Introduction
We constantly make decisions under uncertainty.
From choosing the best route to avoid traffic to skimming through reviews to pick the best restaurant—every day we calculate probabilities and assess risk almost subconsciously.
In Thinking in Bets, former professional poker player Annie Duke explains how to make decisions in environments where information is always incomplete and outcomes are never guaranteed. This mindset—grounded in probabilities rather than emotions—is crucial to navigating a world full of uncertainty. It’s exactly the approach any serious bettor needs, whether they’re using services like WinnerOdds to identify value bets or crafting their own betting strategies.
In this article, we’ll explore four lessons from the aforementioned book that will level up your sports betting results, overcoming common biases and focusing on a long-term strategy.
1. Decisions vs. Outcomes
The first key idea to understand is that good results and good decisions are not synonymous. Annie Duke emphasizes that a good decision (with positive expected value) doesn’t always guarantee an immediate favorable outcome.
This also happens in WinnerOdds. Naturally, if we zoom in on a small selection of bets, any of them can lose—even at very low odds, like 1.08. However, a series of sound decisions over time will inevitably lead to positive results.
As Miguel Figueres often says: “If statistics are in your favor, winning is inevitable”
However, this can lead to another problem: establishing too strong a connection between outcomes and the quality of our decisions can be catastrophic.
For example, when reflecting on certain results, we might fall into cognitive traps like apophenia—assuming a non-existent correlation between two matters—or selecting data that aligns with our preexisting beliefs, known as confirmation bias.
In our field, it’s common to read comments like:
“We’ve had a good streak for weeks, so statistically speaking, we’re due a bad run now…”
“This player had been competing in too many matches back-to-back. He was exhausted, so it was obvious he’d lose today.”
We’re obsessed with devising explanations for everything. But as Annie Duke stresses in her book, not every event has a succinct, direct explanation.
2. Thinking in Probabilities
Have you ever wondered what would happen if we based our Minimum Profitable Odds on a belief or opinion about a player or football team?
You’d likely spot evident patterns and trends in the betting tips.
This explains, for instance, why some bettors favor “longshots”—overstaking on high odds.
It’s easy to get excited about the prospect of a big win, even if the probabilities don’t back it up.
According to a study by Newall and Cortis (Are Sports Bettors Biased toward Longshots, Favorites, or Both?), this bias reveals how personal beliefs can lead bettors to less profitable decisions.
That’s what happens to 99% of tipsters—and trust me on this—in the long run, it’s more problematic than it is beneficial.
In her book, Annie explains how the availability heuristic makes us overestimate the likelihood of events that we can recall, even if they’re rare. A common example is avoiding air travel because of recent plane crashes, despite the data showing that it’s the safest means of transport.
We also fall into the illusion of control. For example, after winning several bets in a row, a tipster might start believing they have a one-of-a-kind skillset, leading them to overstake and underestimate the role of randomness in sports events.
Another common pitfall is the representativeness heuristic: evaluating the likelihood of an event based on existing prototypes instead of considering statistical data. For example, assuming a football team is more likely to win because they’re on a hot streak.
As the book explains, thinking in probabilities means the opposite. It requires basing decisions on data and probabilities rather than opinions or beliefs, which is a challenging task.
In fact, it goes against human nature, as it requires activating critical thinking and rationality.
What sets WinnerOdds apart from human tipsters is that the algorithm is free from biases, doesn’t get discouraged, and doesn’t base decisions on the most recent information it receives.
It views reality through an objective lens, avoiding shortcuts and pitfalls. In just seconds, it analyzes endless data and breaks it down to you in the form of a thousand value bets each month.
3. Patience vs. Quick Earnings
At this point, we know that outcomes and decisions don’t always correlate. You can do everything right and still face unfavorable results—something that’s evident in poker, as we’ve discussed in the past.
That’s why it’s crucial to make probability-based decisions, which align more closely with objectivity. This way of thinking is tightly related to patience, a necessary virtue for achieving consistent results with systems like WinnerOdds.
Annie Duke teaches that discipline and a solid decision-making process are key to long-term success.
In today’s fast-paced world, patience and analysis seem like forgotten virtues. The current mindset is incompatible with paddling through 1,000 bets or understanding the impact of variance. At WinnerOdds, profits don’t come instantly—they require long-term vision, probability-based thinking, and embracing uncertainty as part of the process.
4. Managing Uncertainty
Any time a new user joins WinnerOdds, it’s easy to gauge their sports betting experience based on a few questions.
Most newcomers have used tipsters that output far fewer bets a month. Going from a tipster that releases 300 bets a year to WinnerOdds, which releases around 1,000 value bets a month, is a significant leap.
Imagine compressing a year’s worth of bets into just 30 days. It’s mind-blowing.
While it’s not inherently better or worse, and depends on your personal situation, if your goal is to maximize profits, you have the necessary accounts, a substantial bankroll, and the availability to place the bets, increasing your value betting volume is crucial.
A system that allows you to rotate your bankroll four times a month can grow your profits 4 or 5 times faster than any traditional tipster.
Let’s look at an example
Imagine you’re new to WinnerOdds, and you commit to reaching the 1,000-bet mark to objectively evaluate the service. However, in the first few weeks, you experience poor results stemming from negative variance. At this point, you might wonder:
How likely is it to have such bad results if I’m supposedly placing positive expected value bets?
Well, a few weeks ago, we hosted a livestream (only accessible if you’re subscribed to our newsletter, by the way) where we explained the extent to which variance can impact your betting results.
[Advanced simulation calculator]
Practical Example: Same bets, Same system. Different results?
We simulated the following scenario:
Number of bets: 1,000
Expected yield: 5%
Average odds: 1.80
Subscription cost (4 months): €480
Expected profit (5 times the subscription): €2,400
In the livestream, we generated 1,000 simulations of 1,000 bets each, effectively simulating one million bets in the blink of an eye.
It’s hard to wrap your mind around it. Despite my years of experience, I’m still amazed by the range of different scenarios that can arise from the same configuration. The variability of results—even in a robust sample like 1,000 bets—never ceases to throw me for a loop.
We saw that some graphs even show losses.
Others are flat, and some soar well above the average.
Ultimately, this illustrates the broad range of results our users share daily in our community, and explains why, sometimes, “luck” can heavily influence your performance. As we mentioned earlier, this reinforces the idea that good decisions don’t always guarantee short-term success.
Conclusion
Applying the lessons from Annie Duke’s Thinking in Bets to sports betting can help you grow. While it’s not a book about betting, its teachings are applicable and highly valuable.
By adopting a “betting mindset,” you can better navigate uncertainty, make smarter decisions, and increase your chances of success.
So, I’ll leave you with this quote from the book, which perfectly sums up what inspired me:
“Fewer impulsive emotions, less fear, less anticipated failure. More confidence, more assertiveness, and more long-term success. Become the person who takes the first step—the one who makes the best decisions in any situation.
The next time someone asks you, ‘Wanna bet?’ you can reply, ‘Sure, how much?’”
