“Serendipity is a mercurial muse. She’s like an unbalanced, crazy ex-girlfriend, only slightly less random. Sometimes you mistake her repeated favor as inherent skill, and sometimes her absence as an intrinsic flaw. She deserves neither. When her fortune favors you, be glad; otherwise, fart in her general direction.”
Jacob Stern and Ben McDougherty, both visibly uncomfortable in their dress shirts, sat in Coupa Cafe at nearly the same table where this case was written. Jacob recalled that evening’s conversation with a certain measure of lucky satisfaction. “Meeting Ben was a revelation. I felt like I had been struck by lightning, only, you know, not fatally. Speaking with him was just electrifying....but again, not in a way that would be harmful. I was just positively charged up afterwards. But again, not in a way that would lead to a dangerous electric potential. I’m not sure I chose the right metaphors, but you get what I’m saying.”
Jacob learned that Ben shared a similar skepticism with his education, albeit a few years removed. Ben had graduated from business school a year prior, and spent the last year working as an Assistant Associate Product Marketing Manager for Business within Google’s Eastern European AdSense Division for Education. He finally left after he decided he couldn’t figure out what his actual job was. Business school was, in his words, “two years of confusion that led to a job with no clear responsibilities or duties, other than being an adequate scapegoat for managers above me.” Before school, Ben had been a computer programmer for a monolithic government contractor coding very tiny pieces of products for purposes unknown (apparently coding was done blindfolded for the sake of national security, but Ben suspected his managers hoped to make programming exceedingly boring to create docile, malleable employees).
Like Jacob, Ben received the startup bug from his favorite business school professors, but unlike Jacob, he had delayed scratching that itch to “mitigate risk.” He had more student debt than Jacob, and rationalized his ascension to corporate cogdom by using his steady salary to methodically diminish his student loans. He had lived a spartan lifestyle otherwise; Ben refused temptation by “golden handcuffs” as he received promotions (for being a particularly good scapegoat, he guessed).
The phenomenon of becoming so comfortable with a progressively more expensive lifestyle that it becomes psychologically impossible to leave your career, no matter how unethical, awful, or unhappy it makes you. You are “chained to your gold.” When caught or indicted, it’s the typical motive claimed by millionaire embezzlers, hedge fund swindlers, unethical consultants, drug dealers, and King Midas.
Ben’s desire to absolve himself of debt sustained him for the last year, but that resolve melted away when he spent 60 hours a week wondering what the hell he should be doing to validate his salary. Outside of being a great person to receive condemnations by managers whose only duty revolved around hiring and firing scapegoats, Ben wasn’t sure he was adding any value.
And so he left. He had little idea what he was going to do next, but couldn't stomach a job having little idea of what he was doing. Ben figured a bit of economic uncertainty was a worthy price for eliminating meaningless day-to-day toil. “The moment I quit, I embraced uncertainty. It seemed natural to try my hand at ‘aspiring entrepreneur’ after that,” Ben recalled.
After they caught up on each other’s histories, Ben and Jacob decided to continue their discussion at In-N-Out Burger (given their chance meeting at the cheeseburger slider table, it was only a matter of time before they discovered they shared a love of the Californian fast-food standby). At a deserted parking lot in Mountain View, Jacob convinced Ben of the huge potential of iPhone apps, and the two agreed in principle to work together over two Double-Doubles done Animal Style. Jacob was ecstatic; they seemed a perfect fit. “I knew it was a sudden decision, but at the time I was convinced that gut decisions were usually right. Of course, I had also just read ‘Blink’ and was feeling a bit funny from eating so many damned cheeseburgers, so perhaps I was predisposed to making snap judgments.” Jacob put their early success to that split decision, but in retrospect, he said “I realize we were just lucky. At least, for a time. I mean, we were both suffering from meat sweats. That’s never a good time to make a decision.”
The next day, Ben and Jacob met at one of the many breakout rooms available at the business school and proceeded to furiously brainstorm ideas on whiteboards, flashcards, and any surface that appeared washable. They threw out ideas like a garbage man throws out trash, except the trash was generally more valuable. Here’s a smattering of what turned up in the idea dumpster, in that conveniently readable, reductive analogy format that investors and bloggers love:
Their idea brainstorms went on for most of July, with little structure and even fewer good ideas. Eventually Jacob’s roommate, always one to offer suggestions to improve Jacob’s wellbeing, suggested they both consider adopting “design thinking” into their idea brainstorm methodology. As it turned out, Ben and Jacob were already doing pretty much exactly what “design thinking” advocated, except they weren’t paying consultants an exorbitant pro rata fee to tell them so. “We also weren’t recording our brainstorming sessions, which we promptly rectified.”
That decision was an unforeseeable turning point for their fledgling venture. “It’s funny,” recalled Ben, “in retrospect, I can see exactly what connected us together and what led to our breakthrough. Our love of greasy food, the chance experiences that led to the networking night, Jacob’s suggestion that we start recording our brainstorms...it all seems so purposeful when I think about it now. But it wasn’t. Everything was sort of random. We seized the moment when we could, but it wasn’t part of some grand plan. It never is. A butterfly flaps its wings, I meet Jacob, we both love grease, we order a couple BBQ burgers and sweet potato fries, Jacob records the aftermath...it’s just chaos.”
Ben and Jacob’s breakthrough was certainly unexpected. It was late August, and Ben had just returned to their favorite breakout room with some Counter Burger half-pound patties and the most delicious, stomach-twisting sweet potato fries west of the Mississippi. Jacob had been busy whiteboarding a concept for an iPhone game featuring a slingshot, destructible towers, and adorable cartooned farm animals. (Jacob sighed when he thought about the idea’s quick dismissal. “The working title was Toon Tossin’. God damnable Angry Birds.”) Recording their entire discussion on a Flip cam, Ben convinced Jacob that the concept was a carbon-copy of readily available web games, and consumers wouldn’t be stupid enough to actually pay money for regurgitated ideas available freely online. (Ben cursed when he recalled that discussion. “Motherfucking Angry Birds.”)
And then, something extraordinary happened. The enzymes in the sweet potato fries mixed with the beef patty particulates and began a beautiful, delicate, invisible dance with the inner lining of Ben’s stomach, causing a chain reaction that built up excessive gas in his lower intestine. As Ben rose to erase the whiteboard, he passed a volume of gas from his lower extremities that heretofore medical science had thought impossible. If the Sirens had mesmerized Odysseus with flatulence instead of songs, they would have been jealous of Ben’s magnificent performance. It was the perfect fart. And it was on tape.
Along with Jacob’s laughter. “I thought it was hilarious. I mean, we both ate like pigs at the time, and I wasn’t surprised that Ben had to let one go, but man...what a doozy.” Ben and Jacob left the breakout room early; they feared a hazmat team was required to make the room usable again. But they couldn’t stop listening to the video as they walked back to Jacob’s apartment. Jacob remembered his epiphany; he didn’t think much of it then. “I didn’t like having to pull out my Flip cam to listen to it over and over again, when I had my iPhone right there. It deserved to be more convenient.” As soon as they returned to Jacob’s apartment, he built a (aptly described) “quick and dirty” iPhone app that could serve his purposes. All the app displayed was a big red button and the word “FART!” underneath it. Satisfied that it functioned as expected, Ben spent some time prettying up the button, and installed it on his own phone. The novelty refused to disappear as they pressed the button over and over again; the staying power of Ben’s indigestion was unprecedented.
Jacob’s roommate came home to both of them laughing maniacally at their phones, and was rudely surprised with a double-fart upon asking them how their brainstorming was going. Normally he would have been taken aback by that sort of behavior, but the magic of this audio clip seemed to capture him too. “He thought it was pretty funny. He made a casual aside that he would pay a buck to have that on his phone,” recalled Jacob. “That’s when I knew we had to put it on the App Store.”
At this point, neither Jacob nor Ben had a glimmer of an idea that their app ‘Tootly’ was going to be a business unto itself, but they were both in need of validation for their month of brainstorming. “Frankly, most of the month had been spent eating deplorable foods, so Tootly was a relevant expression of our work. Besides, what did we have to lose?” By midnight of the same night, they had navigated Apple’s labyrinthine app submission process and Tootly, a $0.99 premium fart app, was waiting to be approved. They went out for celebratory In-N-Out fifteen minutes later, while Ben prayed that his stomach could hold up.
“We had done it,” Ben remembered thinking. “I had felt pretty good about our accomplishment, despite my ravaged digestion system. Of course, it was a small victory, and we thought our white whale was still in some undiscovered sea.”
While Tootly awaited Apple’s approval, Ben and Jacob kept brainstorming and whiteboarding. And then, on a normally forgettable day in early September, they received an email confirmation to acknowledge the approval of Tootly.
Not a week later, Tootly surged to become the #1 paid app in the App Store. Their random, completely unplanned novelty app became an iPhone sensation. “And that was the beginning of the end,” a resigned Jacob admitted. “We were thrilled, to be sure. We should have just focused on other ideas and been content with our moderate success. But we were distracted by the dollars and the press...and visions of grandeur. Being ‘1 for 1’ is horrible for an entrepreneur, but we were too proud to know it then.”
Ben offered a more concise view. “We thought we were hot. But it was stupid, blind luck. Soon enough, shit would hit the fan...or iPhone, in this case. And no amount of ‘startup best practice’ would save us. Tootly wasn't our white whale; it was our albatross.”
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