Thursday, Sep 8th
Monday, Sep 12th

Inside CubsFan’s DFS Mind


In this Q&A series, we’ll take you inside the minds of our DFS analysts at One Week Season! Consuming content such as this can help you gain a much deeper understanding of what you’re getting right (and what you can be improving) in your DFS play!

Greatest DFS memory (Loss/Win) – What did you learn?

I have two…
The first ::

It’s funny, but I’m a glutton for punishment and remember the bad more than the good. I vividly remember pulling a lineup that I loved that would have won a high-dollar Milly on DK that had Cole Beasley against the Jags the week he had the greatest game of his life. It was a great lesson to learn, as my research dictated he was a great, potentially high-upside play in a week that lacked any value. I remember thinking that I would likely be the only person rostering him in that contest (as it turned out, literally no one else was on him).

That lineup won some small-dollar Qualifiers, but I pulled it about 10 minutes before lock. It would have won the Milly by 15-20 points, if memory serves.

The second ::

The other most memorable moment was definitely my second or third contest on DraftStreet (RIP). I remember having enough remaining in my account for an entry into a contest that was only half-filled. I had no idea what I was playing for, as it had a “Q” next to the name. I had no idea what I was doing at the time. I was a season-long player who had injuries that season and decided to dabble on DraftStreet. But I am a math guy, and I understood what I eventually found out was labeled as “overlay.” The contest was maybe 1700/4000 filled. So I jumped in and built what I’m proud of to this day: a Bears/Cowboys game stack. The game became a shootout, and I jumped to first place. The funniest thing was second place was for $1500 or so, and I was rooting for second because I honestly didn’t know what the Q was other than it appeared to be a trip! (Note: That “Q” was a qualifier into a Live Final :: which was CubsFan’s first of 20+ Live Final appearances.)

In the end it was a random, unexpected, life-changing moment that gave me my favorite (and highly profitable) hobby. That win allowed me to meet and become friends with Jon Bales and learn incredible amounts about life, game theory, and DFS! Then Jon introduced me to JM. Life is just crazy like that at times!!!!

From JM :: I have a “Third”…
The Third ::

How about that time you did win the Milly, CubsFan???

(This guy…)

The final game of the day was winding down, and CubsFan texted to say, “All I need is a Cowboys pick-six.”

I forget who the opponent was that week (the Bears? — if so…wow; 2 for 2 on Cowboys/Bears games!), but I was watching the game with my dad, and I said, “Man, there’s no way the [Bears?] throw here. But how awesome to be that close to the Milly.” Then, they threw the ball. And the Cowboys picked it off and returned it, like, 10 yards for a touchdown. (And money rained down.)

Describe a moment when a part of your DFS game clicked?

It clicked for me when I was able to befriend Bales and then JM. From that point forward, I drank from a firehose: I read books, articles, courses, studied lineups, etc., etc. It went from gambling to an extremely profitable side hustle!

What I learned was I can leverage from the best minds and analysts in the industry and focus on what I do best:

Taking massive amounts of data and turning it into lineups.

When did you discover your unique angle?

Great question!

I’ve been lucky enough to never have a losing year in DFS. And I’d say my unique angle is that I constantly adapt. When no one dreamed of game stacking in sports like NBA and NFL, I over-stacked those sports. When people were “pay up for RBs,” I tended to go the other way. When it was trendy to pay for WRs, I’d go the other way. I’ve always tried to be early to a trend and early to leave it.

How do you deal with your DFS Psych?

I owe this 100% to Jon Bales:

Probably the most valuable DFS advice I was ever given was him saying to not get excited about winning or losing money.

So learning that the ups and downs are normal (like an economic cycle) was paramount for me.

Being told that some of the top players in DFS don’t even sweat their contests was an awesome eye-opener to me.

Explain your tourney selection strategy any given week?

The industry is obsessed with contest selection. And I’ve never been all that into it. The thing I am obsessed with is overlay and free money. I will max enter and jump on any sport or contest given enough overlay. When the sites put in more money than we do, math dictates we should grab every entry in that contest that we can (and I do!).

When a site issues a deposit bonus, I’ll take 100% of that bonus.

We need every edge to be profitable in the DFS/betting space, and I don’t quite understand why the industry outside of OWS doesn’t speak on it more.

As a DFS player or sports bettor, we need to take every advantage we can! (Note from JM: Xandamere talks about this all the time as well! Overlay. Softer games (Showdowns // prop bets // etc.). Deposit bonuses. Heck, through OWS, you can gain 100+ Edge Points (which means free courses, subscriptions, etc.) and take advantage of deposit bonuses at the same time!!!)

Do you have a favorite Tourney?  And Why?

Any tourney with low vig (rake) or preferably overlay.

What is your goal this year? (DFS or Personal)

With the sites becoming involved in sports betting and the investment world pouring billions upon billions of dollars into the DFS and sports betting space, I want to take as much advantage of the millions upon millions of dollars the sites are offering to retain and bring in new users. It’s a once in a lifetime opportunity and I want to take as much advantage of it as I can. Deposit bonuses. Shopping for the best line. I want all of it. (Note: Again!!! :: check your profile page. (And if you’re not in a state where we’re up-and-running yet, follow the instructions to be notified as soon as we are!) Free money is sharp money!!!!)

What part of your DFS game do you want to improve?

Literally: everything. As I mentioned before, I’m always striving to improve my play, adapt, and constantly learn.

But my main focus in 2020 is going to be on capitalizing on the industry’s free money. Let’s call it discipline! Playing multiple times more when we have free money, and less when we don’t.

Regarding “Free Money” ::

As CubsFan alluded to above…

In these early days of legal sports betting…

>> Every site wants to become “The site” you’ll use in the long term
…and they’re handing out ridiculous deposit bonuses just to get you through their virtual doors.

We talk about finding and hammering edges.

This is an edge!


Lean into these “Free Money” deposit bonuses, and we’ll hook you up with 100 Edge Points per site. Again!!! :: check your profile page; select your state in the “100+ Edge Points” box!