Sharp or Square - THE FUTURE OF BETTING PART 2: Sports Betting Strategy, AI and Tax Battles
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What is the focus of the second part of the sports betting strategy discussion?
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Welcome to Sharper Square, presented by Hard Rock Bet. We are part of the Volume Podcast Network. This is the show that makes the squares sharper and makes the wise guys pay attention. I am Chad Millman. I am joined, as always, by my co-host, my BFF, my companion, my compadre, professional bettor, Simon Hunter. Hello, Simon! Hello, Chad. My man. Today we have part two of a very special two-part episode exploring the future of betting. For part one, we had on Chris Gerlacher talking about prediction markets. Great conversation, animated conversation. But there's still so much going on. We've talked a lot about AI during this NFL offseason, how it's being used, how you're using it, how bettors are using it.
There's tax issues. because of the big, beautiful bill that punishes betters. I want to start there because I do think that's a big issue for people. Can you just remind people what the issue is and how it punishes betters and then how it's impacting you directly this year in 2026? Because I think a lot of people thought it would go away and it doesn't look like it's going away.
Yeah, let's take it from the perspective of just Joe Schmoe, that you're average, better, right? Goes to the sports book. So he has $2,000 on him. He bets $1,000, loses $1,000, whatever. That, back in the day, our whole lives, you bet $1,000, you're petting the juice. The books, that's how they get you, right, Chad? They tax you on the minus $1.10. So they're taking $0.10 off you, whatever it may be. Now... the way it's changed is you bet that thousand to win and you bet that thousand you lost. Not only are you losing on the VIG, the government now is taking 10% off your losses, which means at the end of the year, If you had bet $1,000 total and you had lost $1,000 and you won $1,000, you'd pay no taxes.
Now, you have to pay 10% of your losses, which, again, I don't think people get how big a deal... That's such a big deal. That's so much money, 10%. And someone like me, an obscene amount of money, I don't think people get how insane it is where... Most professional bettors I know, like I'm not a volume bettor. I know a lot of pros who have models where they'll bet all 16 NFL games.
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Chapters
6 chapters
1
What is the focus of the second part of the sports betting strategy discussion?
0:00–13:54
2
How have recent tax laws affected sports bettors?
13:54–19:35
3
What impact has AI had on betting strategies in the last year?
19:35–26:31
4
What challenges do prediction markets pose to traditional sportsbooks?
26:31–34:04
5
How are professional bettors adapting to changes in the betting landscape?
34:04–40:49
6
What predictions do experts make for the future of sports betting?
40:49–45:02
Speakers
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