Money-Making DFS Tips From A Million-Dollar Winner 2022

By Jamie Calandro
Jamie Calandro If you follow me on twitter or if you've read my other DFS strategy articles, you know that I advocate for the safest, easiest way to grind out winnings. This is largely because the millionaire contests are so top-heavy that they're designed for you to lose, and the glitz and glitter of them will keep you donating your money every week. That said, a lot of times we still can't resist going for that life-changing money, and SOMEONE has to win it. I was lucky enough to be joined by one of the best large-field tournament players in the industry by the name of Brian Jester.

Brian is the Co-Founder of Occupy Fantasy and the host of the Emotional Bankroll Podcast, and most importantly for our discussion, is a DraftKings Millionaire Winner and FanDuel World Fantasy Football Championship Runner-Up.

I sat down with Brian to get some advice on how to take down one of these seemingly impossible contests to win, and he was extremely helpful. Check it out below, and make sure to follow him on twitter @BrianJesterFF.

JC: You won the largest single game millionaire contest in DraftKings history. The showdown contest was for the Super Bowl -- Patriots vs. Rams. Do you remember the winning lineup?

BJ: I won a million dollars while surrounded by my friends and family in Vegas. You don't forget that lineup. It famously had zero QBs, which is a rare roster construction in a Showdown winner.

JC: You obviously love DFS, what is your favorite weekly or daily contest to play?

BJ: I grew up on fantasy football, and there's nothing like a full Sunday of action, so NFL will always hold the top place in my heart. However, since UFC was thrust into the spotlight during COVID, I found a huge edge and it's been my most profitable sport outside of NFL since I started playing. Plus, the sweats are unmatched.

JC: When did you first fall in love with sports, playing or watching?

BJ: I fell in love with playing basketball and baseball when I was five years old, but once I was introduced to fantasy football when I was 12, I was immediately addicted to watching sports.

JC: What was the first DFS contest you remember entering?

BJ: I first started playing back in 2014, but I never took it seriously until about 2018 when I put a major focus into the strategy.

JC: What are two pieces of advice you would give to players who are entering lineups into the millionaire contests?

BJ: The first piece of advice is to understand that these contests have top-heavy payouts with tons of competition, so you're likely going to lose. That seems harsh, but it puts you in the right mindset before entering the contests and allows you to take more risks with your lineups. Secondly -- in a sport as popular as football, you can easily find the best projected players by the end of the week. Unfortunately, so can everyone else, and those players are usually the most popular. You need to find the players that most people will overlook that have a shot to outscore the more popular players.

JC: Can you still win the million with chalky players?

BJ: To continue from the previous question, some players take that approach to the extreme and play all unpopular players. You don't have to! You only need a couple of differentiation points, which means you can still roster some chalky players. All of my six and seven figure wins have included some chalky players, while my under-the-radar plays were the true factors in winning a big score.

JC: Are QB/WR stacks essential, or do you think you can win without them?

BJ: You can win without them, but it's extremely unlikely and requires much more luck. Look at it this way -- is it easier to perfectly predict all nine players in your winning lineup? Or is it easier to predict 4-5 players plus one correlated game environment? It's obviously the second, so if you can find a game that you believe will score a ton of fantasy points, and you're right, your lineup shoots to the top of leaderboards. In that case, now you just need to get the other 4-5 roster spots in your lineup correct to have a chance at first place.

JC: How are showdown millionaire contests different from the full week of games?

BJ: Unlike the classic slates, you have to have the perfect lineup 99 percent of the time in Showdown. In classic contests, no one will ever play the optimal lineup, so you can just correlate as much as possible to try to beat all of the other lineups. But in Showdown, you need to get everything right.

JC: Do you approach FanDuel and DraftKings differently with respect to milly contests?

BJ: You have to because of the salaries, scoring system differences, and roster requirements, especially in Showdown. There are a lot of factors, and you need to think about each site in a vacuum.

JC: 90 percent of players lose money on DraftKings and FanDuel. How can they reshape the way they think about playing DFS?

BJ: In most sports, most people know the best plays. Try to find which players are being overlooked. Research the correlation and how winning lineups usually rise to the top. But most importantly, always review the contest payouts and build your lineups accordingly.

JC: How can players use the "Satellite Strategy" to maximize their bankroll potential?

BJ: Take a look at the lobbies for most DFS sites and you'll find satellites or qualifiers, which are contests that award entries to future contests instead of cash. Not only is this payout structure better than a majority of large tournaments, but once you win, it also allows you to enter a future tournament at a higher buy-in level that you could never usually afford. It's by far the No. 1 most attainable way to win a big prize in DFS.

JC: What was one thing that you got for yourself after the big win?

BJ: I "got" my freedom, since the million helped give me the financial flexibility to quit my day job and do this full-time. I also like to travel, so my fiancée and I took a couple of really nice international trips.