The Art of Losing: A Guide to Daily Fantasy Football August 18, 2014  |  Ian Goldsmith


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              1: to fail to win
              2: to figure out how to win in the future


Everybody loses. Everyone (Quiet down, Dolphins fans. I’m talking about people, not teams). Yes, Floyd Mayweather, Jr. may be undefeated in his professional career, but even he lost fights as an amateur. There are always people who seem unbeatable, but the matrix forming their golden glow of victory must inevitably be interwoven with defeat. The great ones, it is said, have short memories (Pippen was, after all, the greatest Chicago Bull to ever live, right?). While that may be true to some extent, becoming great requires the ability to glean insights from losing. Becoming a consistent winner at daily fantasy football is no different.

Now, I’m certainly no Drew Dinkmeyer or Al Smizzle. I don’t play for high stakes and playing DFS is certainly not something I can ever envision myself doing as a profession. While I’ve been playing salary cap fantasy football since 1997 (shout out to Small World Sports/TSN and, baby!), I only regularly started playing daily fantasy sports last year. While I was having fun, success generally came in fits and starts. I’d build up my bankroll, only to see it come crashing down. This repeated itself a couple of times until I was left with change in my account. I took some time to assess what had gone right and what had gone wrong and whether I even wanted to continue playing for money. If I was going to go ahead and continue, I vowed to be more diligent, disciplined and determined to follow a set of rules. With a free ticket left in my DK account, I entered a tournament, won some money and gradually – gradually – started to build my account to a much higher level. The following are some lessons that I learned from my losses along the way. My hope is that you, dear reader, can take these lessons and apply them early on in your daily fantasy endeavor so that you can avoid the pitfalls that I encountered.




Have fun!! This might seem like the simplest rule of them all, but, to me, it is the most important. There is only an incredibly small percentage of DFS players out there that do this for a living. The rest of us are playing because it is a game and it should be treated as such. Yes, we want to win money; who doesn’t? If we forget why we are playing in the first place, however, then frustration can set in during a losing streak and any kind of fun gets tossed aside. My love for the game is twofold. Growing up in Kansas City, my love for the Chiefs became rooted at a very early age. I was nine when the Chiefs drafted Derrick Thomas. Add in the presence of Tecmo Super Bowl god Christian Okoye and I had more than enough reason to become a diehard fan. The other reason I love fantasy football is due to my love of math. I’m the type of guy who, as a kid, played the aforementioned Tecmo Super Bowl and kept running statistics in a journal (well, loose sheets of timeworn wide-ruled paper, but who’s the wiser?). You don’t have to love math like I do, but you do have to recognize that it is an imperative part of the DFS process.




Walter Donovan said it best, didn’t he? There are a plethora of DFS analysis sites swirling around in the cyber ether, all offering seemingly good and well-intentioned advice. While you should use these sites for research (especially The Fake Football, of course!), you need to trust yourself – not others – when making your final roster decisions. In the end, you need to remind yourself that the writers you end up taking advice from – me included – will likely be your opponents on game day. When I’m writing an article and offering my opinion on which player to pick up for the week, I genuinely think that those players have chance to do well. In fact, I guarantee that at least several of the names that I mention will be used on my own teams. That doesn’t mean that I think every player I mention is the optimal choice, but one that could have a great game. You need to use advice for what it is: an educated suggestion (that eliminates hours of research on your end), not a commandment.

Fantasy writers aren’t out to get you. We’re out to help you!  Remember that we are players, too. The more people that play the game – and play it well – means that DFS websites can increase their prize pools and offer people a more exciting game experience.




Once you’ve decided to take the plunge into DFS, you need to sit down and take some time to create a plan for yourself. If you aren’t sure if you’ll like it or not, there are games that you can play for free on all of the major DFS sites. These free contests, or freerolls as they’re called, even offer prizes if you finish at the very top. Try these games first. They will give you an idea of how to set a basic lineup, teach you how many points you can expect to shoot for on a given website and what the scoring system is for each website (the minute differences on websites can make a huge difference in the end); you can also learn the important differences between “cash” games (50/50s or head-to-head matchups) – games where half of the entrants win – and “tournament” games – games with up to thousands of players in which only a small percentage of entrants win.

Once you’ve gotten a feel for how the games are played and which website’s interface and scoring system you like best, think about how much money – if any – you are willing to put into your account. It is important to note that not every state allows people to play online fantasy sports for money. It is your responsibility to know if your state is one of these!!

Just like playing poker in a casino, you can only lose what you put in. Set your dollar limit up front. As a new player, there is no guarantee that you will do well in a DFS format (there’s no guarantee for seasoned players, either). Once you set a limit, you’re ready to deposit funds into your account. Do yourself a favor and see what kind of incentive each website offers for first-time deposits.

You’ll want to spend most of your money wagering on cash games. Aim for at least 80% of your money to be spent in these type of contests. They provide less risk and – if you are well prepared – offer a decent chance of winning. Tournaments are fun – and can reap big rewards – but they are inherently more difficult to win. Why are they more difficult?

  1. You are playing against a lot more people
  2. The best players will enter these more often because their experience gives them a better chance of winning
  3. Winning these type of tournaments requires making risky picks and hoping they pan out


Don’t wager more than 10-15% of your bankroll on any given day. This eliminates risk and minimizes losses if you happen to have a terrible week. Losing is going to happen. You might lose several weeks in a row (or several days in a row if you are playing daily baseball or basketball). Don’t be surprised by it. Be prepared for it.

Enter the contests you want to play in early in the week. You don’t want to get to Sunday morning and realize that the contest that you were most excited about entering has filled up for the week. If you plan on playing 10 50/50s and two tournaments, then enter those contests and don’t enter any more. Your finger might become trigger happy – especially if you are overconfident about your lineup – but you need to stick to a plan. After you are locked into your contests, you can begin to the process of building your lineup.




Building a weekly roster can be done in five minutes. It cannot be done well in five minutes, however. If you are playing on daily fantasy football sites, then you are likely playing for money. If that is the case, then you owe it to yourself to put in at least a couple of hours of research each week.

I like to start my research for the week by recapping the games that were played the weekend before. Were there any major injuries? Who exceeded expectations? Was there a backup that ended up taking over for a starter and earned himself a bigger role going forward? Did any running backs catch a lot more passes than anticipated (this is huge on a site like DraftKings with 1 PPR)? Let’s say, for instance, that Player A ran for 113 yards and one touchdown. How did he get those yards? Was it on 6 carries or 30 (i.e. Will his touches be reliable going forward)? Was the touchdown due to skill and vision, good blocking or just poor defense (HINT: Watch film)? These type of questions will help you understand each player better and guide you to making better final decisions.

My roster building always starts with the value plays that I want for the week. Always. A good example of value is a backup running back that will be getting a start due to an injury to the starting player. After filling in those slots, I look to see how much salary I have left and fill in the remaining positions accordingly. Your work is not over after your lineup is set. Monitoring your lineup for injuries, changes in roles on the team, etc. is paramount to your continued success.  It is an absolute necessity that you monitor fantasy news in the hour before kickoff. If you have something else planned at that time, then you are taking an enormous risk. Health statuses of players change all the time. Don’t be the guy stuck with an injured player as your roster locks.

Remember to spread the wealth! Are you using a QB on every single one of your teams? What happens if he gets hurt in the first quarter and doesn’t return? This happens ALL the time, so be prepared and make a few different lineups. Also remember that your cash and tournament lineups should not be the same. Your cash game lineups should include players that are more consistent in their production. This is your safety net for the week. Tournament lineups need to be riskier. You need to aim for guys that have sky-high potential, but are off everyone else’s radar.




Once your lineup is set, it is SET. There are very few exceptions I make to this rule. Yes, you’ll obviously need to make adjustments if a player on your team is injured. You chose your team for a reason, however. Whether your lineup is based off of some algorithm that you came up with (I reiterate here that understanding the math behind the game is absolutely essential.) or based off of a gut call (DO NOT do this), you chose it for a reason. Stick to your guns and watch how it plays out. If you are making a change at the last second, ask yourself why you are making that decision. Is it actually based on research or is it based on jargon that you read at the last minute on Twitter? Don’t let others make up your mind for you.




OK, let’s say everything went horribly wrong for the week. You entered twenty contests and lost every single one. So, why shouldn’t you worry?

1: You had fun (or at least I hope you did!)! Fantasy sports, to me, is about getting closer to the games that I love to watch! I know WAY more about football and the NBA now by playing fantasy sports. Remember that it’s JUST A GAME!!

2: You didn’t wager more than you could afford. If you followed my (or most other DFS writers’ advice) then you didn’t wager more than 10% of your bankroll on this week’s football games.

3: You learned what not to do!


So you lost. Big deal. Don’t wallow in what might have been. Learn from your mistakes! What did you do wrong? Sit down and ask yourself questions. Reflect. What can you change so that you won’t run into the same issues next week? When you’re done with that, it’s time to start over and play again….the next football game is never more than three days away in Goodell’s NFL.


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