Circles Off Episode 157 - Why Betting on Sports Is Better than Investing in the Stock Market



Mastering the Game: Chris Dierkes on Poker, Sports Betting, and Strategic Insights


Unlocking Winning Strategies with Chris Dierkes

In the latest episode of the Circles Off podcast, we dive deep into the intricate world of poker and sports betting with Chris Dierkes, a proficient player and software engineer hailing from New York City. Chris's journey from battling addiction in the realm of RuneScape to mastering online poker and transitioning to sports betting is nothing short of inspiring. This episode is a treasure trove of strategic insights, personal anecdotes, and practical advice for anyone looking to enhance their betting game.


From Addiction to Mastery

Chris Dierkes's gambling journey began with a family deeply rooted in gambling culture and a personal addiction to in-game gambling in the video game RuneScape. His initial foray into online poker was fraught with losses, but through rigorous study and perseverance, he transformed into a winning player. This narrative of transformation sets the stage for the episode, highlighting the importance of resilience and continuous learning in the world of gambling.


Transitioning from Poker to Sports Betting

The transition from poker to sports betting is a significant theme in Chris's story. He elaborates on the distinct strategies that set these two domains apart, particularly emphasizing the importance of leveraging data-driven tools like Odds Jam and Pinnacle. Chris shares practical advice on finding valuable bets, the challenges of online poker, and the strategic overlaps between poker and sports betting. His insights into the art of finding soft games and the nuances of online versus in-person poker are particularly enlightening.


Benefits and Strategies for Betting Futures

Chris delves into the strategic value and considerations of betting on futures in sports betting, a concept & argument that Johnny has taken the other side of many times in the past. He discusses the potential for significant returns by masking your bets, old edges ranging from 10% to 15%, and offers a unique perspective on the tax benefits of futures bets. This chapter also explores the practical challenges of tying up bankrolls for extended periods and the impact on account perception and longevity.


Betting Strategies and Account Survival

Account management is a crucial aspect of successful sports betting, and Chris shares various anecdotes and strategies related to this topic. From exploiting mistakes by sportsbooks to understanding the pay per head (PPH) system, Chris provides a wealth of knowledge on maintaining the longevity of betting accounts. His role as a head trader in managing accounts and ensuring their survival is particularly insightful for those looking to sustain their betting activities over the long term.


Profiling Sports Bettors

The episode also explores strategies for avoiding being flagged by bookmakers. Chris emphasizes the importance of appearing as a recreational bettor in the initial weeks and suggests tactics such as betting on local teams and leveraging the bets of non-successful gambler friends. This chapter highlights the necessity of consistent sharp betting once profiled and the challenges sportsbooks face in identifying sharp bets among a flood of incoming wagers.


Professional Reflections on Gambling and Investing

Chris reflects on his professional journey, discussing his transition from betting for the love of sports to focusing primarily on maximizing profits. He shares his perspective on the differences between beating the stock market and sports betting, humorously noting that while some people believe they can predict stock prices, sports betting remains the easier arena to master.


Old Edge Revival in Sports Betting

The concept of leveraging old betting edges in new ways is explored in this chapter. Chris shares a unique NASCAR betting strategy involving correlated parlays and encourages the community to contribute their own past edges to spark new ideas and collaborative gains.


Tipping Etiquette and Life Advice

The episode wraps up with some humorous and practical life advice from Chris. From a bold prediction about Yannick Sinner winning the French Open to practical dining tips and a discussion on tipping etiquette, this chapter offers a lighthearted end to a rich and informative episode.



This episode of Circles Off with Chris Dierkes is a must-listen for anyone interested in poker, sports betting, and the strategic insights that can transform gambling habits. Chris's journey from addiction to mastery, combined with his practical advice and personal anecdotes, offers a comprehensive guide to enhancing your betting game. Tune in to unlock the secrets of sharp sports betting and poker playing, and walk away with actionable strategies to elevate your own gambling endeavors. You can follow Chris on Twitter / X at


About the Circles Off Podcast

To support Circles Off, please feel free to look at signing up for new sportsbook accounts using their custom links & offers, which can be found by clicking HERE 


To bet at Pinnacle, the world’s Sharpest Sportsbook, create your account by clicking HERE or clicking the banner below, and use promo code HAMMER to support the show!


To be notified when more Circles Off Content comes out, be sure to hit subscribe on the platform that you listen to & watch on: 


To follow more updates from the guys, you can find them on socials at the following accounts: 


To find more Circles Off Podcast content, and for a completely indexed list of episodes & themes covered, CLICK HERE for our Ultimate Guide to the Circles Off Podcast and find more episodes that could be a fit for you!

All Sportsbooks

Current LocationVirginia

Recent Stories

Loading recent stories

Betstamp FAQ's

How does Betstamp work?
Betstamp is a sports betting tool designed to help bettors increase their profits and manage their process. Betstamp provides real-time bet tracking, bet analysis, odds comparison, and the ability to follow your friends or favourite handicappers!
Can I leverage Betstamp as an app to track bets or a bet tracker?
You can easily track your bets on Betstamp by selecting the bet and entering in an amount, just as if you were on an actual sportsbook! You can then use the analysis tool to figure out exactly what types of bets you’re making/losing money on so that you can maximize future profits.
Can Betstamp help me track Closing Line Value (CLV) when betting?
Betstamp will track CLV for every single main market bet that you track within the app against the odds of the sportsbook you tracked the bet at, as well as the sportsbook that had the best odds when the line closed. You can learn more about Closing Line Value and what it is by clicking HERE
Is Betstamp a Live Odds App?
Betstamp provides the ability to compare live odds for every league that is supported on the site, which includes: NFL, NBA, MLB, NHL, UFC, Bellator, ATP, WTA, WNBA, CFL, NCAAF, NCAAB, PGA, LIV, SERA, BUND, MLS, UCL, EPL, LIG1, & LIGA.
See More FAQs

For more specific questions, email us at [email protected]

Contact Us