One of my favorite people in DFS — Jay Raynor aka BeepImaJeep — is a super-creative tournament player famous for knowing next to nothing about sports. He’s learned a bit more since he started playing daily fantasy, but people are always shocked to learn that Jay, who doesn’t really have much interest in watching sports, at one point didn’t know the difference between a cornerback and a quarterback. And he’s one of the top guaranteed-prize-pool players I’ve ever met.

Jay’s approach has been to solve the game of DFS primarily through means other than predicting player performance. That means looking at things like lineup construction, correlations and, specifically, game theory as opposed to obsessing over whether Mike Trout should be projected at 0.33 home runs or 0.29 home runs.

It might sound ridiculous to say that the most important things for DFS players to focus on aren’t even related to sports, but I think that’s indeed the case for two reasons. First, there’s a much larger potential edge in those areas. If you “win” in predicting ownership, you have a bigger advantage than you do if you win in projecting on-field performance, which is closer to being solved.

Second, it’s fairly easy to outsource performance projections because of all the work others are doing. So although projecting on-field performance matters — duh — it’s perhaps not an incredibly efficient use of time. For my March Madness brackets, for example, it took me like 30 minutes to aggregate the win probability projections from KenPom, FiveThirtyEight and Ed Feng (I highly recommend his book on March Madness strategy, by the way).

This general idea — that winning in DFS is more about solving a game than predicting sports outcomes — extends to March Madness bracket strategy, too (and even more so). I’m actually pretty fascinated with March Madness even though I know next to nothing about college basketball, with the idea being that we aren’t really competing to predict game outcomes as much as we’re competing to exploit flaws in how people think about statistics and general weaknesses in game theory comprehension.

So, coming from someone who almost certainly knows less about college hoops than you, here are five tips for winning your bracket.


1. Pick more favorites.

“More” is of course relative here, but most people pick too many underdogs to win, specifically in the early rounds. The reason people pick dogs seems straightforward: Almost every year, there are lots of upsets.

Here’s the problem with that approach, though: Your job isn’t to determine if there will be upsets, but to pick which upsets will occur. Much different story. And so while it might be statistically likely that at least one No. 12 seed will upset a No. 5 seed, that doesn’t mean you necessarily should be picking one to do it. There are all kinds of possible tournament outcomes, but the most likely single outcome is that every favorite wins. That’s exceedingly unlikely, but of all possible paths, the most likely single one is that each team that’s over 50% to win a game will actually win the game.

Here’s an analogy. If you were to flip a coin 10 times, is it more likely you get 10 straight heads or that you get tails at least once? Obviously the latter. But getting 10 straight heads is just as likely as any other specific scenario of flips, like HTTTHHTHHT or something. If we assume we’re flipping an unfair coin and heads has a 51% chance to show up, then the most likely single string of flips would be HHHHHHHHHH. You shouldn’t pick a single tails — even though tails is almost guaranteed to come up multiple times — because you’re guessing which times will show tails, not if tails will come up in general.

So while it’s unlikely that every favorite will win, it’s statistically the most probable single string of outcomes. If you were going for nothing other than maximum accuracy, your bracket would be nothing but favorites.

2. Tailor your strategy to the size of your pool.

Of course, your goal shouldn’t be to maximize prediction accuracy. Your goal is to beat others in a game. If you’ve read my DFS books, you’re probably familiar with this concept, specifically in GPPs, where players for too long have tried to maximize their lineup scores and not their odds of winning. Those are actually very different things.

To demonstrate why your strategy should change based on the size of your pool, let’s just think about the extremes: One pool playing against a single friend and one pool competing against 10 million people. In the single-friend scenario, you need to beat just one bracket, and so there’s very little reason to get creative. Yes, upsets will happen, but it’s not very likely that your friend will accurately identify those to beat you. In the other league, however, you’re competing against so many bracket combinations that someone is actually likely to hit on upsets.

Each time you select an underdog, you’re effectively increasing the potential payoff for being right. The extent of that payoff is related to the number of brackets with which you’re competing; the greater the number, the more incentive there is for you to get creative. In most pools, though, people tend to pick too many dogs.


3. Think about how seeding and name affect what others will do.

I already mentioned the No. 5 vs. No. 12 example, which is a popular matchup, it seems, for people to pick the dog. I actually think picking all of the No. 5 seeds to win is probably smart because of this.

I also think that in most pools, people are generally going to favor the bigger school in any given matchup if they’re unsure which one to choose (N.C. State over Seton Hall, for example), and so I generally like to choose the smaller school, all else being equal, because I’m probably going to run into lower ownership.

When the Vegas spread is close — meaning the game is probably near a coin flip — choose the team you think will be the least popular. ESPN has some awesome data on how often people are choosing each team to advance to each round, which is arguably the most valuable info you can use to fill out your brackets.

4. Take a stand on one under-the-radar team.

One thing I’ve learned in DFS is that there are different ways to be contrarian, and some are objectively superior to others. In the NFL, for example, I’ve found the best results from pairing high-owned players with a couple of very low-owned guys, as opposed to trying to seek both value and reduced ownership on every player.

Instead of picking a handful of low seeds to advance to, say, the Sweet 16, I think it’s probably preferable to pick mostly favorites and then take a stand on one team, maybe two teams, depending on your pool size.

This is a barbell-based approach similar to what I’ve applied to fantasy football in the past. The idea is that the contrarian dynamic of your entire lineup (or bracket) is different than the sum of its parts. Adam Levitan put it best:



5. Take your friends’ and family members’ money.

As always, make sure you leverage all your research to inflict financial harm on those closest to you.


I’ll leave you with my odds of the top 15 teams winning the tournament compared to the current ESPN tournament selection rates.

Some teams perhaps being underrated in brackets (high payoff relative to their odds): Cincinnati, Purdue, Gonzaga, Tennessee, Texas Tech.

Some teams perhaps being overrated in brackets (low payoff relative to their odds): Kansas, North Carolina, Michigan, Kentucky.

Pictured above: Cincinnati Bearcats guard Jacob Evans
Photo credit: Reinhold Matay-USA TODAY Sports

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