Going Pro in Daily Fantasy: Interview with DinkPiece

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The idea of playing Daily Fantasy Sports for a living has long been discussed since RotoGrinders started up in 2010. Back then, the predominant opinion in our forums was that it was a longshot to see a Grinder quit their day-job to make Daily Fantasy their primary source of income. However, we’ve now witnessed well-respected Grinders CSURam88, Naapstermaan, AlSmizzle and headChopper take down prizes greater than most American’s annual salaries in one day…the concept is starting to feel very real.

Now the title ‘Daily Fantasy Pro’ has become a reality for longtime Grinder Drew “DinkPiece” Dinkmeyer, as DinkPiece has officially announced that he’s taking the plunge. DinkPiece, an Ivy League Grad from Dartmouth, announced he was leaving his job as a Senior Investment Analyst at a respected firm to immerse himself in the world of Daily Fantasy. This is a huge move for “Dink”, and a move that many outside of the Daily Fantasy industry will have trouble understanding. Thankfully, Drew was willing to take some time off his 80+ work hour week to sit down with RG and explain his liberating career-change to us. Here’s what he had to say:

Before you were a ‘pro’, how did you get started in Daily Fantasy?

My introduction to daily fantasy was unique. I’ve been writing for Fantistics for almost 10 years now and over the years you get lots of different questions from our subscribers, typically about trades or FA pickups, etc. One week I kept getting the same email each day from a subscriber asking who the best pitcher of the day was. I was initially really confused because you can’t simply pick up any pitcher you want, so I started investigating and found the interview with HixvilleHunk. Naturally, I found the idea interesting and my immediate thought was “if THIS guy can make serious cash, then I definitely can.” The competitiveness kicked in almost immediately as I kind of thought “How smart can this Hix guy really be?”. (Turns out pretty damn smart) From there I made a deposit (of course $60) and started playing.

Were you a winner right from the start? What strategies did newbie-Dink employ when first playing Daily Fantasy, and how was HixvilleHunk involved in your early days?

I didn’t win right from the start. I definitely went through learning experiences and experimenting with what types of metrics are predictive and which aren’t. Baseball is a great introduction to daily games because there is definitely skill involved but the variance day-to-day allows for new players to have some winning days even when they’re perhaps experimenting with poor strategies. In some regards it can give you a sense of false confidence and I think I went through plenty of learning experiences because of it (bankroll management, roster construction, etc). I was determined to get better though so I started seeking out Hix in chat and we had a lot in common with our thoughts about baseball. We kept communicating over email and I think he really helped crystallize some concepts I was tinkering around with.


How long was it before you realized that you were good and could “beat the game”? What did you notice particularly?

I did OK in baseball season and in football season, but my bankroll really took off during basketball season. For whatever reason I think basketball comes a bit more naturally to me than the other sports and I think there’s a bit less volatility in performance making the game much more math-oriented. I think daily baseball and daily football there’s a bit more art to being good. I think basketball has some art along with the science but I think that art comes more naturally to me. I noticed I was winning more consistently and as the bankroll grew I could move up “levels” in terms of entry fee and my success rates weren’t being diminished. With the fee breaks at the higher levels my returns were actually increasing marginally and it became apparent that this could be a bit more than just a hobby.

Was there an epiphany or “ah ha!” moment you had when deciding to go pro in Daily Fantasy or was it an idea that grew with time?

I’ve been working really hard for the last 4-5 years to create a path where I could work from home, allowing myself to be very involved down the road when my wife and I hopefully start a family. At first the goal was squarely centered around being a fantasy analyst and my involvement with the SiriusXM Fantasy Sports Radio Channel. As I had more success in daily gaming I started to think some combination of the two might be do-able. This NBA season really cemented the idea as an option and at that point it became more of when rather than if.


From what I’ve been told, you were a Dartmouth grad, and had a very nice job in finance…how hard was that to give up to pursue Daily Fantasy? Did your family understand? What made the decision easiest for you?

Very hard. Not only the financial security of the job, but my job was great because of the people I got to work with. I’ve been with the same firm for 7+ years and developed really strong relationships with a lot of my colleagues. It’s just as difficult to walk away from that as it is to walk away from the security of the paycheck. The support of my family and specifically my wife is what has made the decision easier. We’re in a good place in our lives for me to be able to chase this dream and knowing that she not only has supported me but pushed me to make this jump means everything. The other factor that has made it easier has been the support of Anthony Perri, our founder at Fantistics. He’s always been gracious in the opportunities he’s given me at the site and this transition isn’t just about the daily gaming side of things, it’s about continuing my path as a fantasy analyst and allowing that to become a bigger part of my income as well. I’ve worked really hard to put myself in position to have this as an option, but I’m not sure I’d have had the fortitude to make it official without any of the people in my support system. They’ve reassured me when I’ve had my doubts and encouraged me to chase. I couldn’t ask for a better group of people to have surrounded myself with. I’m very lucky.

Have you told your wife or parents yet? How did they react to the news?

My wife is actually the one who pushed the timeline up considerably. At the beginning of the year we had talked about this as a goal and she has always been exceptionally supportive. The initial idea was to get through this full year, continue to do more on the analyst side (such as producing more daily content) and keep setting myself up where I have a combination of stable income (the analyst jobs) with the variable income from gaming. Once we got into baseball season and I started taking on more writing responsibilities and frankly I was taking on way too much. I’ve been working a 45 hour work week with my regular job and probably another 30-40 with the fantasy stuff (content, radio, gaming). I was sleeping 4-5 hours a night and just really worn down. My wife approached me and said it was time. My parents and friends have also been very supportive. It’s truly been overwhelming.

What goals have you set for yourself now that you’re ‘pro’? What do you envision your daily routine being?

I’m still working for the next few months so I’m working on what my daily routine will be once I finally depart the day-job. I have some ideas, but it’s not set in stone. Right now I’m just looking forward to getting a more consistent sleep schedule in my life. As for goals, most of them are process as opposed to results-related. I intend to get better at understanding very specifically where I have my success (what types of games, which sites/sports, etc) and even more tactical in the games I’m playing. I feel like if I control the process the results will follow.


Is there an actual “process” to going pro? Did you have to file any paperwork or form a company? Or is it just a mental commitment you’ve made with yourself?

There’s a mental commitment that is significant and shouldn’t be overlooked. I’m doing all of this with a pretty solid financial background (reserve funds, bankroll, etc) in order to help limit the stress associated with this being a primary source of income. The stable revenue from my analyst work also helps in this area. I also have the benefit of having a wife who is very successful in her industry. In terms of forming a company, I’m in the midst of meeting with my CPA and Attorney to evaluate my options.

What Big Events will you specifically be targeting in 2013? What game-types and which sports will you be playing in the heaviest volume?

I think it’s very likely basketball will continue to be the sport I play in the heaviest volume. In terms of big events, I’ve been dabbling in most of them early in the baseball season with limited success. I think the extra time should allow me to really hone in on a few of the unlimited entry qualifying events. I’ve always admired some of the guys who are so good in those (Naap, Primetime420, Chop, Smizzle, etc – forgive me if I’m missing someone) and always kind of thought “well I don’t have the time to enter a competitive number of entries”. I’m hopeful that will change and I can be more of a presence in those events.

What advice would you give a ‘Grinder’ who is considering going ‘pro’? What are indicators they should look for? What are the negatives they might be overlooking

I think it’s really important to have a good handle on your personal finances before you consider a decision like this. You need to not only have a bankroll to work with but a reserve fund set aside that isn’t considered part of the bankroll. Fortunately I have a background in finance that helps and my wife and I already live a pretty conservative financial lifestyle. That side is the most important in my opinion if you’re going to make this decision. In terms of indicators I actually think a really good test is how you handle extended losing periods. They happen to everyone and I think your ability to manage your bankroll and your emotions during those periods is a really good indicator. Outside of those two things it’s probably the stuff that first comes to mind – how consistent your success is and how many different sports/sites you can have success in.

About the Author

Cameron MacMillan (Cameron)

Cameron MacMillan is an entrepreneur and angel investor, who co-founded RotoGrinders in 2010, alongside Cal Spears and Riley Bryant. Cameron operated as the COO, creating & implementing a multitude of business & content systems for the company over the course of 11 years, before Better Collective completed its acquisition of RG in 2021. In 2022, Cameron stepped back into an Advisory Role.