The Icy Weather System that trundled up the Atlantic Seaboard and glazed New York City on February 14, 2007, was nasty, but not the worst that airlines had ever confronted. Mainline carriers such as American and Delta knew the drill. They canceled flights in anticipation while moving equipment and crews to sidestep the storm and minimize disruptions. The newer kid on the tarmac, JetBlue, flew into the storm face first. And flopped.
The low-cost carrier was barely seven years old, growing rapidly and happily because customers loved its panache, pricing, and product—comfortable seating, free satellite TV, and freewheeling yet attentive flight crews. Concentrating its fleet in New York and Boston made the carrier more vulnerable to winter weather, though, and as the storm began to wreak havoc on operations, JetBlue swiftly learned that its communications and logistics networks had not scaled with the rest of the outfit. With crews stuck out of place, the airline would cancel more than 1,000 flights over five abysmal days, stranding customers from the Caribbean to Queens. One jet full of passengers sat on the tarmac for eight hours. The debacle ultimately cost the airline $30 million.
Even before the storm had passed, Jet- Blue founder and CEO David Neeleman was conducting a nonstop apology tour, vowing to upgrade systems and make things right by customers. “This is going to be a different company because of this,” he told The New York Times. He was right about that. Three months later, JetBlue announced that Neeleman was leaving the CEO post and becoming chairman. At least Neeleman wasn’t aboard a flight when his own board shoved him out the door.
If you are looking for a case study of an entrepreneur who gets repeatedly suckerpunched by exogenous events, Neeleman is it. He’s also a study in rebounding. In the early 1990s, he built his first airline, Morris Air, out of the wreckage of his own failed travel agency. He launched JetBlue less than two years before 9/11 grounded the airlines for weeks, curbed travel for a year, and bankrupted most of the industry. Then came that storm. “You can’t control everything,” he says now, without any particular malice. “I wrote an email to the crew and said, ‘It doesn’t really matter what happens to you in life; it’s how you deal with it.’ ”
Neeleman began to build Breeze, his fifth airline startup, just before Covid-19 emptied the nation’s airports. That was after he’d returned from Brazil, where he started the wildly successful Azul Airlines in 2008. “I had 50 people hired for Breeze and we were moving along the track,” he says, munching airline snacks on a recent Monday in the upstart’s empty offices in the basement of a beige building in Darien, Connecticut. “It would have been easy for me to say, ‘Sorry, I just can’t do this.’ ” While major airlines, including Delta, United, and American, would get more than $50 billion in loans and grants from the federal government to weather the pandemic, Neeleman would have to plow his own money, some $30 million, into his fledgling business. (The company later got less than $1 million in PPP money.) “But a lot of the Breeze team left their jobs to come here,” he says, “and I just felt that I owed it to them to do it. So I said, OK, let’s make this happen. Let’s keep a foot on the brake and a foot on the gas.”
We tend to think of the airline industry as a business with a high barrier to entry— all those pricey planes and terminals. But entry is not nearly so difficult as keeping an airline flying profitably over a long period of time, as dozens of defunct carriers (Braniff, anyone?) can demonstrate. Neeleman’s ability to spot opportunity and pair the right customer service with exacting operational efficiency has helped him defy the odds more often than any other airline entrepreneur. So has a sort of tunnel vision that comes with attention deficit disorder—a disability that led to one huge career setback but also fueled his success.
“There are two phrases I’ve heard a lot,” he says. “One is, ‘Well, David, if that was such a good idea people would have done it already.’ Really? The other is: ‘David, It’s not that simple.’ ” He pauses. “Well, yes, it is—it is that simple.”
THE HISTORY OF AVIATION is filled with dashing figures. Pan Am co-founder Juan Trippe was a true titan who made air travel glamorous in the 1930s and introduced the jet age. Eddie Rickenbacker, the unkillable racecar driver and World War I fighter ace, bought and built Eastern Air Lines. Howard Hughes, the wildly eccentric entrepreneur, airplane designer, and Hollywood producer, largely created TWA. Fast-forward and there’s Richard Branson, the music mogul who brought his personal Cool Britannia brand to Virgin Atlantic. And let’s not forget Herb Kelleher, a fun-seeking Texan lawyer who loved people, cigarettes, and Wild Turkey (not always in that order) and co-founded Southwest.
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