10 Things I Wish I Knew When Starting DFS

Justin Freeman discusses the DFS lessons he learned the hard way.

“Peyton Manning is the greatest quarterback of all time.” That was my take in 2013 as Manning rewrote the NFL record book with 5,477 passing yards and an absurd 55 passing touchdowns. He orchestrated the Broncos' offense to perfection before taking a brutal beatdown at the hands of the Seahawks’ Legion of Boom in Super Bowl XLVIII. I had never seen a player show such command of an offense. I had never seen a player so clearly playing chess on the field, moving his pawns with pre-snap motion, and audibling once, twice, even three times at the line of scrimmage before settling in on the perfect route combination and the optimal pass protection in place. “Omaha… set-hut” was a signature death sentence for defenses.

Thinking Peyton Manning might be the G.O.A.T. in 2013 was no hot take. The options at that point were Manning, his infamous rival Tom Brady, prolific peer Drew Brees, and some of the historical greats such as Montana, Young, Favre, Marino, Bradshaw, Namath, Unitas, and Starr. Among the peer group, Manning and Brees were hung up on a single Super Bowl victory while Brady boasted three (with two more losing appearances). That season, Brees posted his third straight 5,000-yard season before also falling to the Legion of Boom in the playoffs. Manning’s Broncos outdueled Brady’s Patriots in the AFC Championship Game.

At that point, each of these three peers had a unique claim to G.O.A.T. status – Manning because of how cerebral he was, Brees because of how he stuffed the stat sheet, and Brady because of how he just seemed to will his team to victory so consistently.

But over time, the legacies of each player have changed. Manning limped into one more Super Bowl, then quickly retired. Brees led the league in passing yardage three straight years and then in completion percentage for three straight years after that! And Brady? Well, he stacked up four more Super Bowl rings including one away from the influence of Patriots coach Bill Belichick.

So, did any of that change my mind? Do I still consider Peyton Manning the G.O.A.T.? Does any of this even matter? Yes – I did change my mind. No – I don’t still consider Peyton the G.O.A.T. Yes – this does actually matter!

It doesn’t matter who I think is the greatest. After all, we’ll never really know. It’s more bar talk (remember bars?) and speculation than provable fact. But what does matter is how we make decisions. More importantly, how do we adjust to changing information? This is the name of the game in DFS on a week-to-week and even a minute-to-minute basis. The best players in DFS are the ones that best adjust to changing information.

Number 1 – The best players in DFS know how to adjust to changing information

Knowing how to adjust to changing information sounds relatively easy but let me assure you that our brains are horrible at it. Our minds are wired with many biases that keep us from properly adjusting to new information. We are great at overreacting. We are great at anchoring to our original opinions. We are great at buying into groupthink. We are great at thinking we know best. But we truly are inherently awful at giving proper weights to changing information.

And there is so much information in the context of DFS decision-making. We must consider projections, ranges of outcomes, ownership projections, lineup construction, salary, and the fragility of anything forward-looking. And this is just the tip of the iceberg.

How do we deal with a player who just saw twice as many carries as he normally does? How do we deal with a player who is $1,000 cheaper than he should be? How do we deal with a player who is great but over-owned? How do we deal with a player who is playing out of his mind for the past month? How do we deal with every single news blurb? Perhaps most importantly, how do you deal with the 90 minutes before lock when inactives are announced? With so many changes, what should we do?

Flush it and start over. Reset your understanding. Reconsider the impacts. Our brains can only accommodate so many changes before being overcome with the dreaded “paralysis by analysis.” We are much better at approaching new situations with fresh eyes than modifying our opinions on existing situations. When the information changes, the game changes. Don’t be afraid to push your “reset” button.

Number 2 – The best players in DFS know how much they don’t know

DFS is a game of variance. You don’t have to play for very long to figure that out. The best NFL players in the most optimal situations can flop in a big way. Relatively unknown players can come out of nowhere for a monster performance. And there is plenty of real estate in between those two examples where the vast majority of player outcomes reside. There is a major advantage in embracing this uncertainty.

Most DFS players are debilitated by overconfidence bias, a psychological tool that keeps us from embracing a full range of outcomes and assigning proper weights to the likelihood of each outcome. But the best in DFS understand that good players in good situations are not guaranteed good results.

Number 3 – The goal of DFS is NOT to score as many points as possible

Okay – this one might sound like the dumbest thing you’ve ever heard. “The goal of DFS is NOT to score as many points as possible? Where can I unsubscribe?” But this is perhaps the most important principle I’ve learned and the one that took me the longest time to truly understand. So, what’s the idea? The goal of DFS is to score more points than your opponent.

That may seem like semantics at first but let me walk you through the point. When you build lineups with the goal of scoring as many points as possible (specifically for tournaments), you are going to severely limit your likelihood of a first-place finish (where all the money is). To score as many points as possible, you are naturally going to play the best players available. Guess who else is going to play the best players available? Pretty much everyone! Guess what rarely happens? All the best players all do very well all at the same time. With this strategy, you will be competing against so many other similar teams, that unless you absolutely nail it across the board, you are drawing dead to first place.

What we want to do in tournaments is to find situations that allow us to cut down the size of the field and have our lineups succeed when those things happen. It’s extremely hard to win in a field with 10,000 people in it. But let’s say that we think that Derrick Henry is going to be owned by 50% of the field. Wouldn’t it be great if Henry had a subpar game? Is there a teammate of his that would likely do well in games where Henry struggles? So maybe we play A.J. Brown instead of Derrick Henry and if we guess correctly, we have eliminated half of the field from contention all while improving our own lineup’s scoring upside. While Derrick Henry might be the objectively better play if our goal is to score the most points, A.J. Brown might be the one that helps us score more than our opponents.

Number 4 – In DFS, you can select your opponents

Playing DFS is hard. Not many can simply roll into the lobby, register for contests, submit lineups, and print cash. Instead, we are grinding edges like crazy, looking for every possible angle that can gain us some expected value (EV). One of the biggest angles still out there is opponent selection.

It’s not extremely difficult to figure out which DFS handles are good players and which ones need to withdraw their funds immediately. With a modest amount of research, you can pretty quickly identify some awesomely bad DFS players. And guess what – you can play against them head-to-head!

Especially in cash games (but also in tournaments), opponent selection is the biggest edge left. Not enough players are dedicated to discriminating against their opponents. Picking good players in your lineup is only half of the game. Picking bad opponents is the other half. And believe me, there are plenty of bad players floating around the lobby of your favorite DFS site. Figure out who the bad players are and do your best to enter contests with them.

Number 5 – If it matters, measure it – be consistent

When I first started playing DFS, I was bad about picking contests all willy-nilly. There was no rhyme or reason for my strategy. I had my two or three lineups put together and I’d throw them in whatever contests looked appealing. I’d play on FanDuel one week, DraftKings the next week, and FantasyDraft (RIP) the next. There were a handful of problems with what I was doing.

First, and most importantly, I was building lineups and then throwing them into contests that they were not suited to win. The proper order of operations is to first select a contest and then create a lineup that fits the demands of that contest.

Second, there was no consistency to my play which made it impossible to tell if I was any good. And if I actually WAS any good, I wouldn’t exactly know which site or which format or against which opponents I was finding my success. I wasn’t getting enough of a sample size anywhere to determine my EV. Pick the contests you like and ride it out for the year. Sure, you may want to amend your strategy to hop in on overlay or something else that presents an edge for you but continue to be consistent in the bulk of your play. Have a strategy that can get you a large sample of results and evaluate your strengths and weaknesses in the offseason.

Number 6 – Even an entire season is no sample size in the NFL

While I recommend using the offseason to evaluate results, I should also say that a single NFL season is a blip of a sample size. Perhaps if you are playing hundreds of head-to-heads per slate and multiple slates per week (main, early only, afternoon only, Thursday-Monday, Monday-Thursday, etc.), maybe you have a sample size with signal. But there is no chance that you can find out how good you are at NFL tournaments in a single season.

Elongate your ROI horizon as a tournament player if you want to calculate your EV and evaluate your results. And beware of the potential risk of a tremendously positive result early in your play. A big payday early in your DFS career can have a harmful distorting effect on your expectations moving forward.

Number 7 – Can your bankroll match your goals?

What is your goal when playing DFS? Is it simply to make money? Or is it to make a certain amount of money? Fill in the blanks: I’m willing to lose $______ to win $______. That sentence will determine the kinds of contests you should consider and can help you arrive at the necessary bankroll needed to execute.

Many DFS players have entirely unrealistic expectations. I can’t tell you how many people have told me they are going to get rich playing cash games. Let me tell ya – you better already be rich. For example, let’s say you were willing to put $1,000 in play per week and you were only interested in the Sunday main slate for twenty weeks per year including the playoffs. And let’s say you are a phenomenal head-to-head player with a 65% win rate. How much money would you make? Hold on – let me grab my TI-83.

After a 10% rake, you are left with a weekly expected profit of $170. Over a twenty-week sample, you’ll haul in $3,400 total. You’re probably not going to want to quit your day job. So what if you wanted to make $100,000 playing cash games – how much would you need to play weekly? Answer: just shy of $34,000 per week. That is going to take a pretty big bankroll to pull off. And keep in mind, this is assuming a pretty ridiculous 65% win rate.

Number 8 – Find a unique approach

The best move I ever made in DFS was diving into NFL showdown. In the summer of 2020, I fully immersed myself in the format by digging up historical slates, and eventually co-authored a book that some (fine, just my Mom and my Grandma) are calling the best showdown e-book ever written! I went a few steps further and build out a simulation program to help me fully account for in-game correlations. I started doing content around showdown and I got pretty dang good at it with several first-place finishes in the largest field GPPs.

And there are still so many unique contest formats out there to explore. Find one where the available content is not as robust and people are treating it recreationally. Maybe it’s second-half or fourth quarter showdown. Maybe it’s Tiers. Maybe it’s salary multiplier format on SuperDraft. Maybe it’s Yahoo!’s new showdown product. Maybe you could be a mini-slate specialist (two-three games). Maybe you learn how to beat one-week snake drafts. There are so many options out there without hundreds of hours of accessible YouTube breakdowns. And if you still just love the traditional classic slates, find a unique approach. Try to solve this puzzle with a different methodology than everyone else.

Number 9 – Resist temptation and find smaller contests

I get it – we all love the idea of winning a life-changing amount of money on a single slate. But if your goal is to build a bankroll sustainably, the best way you can grow your bankroll is by limiting your tournament exposure by field size. Make it a rule to never join a tournament with more than 100 players. You’d be surprised what doing this will do to your bankroll.

It also allows you to focus on nailing the plays without going overboard with game theory. You won’t have to wait as long to realize your expectation and you can consistently churn your bankroll with enough diversification and smart play.

Number 10 – Don’t forget to have fun

Listen, it wouldn’t be a top ten list without an extremely cheesy closer - hear me out. Playing DFS can be an absolute soul-sucking grind if you’re not careful. Week one will show up and you’ll be pumped and you’ll have a few big weeks that will send you to cloud nine. But there is a LOT of time between slates for football. That means there is a LOT of time to dwell on your mistakes during a losing streak. And trust me, you will have losing streaks.

Mentally, you can’t afford for this to not be fun. It has to be fun when you win and fun enough still when you lose. It has to be fun to do the research. It has to be fun to make the lineups. It has to be fun to scramble to adjust to late-breaking news. If it’s not fun, you’re going to have a really tough time staying disciplined and confident throughout the course of the season.

Wrapping Up

Leaning on these principles has been something I’ve come to appreciate after years of trial and error. Slate after slate of testing hypotheses and being proven wrong have cemented these ideals in my approach to DFS. But now I have a process that I can count on and in so many ways it has been delivering unbelievable results.

On a Sunday evening in January, the four-game Divisional Round weekend was drawing to a close. The Saints were hosting the Buccaneers to see who would travel to Green Bay the following week in the NFC Championship Game. It was Brees versus Brady – the same guys who threatened my Peyton Manning G.O.A.T. claims eight years earlier were playing each other for the last time.

I had seventeen sizzling hot lineups that were in contention to take down the DraftKings millionaire maker heading into that evening. By the fourth quarter, just one of the seventeen lineups was poised to make a real run. With 4:25 left, I needed this game to hurry up and end as I sat in third place with no viable path remaining to first. Then, with the Saints down ten points, Drew Brees threw an interception on his final play in the NFL, and Brady’s Bucs were able to salt away the clock on their eventual path to claiming Brady’s seventh Lombardi trophy. As the clock hit zero, my third-place finish was cemented for a cool $100,000 – the biggest hit of my DFS career. All thanks to my two biggest rivals – Tom Brady and Drew Brees. What a world.

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