Thursday, Sep 29th
Monday, Oct 3rd

Thinking Like a Coach and Investor

In July of 2021, I received an email from a website I had been a subscriber to for three years. That email changed the course of where I was heading personally and professionally. The email in question was from this very website, One Week Season, and it was an update for subscribers about some new things on the site as well as a couple of job openings they had. I responded to the email and sent in a writing sample as well as a history of my DFS successes. Aaron (Rotomaven) and JM responded to me in just a few days and set up a meeting. The initial job posting was to do game breakdowns for the NFL Edge, the OWS flagship product. The meeting went extremely well, and we even jumped into ideas for other content I could provide during the season, such as the option to write one or two training courses for the “Marketplace.” There was a relatively short (under a month) amount of time to put this together, but I was up for the challenge. I will never forget JM’s advice for what I should write about for my courses: “just think about what makes you successful in DFS and write about it.” 

Those words of wisdom led me to write a course breaking down my player pool selection process, as well as a course about what +EV (expected value) means and the things I do to make myself +EV over time. I really enjoyed digging into those areas and putting those courses together for subscribers to read and learn from, as I think both have a lot of lessons that are evergreen. 

After my first year providing DFS content, I started thinking more about what JM had said to me. While I had provided a couple of (in my biased opinion) quality courses that people could learn from in a relatively short period of time, I felt like there was a lot more I could provide. Also, in interactions with the OWS fam in Discord and the fantasy community in general, it became more clear to me that the things I do and the ways I think allow me to have consistent success year over year. 

no one thinks like you do

So, what to do next? Well, that is the story of how this course came to exist. I thought about all of the content I’d seen and heard over the years on DFS theory and how to win. I thought about all of the people (in person, on Discord, on Twitter) who had shared lineups or shared thoughts on what they were doing in DFS. And that’s when it occurred to me that DFS is broken down in so many ways: lineups, roster construction, contest selection, player selection, etc. However, the one thing that people hardly ever talk about just may be the most important: the person playing the game. 

Going back to JM’s comment: “just think about what makes you successful in DFS and write about it.” The greatest strength I have in DFS is who I am and how I think. That may sound arrogant, but the reality is that I have such a unique background and mindset that fits perfectly with DFS, that it allows me to naturally think about and see things that seem obvious to me, but that other people miss:

  • Math and Markets – I have always been a numbers person. In high school, I scored a 34 out of 36 in the Math portion of the ACT. I have a business degree with a major in Finance. In college, I was in a program where students managed an endowment fund for the university and made investments. This part of my life has been wired into me for many years and allows me to take a bigger picture look at the DFS landscape and weigh short and long-term risk/reward decisions. While some of the things in my past can’t just be passed along, there are things I look for and evaluate that just about anyone can use to make themselves a better DFS player.
  • Coaching – I’ve been around sports my entire life and have coached for my entire adult life. I have spent so much time watching and learning about the games and studying coaches that I strive to be like, that I am always acutely aware of the mindset coaches have and the things they are thinking about. 

Having both of those perspectives and strengths is very unique, especially given that many people have experience in one of those areas, but very few have a background in both math/markets and coaching. This makes sense, as most people who have a lot of experience in math/markets are putting those talents to use in other ways that keep them from diving deep into the coaching world. Likewise, most people who fully understand the depths of a head coach’s mindset are coming from a background of playing sports at a high level and/or education, both of which are unlikely to also come with math/market experience. To reference one of Hilow’s favorite terms, these two strengths have very low combinatorial ownership.

This course will dive into each of those areas and specific “ways that I think” that give me an edge. It will break down different perspectives that you can be aware of and consider, while also challenging you to think philosophically about yourself and how you play. I believe this will help you do two things:

  1. Try to think in some of the ways I do, so you also start to see those edges on your own
  2. Be aware of who you are and how you think, and leverage your strengths while minimizing the effects of your weaknesses