Guest: WinThatPool.com founder Tom Anichini

When I first started ConfidencePoolPicks.com, I kept looking for other sources I could learn from. I found WinThatPool.com and followed it throughout the years. It seems like their win probabilities were pretty accurate, and I’ve always wanted to find out if there was a way to incorporate it into our picks here. 

This year, I saw a post that WinThatPool.com was no longer offering up picks and instead the founder, Tom Anichini, was going to release a book. I jumped at the chance and ordered the book right away. I was lucky enough to get a hold of Tom to ask him about the site and his analysis of confidence pools. Here are his answers:

CPP: How did you get into doing confidence pool analysis and what’s the story behind starting up WinThatPool.com?

Before I ever played in a confidence pool, I played in a college football pool called a 3-teamer. In a 3-teamer entry, you select three teams to beat the spread in their game. It impressed me how picking against the spread was (thanks to pushes) worse than a 50/50 proposition. I kept this lesson in mind a few years later when I worked at a different office where they had a confidence pool. I figured, if the point spread is such a good predictor of the eventual point differential, why not just pick the favorites, sorted by point spread? So, I did. And I won a lot. Back then you had to hunt for point spreads in the newspaper, or on Bloomberg if you had access to one. Using them was an unfair advantage.

Years later I learned that Wayne Winston, author of Mathletics, imputed win probabilities from point spreads by assuming a normal distribution. I found this technique to be valid and it greatly simplifies calculating win probabilities.

Working in the investment industry, instead of winning small stakes I thought it might be interesting to post picks and win probabilities, the same way analysts publish research on stocks. By the time I launched in 2009, I had read two highly informative academic articles, one by Avery and Chevalier on the efficiency of NFL betting market information, and an in-depth analysis and simulation on winning pools by Clair and Letscher. The first work (to me) validated the use of point spreads, while the second one validated that there isn’t some secret better way out there.

CPP: Did you have any interesting interactions with a WinThatPool reader over the years? Fans? Haters?

I’ve enjoyed mostly messages of appreciation. I imagine if the site had haters they simply ignored it. A few loyal readers I could count on to correct errors I had made in posting results. Many readers asked for my methods, which I finally reveal in the book.

CPP: What made you decide to write a book on this subject? What was that process like? Were you friends/family supportive or skeptical?

I announced in 2017 that the site would cease publishing picks. In addition to my investment tasks, I serve as CFO of an anti-bullying nonprofit, ActLikeYouMatter.org (ALYM). ALYM presents bullying solution seminars and assemblies at K-12 schools throughout Southern California. Demand for ALYM’s service is growing. We just obtained 501(c)(3) status so we expect our funding to increase, demanding more of my time. I didn’t want incorrectly predicting Super Bowl LII to be WinThatPool’s last word, so I thought I would finally offer readers all the secrets they care to have.

CPP: Do you play confidence pools yourself? How have you done?

Not anymore. When I began publishing on the site, I continued to play in different pools under different avatars, changing my team name each year. One commissioner privately suspected me of being a professional gambler on the DL. I won his pool the first year I played. Up to about 2012 I applied a season-long strategy. Since then I have experimented with weekly strategies to test the algorithms I list in the book. I didn’t win all the time, but I won more than my fair share, and I am confident that the methods in the book are worth sharing.

CPP: What’s your personal strategy (that you are willing to share)?

In a nutshell, I prefer a pool that continues into the playoffs. I aim to be near the top of the leaderboard heading into the playoffs, which requires picking favorites week after week and making no errors entering my picks. Come playoff time I switch to tactical mode and rely on Monte Carlo simulations, considering the likelihood of picks by the other leaders, to make picks. In 2013 I won a pool where entering the playoffs I was in 5th place. During the playoffs I clawed my way to the top, one week at a time, by identifying which combination of favorites and upsets put me in the best position to pass people ahead of me. Entering the SB (Ravens vs. 49ers) I was in 3rd place, which was in the money. I calculated the game theoretical optimal pick for me, Baltimore. Of course, the two guys ahead of me picked the favorite, SF, so I won it outright.

CPP: What’s the biggest mistake a confidence pool player is making?

  1. Entering your picks incorrectly. If you play in a lot of pools on different platforms, it is easy to make an error.
  2. Picking emotionally. Do not allow emotions to affect how you rank or pick teams you love or hate.
  3. Hubris, believing that you know better than the betting markets do. You probably don’t.

CPP: What advice do you have for the readers of this site?

Don’t lose confidence (no pun intended) in the picks based on a few bad weeks or even a bad season. If you hope to win a season-long prize, stick with the favorites until you feel you’re out of reach of your pool’s leaders. At that point (hopefully Week 14 or later), switch to using the Money Pick, and assign it the most points possible.

Tom’s book, Win That Pool! Your starting point for winning office football pools, is available on Amazon. If you’re a stats junkie, it’s a great easy read and you really appreciate the work that was done behind the scenes on the site. If you have any questions for Tom, please post in the comments!