Meet The Team: A Q&A With Huddle’s VP of Trading, Drew Gearsbeck

In this "Meet the Team" Q&A, we dive into the journey and insights of Drew Gearsbeck, our newly appointed VP of Trading. From his early days transitioning from a career in education to making a bold move to Las Vegas, to his rise through the ranks in the sports betting industry, Drew shares his passion for combining math and sports, the challenges and opportunities that come with his new role, and what drives his continuous enthusiasm for the work he does every day. Get to know the strategic mind behind our trading team and the vision that guides Huddle's success.

Can you tell us about your early days in the sports betting industry? What initially drew you to this field?
My journey into the sports betting industry began after spending nearly five years as a teacher, athletic director, and coach in northern New York state. While I loved working in education, I found myself yearning for a new challenge—something that would allow me to combine my passions for both math and sports in a more dynamic environment. That desire led me to make a bold decision: I packed up and moved across the country to Las Vegas, the heart of the sports betting world.

Once in Las Vegas, I landed a position as a trader at Deck Prism Sports. This role was transformative, offering me the opportunity to immerse myself in the world of sports betting while learning from some of the best in the industry. The experience was invaluable, not just for the technical skills I acquired, but also for the insights and mentorship that shaped my understanding of the industry. Looking back, I know that this experience was pivotal in shaping both my career and the person I've become. It set the foundation for everything I've accomplished since and fueled my passion for this ever-evolving field.

Congratulations on your recent promotion to VP! Can you share how this new role differs from your previous responsibilities, and what strategic vision you have for the trading team at Huddle?
Thank you! I'm excited about the new role and the opportunities it brings. The biggest shift for me will be moving away from the day-to-day trading activities that I've been deeply involved in over the past few years. Instead, my focus will be on leading and managing the trading team, providing guidance and training, and engaging more with other departments and clients through meetings and collaborations.

In terms of strategic vision for the trading team at Huddle, I don't anticipate any major changes. We've built a strong foundation with a core group of traders who have been working together for the past 2-3 years, and that continuity is something I value greatly. We'll continue to rely heavily on our established projections process, which has served us well. However, as we grow and evolve, it's also crucial that we remain adaptable and responsive to our clients' needs and expectations. My goal is to strike the right balance between maintaining the standards of our trading processes while also being flexible enough to meet the unique demands of our clients. By doing so, I believe we can continue to deliver exceptional results and drive the success of the team and the company as a whole.

What are some of the biggest challenges you foresee in the current trading landscape, and how is Huddle positioning itself to overcome them?
I think the obvious answer is the increased need for providers who can offer player props, micros, and same game parlays. A lot of bettors want to focus on individual players that they know as opposed to betting on the full game. We’ve seen a trend towards instant gratification when it comes to technology in general. Micro markets give you an option to bet on what will be the outcome of the next pitch, or which team will score next. You can find out the result of your bet in a matter of seconds instead of waiting a few hours for the full game to conclude. Huddle has been focused on this for the past few years and has built a product that can create, price, and settle these markets in real time. I’m excited to see what the future holds.

What qualities do you believe are essential for building a successful trading team?
I believe anyone is capable of becoming a successful trader if you have a basic understanding of probabilities and a deep knowledge of the sports you are trading. We work with very complex models and you must have an understanding of what goes into the model, what is not included in the model, and how to make the necessary adjustments in order to get the best price.
Communication, trust, attention to detail, accountability, and confidence are some qualities that come to mind for our team. I think an important thing is leaving your ego at the door and being open minded. We learn new things every day from each other in the trading room and it's key to our growth and success. Attention to detail is everything when it comes to trading. If our pricing is consistently off by 1-2% it can be the difference between winning and losing long term. Also, it’s on myself and other leaders to make sure we are putting everyone in a position to succeed. You’ll be more productive if you get to work on something you are passionate about and your confidence will allow you to shine if you are trusted to do your job.

Lastly, what do you enjoy most about your role as VP of Trading? What keeps you motivated and passionate about your work every day?

What I enjoy most about my role as VP of Trading is the constant opportunity for learning and growth. Every day presents new challenges and insights, and I get to immerse myself in the world of sports while working with numbers—two things I'm deeply passionate about. It's incredibly rewarding to be able to combine these interests into a career that keeps me engaged and excited.

But above all, what truly motivates me is the people I work with. I’m fortunate to be surrounded by a talented, dynamic team that makes every day interesting and energizing. There’s a unique camaraderie in our office, and no two days are ever the same

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