Pool Guide
How to Run a March Madness Pool
The tournament is the fun part. Here's how to handle everything else — entries, money, tracking, and paying out winners without the headaches.
Every year, the first two days of March Madness basically shut down American productivity. People are refreshing scores in meetings, watching games on their phones under conference tables, and absolutely losing it when a 12 seed knocks off a 5. It's the best three weeks in sports.
Running the pool that makes it all more interesting? That part has some landmines. Collecting from 30 people before the first tip, figuring out who paid and who's still "on the way," keeping track of standings across six rounds — it adds up fast.
This is how you do it without wanting to pull your hair out by the Elite Eight.
Heads up for 2027: The NCAA is expanding the tournament field from 68 to 72 teams starting in 2027. That means four more first-round games to track — and potentially four more upsets to either celebrate or cry about. If you're building a pool with long-term rules, it's worth noting now so nobody's blindsided when the bracket looks a little different.
Lock In Your Format Before You Open Registration
Don't take a single entry until these are decided and written down. Disputes almost always start because the rules weren't clear upfront — and someone who lost always seems to find an ambiguity when there's money on the line.
- Entry fee: Most casual pools run $20–$50. Higher-stakes pools are fun but make sure everyone's comfortable with the number before you lock it in.
- Multiple entries? Allowing two or three brackets per person changes your payout math and keeps more people engaged when their first bracket implodes in the round of 32.
- Scoring system: Standard scoring gives 1 point per first-round correct pick, doubling each round. Upset multipliers (rewarding correct picks on higher seeds) are popular and keep people in it longer.
- Payout structure: Winner-take-all is simple and creates drama. Top 3 (roughly 60/30/10) keeps more people invested through the Final Four. Pick one before anyone pays.
- Tiebreaker: What happens if two people have the same score? A common fix is a predicted final score for the championship game — whoever's closest wins the tiebreaker. Decide this now.
Write it all down and send it with the entry link. A five-sentence rules doc saves you three arguments in week three.
Collect the Money Before the Tournament Starts
This is where most pool runners get burned. People commit enthusiastically in February and then somehow can't find ten minutes to pay before Selection Sunday. Set a hard deadline — 48 hours before the first game tips — and enforce it. Anyone who hasn't paid by then doesn't get an entry, no exceptions.
Yes, someone will complain. They'll complain a lot less than you will if you're chasing dues while simultaneously trying to enjoy the Sweet Sixteen.
For actually collecting the money, you've got a few options:
Cash at a gathering
Works if your pool is local and you can physically get everyone in the same room. Still results in one person forgetting their wallet and promising to Venmo you.
Venmo or Zelle
Easy to use, but everything goes directly into the commissioner's personal account. No accountability to other members, no protection if something goes sideways. Worth knowing: both Venmo and Zelle have terms of service that prohibit using their platforms for gambling or contest-related payments — and cash pool entries can fall into that bucket. They reserve the right to freeze or confiscate funds flagged for those violations. Fine for splitting a dinner tab; not ideal for a prize pool you've been building all February.
LeagueSafe
Handles collection and holds the funds in escrow until you're ready to pay out. Members pay via credit card or e-check through a single payment link. LeagueSafe will even send reminders to anyone who hasn't paid yet — which means you don't have to. It supports up to 1,000 entries, so it scales whether you're running a 20-person office pool or something significantly more ambitious. Set up your pool
Why does it matter where the money sits? When pool funds go into someone's personal account, they're just money. They get mixed with rent, groceries, whatever. By the time the championship game tips, that prize pool has been mentally spent three times over. Escrow means the money is locked and accounted for from the moment it's collected.
Lock Entries When the Field Is Set
Once Selection Sunday happens and the full 68-team bracket is revealed, your entry window closes. No late brackets. No "I swear I submitted it." No exceptions.
Make sure every participant has submitted their picks to the same bracket tracking platform before the first game tips. If someone misses it, that's on them. You set the deadline — stick to it, or you'll set a precedent that the deadline is negotiable.
Keep People Updated Through the Tournament
You don't need to send daily dispatches. A quick standings message after each round goes a long way. It keeps people engaged even after their bracket has become a crime scene, and it dramatically cuts down on "wait, who's winning?" messages in the group chat.
People who feel like they're part of something come back next year. People who paid $30, got no updates, and found out they lost via a Venmo notification often don't.
Pay Out Quickly After the Championship
The championship game ends and your job is basically to pay people immediately. Sitting on the money for a week after the tournament feels disrespectful to the people who won, and it creates unnecessary friction and suspicion.
If you collected through LeagueSafe, the payout process is straightforward — the majority-vote window ensures everyone agrees on the final breakdown before any funds move, and then winnings are distributed directly to the winners. No awkward Venmo requests. No one wondering if the commissioner "forgot." Set up your pool
Send your payout math to the group before you distribute anything. Show the final standings, the payout structure, and who gets what. Transparency prevents the one complaint that would otherwise live in the group chat forever.
The One Thing That Kills Good Pools
Unclear rules. Every time. The actual picks don't ruin pools — ambiguous tiebreakers, disputes about who technically finished third, arguments about whether the scoring was right. These are all preventable with five minutes of documentation before the pool opens.
The pools that run smoothly year after year are the ones where the commissioner took ten minutes to write down the rules, sent them to everyone with the payment link, and enforced the deadline. That's genuinely it. You don't need to be a spreadsheet wizard or a professional event organizer — you just need to do the boring stuff before the fun part starts.
Run Your Pool the Right Way
One payment link. Up to 1,000 entries. Funds in escrow until you're ready to pay out.
Set Up Your Pool