to a full calendar year after the project's inception. "But we lost control, and each time there were more bugs to fix and more beta tests to run, the joy was drained out. But we still brought a game to market. We accomplished a lot."

The term "Bosshole" first appeared in Entrepreneur in 2010, "a mashup of the words 'boss' and 'asshole,' used to describe an employer who makes life hell on earth."

Not coincidentally, the evil boss archetype is a gaming staple dating back to the mid-1970s, a decade before multinational brands like Nintendo and Sega took control of the video game sector, building console titles that sold for $50 to $60. The 2007 introduction of Apple's iPhone and the rollout of its App Store changed all that, handing third-party developers the keys to application programming tools and giving them a direct-to-consumer digital distribution channel. Virtually overnight, it became possible for unheralded, unproven garage startups to develop and sell mobile games for a fraction of the console cost or even offer them as free downloads, subsidized by revenue from mobile advertising. In the fourth quarter of last year, consumer spending on games optimized for devices running Apple's iOS and Google's Android operating systems eclipsed spending on handheld titles published for the Sony PSP and Nintendo 3DS platforms.

The mobile gaming opportunity was simply too potent--too quintessentially entrepreneurial--to pass up, Cosper decided last year. "We have to do this," she explained. "We're a media company. This is a new media idea, and we should be playing in this sandbox. All companies have to innovate. This is a way for us to innovate."

Bosshole beat out several other proposed concepts. "Bosshole just fits so well with what we do every day," Cosper said. "It resonates across all aspects of our brand."

But she also harbored misgivings. Specifically, she questioned the ethics of leveraging that brand, as well as Entrepreneur's subscriber reach and marketing muscle, to bring attention to a product so far outside the magazine's wheelhouse. "By essence of writing about it, we're promoting it. It's a Catch-22," she said. "Where is the benefit to our readers? I think the value lies in discussing our experience. We want to help. That's the goal. And that means we have to be completely honest and authentic about everything we do."

After Entrepreneur Media president Ryan Shea signed off on the project, Cosper began marshaling the troops to spitball ideas via conference call, recruiting me, executive editor Carolyn Horwitz (whose main contribution--rejected--was the concept of a "phantom turd" in the office bathroom that must be flushed before moving on to the next level), associate editor Michelle Juergen and staff writer Jennifer Wang.

"The goal of this game is to ascend various levels of ineptitude, humorous obstacles at an organization. Each level of the game represents a layer of bureaucracy and the ascending floors of an organization," read an early Cosper synopsis. "The ultimate goal here is to become your own bosshole, off the current boss and be in charge."

The plan was for Bosshole to hit the App Store in September 2012, with my corresponding article running in Entrepreneur the same month. For a nanosecond we considered developing the game in-house, but the DIY approach was abandoned given our nonexistent coding skills. However, outsourcing the project proved far more expensive than the $15,000 Shea allocated originally; in all, Entrepreneur would spend about $131,000 to make Bosshole a reality.

There will be blood: The team holds an early-stage meeting about game mechanics.

"I met with a developer in Boulder yesterday--Rage Digital--to talk about our game app project," Cosper, a resident of nearby Fort Collins, Colo., wrote in a late April 2012 e-mail. "After several failed and unsettling meetings with developers, I feel pretty good about these guys." 

Rage Digital got its start building mobile apps for clients such as Pepsi, Hyundai, HTC and Red Robin, as well as its own TextUs.Biz text-powered business apps--Messages, iPad Receptionist and Waitlist. Bosshole signaled Rage's entrance into mobile gaming, a segment the firm was itching to tackle. In fact, the team took on the project knowing they would lose money, convinced that the creative possibilities and attendant media exposure would make up the difference.

"Games can be very risky and very time-consuming, and they can also be very difficult to distribute in terms of marketing," Rage president and CEO Ted Guggenheim says now. "What Entrepreneur brought to the table is enough money to where we could afford to take a loss but still have the opportunity to do a top-notch game. They also gave us complete creative license. They didn't say, 'Here's the game, here's what it has to do.' They said, 'Here's a 10-word idea--can you make a game of it?' That was huge."

Guggenheim is a music industry veteran who transitioned to the technology space in 2001, becoming a partner at, an online resource for concert industry professionals. He and creative director Andrew Kimmell launched Rage Digital in 2008, setting up shop in an eyeball-shape stucco building, originally commissioned by an ophthalmologist and designed by modernist architect Charles Haertling. Ed Hahn, a lifelong gaming enthusiast with a background designing e-learning software, joined Rage in early 2011 to spearhead the company's game development efforts.

"For me [Bosshole] is a dream come true," Hahn told me. "It's the first project that has allowed me to flex my game design muscles--to take all I've learned, and all my years and years of experience playing games and thinking about games, and figure out what's going to be a good, fun game mechanic wrapped around [Entrepreneur's] concept. I want to shoot for longevity. I want to have a game that people will come back and play a lot, because that's how you make money on it."

Stop, drop and roll: Game developer Ed Hahn shows a character's stages of movement.

Hahn fleshed out the Entrepreneur team's ideas, producing an exhaustive 33-page document that outlined all aspects of Bosshole in precise detail. "The player selects his or her character and begins as a new hire in the lowest ranks of Jabberwocky Industries, the global leader in innovative (and questionable) technology. The player must work their way up the corporate ladder by performing tasks for the bosshole of each department," Hahn wrote. "As the player ascends to higher ranks in the company, it is revealed that Jabberwocky Industries is disturbingly unethical. This fuels the character's determination to one day take over the company and clean up Jabberwocky."

The document went on to describe the obstacles that impede the player's progress, as well as bells and whistles such as multiple gameplay modes that allow players to take over each others' companies; unlockable content like weapon upgrades and special powers; Facebook and Twitter interactions; and integration with Apple's Game Center social gaming network. It was a wildly ambitious proposal under any circumstances, let alone for a small startup building its first mobile game on an aggressive schedule and limited budget. And there was no margin for error: Beginning in late autumn, Entrepreneur would run Bosshole teaser advertisements in its pages, promising readers a holiday-season App Store debut.

"I don't know what to expect," Guggenheim confessed. "But I have to take Ed's word that we have enough time and that he has the skills."

Confidence was high when we convened for an August strategy session in Rage's offices. Cosper arrived from Fort Collins on her motorcycle; Entrepreneur director of business development Charles Muselli and vice president of marketing Lisa Murray hopped an early-morning flight from the magazine's Irvine, Calif., headquarters; and I flew in from Chicago.

Geek squad: (from left) Ted Guggenheim, Jason Ankeny, Amy C. Cosper and Ed Hahn.

The beta version the Rage team screened for us looked even more dynamic than we had hoped. Hahn had hired Los Angeles-based graphic designer and storyboard artist Eddy Mayer to create characters and office environments; in addition to male and female player avatars, there were the bossholes, plus over-the-top secondary characters like the office drone, the gossiper and the regrettable workplace fling.

"Big heads, small bodies--that's the look we're going for," Mayer explained. "Because of the small screen size, it's important to simplify the characters. You can't go too crazy with detail, because you lose so much of the line work when you shrink it all down."

Oohing and aahing over the prototype gave way to talk about the business model. Bosshole was built for Apple's iOS platform. Instead of marketing it as a premium download, Entrepreneur decided to offer it for free, monetizing the game via in-app purchases--specifically, "reputation points" offered to enhance and accelerate the gameplay experience, beginning at 5,000 points for 99 cents.

So-called freemium titles available gratis and supported by in-app goods like virtual currencies, additional levels and power-ups have emerged as the de facto mobile gaming monetization model: As of March 2013, in-app sales generated 76 percent of total iPhone app revenue in the U.S. and at least 90 percent in some Asian markets, mobile analytics firm Distimo reports.

But developing any application for iOS--let alone one called Bosshole--presents challenges. For starters, App Store gatekeepers are notoriously persnickety about which apps they approve, and anything they deem too edgy or risqué can be problematic. Muselli, who spent weeks studying the App Store ecosystem, warned that Apple's seal of approval was no sure thing and underlined the importance of allowing extra time at the end of the project calendar to accommodate changes necessary to conform to the store's developer rule book. It was also critical, Muselli added, that Bosshole be available in time for the 2012 holiday season, when millions of consumers would unwrap new smartphones and tablets and begin populating those gifts with apps.

There was also the question of visibility. As of this writing, the App Store offers more than 850,000 iOS apps and games, with roughly 1,000 more submitted each day. Precious few break out and go viral; most iOS success stories are vaulted to prominence by earning a spot in the coveted New and Noteworthy homepage spotlight, curated by Apple editors. But Apple is a cipher wrapped in an enigma and smothered in secret sauce, and no one knows what criteria its editors apply to New and Noteworthy selections.

There was hope that the novelty of an established business magazine designing a game would appeal to Apple's own marketing sensibilities and help score a New and Noteworthy slot. But Entrepreneur also decided to take matters into its own hands: The more content published online, the greater the consumer anticipation, or so the thinking went.

Alongside the print ads, the team rolled out a Bosshole website, highlighted by a "Which character are you?" quiz written by Esquire editor (and Entrepreneur contributor) Ross McCammon, as well as an @Bosshole Twitter account. I committed to writing a blog, documenting the app's ongoing evolution and the intricacies of the mobile gaming business.

The meeting stretched more than three hours, followed by a celebratory drink. "What a great meeting, great energy and, perhaps, the funnest project of all time," Cosper wrote a few days later in a thank-you e-mail to the Rage staff. "In the name of Bossholes everywhere, we salute you."

Then it all went sideways.

It's impossible to identify exactly how and when Bosshole flew off the rails. In September 2012, five weeks after the Boulder meetup, Hahn told me the single-player story was about 70 percent complete. "We're still on schedule," Hahn assured me. "There are a lot of late nights and lots of coffee."

But he had made erroneous assumptions about the multiplayer experience, believing it would be largely similar to coding the single-player version. Bosshole began to slip hopelessly behind.

"The multiplayer version is a lot more taxing than I originally anticipated," Hahn admitted in October during a tension-filled conference call. "The volume of code is so enormous. Every tweak or change takes more time to add than it did at the beginning of the project."

Muselli chalked up the delays to Rage's inexperience. "They've done many other apps, but with Bosshole they started doing a lot of things they hadn't done before," he told me. "Perhaps allowing only three months of game development was too aggressive."

By early December Bosshole encompassed more than 2.5 million lines of code. The holidays came and went, and the game remained vaporware. The schedule was revised time and again. ("Ed's infected uvula took away three dev days from our timeline," Guggenheim explained in one e-mail.) Rage Digital was losing money with each passing day, and by the time February came around, Hahn was forced to abandon some of his more grandiose ambitions in the interest of putting the game to bed. "The idea was that we would do this at a loss, but no one anticipated just how much money we would have to eat," he says now.

When Bosshole finally went live in the App Store on Feb. 23, there was no fanfare, no excitement--no anything, really. Contrary to our initial concerns, Apple approved the submission in about seven hours. Not much else fell in line with our expectations, either.

"The final product is pretty close to where I wanted it to be, but the gameplay doesn't work very well, and the graphics could use an overhaul," Hahn acknowledged. "But I am proud of what it is. It's quirky, tongue-in-cheek and fun. We accomplished a lot in a short time."

By the end of May only 5,207 gamers had downloaded Bosshole, but work on the title is not finished--not by a long shot. Hahn continues to update and improve the software, with a focus on implementing the social features envisioned in his original game document.

Hahn is not retooling Bosshole from Rage Digital headquarters, however.

He left the firm in the spring to launch his own gaming startup, Singularity Interactive.

"Ed figured out after all these horrible 18-hour days that he wanted to be in the gaming business more than ever, so he went on to start his own company," Guggenheim says. "I realized that I don't want to be in the gaming space at all.

For Andrew and myself, working on Bosshole has solidified the fact that we are a design and development company that is best suited to working with brands. None of us knew how challenging [Bosshole] would be. But we came out of it with something to be proud of."

With one chapter of the Bosshole odyssey ending and another just beginning, I ask Cosper the obvious question: Knowing everything she knows now, would she do it all over again?

Cosper lets me in on a secret: She's already mulling a second Entrepreneur-themed game. "There are potential ideas in all the things we cover," she says. "The magazine is one big, giant gaming opportunity. There's so much more we can do."  

Game Theories

Entrepreneur asked some mobile game experts to play Bosshole and tell us what they liked, what they didn't like and how it could be improved. Here's what they had to say.

I think the name and idea are cool. I also like the framework of the game … [but] the feel of the game is off. It feels a bit clunky, and it's hard to get in a rhythm when playing. It feels hard to gauge when to jump or hit a zombie, and when I get hit, it feels like I'm stuck in mud rather than just slightly penalized.

Many people get lost in the clever idea of their game and completely ignore the feel. The feel in addition to the presentation is the most important [part] of development. --Dave Castelnuovo, CEO of Bolt Creative (developer of Pocket God)

I found the game to be frustrating due to the way the player controls the character, and also the responsiveness of the controls/gameplay in general. I would look at the core gameplay mechanics (run speed, melee attack, jumping and sliding) and make sure that those core components were as finely tuned as possible. If the game doesn't do those core mechanics well, then users won't be compelled to play past the first level."
--Billy Delli-Gatti, senior producer at mobile game development platform provider CocoaChina

The office theme is a good choice as it can carry itself on its own (see the success of other apps like Kick the Boss, Office Jerk, Paper Toss). However, mixing it with other popular zombie-themed games could be a challenge. While overlap/fusion apps (Zombie Farm, Plants vs. Zombies) have had some success, they are quite rare. It might be a better use of time and resources to focus on building strictly around the office theme, as it'll also bring better appeal to the targeted demographic. --William Siu, chief product officer at Storm8 (developer of Bubble Mania)