Pro Sports Gambler Who Has Won Millions Tells Us The Keys To Betting (And Winning) On Daily Fantasy Sports

Photo by Nick Fewings on Unsplash

When bros think about a dream scenario, I wonder where going from professional poker player to professional daily fantasy sports player would rank on the list, with stories and successes coming from them both? For Cory Albertson, he would know, because that’s exactly how his life has played out.

After realizing that he was pretty damn good at digging into statistical analysis and breaking down daily fantasy sports lineups with his playing partner Ray Coburn, Cory found himself winning millions of dollars while at the University of Notre Dame during his MBA program, even starring in a documentary on daily fantasy sports entitled Living The Fantasy.

I got to chat with Albertson to discuss how he landed himself in such a lucky spot, for tips on how a normal bro like you or I could, possibly, score some serious cash doing what he has done, and why he could totally give better advice than Matthew Berry.

BroBible (BB): I need to ask, how did you even get into playing fantasy sports so competitively?

Cory Albertson (C.A.): “I first started playing fantasy sports when I was in high school, so about 15 years ago, and it really just sort of clicked for me because I really loved stats and sports and competition. So it was really just natural for me to play daily fantasy sports when I first discovered it.”

BBAnd from that, it just sort of became a full-time gig?

C.A: “So I graduated last May from Notre Dame with my MBA and I think that, around the time I started really playing daily fantasy, it was about the same time that I started thinking about going to business school.

At the time, I didn’t think I was going to have nearly the success that I would have playing fantasy, so getting my Masters seemed like the very pragmatic thing to do.

It probably wasn’t until after I started that program that I realized just how lucrative a possible career in daily fantasy could be, and, at that point I was so committed to getting my Masters that I decided not to dropout, so those two years were pretty crazy—playing fantasy at a high level and getting my MBA—but somehow I got through it.”

BB: On average, how much time during a day do you spend updating fantasy or doing some sort of research?

C.A.: “You know, I used to spend a lot more time on it than I have lately. I think lately, especially since this NFL season is just about ending, that I’m winding down how much time on spending on daily fantasy, and there’s a couple of reasons for that.

The first reason is that the process for playing these sorts of games online is becoming easier and more automated, so it doesn’t take as much time as it used to do get the information I would need to play in these fantasy games.

And the second thing is that the games are getting tougher and there are a lot more people that are playing really well and are really good at playing daily fantasy, which wasn’t the case three or four years ago.

Because of that, the expectation for me to win in these daily fantasy games has gone down a lot, so I don’t spend as much time on them as I used to.”

BBInteresting, I would’ve thought it was a hell of a lot more time than that.

C.A.: (laughs) “Sorry, that was sort of a longwinded response to your question, but at my peak, I was probably spending about three or four hours playing per day for an NFL weekend, whereas now, it might be about an hour per day, potentially.

There are people who spend a lot of time on it, but I teamed up with a really smart guy and one of my best friends, Ray Coburn, and Ray has taken on a lot of the innovation in playing daily fantasy, so he’ll probably spend a little more time on it per day than I do.”

BBYou briefly mentioned how competitive daily fantasy has become over the past few years, so, with that, do you have any tips for people on what to look for when playing? Any expert secrets to become successful?

C.A.: “You know, its just become a lot more important to think about how popular certain players are going to be on a given night.

There are some players who are owned by so many people, that it’s almost better to not even have that player in your lineup. It’s not enough to just know who the good picks are, you also have to have a sense of who else to pick that no one else is going to have.

All else being equal, would you rather have a guy that everyone has, or someone who almost nobody has? It’s about understanding which players will do really well on a given night, but trusting yourself to go with someone with a cheaper value that might do nearly as well, but no one is going to draft.”

BB: Exactly. So finding that diamond in the rough, like a Blake Bortles, who had an awesome season that sort of went under the radar.

C.A.: “Yeah, but, you know, I would use an even better example and say Alex Smith of the Kansas City Chiefs; who I pretty much used all season long.

He’s a great fantasy pick because no one ever wants to draft him, but he’ll go out and get you two touchdowns and 40 yards rushing and get you a solid 20 fantasy points. He’s sort of the perfect daily fantasy quarterback in that kind of way.”

BB: Uh oh, man, you sure you’re OK giving away your secret guy?

C.A.: (laughs) “You know, I’d like to think that next year will be a clean slate, so, you know, I doubt it’ll just be a repeat of this season where Alex Smith will be my main guy, but if it is, I’m sure other BroBible people will be thinking about him, too.”

BBOutside of Alex Smith, any go-to guys you always lean on, or do you just go by what your calculations and research always says?

C.A.: “If someone is such a go-to guy that you ALWAYS lean on him each week, then there are probably a lot of other people out there who feel the same way about that player, too, so if everyone is drafting a player, then you don’t want to draft him.

I can name names of those guys that EVERYONE knows is going to put up big numbers on a weekly basis, but the key to daily fantasy is trying to find the diamond in the rough guys that will do a lot for your team, but are cheaper and won’t be on many other people’s teams.”

BB: I know you took party in the documentary Living the Fantasy that’s all about daily fantasy sports, can you talk about that experience and what it was like to be featured in that?

C.A.: “Oh, man, it was so cool.

To give a little bit of background, I was in a Wall Street Journal article in the summer of 2014, and that was really the first time that I was featured for daily fantasy sports in the mainstream media. After that article came out, it brought on quite the wave of attention—including the Living the Fantasy creators, Josh Adler and Andeep Singh.

They reached out to me and told me about how they were making a film about people who play fantasy football for high stakes and if I’d be interested in being in it.

The guys seemed like really cool people and I liked the idea of the movie, so I agreed to do it.”

BBSo they just started following you around with a camera then, huh?

C.A.: (laughs) “Pretty much, yeah. They came to South Bend, which is where I was for school, and they followed me around for the weekend, getting shots of me sitting in the classroom and that type of stuff.

That was weird because the professor didn’t want to give the filmmakers any time to record during the actual class, so the footage was basically us acting things out after the real class had ended, giving other students who wanted to stay around to be involved. We basically reenacted the entire class with about half of the class actually in it.”

BBDo you have a favorite part of the movie?

C.A.: “I do, yeah. My favorite part is the footage from when I won $1 million in a fantasy sports event down in South America, where I was studying abroad in Santiago, Chile.

They had cameras out with me and my friends on only the second night that we were in the country, and they have this part in the film that captures Ray (Coburn) and I celebrating the touchdown that put us in the lead for this daily fantasy football contest, and that was pretty cool.”

BBOh, man, I bet. The fact that it was so organic and unscripted had to be so cool, too.

C.A.: “Yeah, yeah. It was definitely the moment that made me so glad that I said yes to being in the documentary, because that’s what I was hoping would end up on film.

It was just such a good memory because I was out with a bunch of my friends and, when you watch the scene in the film, you can just tell that everyone’s having a good time and we were all so happy.”

BBLook, you’re a smart guy, so anything you can tell us regular Joe’s as to the crazy algorithms you use to bet daily?

C.A.: “You really need to come up with one number, which is how many fantasy points you project for any given athlete, and then once you have that projection, which, by the way, there are plenty of ways to get that research—like Google, it will become your friend—you just couple it with the price of that player on whatever website you’re playing on.

You just want to look at ever players’ value ratio and determine how you’re best served at spending the daily fantasy money on how to properly draft a winning team.”

BBYou make it sound so easy, man.

C.A.: (laughs) “Yeah, but I do feel like it’s becoming easier for anyone to do it.”

BBCan I ask the most you’ve made in one day or one week from fantasy sports?

C.A.: “Yeah, I think Ray and I have about $1.5 million in winnings in one day before.”

BBThat’s insane, man. It’s more than just the big payout you mentioned earlier from the film, right? There was another big payout?

C.A.: “Yeah, Ray and I were the first people in daily fantasy to ever win multiple $1 million-plus payouts.”

BBI’m literally speechless. That had to be so awesome, congrats.

C.A.: (laughs) “Thanks, man, it really was awesome.

The second one was FanDuel’s fantasy baseball world championship in Las Vegas, and one of our lineups was really hot and it sort of separated itself from the pack and never looked back.

It was cool because one of my childhood heroes, Bo Jackson, who gave us the trophy and presented us with the winning check. It was kind of a tough day to top. It didn’t feel like real life.”

BBBiggest gamble you’ve ever made and biggest loss ever… GO!

C.A.: “I was 23 years old and my buddy was playing in a poker cruise that had a $8,000 buy-in, which was pretty much all I really had to my name at the time. So I decided to go with him and play in the tournament—which isn’t really optimal bankroll management at all—but I ended up finishing third place and winning, like, $160,000, which, at the time, totally changed my life.

BBAnd your biggest loss?

C.A.: “I think that I’ve had a few losses over a couple hundred thousand dollars in daily fantasy sports on a few occasions, which, you know, always kinds of sucks.”

BBLastly, could you give better fantasy advice than Matthew Berry? Be honest.

C.A.: (laughs) “With no disrespect to Matthew Berry, I think so, definitely. I couldn’t give advice in as nearly entertaining a fashion as he does, but that’s really why he’s the man, because he’s both a fantasy expert and a guy who can deliver it in a unique fashion.

So, while my advice might be slightly better than his, there’s no way I could present it as well as he does.”

Nick Dimengo avatar
Nick's a Sr. Editor for BroBible, mainly relying on his Sports Encyclopedia-like mind to write about things. He's also the co-host of the BroBible podcast "We Run This," and can be seen sweating his ass off while frequently running 10+ miles around Seattle.