Ask The Commish: Investing Pool Money and Bonus Payout Ideas

By Reginald James
Reginald James



Any suggestions on what to do with pool money? I feel like I could be doing something creative with it. I saw your story about the bitcoin guy, that’s not what I’m talking about. I’m asking for next year.


Honestly, I personally feel comfortable letting the money sit until you need to pay it out. That’s what I do. During the preseason, I took a survey to see what pay clients everyone in the league used i.e., Venmo, CashApp, GooglePay. Everyone was okay using Venmo, so that’s what we’re doing this year. Before that, I was accepting money through various means. When it came time to pay the money out at the end of the season, I often had to make multiple moves to pull it all together.


This isn’t exactly the answer to your question, but I just wanted to give (the readers) an example of the most basic way to handle pool money. I know it’s boring, and not very creative. As the custodian of our fantasy league money, I’m cool with that.


That said, what do you mean by creative? How creative can you be? Either the money sits, or you do, what? You either hold it, or invest it. I don’t know what else you can do with the money.


You said you read the question about the commissioner who was investing in bitcoin, and you weren’t interested in that. If investing is what you mean by being creative, then you’ll recall that I wouldn’t recommend investing in something with such high risk, so we’re in agreement about that. If you’re going to invest in say, a certificate of deposit (CD), you’ll have less to worry about. I would not buy stock or options.


If you’re in a league where your members are reliable in paying you their money, maybe you could consider collecting the money earlier than you normally would. For example, collect the money in April. Then, you’ll have more time for a CD to collect interest. CDs aren’t paying a lot, but the longer you hold one before cashing out, the better.


Buying a CD in April will give you a longer time to collect interest, as opposed to investing in August. Any interest you collect, could be used for an increased payout, or as a bonus payout for something like, the widest margin of victory of the season, or the highest total points scored for the season. Frankly, it’s not likely going to be a lot of money, but it’ll be more than what you started with.


I’m not sure if this is creative, or maybe it’s just crazy, but if you could pull off collecting the money in January (just as your current season is ending), that would give you a whole year for your league CD to collect interest.


I’m not sure if I helped you in coming up with creative ideas. Maybe your league mates will come up with something better than me. At the end of the day, just be transparent in your actions - no surprises. The whole league should be onboard with whatever you want to do. I do mean the whole league. Since you’re dealing with someone else’s money, I would want full agreement from everyone when deciding what to do.




I won some nice stash of cash with a scratcher! I want to share some of it with my league. I think I will give a prize for the highest scorer for the year. I’d like to do some others that might be a bit different. Have any ideas that might be fun?


Cool, congrats. Sharing some of your wins with your league is even cooler. I probably wouldn’t do that myself, LOL.


If your stash is big enough, you could offer a weekly payout for whichever team wins by the biggest margin of victory, or simply the best margin overall at the end of the season.


You could offer a bonus for the team:


whose bench scores the most points (weekly award or for best single season match)

• with the longest winning streak over the course of the season

• with the highest single-game score of the season

• that scored the most points during a regular season game while recording a loss


You could have everyone predict what their total score will be for the season, and whoever comes closest wins some cash.


How about if two teams actually tie? Give them a cash prize.


The Unicorn Bonus - something that’s not likely to happen (especially in leagues that have fractional scoring) so make this bonus a bigger one, just for fun: offer a bonus for any team that puts up a score of all the same digits e.g., 222.00, 333.33.


Let me know what you decide to do!


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