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- Issue #42
Sports Betting: May 5 - 11, 2025
In Issue #42:
Weekly Betting Recap
Last Week: 2-1 | +1.36u
Ronel Blanco Under 5.5 Strikeouts (-105) ❌ / UNDERground Lab
Cincinnati Reds -1.5 (+162) ✅ / Locksmith
Florida Panthers Moneyline (-135) ✅ / Peak Picks
2025 Record: 27-26 | +2.68u
No bets this week…
Taking a break from bets this week—curious how that lands with you.Your feedback shapes what we do next. |
Think Like A (Winning) Bettor
When the Seahawks opted for a pass from the one-yard line with 26 seconds left in Super Bowl XLIX, most saw only the interception—and judged the choice as madness.
Many argued that running the ball, especially with a strong running back like Marshawn Lynch, would have been the more logical choice.
What if Pete Carroll had chosen to run the ball with Lynch and they didn't make it? Would people then say, "He shouldn't have done that; running up the middle was too obvious!"
The point is this: Focusing solely on outcomes obscures the quality of decision-making.
The best decision-makers understand that outcomes involve both skill and luck—good processes can lead to bad outcomes, and poor processes sometimes yield favorable results.
So how do you start thinking like a (great) bettor?
4 Must-Reads to Elevate Your Betting IQ
Also available in audio form for the non-readers out there (Linked at end of each section).
While you won't find explicit sports betting tactics here, these books deliver something more valuable: decision-making principles that create lasting edges.
Pick up just one, and you'll see immediate improvements in your betting approach, regardless of your experience level.
"Thinking in Bets" by Annie Duke
Annie Duke is a former World Series of Poker champion, and uses real-world examples from business, sports, politics, and poker to teach others how to make smarter decisions - even when you don’t have all the facts.
This one is all about treating uncertainty like an ally rather than running from it - A true "masterclass" in probabilistic thinking.
Why is this one first on the list?
Extremely easy to digest & understand
Whether you bet $5 vs $500 per wager, or 10 vs 100 bets per day, this book applies.
No one has ever made a decision with 100% of the facts. Learn how to embrace this way of thinking.
"Improving decision quality is about increasing our chances of good outcomes, not guaranteeing them."
"Gambler: Secrets from a Life at Risk" by Billy Walters
A raw, insanely powerful blueprint from Billy Walters - Quite possibly one of the greatest sports bettors ever.
His memoir details his billion-dollar bookmaking operation, advanced betting concepts he used in his career, and everything else from the highest highs to the rock bottoms he faced in life.
Why you should read it:
Unprecedented access to the methodology of a genuine betting savant
Follow his evolution from small-time Kentucky hustler to betting syndicate kingpin
Reveals the psychological discipline required to withstand massive swings of fortune
"There are a very small number of gamblers who gain an edge by specializing in one sport and betting as soon as the line comes out. Those guys make a living, but not what I would consider serious money. Most of them last fewer than five years."
Originals by Adam Grant
This book has zero (0!) mention of sports betting - And yet here it is on this list.
Why?
Because Adam Grant gets to the heart of how true innovators think and operate, precisely what separates winning bettors from the public.
While everyone else follows the herd, "Originals" provides the blueprint for developing genuine contrarian thinking.
Why you should read it:
Provides frameworks for recognizing value others miss
Shows how calculated risk-taking differs from recklessness
Without explicitly mentioning it, the parallels to successful betting are unmistakable
"Progress always involves risk. You can’t steal second and keep one foot on first base."
"Superforecasting" by Philip E. Tetlock and Dan Gardner
If you want to know what separates the elite 2% of forecasters from everyone else, this is for you.
Based on Tetlock's groundbreaking Good Judgment Project, this book doesn’t just theorize about prediction - it reveals how anyone can approach prediction as a skill that can be developed rather than an innate talent.
Why bettors should read it:
Exposes the thinking patterns of world-class predictors ("superforecasters")
Teaches how to break down complex predictions into trackable components
Shows when and how to avoid the psychological traps that destroy most people’s predictive accuracy
After reading this, you’ll never make another prediction—or place another bet—the same way again.
"Knowing what we don’t know is better than thinking we know what we don't."
The Bottom Line
These books won't tell you which teams to bet on this weekend, but they'll transform how you approach every betting decision you make.
The principles in these pages have helped build fortunes in poker rooms, trading floors, and sportsbooks worldwide.
Your edge in betting doesn't come from more information - it comes from processing that information better than everyone else.
This Week In Sports Betting
NBA Conference Semifinals: May 4-20
Tonight: Knicks @ Celtics (7pm ET) / Nuggets @ Thunder (9:30pm)
NHL Playoffs 2nd Round: May 5-20
Tonight: Panthers @ Maple Leafs (8:00pm ET)
Week 6 MLB (view MLB schedule this week)
PGA Tour: Truist Championship May 8-11 (Formerly Wells Fargo)
WNBA Preseason started 3 days ago, and lasts until Sunday, May 11th
Regular Season tipoff: Friday, May 16th
UEFA Champions League Semi-Finals: Tuesday & Wednesday
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