What do we think of when we think of playing fantasy sports? When I started playing season-long fantasy football, I thought it was fun to have some competition among friends to see who could build and manage the best fantasy football team. I enjoyed watching football and rooting for my team, so why not build my own virtual team with real competition? This makes the games more exciting to watch and gives me more teams to root for.

My season-long fantasy teams are money leagues, but the money aspect is secondary to the thrill of competition and becoming part of my league's hall of fame when I win. The money aspect of season-long makes it more fun because it adds to the thrill of winning and the consequence of not winning, giving the “fantasy” a touch of "reality", but it isn’t enough to change how I live.

The focus on monetary gain is greater with Daily Fantasy Sports than with season-long fantasy sports.

But here’s the thing – it doesn’t have to be the sole focus.

What are other reasons to play Daily Fantasy Sports?

We play it for entertainment. We like to be the captain of our own ship. We like to compete.

The mindset that we enter into playing Daily Fantasy Sports can make all the difference in the world in terms of it being fun, and keeping the chance of hitting the dream of winning a big prize alive, versus becoming a real nightmare of financial lose.

So, I have created rules for myself to ensure that Daily Fantasy Sports remains fun for me. With that said, even though I haven’t hit a big prize, I am winning, having doubled my money since the 2020 NFL season began.

These are my rules, and I share them with you so that they might help you enjoy Daily Fantasy Sports more without the stress of possible financial loss.

Rule 1: Play for the entertainment value. When I rent or buy a movie, I recognize that the enjoyment of watching the movie has monetary value. I don’t expect any money back. The money I pay to rent or buy the movie is within my budget, and I don’t have buyer’s remorse later thinking I lost a ton of money watching a movie. Even if the movie is bad, I don’t think about how much I paid to watch it.

Rule 2: Set a per season budget. Figure out the entertainment value that Daily Fantasy Sports has for you and set a budget for playing per season that won’t change your lifestyle if you get none of it back. Is it $10, $100, $1000? Whatever the amount, settle it in your mind that this is your entry fee, and everything from there is upside.

Rule 3: Keep the dream alive. Have a rule about how much you are willing to spend on any one contest. For example, I typically only put 5% of my FanDuel account into any single contest, but the maximum I will put in any single contest is 10%. If I am winning, I can spend more per contest as my account grows. If I lose, I am still in the game, but I must enter smaller contests. As long as there is money in my FanDuel account and as long as I keep playing, I continue to have a chance to hit a big prize, even if I am entering a single lineup in a contest at $0.05 per lineup.

If you lose with a little money, then you saved yourself from losing a lot of money. If you consistently win with a little money, it will grow exponentially as you enter larger contests and the winnings will become more significant. So, you are winning either way if you stick to a rule like this.

The goal here is to keep the dream alive by never losing more than 10% of my account in a single contest. No matter what happens, win or lose, I can continue to enter more contests. One way to think about this is that breaking even is winning, because you continue to have more opportunities to hit a big prize.

Don’t feel that you must enter 150 lineups in a multi-lineup contest because that will give you the greatest chance to win the big prize. This thinking is mathematically flawed. Without going into the math, your odds of winning a big prize are higher if you enter 10 lineups in 15 different contests than if you enter 150 lineups in one contest.

Rule 4: Don’t chase after losses. If you lost money in the past, don’t have the mindset that you must win it back. More times than not, this mindset leads to greater loses. This might be because you lose, or it might be that even though you win it isn’t enough, and you never cash out.

Rule 5: Cash-out sometimes. You don’t ever win, no matter how much your account grows, unless you cash-out. Decide your cash-out point. My cash out point is that I will take out half the winnings at the end of a sports season. You could pick some dates every year that you will cash out, your birthday, your anniversary, before summer vacation. It doesn’t matter, just pick some dates to harvest your winnings. If you didn’t win, these are the dates when you can replenish your funds for your next period of play.

Don’t put money in in-between these dates. Stay disciplined. Just like full-season fantasy sports, when you are out, you are done for that sports season. Stick to the mindset that this is entertainment. If your account runs out of funds, use the offseason to think about your winning strategy for the next season that you have determined for yourself.

Winning is a matter of mental discipline. The hardest part of that discipline will be to stick to your own rules. Think about the rules rationally before you put your money in. In the middle of the season, it will be tempting to take chances and break your own rules. If you give into the temptation to break your own rules, you start down a slippery slope. If you can avoid giving into that temptation, then you will have more Daily Fantasy Sports success in the long run.

From a monetary standpoint, the only sure winners are the sites that host the Daily Fantasy Sports contests. If you multiply the number of entries by the entry fee and subtract the winnings, this is how much money the site takes from a contest. Typically, it is around 20%.

So, if you are an average Daily Fantasy Sports player, you are losing, on average, about 20% per contest. You are not a loser if this happens, you are just an average player.

The team here works hard to provide products that can truly help our subscribers win. We try to keep our subscription price low to minimize the additional money that you must budget to play Daily Fantasy Sports with the hopes that you have fun and win enough that you become a long term subscriber. Therefore, I am writing this article because I want you to be successful in Daily Fantasy Sports long term and avoid financial stress that can occur without a disciplined approach.

We believe our products have features and capabilities that outperform products that cost 10x more per month but we are taking the long term view, which depends on having a top performing product. We know that if you enjoy playing long term, you will continue your subscription long term.

As I mentioned, I have been consistently winning since I started playing Daily Fantasy Sports earlier this year (hadn’t played since 2016). I am truly enjoying playing and I use our own optimizer to decide my lineups. But there is not guarantee my winning streak will continue or that our subscribers will win. So we are not standing still, but are constantly improving our Daily Fantasy Sports lineup optimizer. 

Watch for more articles on ASL's site including in the FAQ section (under Support). We plan to add articles that show what strategies have worked well.