Reassembling the Case Writer

“Never regret the past; time expires like farts in the wind. Instead, regret the possibility of squandering time yet unexpired; embrace the unexpected future and the failure yet to happen. Life would be boring otherwise.”

Satisfied with his effort, the case writer completed his marathon writing session after finishing his tenth hour and fifth lemon tart at Coupa Cafe. He closed his last generation Macbook, doubly content with his work and its expected outcome. Yup, I’m going to get fired. The case writer was always an insufferable smart ass; his intimate knowledge of Tootly guaranteed a healthy milieu between his sarcasm and the official-sounding narrative of a case study. But he had gone above and beyond his normal subtlety.

Since reluctantly accepting this assignment, the case writer knew he wouldn’t return to Boston. If he had done a normal account of Tootly, it would have been shuffled away with the rest of the “Understanding Failure” fodder, briefly read and then summarily dismissed, as Professor Bonhoeffer predicted. With his prior performance “issues,” he would be juggled between assignments before ultimately being dismissed. Besides, he was tired of powerlessly ending careers with a whimper.

Instead, he would leave with a bang that would put Ben’s infamous toot to shame. He diligently placed most of his heart, and a fair amount of heartburn (courtesy of Coupa’s pretentiously potent Venezuelan Americanos) into Tootly’s case study. When he submitted this case, he wanted the controversy to reach a pungent fever pitch. And he was sure it would. Because even if the Dean buries the case, it would undoubtedly leak, either from the case writer himself or some other malcontent in his office.

Either way, he carried no illusions about his bias. But to him, an extra pinch of persuasion thrown into historical record didn’t diminish its value. What’s a little hyperbole here or there to help the little guy? The serial loser, bereft of luck? His story matters too. The case writer believed himself a noble crusader, defending the outcome of the failing underdog; exploratory prose was his sword, experience his shield, and medieval war analogies his bard.

There was, of course, an ulterior motive, outside of submitting this tragedy of a case against a horde of stuffy, Middle Aged management professors/infidels. As he wrote in the cafe, soaking in the strange mixture of diligent students, flashy entrepreneurs and harried venture capitalists, the Valley’s infectious optimism had taken hold. It didn’t prevent him from displaying rampant cynicism in his case writing (few forces in the Universe could have stopped that), but its effect was powerful enough to change him.

His Californicated optimism generated an epiphany reminiscent of Ben’s social impropriety in that fateful, now uninhabitable break room. The case writer knew spreading the “Tootly-afied” view of the world would cultivate an environment that could maximize the chances of his next enterprise. He was leaving case writing, whether he wished to or not; but he’d be damned if he didn’t give himself an advantage on the way out.

His next move was obvious to him, now that the case was finished. He left Coupa Cafe practically beaming with inspiration, and decided to stroll past Tootly’s old office as he returned to his rental car. He paused in front of the windows, gazing upon the logo of a fancy new mobile gamification startup. This screams failure. He took a picture from his iPhone for posterity’s sake, and returned to his car before driving back to his hotel.

There, he proofread his case before writing a terse message to Bonhoeffer alongside the final text of his case.

I don’t think “Understanding Failure” is failing fast enough. Hope this helps.
A Lover of Warmer Weather and Perennial Quitter

Happy with his submission and his tacit resignation, he spent the beginning of a sleepless night making arrangements to sell what few possessions he had in Boston and deftly negotiated out of his studio apartment’s lease. And then, he did what he did best: he crafted an elegant vision for a new kind of company.

As he wrote his last case, an opportunity slowly dawned on him. The startup investment climate was heating up; indeed, as valuations doubled and tripled in the last few months, with no commensurate increase in revenue, murmurs of “bubble” starting spreading across the tech community. Any monkey with a few months of coding experience and a slick presentation could receive funding these days. And the case writer was better than any monkey. He was a monkey with a long list of failures, but he’d rebrand as he always had: it wasn’t failure, it was experience. Experience better ignored, but experience all the same. And credibility, thanks to the soon-to-be-leaked case he had just finished writing.

This has to work. It must. Anyone can see the opportunity with the right perspective. As he crafted the skeleton of a business plan, he was surprised he hadn’t thought of this before. He must have been too jaded to care before, but the California sunshine had pierced that shroud. Either that, or the freshly unearthed memories of Tootly.

The daylight peaked through his window as he finished his outline and practiced his pitch. He knew he could get people behind this concept. The industry he would attack is entrenched, bloated, and ripe for disruption. It fit all of the criteria of a disruption framework he had once learned -- one of the few frameworks he believed served any purpose. I’d be disrupting the platform for all startups. As a startup. How can something this meta fail?

Before long, he was driving to the same sprawling Californian apartment complex he had visited just a few days ago. Authentic though he may be, he couldn’t start a company without a respected co-founder. This time, he knew where to find one without suffering through another networking event. On the ride over, he did a final gut-check (thankfully without cheeseburgers kludging up the process). Was this a real opportunity? Or was he just petty and vindictive? Can’t it be both? The case writer didn’t believe in mutual exclusivity.

He pulled up to his friend’s ascetic abode, while suppressing his lingering fears, uncertainties and doubts. He knew that walking this path made him some kind of masochist, and went against the lessons he innately understood from so many failures -- to the point of documenting them. Fool me once, shame on you. Fool me twice, shame on me. Fool me thrice, then I must be an irrational entrepreneur. But who cares? Progress depends on the unreasonable man, right? Apple toasts the “crazy ones,” and they’re a monolithic multi-billion-dollar organization, so they’re probably on to something. It takes a wise man to learn from experience, but it takes an entrepreneur to repeatedly ignore it. And as the case writer walked to the door of his former co-founder, he decided he wanted to ignore it once again.

Jacob Stern, a former case writer and a living monument to failure, stood outside his friend’s door, ready to pitch his latest idea.

Jacob Stern, who had been badly burnt from the startup world (but with fingers still intact), was steeling himself for another invisible scar of failure.

Jacob Stern, a startup insider, had an ingenious scheme to disrupt the entire early-stage funding industry. He was especially looking forward to the delicious irony of a venture capitalist investing in their own downfall. I bet that won’t even be that hard of a sell. But this might.

Jacob held his breath as he knocked on Ben McDougherty’s door. Would he join me? Would he even want to? Will he want to grab a burger? Would we finally dine on a success we only tasted before? Does it even matter if we don’t?

Unsure of the answers, the door opened, and Jacob stepped optimistically into his undiscovered future.

Appropriately, he farted on the way.

Copyleft MMXIV Josh Cincinnati