Winning At Sports Betting Is Easy... This Is The Hard Part

This week on Circle Back, the crew dives into a heated debate sparked by Alex Monahan’s claim that winning at sports betting is actually easier than most people think—and why the real challenge isn’t winning, but scaling. Plus, we break down a deeply concerning discovery on Polymarket, where a market appears to be designed to exploit users who don’t fully read the house rules, raising serious questions about predatory structures in betting platforms. And finally, we discuss Steve Fezzik stepping away from his pick selling service—for now—and what it could mean for the broader betting ecosystem.



Jacob Gramegna, Rob Pizzola, and Geoff Fienberg are joined by George Tsilfidis to react to the latest stories and controversies from gambling Twitter and beyond. From sharp betting theory to industry drama, the panel gives their unfiltered thoughts on everything shaping the sports betting space right now.



📅 New episodes of Circle Back every Monday at 1pm ET and Friday at 8am ET. Plus, watch for additional content every Wednesday, ranging from interviews with industry experts to instructional videos!



📊 Building in prediction markets? Get your trial API key for unified prediction market and sportsbook data: https://bit.ly/4blx5BR



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SHOW INDEX

0:00 - Circle Back w/ Rob Pizzola, George Tsilfidis, Geoff Fienberg and Jacob Gramegna

16:14 - The weekend of sports

33:29 - Is it easy to win at sports betting?

39:10 - Predatory markets are getting worse

48:20 - Online Twitter beef

1:01:29 - Reading your comments

1:11:50 - Steve Fezzik stops selling picks

1:26:09 - So you think you can tout

1:30:18 - Jeff Benson vs. Sean Perry

1:36:18 - Chopping block



Disclaimer: The content presented in this show is intended for entertainment purposes only. All opinions expressed are those of the hosts and do not necessarily reflect the views or opinions of any individuals or organizations mentioned. Statements made about public figures or entities are based on publicly available information and are not intended to harm or defame any person or business. This show relies on the fair use of social media posts, which are presented in good faith for the purpose of commentary and criticism. Viewers are advised to form their own opinions.



Circles Off podcast is an entertainment podcast. The opinions expressed in the podcast are for the purpose of discussion in the area of sports betting, online gaming and other like markets. Circles Off podcast does not condone unlawful or illegal activity, and if you are unsure of the laws in your jurisdiction surrounding these markets, please seek the appropriate legal advice about strategies that you intend to implement. Please gamble responsibly.
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