Meeting the Broken Businessman

“Acquiring business acumen closely resembles learning to juggle knives. Anyone can become a master, but only the especially masochistic will persevere. You also may lose a few fingers along the way.”

The case writer surveyed the single bedroom apartment as he waited for his tea. Seems tidy. The apartment was an exercise in minimalism, best described by what it didn’t have. No messy whiteboard with the faint traces of permanent marker mistakenly applied. No Hollywood movie posters or ironic Soviet-era propaganda. No over-sized furniture or exercise equipment. All the accoutrements -- a simple desk, chair, couch, and featureless coffee table, all black -- served to remind you that it wasn’t quite empty enough to achieve zen. It was even empty of emptiness. The entire place fell into a feng shui limbo -- in layman’s terms, it was pretty creepy.

“Nice place,” he called to the kitchen as he heard the water boil. “Very...efficient.”

“Thanks,” his host called back. “I hope you like your tea green. And hot.”

The case writer didn’t, but withheld his complaint silently. His host returned to the living room clutching two black featureless teacups in his left hand. He seemed the prototypical entrepreneur. He was in his late-20s, average build, maybe a little taller than most, with dark scruffy hair and a matching unkempt beard. His face was made complete with thick-rimmed black glasses, and was wearing the standard plaid and jeans garb of the self-starter caste. Nothing really to distinguish him, until the case writer glanced at his right hand, which seemed to be missing its two lower digits.

The host caught his stare as he set the teacups down on the coffee table. “Juggling incident. Next time I’ll stick to torches.” He pulled up his right sleeve with a sly smile, revealing a nasty pink burn scar.

The case writer chuckled as he cautiously sipped. “Maybe you shouldn’t have a next time?”

“And miss the thrill of unanticipated amputation? You clearly aren’t a juggler.” The young entrepreneur was strangely whimsical for someone who had lost two fingers. Then again, he was a juggler.

“Not anymore anyway. And never with knives, though I lost a fair bit more than my fingers, I’m afraid,” the case writer responded. He should have expected a witticism pissing match, but was more concerned with getting his source material than one-upping hotshots.

After a long, contemplative sip of tea, the entrepreneur understood the confrontational portion of their tete-a-tete was over. “Haven’t we all?” He revealed a hint of something the case writer recognized; this man had been sucker-punched by the invisible hand of the market. Invisible, but it leaves a mark. “But you came to listen, yes? About Tootly?”

The case writer thought over his next words carefully. After a few seconds, he had internally crafted an elegant, tactful response that would craft an enduring bond of trust between them. In his extreme focus, he neglected to keep track of his scalding hot cup of tea, which casually spilled on the side of his khakis, destroying his inner monologue and forcing him to blurt out, “Yes, Tootly! And its failure.” Whoops.

Our entrepreneur shrugged with a brave smile, swallowing the case writer’s curt response like a child forcing down a bitter elixir to impress his parents. “And its failure. So that others may learn from Tootly's mistakes?”

The case writer was too distracted from the pain of hot tea on the upper thigh to construct an appropriate response, and spoke honestly instead. “I’m afraid I’ll be the only one who will learn anything. More likely, it will be carelessly tossed into a ‘well rounded management curriculum’ and summarily dismissed by our success-crazed graduates. Apologies.”

The entrepreneur betrayed no surprise, but some of his smile was gone while he fetched napkins for the case writer’s spill. “Ah, well, that’s just as well. Perhaps retelling the story will help me build perspective -- a trait I find lacking in most. Not that I’m much better; I find that I’m occasionally out of...touch?” His smile returned as he wiggled the remaining three fingers on his right hand.

With that, the case writer felt they had recovered a baseline of amicability. He set down his dripping tea cup and took out his laptop. “I’m glad you’re optimistic. And who knows, you may get a speaking engagement or two for your trouble. Mind if I record our conversation as well?”

He looked about to laugh at a joke only he knew, but kept his composure. “Yes, why not? A recording nearly made me rich once, wouldn’t want to pass up that opportunity again. So what do you want to know?”

“Everything, for a start.”

“That’s not a very helpful starting point.”

“I’m not a very good interviewer.”

He sighed. “Well, let’s try to constrain things a bit. ‘Birth to expected death’ everything, or ‘how I co-founded, built, and grew a mobile app company based purely on novelty, only to watch it implode’ everything?”

The case writer considered for a moment. “Birth to death would be droll but unhelpful. The latter sounds more edutaining.”

“Fair enough; your interview. In that case, for perspective’s sake, we should probably start a tad bit earlier. I didn’t even know I wanted to be an entrepreneur until business school.”

The case writer brought out his notepad. “Did you really want to be an entrepreneur in business school? Or was it more about not wanting to be a consultant, banker, or middle manager?”

The eight-fingered man laughed. “What did you not want to be?”

Chuckling, the case writer brought up his laptop’s audio program and started recording. The interview lasted well into the evening, and he returned to his hotel room, content as a dread pirate after a particularly fruitful raid. The next morning he traveled to Coupa Cafe in downtown Palo Alto; the case writer, like many self-starters, worked best under the din of other procrastinating cafe patrons. He wrote the bulk of his case writing opus while tasting Guayoyos (pretentious Venezuelan Americanos), fruit tarts, and the faint aroma of nostalgia.

Copyleft MMXIV Josh Cincinnati