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United Airlines placed the largest aircraft order in history during COVID: 200 wide-body jets plus several hundred narrow-bodies, at a time when every other long-haul carrier in the world was permanently retiring part of its wide-body fleet.
The industry consensus was that travel demand would stay 50% lower forever. Scott Kirby, CEO of United Airlines, told Stripe co-founder John Collison and Stratechery's Ben Thompson on Cheeky Pint that he did not consider the bet risky at all.
"This is one of those cases because everyone else is shrinking, we don't have to be right. We just have to be not totally wrong." — Scott Kirby
Scott took over United in May 2020 and has since put Starlink Wi-Fi on nearly half its flights and pulled software that other airlines rent from vendors back in-house. He now says the main thing holding his business back is the US air traffic control system.
The full interview is covered here so you can skip it. 1 hour 20 minutes of audio, 10 minutes of reading.
Here are the 13 lessons that matter.
Stripe · Oct 27, 2026 · 1h 20m · 70m saved
With Scott Kirby, CEO of United Airlines
Key Takeaways
United ordered 200 wide-bodies during COVID while every other long-haul carrier was retiring them
Scott's rule: "ignore the experts outside of two sigma"
Air traffic control is "90% of the issue" limiting United, and annual funding is why it cannot be modernized
Sending delayed fliers a radar image of the storm moved satisfaction by 120 points, with no change to the delay itself
American will lose about $1.5B in Chicago this year, Scott estimates, because split hubs waste flight slots
Starlink is United's biggest point of difference from Delta, and some customers now pick regional flights to get it
Every US low-cost carrier abandoned low-cost airports, which Scott says is why the model failed here and not at Ryanair
Six of 10 US airlines will lose money this year, and United and Delta are the two winners
1. 200 Wide-Bodies in COVID
The order covered planes that list for roughly $400 million each. Scott said surveys taken in the middle of a crisis reliably mispredict recovery, and that expert consensus is at its worst exactly when conditions are most extreme.
Scott Kirby said the COVID order was not risky because experts are wrong in the tails
"I didn't think it was [risky]... every single expert in the world said travel demand is going to be down by 50% forever... you should ignore the experts outside of two sigma. In the tails, the experts are terrible." — Scott Kirby
"Two sigma" means two standard deviations from normal, the extreme outcomes. Because the market had shrunk, aircraft pricing was favorable, and Boeing could point to United as proof that demand still existed. The downside of being wrong was smaller than the upside of being right.
United uses surveys to judge what it has done, never to predict what customers will do
"We use surveys for how did people feel about stuff we've already done. I ignore surveys for what are we going to do in the future." — Scott Kirby
Scott also used COVID to start a several-hundred-million-dollar project moving United off mainframe computers and onto modern, cloud-based systems, with no clear return-on-investment case. He says it is paying off now, because it lets United ship products other airlines structurally cannot.
