A few weeks ago, Flighty quietly pulled off something remarkable. In the middle of a nationwide travel meltdown, it rocketed to number one in the App Store’s Travel category, and number 17 most popular overall. During what was one of the most chaotic weeks of travel in recent memory, it seemed as though everyone was suddenly depending on the same app.
If you only looked at the charts, you might think Flighty came out of nowhere. The thing is, there’s a lot more to the story. First of all, Flighty has long been a favorite among frequent travelers, pilots, and anyone else who cares about knowing everything you could know about their next flight. I recommend Flighty to anyone I know whose plans include getting on a plane.
The real story, however, is that Flighty is the product of a 12-year journey that started on an oil rig, wound its way through a brief stint at Apple, and eventually arrived at the exact moment when millions of travelers needed it most. It is, you could say, an “overnight success” that just happened to have taken more than a decade. Which, by the way, is how these things almost always work.
A data-obsessed weather app
Long before Flighty, its founder, Ryan Jones, was a mechanical engineer working in the oil industry in East Texas. And then the iPhone happened. Somewhere between long shifts and long drives, Jones found himself following a handful of indie developers on Twitter and realized that most apps are just made by normal people, not giant software companies.
So he gave himself six months to make one. Not only that, Jones wanted to prove he could make an app that made it into the top 100 apps on the App Store. That’s a big bet for someone who didn’t even know how to code. But he had an idea: take weather data—something inherently nerdy and hard to parse—and make it visual.
That idea became Weather Line, a beautifully simple weather app that turned forecasts into a clean line graph that looked like it was designed for the iPhone on purpose. The app launched in 2013, and proved something important. Jones told me that the experience “gave me the confidence that there wasn’t this secret group of people in California who only knew how to build software and make great products, and like no one else could figure it out.”
On the contrary, he could just make something great, and people would use it. As for his goal, Weather Line reached number 17 on the App Store charts.
Then, he took detour number two and “accidentally” got hired at Apple. For two years, he sat inside one of the most product-obsessed companies in the world, absorbing how it thinks about design and product. That would become incredibly important for what came next.
The app he wished he had
Flighty didn’t start with a grand plan. It started in an airport Chili’s.
Jones has told this story before: he was stranded during a brutal delay and couldn’t get reliable information from anyone—not the gate agent, not the airline, not the apps that were supposed to help. The data clearly existed. It just wasn’t getting to the people who actually needed it. So he decided to build the app he wished he had.
He tweeted about the idea that night and ended up assembling a small distributed team that would spend the next few years obsessing over a single problem: turning an overwhelming amount of aviation data into something normal people could understand instantly.
“I think what I’m great at is taking nerdy data and making it really simple and visual on small screens,” Jones told me. “That’s what Weather Line was. That’s a lot of what Flighty is.”
Flighty launched in 2019, and from the beginning, it has always done one thing better than anything else: tell you what’s happening with your flight. I cannot even tell you the number of times I’ve been sitting in an airport and Flighty let me know a flight was delayed or canceled long before the airline did.
There’s no magic behind that. It’s the same instinct that powered Weather Line—making something complicated, simple enough for everyone to understand. In this case, it just happens to be applied to a much harder domain.
It also required a different kind of superpower: learning how to negotiate with the obscure companies that sell flight data to airlines, hedge funds, and large industrial customers. That experience became one of Flighty’s not-so-secret advantages. The team figured out how to get world-class data, stitch it together, and wrap it in a design that makes it feel obvious.
Success is a long game
What’s most interesting about Flighty is that none of this came with the typical trappings of a startup “success story.” There’s no giant funding round or massive ad spend. The team is seven people. Marketing is mostly people sharing screenshots because the product gives them something worth sharing.
Even the business model is unconventional. Flighty offers a free tier, along with monthly and annual subscriptions of its Pro tier. But there’s also a flexible weekly plan—one of the only legitimate uses of weekly subscriptions, in my opinion—that aligns with how people actually travel. The annual and lifetime plans serve the frequent-flyer crowd while the free tier gives people a taste without forcing them into a trial they’ll forget to cancel.
Still, nothing compared to what happened during the shutdown.
Becoming an overnight success
When flights started melting down, Flighty didn’t have to reinvent itself. It simply did what it always does—only this time, millions more people were watching. Downloads and subscriptions grew and, for a brief window, the most popular travel app in the world was the one built by a handful of people who spent a decade getting ready without knowing it.
From the outside, that looks like luck. But when you zoom out, it’s the opposite.
This is what it looks like when someone brings a very specific set of skills—visualizing data, designing for clarity, negotiating for obscure inputs, sweating the details—and applies them to a hard problem that almost everyone would like solved.
The truth is, “overnight success” is almost never about timing alone. It’s usually about what happens when someone keeps going long enough for all of those oddly specific experiences to line up at the right moment. For Flighty, that moment was a government shutdown that wreaked havoc on travel.
The thing is, Flighty didn’t become the world’s most useful travel app just last week. It was just the moment everyone finally noticed.
The opinions expressed here by Inc.com columnists are their own, not those of Inc.com.
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Jason Aten
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