Five Daily Fantasy Lessons I’ve Learned the Hard Way

What initially attracted me to DFS is the possibility of making some big bucks. Who wouldn’t want to win a million bucks in a day? But as I delved further into daily fantasy, I found out that by putting in a little time and effort, you can come out ahead.

At first, I dabbled a little bit with the Perfect Lineup on the now defunct DraftDay winning $40 for 2nd place, while playing poker full time, but quickly realized that to be successful in fantasy I would need to learn a lot. I couldn’t just build a lineup a few hours ahead of time and expect it to do well. Condia taught me that lesson when Rajon Rondo was ruled out because he didn’t play back-to-backs.

I was successfully grinding online poker but noticed many pros hung up their chip protectors to play fantasy football for a living, and these guys were better at poker than me. I quickly realized that the dream wasn’t a fantasy; it was attainable. Everyone wants to make money playing games that they love, especially when there are such large amounts of money at stake. I had to learn the tricks of the trade to make it reality. This is what I’ve learned so far.

Lesson #1 – Contest selection

Who you play against is as important as who you play in your lineups.

Over time, the data has shown DFS players have a strong preference for contests that offer a large prize for first place. But even if you’re a good player, you could go weeks or months in these contests without coming in first. This creates two challenges: knowing if your strategy is profitable and being able to survive cold streaks.

Enterprising people hear about DFS and the level of competition has gotten quite strong. But it varies so much from tournament to tournament! In some tournaments, often 60% or more of the competition are semi-professional or professional players. I’ve learned you have to be on your game to come out ahead in those contests. But in low stakes tournaments, people entering don’t try nearly as hard to make a strong lineup. The margin of error in these tournaments is much larger so you don’t have to quit your job to dedicate all of your time to fantasy to be a long-term winner.

In smaller stakes tournaments, I found it possible to make a steady profit year after year. In the $20 and under contests that I graphed my results from above, my risk of going broke was low because the variance was small in comparison to the potential profits. Still, I had a downswing of six figures during this stretch. That shows that even if you’re a very profitable player like I was over this period, you can take significant losses in a short-term period. Most people probably quit DFS when they lose money like I did over many of the intervals in my graph above. That’s why you need a solid gameplan from the get-go. There are tournaments available as low as $.05 so there’s a level for anyone to get started on making DFS a profitable hobby.

The higher stakes tournaments ($20+ per entry) can be profitable, as well, but I’ve found the experience playing these tournaments challenging. I can’t recommend focusing on them except for players who have already reached their potential playing the lower stakes tournaments. These tournaments can be appealing because there are less entries to compete with, but the money is really in the small stakes games. While only 82% of my entry fees have been in contests $21 or more, these tournaments make up 57% of the profits in my career. My best advice is to wait to enter these tournaments until you’re an advanced player.

I’m well known for the volume of my play which is how I have held down the number one-overall ranking on RotoGrinders since 2017. But the bankroll requirements of playing tournaments that are hundreds of dollars or more per entry are insane: up to seven figures depending on the stakes. There might be a few guys out there that win big but most go broke. If you want to “get rich or die tryin’,” disregard this advice and knock yourself out. For this graph below, I selected only contests $21 and up and the dates of one particularly crazy stretch of my career. It happens to be this year so far!

The sites you choose to play on are of the utmost importance. Because DraftKings and FanDuel offer the highest volume of play they attract the best DFS players in the world. It’s possible to win the most money on those sites if you’re a shark because of the volume, but other sites like Yahoo and FantasyDraft offer a better profit margin on the money you enter. Yahoo has a model of encouraging friendly competition among players so the ratio of bad to good players is much more favorable. FantasyDraft charges less money than the other sites with their rake-free model, allowing you to pay less than half of the money to play than the other sites. Yahoo and FantasyDraft provide ideal places to learn the game while you start to scale up your play.

The other leagues that people focus on to make money at DFS are ones where the return on your entry is limited, commonly referred to as cash games. The dirty secret of cash games is that they are a fraction as complicated as GPP’s because you only need to consider the one factor of projections and not correlations or ownership. If you find yourself figuring out who the best plays are on a given night based on salary and not worrying about playing the poker game that is ownership, cash games could be the right format for you.

You need to have a big enough edge to overcome 10% rake in most instances and this can be measured in terms of the gap in projection between your lineup and your opponents. I’ve found the easiest way to ensure this gap is large enough is to seek out weak opponents. That’s why I’ve found the most profitable way to play cash games is head-to-heads, especially on sites that allow you to have greater control over who you face, such as Yahoo and FantasyDraft. If you develop a reputation for being solid, smart people will choose not to face you and the only ones who do aren’t putting in as much effort. The way to find these opponents is to create your own contests instead of joining currently existing ones. Some other formats of cash are very favorable like large single entry double-up tournaments, but others such as multi-entry double-ups can be rake traps where no one is doing that well.

My mantra has been always to follow the formats that people play for recreation, and that’s why I think large-field and beginner/microstakes tournaments are both the most fun and lucrative way to play fantasy sports. Cash games don’t attract nearly as much attention from casual players as tournaments though because they lose their money quickly and don’t even have the chance for a large score. The key feature of any contest you play should be that the skill level of the field isn’t nearly as high as yours when you’re playing at your highest level. You have to overcome not only your opponent but the cost the sites charge you to play.

Lesson #2 – Projections

You can make a good lineup optimizing based on projections but to make a great one you have to sacrifice projected points in favor of ownership and correlation.

When I started fantasy, my approach was simple: pick the best players I could and fit them into a lineup. Creating more accurate projections are how I made my bread and butter for years. Over time, my lineups started to look more like my opponents’. Now, the best plays are always highest owned, so I realized I have to play more strategically. If you just want to win your head-to-heads or double ups, projections can be the ticket. But if you’re like me, you want to win the large field tournaments for the big prizes and glory.

In tournaments, the challenge is that it’s easy to identify the best players to fit the salary cap. The challenge is figuring out the best ways to deviate from projection in favor of accounting for other factors. The most likely result if you optimize solely for projected points is you’ll end up with a lineup with a great overall outlook for cashing in a tournament, but a small chance of winning it outright. I’ve learned the hard way that the nights where I put up personal-best fantasy scoring lineups aren’t usually the ones where I win the slate.

This is one of many examples where I found that even though I picked players that far exceeded their expectation, they were all relatively high owned and as a result I finished 49th with a score that would have easily won most slates. I’ve found I tend to do better on slates where the winning score is lower because that means the most popular plays probably didn’t all do great.

It makes a lot of sense strategically to aim for less likely outcomes in your lineup because less people predict them. If you go for a lineup with a good projection instead of a great one in favor of reduced ownership, it will be less likely to cash but more likely to take first. The more of the prize pool that is paid out to first, the more you should be willing to make this sacrifice. You’ll need accurate projections though because picking out the 9 best values on a slate is easier than the lower-owned players that have a decent shot that day. I’ve had success using my projections to evaluate my lineup’s potential and you can too.

Lesson #3 – Ownership

The best way to construct a lineup is with a mix of high-value popular plays and lower owned sleepers.

In 2017 I won a trip to the Scottish Golf Experience through a FanDuel satellite and I didn’t realize how much it would affect my DFS career. In Edinburgh I met future Awesemo.com co-founder Tomjk321 who had recently become a fantasy sports pro. He developed ownership projections for each contest he played in and showed me how integral it was to his process. What percentage of lineups contained each player wasn’t something I had tried to project. Previously I tried to account for being contrarian by diversifying my exposure to different players, but I still put in a lot of lineups that had too many popular players in them. I realized this was an opportunity to step up my game.

I understood the concept of using ownership to build fantasy lineups but I hadn’t put it into practice. If each lineup in a contest represents a set of potential outcomes for the games of the evening, then you’ll have the best chance of winning if your lineup covers the most possible outcomes. You want a lineup to be relatively unique to give yourself the most margin of error for victory.

The ideal way to incorporate ownership into your process depends a bit on the sport. In NBA DFS it’s often unlikely a low projected player will put up a good enough score to win you a tournament but in NFL DFS you might get lucky with a touchdown or two giving any player the possibility of being a top scorer. Remember: A good way to learn the DFS strategy is by following content from articles, websites and streams and a great way to learn is to study the strategies top players are putting their money on.

The two best ways to evaluate ownership are to take the sum or the product of the individual ownership percentages and compare them between your lineups. When you multiply ownerships, it gives you an idea of how likely a combination of players is to be duplicated; if Tom Brady is 10% owned and LeVeon Bell is 25% owned, a good estimate is that 2.5% of lineups will have that combination of players. If you multiply all of them you’ll get an estimate of the chance that your whole lineup will be duplicated; however, some players fit better together due to stacking or salary constraints. Like if you have Brady you are far more likely to have Julian Edelman, so at 10% and 25% many more than 2.5% will have this combination. The sum downplays the value of lowowned sleepers but eliminates that bias by just evaluating ownership on the individual player level. The fact that it’s integrated into FantasyCruncher Pro is a bonus.

If you’re not an Excel whiz to calculate the ownership sum and product of each lineup, no problem. The lineup builder on Awesemo will tell you how sneaky your lineups will be on any given night as well as how high your lineup projection is compared to the competition. Having a lineup that is strong considering both ownership and projection is essential to DFS success. The following lineup is a good example based on the projections because it’s above average in both projection and below average in ownership. That’s why I used it in my GPP’s that day!

The payout structure of the tournament you’re in is a relevant factor. Tournaments with a high degree of top-heaviness reward lineups that are more contrarian whereas tournaments with flatter payout structures reward lineups that have a better chance of a top 20% score. DraftKings tends to be the top-heaviest followed by FanDuel. FantasyDraft and Yahoo reward players more for cashing their lineups.

DFS content can be misleading because there is no one-size-fits-all strategy. The highest value play of the night could be the best player to complete a lineup that’s otherwise contrarian but in a lineup that’s more conventional they could be a net negative. You may even want to pick a player that is over-owned to pick on other DFSers that have that player in case they’re essential that day. So much depends on the context of your lineup. In my experience the best approach is to have a mix of high value high owned players and low owned sleeper plays. The value gives you a good chance to cash and the sleepers a great one to win your tournament outright.

Lesson #4 – Correlation

The odds of picking 9 players that all excel are astronomical; the more correlated players you have in your lineup, the less luck you need for them all to excel.

Once the number of games goes above a certain threshold, predicting the highest scoring lineup is about as likely as winning the lotto. DraftKings pointed this out by offering a billion dollars to anyone who could accomplish the feat in week one of 2017 with a free entry. The chance that each one of your individual players has a big game is remote if you consider each an independent event.

You can increase your chances of making the best scoring lineup by stacking: pairing players who are likely to do well on the same night. The classic situation is pairing a quarterback and wide receiver together: when the WR scores fantasy points by getting a catch, the QB also scores. If your wide receiver has a tournament winning performance your QB is also likely to do very well. Instead of picking a random player to be the best, you already have a good idea based on the scenario of your lineup who will do well at the QB position. This improves your odds greatly.

In some sports taking stacking a step further and creating a game stack, including players from both teams can be advantageous. A prime example is NFL where teams in the lead chew clock and don’t try to score, stunting fantasy production. You really want your players to be either on teams playing catchup or tied, and one scenario where that happens is in a shootout where the team behind scores and takes the lead, forcing the other team to play aggressively. If you get lucky you might even get some additional overtime minutes.

In sports where stacking dominates like NHL and MLB it can often make sense to pick your stack and just fill out your roster with players who fulfill the position and salary requirements of your lineup rather than the other way around. In these sports stacking the team that scores the most points on a given night is almost a pre-requisite to winning the tournament you’re in.

The easiest way to get started is just pick the most popular stacking scheme among pros and run with it. That will guarantee that your lineups will have good correlations. As your process gets more advanced, you can start working in multiple stack types and develop a system to balance the correlation with the projection and ownership.

I found that just considering overall projections and ownership in my lineups I was overlooking low-owned team stacks of great teams that were just expensive. Assuming that the top scoring team will win the slate for someone, I realized these teams were going far too low-owned given their potential.

That’s why I developed my top stacks tool.

Cheaply priced teams are often popular to stack because but while each player is a strong pick by projected points/$ the stack itself is relatively unlikely to succeed compared to their popularity. Looking at the probabilities of team success compared to the projected ownership of the players is the best way to identify stacks that are going over or under owned.

If you operate with the assumption that you will need the highest scoring stack to win your tournament, this tool provides you a great resource to start your research by giving both the popularity of each stack and the probability that each will be the highest scoring of the night.

Lesson #5 – Software

It’s a better strategy to scale up your play by entering a lot of good lineups in small stakes tournaments than to enter one great lineup in higher stakes tournaments.

Being able to scale your approach up by entering multiple lineups as opposed to entering higher buy-in games is critical to your success. Regardless of your skill level, your success measured by Return on Investment (ROI) will be the highest in large field low dollar tournaments. My rule of thumb is that as you increase your investment into a slate you should preferentially enter the lowest buy-in tournaments to the max before entering any lineups in higher dollar games. If you assume a 6% return on $333 tournaments vs. a 20% return on $10 tournaments, you’ll make 14% more money with the same dollar investment. Building more lineups in low stakes contests will not only give you a greater return for your money but will offer a lower risk portfolio overall.

Building 150 lineups while managing the projection, ownership, and correlation of each quickly becomes too complicated to manage by hand. You need to use software to build lineups according to your specifications and then identify the one you want to use. The two pieces of software I use daily are FantasyCruncher and Excel.

FantasyCruncher allows you to build lineups according to any specifications you have, and the customization is second to none. My favorite settings include unique players (how different your lineups are from each other), randomness to give you a good mix of sleepers and popular plays, player exposures to ensure a wide range of different players in your lineups, and stacking according to any scheme you set. I like to build a lot of lineups compared to the 150 I’ll end up using for a tournaments. The more lineups that I have to choose from, the stronger lineups I can pick. Having a desktop computer helps the speed along with using Firefox instead of Chrome. I’ll generate hundreds if not thousands of lineups and sift through them to pick the ones I like. For more information, refer to my series The Fantasy Crunch that I did with Chris Randone dissecting exposure, randomness, ownership, and stacking.

In order to be a successful fantasy player, you need to be well organized. Excel is a great way to start. It automates many routine tasks: and because so much of the game is accruing the information you need to build your lineups and meeting the deadlines for your locks, it’s an important time saver. Excel is crucial for managing my projections but also to work with my lineups. One worksheet that’s essential to my system is my player upload sheet for use with FantasyCruncher where I specify the exposures and randomness for each player. Then once I make my crunch I have a system to pick the lineups I want. You can accomplish this several ways: by hand, through Excel, or in FC itself. It’s important that your process is timely because situations can change quickly in sports. Having a process that is executable within an hour before lock is important for getting the most return on your money.

Putting it all together

DFS is an awesome hobby because not only can you play in the fantasy games that you’ve always loved but you can make money while doing it. A lot of people want to make a profit playing daily fantasy but most people fall short of the goal line. There are so many pitfalls along the way – bankroll management, strategy, what information to incorporate into your process. It’s easy for anyone to get tripped up along the way and get discouraged.

Realistic expectations are key to long-term success in DFS. It’s easy to go back to your lineup that cashed and take too much credit for your success or one that didn’t cash and have FOMO for what you could have done differently. A good return in DFS is anything above 0%, while a great one is 5-10%. The winnings (or lack thereof) that you have in a single day or week are more noise than valuable data. Relying on proven resources is crucial because it takes a long time to figure out what works and what doesn’t.

Everyone wants to go from start to finish as fast as they can in DFS but it’s a slower process in practice. Because reliable feedback isn’t immediately available to you after playing a tournament, it can take a long time to go through the trial and error process. You can speed up your process along the way by taking advantage of all of the resources available to you. Learning from the collective experiences of the industry will save you the trouble of learning each lesson on your own.