As a security researcher, Ian Carroll found vulnerabilities for a living.
He would probe TSA databases, hotel door locks, even Formula 1 infrastructure. He even reported bugs to United’s bounty program and got paid in miles.
When he turned that same lens on award travel, treating opaque airline booking systems as puzzles to crack, he was so good at it a national airline tried to shut him down.
Seats.aero now generates $8M annually.
Carroll runs the company from Michigan, and he’s never written a newsletter or posted a content calendar.
So what pulls half a million users through the door each month and converts them at five times the industry average? The answer lies in one of the oldest methods in business and a paywall in exactly the right place.
How a side project hit $1.5M in 18 months
In mid-2022, Carroll was frustrated.
Award travel is a game of hidden inventory. Airlines release premium cabin seats, sometimes worth $5,000 or more, for a fraction of the usual points.
The catch is to find them.
It means clicking through calendar grids day by day, program by program. A first-class seat to Tokyo might appear at 2am and vanish by breakfast.
Carroll decided to build a tool for himself that searched 24 loyalty programs, delivering results back instantly.
Once he saw it was working, he opened it up to others.
At first, he seeded it himself. The tool was originally called awards.pnr, and Carroll would drop links in Reddit’s r/awardtravel, a community of half a million points obsessives who vet every tool that crosses their feed.
They’re skeptical of anything that smells like marketing, but they’re evangelical about things that actually work.
The tool looked like a spreadsheet. No polish, no lifestyle branding. One reviewer called it “a geeky travel-hacker playground.” For this audience, that was the appeal.
Someone would find a business class seat to Europe, post about it, and mention the tool that surfaced it. Others would try it, and the cycle would repeat.
Within a year, AwardWallet named it one of the best new points-and-miles utilities. Traffic crossed one million pageviews monthly.
By December 2023, eighteen months after he started, Carroll posted a reflection on LinkedIn: Over a million pageviews per month, $1.5M in annual recurring revenue and not a single employee on the books.
Then came the lawsuit from Air Canada.
What Air Canada couldn’t shut down
In October 2023, Air Canada filed suit. They claimed Carroll’s scraping placed “immense strain” on their systems and sought up to $2 million in damages.
Carroll didn’t shut down. He didn’t settle. He offered to work with them on how he retrieved the data. Air Canada refused.
A judge denied their request for an injunction in March 2024. The tool kept running.
Over the next fifteen months, Seats.aero grew from $1.5 million to $8 million in annual recurring revenue, while being sued.
The system that made that possible is simple.
The free version lets anyone search award availability within 60 days and set up to five alerts. Email notifications only.
The Pro version costs $9.99 a month or $99.99 a year. It extends the search window to 365 days, unlocks unlimited alerts, adds SMS notifications, and includes advanced filters for direct flights, passenger counts, and fee caps.
That 305-day difference is the entire business model.
Premium cabin awards often release 330 days in advance. A family trip to Japan next summer, a honeymoon in the Maldives, a business class seat during peak season.
These require planning horizons that the free tier can’t reach.
The moment a user tries to search beyond 60 days, they hit the wall.
Five alerts sounds generous until you’re tracking multiple routes across different dates and programs. Serious award hunters burn through five alerts on a single trip search.
The gate appears at the exact moment someone has demonstrated they need more.
What Carroll sells is time horizon. The people who need to see further are the same people willing to pay.
By March 2025, Seats.aero had 500,000 monthly active users. Roughly 70,000 to 80,000 of them were paying for Pro.
That’s a conversion rate between 14 and 16 percent. Most freemium products sit around 2 to 4 percent.
The difference is where the paywall sits.
The gate that converts at 5x the average
Most freemium products limit what you can do. Carroll limits how far ahead you can look.
A user searching within 60 days gets everything. The tool works exactly as promised. They find award seats, set alerts, book flights.
The friction only shows up when they need more. When they start planning a trip six months out. When they learn the seats they want open almost a year in advance.
By then, they already know the tool works. They upgrade after they’ve seen the proof.
This is why Carroll doesn’t need a sales page, a webinar, or an email sequence. The free version is the sales pitch. The paywall shows up when someone is ready to pay.
The same logic drives the growth.
Carroll doesn’t write blog posts or record podcasts. Affiliates and press do that work for him.
Travel sites like The Points Guy, NerdWallet, and Upgraded Points publish guides on how to use Seats.aero. These sites survive on trust. They need to recommend tools that deliver.
Carroll’s affiliate program pays 100 percent of the first month or 20 percent of the first year. For points bloggers, featuring the tool is an easy call.
Word of mouth fills the gaps. When a user finds a first-class seat worth $8,000 for 70,000 points, they tell people. The result becomes the ad.
Three lessons from a tool that sold itself
Carroll’s model holds a few lessons for creators who have engagement but struggle to convert.
The first is about simplicity.
One product. Two tiers. A clear line between them.
Carroll was scratching his own itch, building a solution to a problem that already had an active market.
He just needed to do it better than the alternatives.
For creators stuck in the cycle of launching new offers that fail to convert, this might be the harder lesson.
Sometimes the answer is fewer products with sharper gates.
The second is about where to place the gate.
Most creators give away complete value hoping it builds trust.
Carroll gives away complete functionality within a limited window.
The user gets everything, just not forever. The upgrade happens when their needs grow.
David Senra does something similar with his Founders podcast.
Free listeners get the first thirty minutes. The episode cuts off mid-story.
If you want the ending, you pay. The gate sits at the moment of peak curiosity.
For creators selling courses, templates, or tools, the question is worth asking: where does your audience’s intent peak? That’s where the gate belongs.
The third is about who does the marketing.
Carroll built something useful enough that the existing ecosystem wanted to talk about it.
Affiliates, bloggers, and users did the distribution. His job was to make the tool worth mentioning – age old ‘word-of-mouth’.
It worked.
With the business now at $8 million in annual revenue and still growing, Carroll recently brought in Chris Lopinto to run operations.
Lopinto co-founded ExpertFlyer, an award search tool in the same space that was later acquired by Red Ventures. He’s built and sold a company in this exact market.
The lawsuit with Air Canada is still active, the tool is still running, and the new hire brings experience in successful exits. It may be a signal for where Carroll plans to take Seats.aero next.