SquadJet blog
Why We Started SquadJet
2026-08-09
SquadJet started as an idea I could not stop thinking about.
For years, my friends and I wanted to get together for a weekend. We missed each other. We wanted to reconnect. And we did not particularly care where we went. Enthusiasm was never the problem. The problem was that we lived all over the country, everyone had a different home airport, and the trip had to stay affordable for all of us or it was not going to happen at all.
That turns out to be a genuinely hard thing to work out. Hard enough that most years, we did not.
The question nothing could answer
Planning one of those weekends meant opening what felt like twenty browser tabs. Different destinations, different dates, flights from every city, all of it copied into a spreadsheet or pasted into a group chat that scrolled past itself by lunchtime.
The tools already existed and they were good. They were just built to answer a different question. Every flight search on the internet is excellent at this one:
What is the cheapest flight from A to B on these dates, for this person?
Ours was:
Where can all of us meet without making the trip too expensive for anyone?
Those are different shapes of problem. The first has one origin. The second has six, and no candidate city tells you anything until you have priced it from every single one of them. For a group of eight, doing that by hand is somewhere around fifty separate fare searches.
Somebody has to volunteer for that. And the person who volunteers is doing hours of unpaid research to find out whether a trip is even possible, before anyone has agreed to anything.
Cleveland, in the middle of winter
One year, all that searching landed us in Cleveland in January.
It was not an extravagant destination. Nobody had it on a list. It won because it was the cheapest place all of us could actually get to, and by that point in the process, that was the only criterion left standing.
It was one of the best trips we have ever taken.
Not because of Cleveland. Because six people who lived in six different cities were in the same room for three days, and that had not happened in years. The city was a container. What we were actually there for was each other, and once the weekend started, the destination stopped mattering almost entirely.
That trip is the one I keep coming back to, because it quietly proved something the whole travel industry is set up to deny: for a lot of group trips, the destination is doing far less work than the effort of choosing it would suggest. We spent hours optimizing for a place that turned out to be beside the point, and we very nearly did not go at all.
And the years it did not happen
That is the other half of it, and it is the part that actually pushed me to build something.
Plenty of years, the trip died. Not in an argument. Nobody fell out over where to go. Everyone said they wanted to go, everyone meant it, and then the thread went quiet, because taking on the research meant taking on hours of it for a group of people who might still say no at the end.
Group travel does not usually die in a disagreement. It dies in a tab nobody reopened.
There is a version of that failure with a price tag on it too. A destination that costs four people $250 each and the fifth person $700 does not produce a fight. It produces one person who gets vague about their calendar and then quietly drops out. The group optimized for the place, and the place vetoed a person. Nobody notices until the trip is smaller than it was supposed to be.
So I built the tool I wanted to have
The idea sat in the back of my mind for years. Eventually I stopped waiting for someone else to build it.
SquadJet starts where those weekends actually started: with the people. You add each traveler's home airport, then either pick your dates or stay flexible, because flexibility is the cheapest lever a group has. From there you can let SquadJet look for affordable places the group could meet, or compare up to six cities you already have in mind.
It prices every candidate for every person, up to 24 travelers, and ranks them by what the squad pays together rather than by what the organizer pays. That difference is the entire point. The organizer's fare is the least useful number in the exercise, because the organizer is the one person guaranteed to come.
Then everyone gets a link and a vote, because the cheapest destination is not always the one the group wants to visit, and people commit to trips they helped choose. Flights and hotel sit in the same view, split evenly, so nobody is doing group math at 1am. Once the city is settled, one trip dashboard tracks who has paid their share and who has actually booked, which is the other unpaid job the organizer never asked for.
The scan that used to be an evening takes about a minute.
What we are building toward
The goal is not a cheaper flight. Cheaper flights exist and other people are good at finding them.
The goal is to remove the part of group travel that makes plans stall before they ever begin. We are building SquadJet into a full group-travel platform, so that comparing options, making a decision, coordinating everyone and getting the trip actually booked all happen in one place instead of across twenty tabs and a group chat.
There is no subscription and nothing is locked behind a tier. Every account lands with 100 free credits, and the only thing that ever spends one is pricing a trip. You can read how it works, see what a search costs, or read more about the company.
We want "we should all get together sometime" to turn into a weekend that actually happens.
Because sometimes the destination is not the most important part. Sometimes, you just want to get the squad back together.
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