Like Brie Larson, Chesky was open about his barriers. In the summer of 2015 he shared screenshots of those original rejection emails in a Medium blog post. They're peppered with such phrases as "not something we would do here," "not our area of focus," "the potential market opportunity did not seem large enough," and "we've always struggled with travel as a category." Obviously Airbnb weathered these early storms and emerged intact. The team met with dozens of its early hosts to learn what did and didn't work about the product. That year, the founders lived in Airbnb-hosted apartments to experience the service firsthand. What made the difference between a three-star experience, a five-star experience, and—as Chesky likes to call a sublime review—"a seven-star experience"? Airbnb eventually grew, first in New York, and then in other US cities, and investors began to take the company seriously. The company raised $620,000 in 2009, $7 million in 2010, and $112 million in 2011. Despite its many hiccups, most people most of the time focus on the company's successful destination rather than the barriers that hampered its journey.
Airbnb isn't unusual in its bumpy path to prosperity. Take another behemoth, Amazon, and you'll find the same hurdles. Dan Rose managed retail divisions at Amazon from 1999 to 2006 and helped launch the Kindle. In September 2020, Rose posted a thread of tweets recalling how the company teetered shortly after he joined, in November 1999:
Amazon launched in July 1995, and every Xmas was a near death experience for the first 7 years. I joined in '99 and got to experience this first hand. Starting in late Nov, all corporate employees were shipped to fulfillment centers to pack boxes for 6 weeks. Here's what I saw:
Despite efforts to plan ahead, the company literally couldn't keep up with holiday demand. 40% of all annual orders would come through in 6 weeks from Thanksgiving through New Year's&. Xmas '95, every employee including [CEO Jeff] Bezos packs boxes for 6 straight weeks, then vows to never let that happen again&. By the time I joined in '99 it was an annual tradition&.
Picking items, packing boxes, wrapping gifts for 10 hours/day x 6 days/week is fucking hard work. I have immense appreciation for the people who do these jobs. Your legs ache, your eyes go blurry&. [It's] exhausting.
Jeff Bezos ultimately brought in Jeff Wilke, who saved the growing company from itself. Wilke's background in manufacturing gave him the tools to turn Amazon's warehouses into finely tuned machines, ultimately allowing the company to promise the same-day and next-day delivery options that fueled its Prime membership service. Wilke's role was so instrumental in Amazon's success that he ultimately became the company's CEO of worldwide consumer business—a position that placed him second in charge behind only Bezos himself. In an interview Wilke gave shortly before he retired in January 2021, he remembered those early days when Amazon's fulfillment process was stuck:
So I took the playbook that I had, which came from manufacturing, and implemented it in retail. It was really the first time that some of these techniques had been applied in a retail environment. And fortunately, they worked, [producing] very short cycle times, lower waste, lower defects. And that's what enabled us to launch Prime. Prime is basically a subscription to this.
What we focus on is Amazon's immense success, rather than its struggles. But what might have happened in an alternate reality where the company failed to overcome these early hurdles? In this universe, like so many other fledgling companies, Amazon might have collapsed beneath the weight of its own success. By its third or fourth holiday period, in the late 1990s, this alt-Amazon was receiving hundreds of thousands of online book orders. Its ersatz fulfillment team was forced to work twenty-plus hours a day to keep up with demand. Many orders arrived late, and customers were furious. Kids were denied the latest Harry Potter book on Christmas morning, and their parents were left without Stephen King's holiday bestseller. The company had gone public in May 1997, but by 1998 or 1999 its stock price tanked in the wake of terrible reviews. (Even in reality, many early reviews of the company were quite negative. 'Slate' called the company "Amazon.con," and the 'Wall Street Journal' called it "Amazon.bomb.") By the early 2000s, alt-Amazon imploded. And since it no longer captured the attention of major newspapers, websites, and reviewers, its struggles faded from view. The company was stuck, but, as with the thousands of other companies that close every day, nobody was there to document its decline.
The bottom line is that entrepreneurial struggles are hard to see regardless of whether a business succeeds or fails. Success eclipses the struggles that preceded it, while failure is so commonplace that it tends to escape our attention. Instead, we're exposed to story after story about Apple, Google, Facebook, Netflix, and an elite group of similarly exceptional successes.
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Brie Larson, Airbnb, and Amazon are just three examples, but you don't need to cherry-pick. Just dig one or two layers deep into our culture's most prominent success stories and you'll find frustrated protagonists. A young Fred Astaire complained of being stuck after a Hollywood producer rejected him with the statement "Can't act. Slightly bald. Dances a little." When Walt Disney's first studio, Laugh-O-Gram, went into bankruptcy, he endured five years of inertia before designing a cartoon mouse who would go on to become his new studio's mascot. Photorealist painter Chuck Close suffered what he called "the event" in 1988—a seizure that partially paralyzed him from the waist down. For decades his hyperrealistic paintings had relied on fine motor movements that were now impossible. Close was initially despondent, but in time he learned to paint in a new, expressive style with a brush strapped to his wrist. As he emerged from the fog of grief, Close famously claimed, "Inspiration is for amateurs; the rest of us just show up and get to work. If you wait around for the clouds to part and a bolt of lightning to strike you in the brain, you are not going to make an awful lot of work."