So, full disclosure: We originally kicked off this idea by asking members who they wanted to nominate for Commissioner of the Month.

This past week, however, we received more than 200 replies nominating one fellow for the award, and we just felt like a monthly award just wasn’t enough for somebody who’s built that sort of loyal community — all by himself. Literally thousands of people play his pools, across multiple sports and games.

So we put our heads together and instead of giving him the award for 2022 — we thought it would be fairest to give him the award he deserves: Commissioner of the Year 2021

His name: The Tutor. (Clearly a pen name — or a pool name, as it were — but we wanted to respect his privacy.) We were able sit down and ask The Tutor a few questions, so if you’re interested in how to build such a huge following yourself, check out his advice and story below.

So let’s start off simple! How long have you been a commish?

Since graduating college, I’ve always done something. Fantasy football and brackets with my core set of friends. I was even a real golf league commish for a few years. Help started a corn hole organization. Running yard or drinking Olympics. Simple things. My friends and family think I would be a great wedding coordinator, city event coordinator, or professional sports team event management. I probably would be — if the money was right. Looking back, it looks like I got some NFL stuff going for the 2013 season, and March Madness going in 2014. I had my “official” new email around that time, so let’s say nine years being the actual “Poolguy” officially.

Why do people call you the Tutor, then?

Because that’s USUALLY what I name all my entries in games.

Tell us how you started your pools, how it’s grown.

It’s actually an incredible story that I talk about in my Hall of Fame speeches.

You have a Hall of Fame?!

Yes, I have a Hall of Fame for my followers. I try to be serious and fun at the same time. I nominate three people every year. They love it. It’s like a four-page Google document every year that gets bigger and bigger. Probably won’t be near the size of this speech though!

Go on.

Anyways, I became the Poolguy, because I was in a fantasy MLB and Nascar league with a dude named Jon Roy. He also had some survivor and pick’em pools too. (PLEASE, if anyone remembers this guy, please email me!).

Anyways, he skipped town. A few of us had an email list of his and some of us tried to play detective to try and find him. We never did. But I had his list, so I capitalized, took some initiative, and emailed everyone that I was going to do some NFL stuff. I was good at fantasy football so I was actually trying to recruit folks to beat. Literally, that was my initial motivation.

At the time, Jon only had about 30 guys on the email list, nothing special. I also had some friends I got involved with too. I started four fantasy leagues: one squares grid, confidence, and spread pick ’em. So seven things. This year, I had over 65 different contests for the NFL season.

That’s quite the growth!

I know, right? The Tutor tooting his horn. I just got done doing my March Madness list. I have 36 separate contests for that. I only had eight in my first year. If you think about it, not to brag or anything. Ok, I’m bragging.

Brag away. That’s a lot of contests for an event that only runs for three weeks.

In 2014, I had 174 entries in my first NFL Survivor try. This year, I had 2,058. I had to make a new email, and also use Google group because I have too big of an email list that Google spams me or sometimes blocks me. Started Twitter, Facebook, and Discord to help with communication. I remember it being a big deal that I had an email label with 100 guys. Now I have a Google group with over 1,000 people! I really do appreciate all of my followers. I hope to continue to grow. Just being nominated for this means a lot, but what I really want is, 10 years from now, people all know who the Tutor or the Poolguy is.

So how many pools do you run? Which sports?

Officially, 170ish. Unofficially, over 300.

Unofficially?

So if I do a random pool that RYP doesn’t have, like Predicting the NFL Draft, MLB Opening Day Pick em, Tennis, Daytona Draw, Golf Calcutta, WWE Royal Rumble, then I go a different route. Especially if only 10 to 20 guys want to play. Would love for RYP to get all those on the site!

Us too! What are your favorite game types to run? Why?

Fantasy football because I’m good at it! I can run it and also win! Outside of fantasy, I have a few unique paper pencil leagues that I run that are personal to me. It’s much more enjoyable when you have to put a little work into it, no offense to RunYourPool, but those are probably a few contests I’ll never let you run!

No offense taken! Haha

However, if I could, I would LOVE to run all kinds of survivor type games, for all the sports. That’s my dream. Be a Survivor King.

What’s the best part of being a commissioner, to you?

Well this nomination was great, but I love it when I get emails saying, “Hey, can you put my friend on your list?” Because I know I’m doing something right when people want their friends to join in. Being a commissioner isn’t always fun and games, and there’s a lot of bad situations, but the good outweighs the bad.

Got a favorite story of your time as a commish?

Literally, I was picking up my daughter from school, and a guy came up to me and said, “Aren’t you the pool guy?” That’s the first thing that comes into mind. I’ve met guys at the Kentucky Derby and baseball games from my list.

Got any advice for aspiring commissioners to make their lives easier?

Get rid of toxic people fast and don’t feel bad about it. You are doing this for free, so it is much easier to just block, or delete people who ask a million questions, disagree with rules, won’t follow the rules, negative remarks, etc etc. You aren’t a little league coach that has to put up with parents. Trust me, IF your list gets bigger, you are going to run into a lot of these people and a lot of moments that stress you out.

Good advice.

Another bit of advice would be to find that ONE unique pool and concentrate on doing THAT particular one.

Not trying to scare anyone off, but I think the market of becoming someone like ME is unlikely. By now, everyone has a “guy,” for whatever pool floats their boat. It took me 10 years to get where I am, and by no means do I have the market cornered in anything, except maybe this ridiculous Super Bowl Pool I do. So my advice would be that you put your energy into being the DUDE who runs that “ONE pool” that everyone knows about.

From there, your popularity will rise, and if you wanted to, you could sprinkle other pools here and there. I’m just a dude who does them all, that’s my speciality.

There’s no difference in having ONE pool with 2,000 entries versus ten pools with 200 entries each. Find your one thing, and build from there, or see if RYP can help you build it. One thing you all should know is that RYP is under new management and they are committed to making this site the best. So hit them up with your ideas. Another idea could be to hit up other big time pool guys, like me, and “trade” users as long as you have two different games so you aren’t stepping on anyone’s shoes or poaching entries.

Where do you think you’ll go from here in terms of pools and game types? Anything interesting on the horizon for The Tutor?

I might just be content doing what I am doing, and hope RYP can accommodate most of my ideas going further. Pipe dream would be my own site (involving my Survivor ideas), but I’m 40 years old, and probably not worth all the headache and hassle. I have a lot of great ideas for pools, not on RYP, but I can’t give away ALL my secrets just yet.

What do you hope is in RunYourPool’s future?

If I could address the audience: Folks, RYP seems to really, really be invested in being the best. Reach out to them. Maybe you have an idea that I didn’t think of. That’s a great start to begin with. If you are running pools on other sites or paper/pencil when you shouldn’t be, please consider doing it on RYP. The more we run pools and bring traffic to the site, the better chance we get MORE options and a BETTER product.

Email me if you are a serious pool runner and want to know the ideas I ran by them. My personal wants are text alerts when you have picks due and also having golf/NASCAR/spread survivor and NCAA regular season basketball and football pools.

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