You already know how this goes, because you have done it for a tournament entry or a bar tab or a Christmas collection for the league operator. You put it on your card, you tell everyone to get you back whenever, and eleven weeks later you are still owed twenty-four dollars by someone you see every Tuesday and cannot bring yourself to ask again.
That is why teams don't have shirts. The design is the fun part and the sizes are only annoying, but the money is the part that makes a captain quietly decide it isn't worth it.
Collect first, order second
That is the entire method. Everything below is detail.
The moment you front the money, you are the one five friends owe, and you carry that until the season ends. Collect it first and you are holding everyone's cash until the order goes in. It is the same money either way, and only one version leaves the friendships alone.
The message that gets answered
One number, one date, one action. Send something close to this.
Shirts are happening. $32 each, covers everything including the design and shipping. Bring it to the match Tuesday or send it to me before then, and the order goes in Wednesday morning. Size chart is below, check a shirt you already own.
That removes every decision except paying. The message most captains send instead asks whether everyone still wants shirts and how they feel about the color, and it produces four thumbs-up and no money.
The number you send has to be the final number. If you come back two weeks later for another four dollars a shirt, you are chasing people again, this time for money they thought they had already handed over. Build in the shirt, the design, the shipping and a dollar of slack, and quote that.
Make the date the next league night. It is soon and specific, and everyone is already going to be there. A deadline three weeks out reads as a suggestion, and suggestions get answered on the last day or never.
Take the money in the room
The message sets it up. League night is where it actually happens.
Payment apps are easy and people still forget them, because paying you is not on anyone's list. Standing in front of someone between racks fixes that. If you know they use Venmo or Cash App, open it and send the request while you are standing there, so the only thing left for them to do is tap it. If you don't, they pay you on their phone right then while you watch. Cash is fine and honestly faster.
Collect the whole amount, not a deposit. A deposit is just a reason to collect a second time.
Take the sizes on the same trip. Six names, six sizes, six payments, one league night, and there is no follow-up to send.
Whoever has not paid when you order
Order Wednesday for everyone who paid. Whoever has not paid goes in a second batch a few weeks later, or places their own order whenever they're ready and pays a little more for it. Say that once, up front and with no edge on it, then actually do it. The rule does the work, so there is no chasing and no one gets singled out at the table.
This works because of how the ordering is priced. There is no minimum, so a first batch of four is a real order. The second batch carries no setup charge. And the design is paid for once, so a late shirt costs what a shirt costs.
Ordering late costs a little more on its own, without you adding a word. Six shirts or more takes 15% off the order. Three to five takes 10%. Free shipping starts at $65. Someone who lands in a batch of two clears a smaller discount and may cover shipping, so they pay a few dollars over what the Tuesday crowd paid. Every player who has ever missed a deadline understands that the moment they see it.
A team with four shirts on the floor in week two usually has six by week five, because the holdouts start asking where theirs are. And since the money came in before the order went out, a player who leaves the team in week four costs you a teammate and nothing else.
The version where nobody pays anything
Before you collect a dollar, ask the room to pay for the shirts. Bars sponsor league teams all the time, most captains never ask, and a yes changes the number in your message from $32 to zero.
Ask the room first, collect from the team second, order third. In that order you never have to hand anyone's money back.
One list, one night
Name, size, paid. Three columns on paper or in your phone. Take it around the table on league night, fill it in while people are standing there, and order from it the next morning.
The rest of the process, from the team name to reordering next session, is in the captain's guide to team shirts.