I Was a Losing Bettor for Years... Then I Figured This Out | Presented by Kalshi

2025-11-12

 

 

Welcome to a transformative journey into the world of sports betting! If you're ready to elevate your betting strategy and achieve long-term profitability, this podcast episode is your guide. With insights drawn from personal experience, this episode is a masterclass on how to turn sports betting from a game of luck into a calculated market endeavor.

 

From Losing Streaks to Sustained Success

 

We begin with a story familiar to many bettors: the early days of losses driven by gut instincts and fandom. Like many, I believed my deep knowledge of sports, particularly the Toronto Raptors, would naturally translate into betting success. But, as many have discovered, fandom can cloud judgment. Tracking over 5,000 bets with Betstamp revealed the hard truth—success in betting is about market understanding, not team loyalty. The shift to viewing sports betting as a market, where price sensitivity and odds matter more than the game itself, marked the beginning of a profitable journey.

 

Embracing Logic and Patience

 

In sports betting, emotion is often the enemy of logic. This episode emphasizes the critical mindset shift required to see betting as a mathematical endeavor rather than a game of picking winners. By eliminating biases and focusing on the math behind bets, we can aim for long-term profitability. Patience and perseverance are essential, especially when facing the natural ebb and flow of variance. Tracking every bet, understanding market movements, and maintaining confidence in a solid strategy are the pillars of sustained success.

 

Mastering the Basics: Math Over Emotion

 

Understanding that betting is a math problem, not a prediction game, is liberating. It removes the emotional baggage and focuses on identifying when the market is wrong. This episode discusses how sportsbooks use information to refine odds and how adopting a top-down strategy to identify market inefficiencies can lead to success. Whether you're betting on a beloved team or a sport you know little about, the process must be the same: focus on prices, not teams, and bet only when you have a real edge.

 

Continuous Learning and Adaptation

 

In the ever-evolving world of sports betting, continuous learning is crucial. The episode highlights the importance of adaptation and curiosity in keeping pace with changing markets. Successful bettors never stop seeking to understand why something works. This mindset, coupled with diligent tracking and analysis, can turn losses into gains and transform betting into a strategic pursuit.

 

Conclusion: Building a Foundation for Success

 

This episode provides a blueprint for turning from a losing bettor to a winning one. It emphasizes the importance of tracking, understanding markets, eliminating biases, and focusing on the process rather than results. Resources like the Circles Off channel offer valuable insights for beginners and experienced bettors alike. Remember, the goal is not to chase immediate wins but to build a foundation for long-term success. Engage with our content, share your thoughts, and continue learning. Your journey to becoming a successful sports bettor starts here.

 

Tune in, take notes, and transform your sports betting strategy today!

 

 

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Episode Transcript

00:00 - Jacob Gramenga (Host)
When I started betting, I was the definition of a losing bettor. I thought I had an edge because I followed the Toronto Raptors closer than anyone else I knew. I tracked lineups, rotations and even went as far as to look at which rest disliked them the most, but none of it mattered. I was still a losing bettor. Fast forward a few years and over 5,000 bets later, tracked and verified on Betstamp, I'm showing a 2% ROI and nearly 2% CLV. I'm a profitable bettor and I understand why. So in this video, I'm going to break it down for you how I went from the guy who was chasing parlays to now the guy who's winning long term. I'm going to give you the habits, the mindset shifts and the lessons I learned along the way to make the difference. And hey, before we jump in, if you actually want to get information that's going to make you a better sports bettor, not just somewhere where you're just going to tailpicks, then this is the channel for you. Make sure you do subscribe for more content, just like this, and also make sure you've hit the like button if you find out something new along the way. 

01:13
When I first started betting, I thought that I could beat the book simply because I knew sports. It was your classic example of learning about sports betting thinking well, I know sports really well. I watch every toronto raptors game. I watch every english premier league game. I know a lot about sports. Naturally I should be able to beat the sports book. I used to just pick teams based on who I thought was going to win the game. There wasn't a lot of thought, or nearly enough thought, that went into actual price sensitivity. There was no process. There was no tracking of bets. There was no line shopping to try and get the best price. Oftentimes I'd be chasing parlays. Every Sunday I'd throw down an NFL parlay. None of this was working and I was struggling to understand why. I got a few big wins then I would feel smart, but then I would lose it all again. In the end I just blamed it on luck and didn't actually put the onus on myself to be better as a sports better, because I just didn't understand how to do that. It took me a long time to realize that just being passionate about sports doesn't automatically make you good at sports betting, and oftentimes it can actually make you worse. You start thinking that fandom is knowledge, but in sports betting, emotion can be the enemy of logic. If you've ever been at that stage where you feel like this team can't possibly lose again, or you think maybe there's no way this team can beat this team, well, that was me. I was in the same position. But then that's when it all started to turn around. 

02:34
The real turning point for me was when I started working at BetStamp. Initially, I wasn't tracking any of my wagers, but when I started to track and I started to see the analysis behind my wagers, that's when the gears started to turn. When you actually log every play, there is nowhere to hide. You can't cherry pick your winners. You see the results for what they are. You can't just remember the heaters, because those losers are still going to be very prominent within that tracking. 

03:01
My first few months of tracking were truly humbling. I realized that I was taking bad numbers constantly. I thought I would be making a really good wager and then the number would move against me at post. But seeing that data is what flipped the switch. I started caring less about who I was betting on and cared more about what price I got on that wager. That is the shift that changed everything. It's when I started to process sports betting as a market and math, rather than just knowing sports and picking winners. Now, 5,000 bets later, where I'm doing my verified tracking on Betstamp, I'm showing 2% ROI, 1.9% CLV and I'm up over 116 units. And even behind the scenes, for stuff that isn't verified, my numbers are even greater. It's not because it became some genius better. It's because I just started to understand how markets work and you kind of realize that it's way easier than you think. This is where the next chapter starts. It's about understanding why bets win and lose, not whether they do that. First real aha moment for me was when I started to understand how sports betting markets actually work. 

04:06
Most bettors think that they're placing a prediction against a sports book. It's a me versus a sports book type of dynamic. But the more you learn about the industry, the more you understand that that is not the case at all. A sports book isn't trying to beat you with better predictions, nor are they necessarily trying to balance action 50-50 on each side. They're trying to gather information, and the more information they have, the sharper they can make their number. This information comes throughout the week as we learn more about the event that we're wagering on. But sportsbooks also gather information based on the people that are wagering on the event. Specifically, when sharp people are wagering on events, they take note and shift prices in whichever direction. As a result, they take all of this sharp, betters, respected accounts, syndicates, injury news and even a little bit of their own internal model. All of this is put together to shape the line to where it is. It's not a you versus sportsbook. Once again. All the sports we're just trying to do is figure out what the true price of the event should be, and you need to start trying to figure it out before they get there. 

05:06
Once I learned that, I started to understand why lines move and what those line movements actually represent. That's when top-down betting really started to click. For me, it's not about handicapping each individual game from scratch. It's about being able to identify when the market was wrong, even temporarily. If sharper books were moving in one direction and other books weren't as quick to catch up, that presented itself an opportunity. Not because I suddenly knew who would win. It was because I was placing a wager at odds that were better than what should have been the actual price for the game. 

05:38
Now, top-down betting isn't for everyone. For a lot of people, it takes a lot of the excitement out of the equation A lot of people. It takes a lot of the excitement out of the equation. A lot of people want to feel rewarded with being able to model or handicap a game and be able to make their own prices to beat the sports book. And sure there was a lot to that. 

05:53
But even along in this process, still understanding the market movements and understanding closing line value are significant to anybody who wants to get into sports betting and be successful at it. It teaches you to recognize which information matters, which information doesn't, and what you can do with it. That's when I started to understand that sports betting isn't about being right. It's about identifying when the price is wrong. That's a math problem, not a prediction, not thinking who's going to win this game. As I started to view sports betting as a math problem, things really started to pick up steam. 

06:26
Most people bet based on predictions. They predict who is going to win this game. They predict who's due, who's hot. But every bet you make has a price. That price has a probability and you're betting on something that happens less often than the odds would suggest. Well, that's going to make you a losing better long-term, no matter how much you know about the sport. You could win that bet today and you could reaffirm your position that I know sports really well and I can beat sports betting. 

06:49
But it's not about the one day approach. It's about long term profit. That is what we should all be after. That is the goal of every sports better to find long term, sustainable profit. The goal is not to be right more often than you're wrong. The goal is to get a better price than the true odds of the event. If you can do that consistently, it is going to show up in your results almost guaranteed. Even if it doesn't quite show up right away, we're in this game for the long term. 

07:15
Once again, every market has the math already baked into it. It is your job as a sports better to find the mistakes in that math. And this is the part that people just don't realize. Even you right now might be watching this video, maybe having some doubts over what I'm saying right now, but trust me, while I'm here, sports books are trying to fool the masses into thinking that sports betting is about intuition, having that hunch, having that gut feeling. But it's not. They want you to focus on who's playing, who's clutch, who's hot, who has to win. But in reality, all of that is already baked into the line that they are setting you knowing who's been hot, who's been on a good run, who's cold, who's been on a bad run. You think the sportsbook doesn't already know that themselves. 

07:58
Accepting that sports betting is just a giant math problem made the game a whole lot simpler. The noise started to fade away, I stopped worrying about being right and I actually started focusing on being profitable. It was extremely liberating to be able to take the emotional side out of sports betting. Sure, I want my wagers to win, but at the end of the day, if I place a wager at a good price, I know that as a sports bettor, I have done my job job and the results are going to take care of themselves in the long run, even if in the short term there may be some ups and downs. That was a real big lesson for me, removing the personal bias. 

08:31
When I first started betting, I thought my deep knowledge of certain teams gave me an edge. I'm a massive Toronto Raptors fan. I'm a massive Manchester United fans. I knew all the players. I knew all the coaching tendencies. I knew all of the rotations, advanced stats, everything, all of it. But that level of fandom actually worked against me early on. I justified bets because I wanted them to be right and I was looking for confirmation bias. I was looking for statistics that supported the opinion that I wanted it to be right and I used that as justification in order to make my wagers. But this was the wrong approach from the jump One of the hardest things to realize that you can be biased without even knowing it. 

09:10
And I felt like in the early stages and I was learning to eliminate these biases I had that was better to bet on sports that I didn't know much about, because those biases weren't present, therefore couldn't exist in my betting. Sure, it took time and it took a lot of losing bets to understand. The market doesn't care who I like or what I think. I know. The number already reflects everything that is publicly available, like the statistics I was diving into, like a player being injured. They know the significance of those statistics, they know the significance of this player not being available to play and they probably know it a lot better than I do. So if I'm betting on something I believe, then I better believe that the sportsbook doesn't know it as well, or else I am not betting with an edge. 

09:50
Now I treat every bet the same, whether it's the Toronto Raptors, who I love, or the Boston Celtics, who I hate, or two random teams I never watch. The process has to be identical. You're not betting teams, you are betting prices, and anyone who tells you otherwise, I can virtually guarantee, is not presenting any verified tracking to showcase that they are a winning better. That mindset is huge. Once you start to take the emotion out of things, you start to see the game differently. The goal isn't to prove yourself right. The goal is to make money, and oftentimes you can eliminate your own biases completely, even by maybe even betting on a sport you do not know anything about. If you know how to exploit markets well enough, you don't need to know anything about the sport to be profitable. 

10:33
Another tough lesson I had to learn was that results don't always tell the story Process does. When I was new to betting, I judged everything pretty much based on whether a bet won or lost, or by watching the game. How did the team perform? Did they deserve to win? Did the bet deserve to win? If I lost three in a row, I would question my entire approach. If I won a few, I'd think I was on to something genius. But variance is brutal in this game and it's something that even today, I can sometimes struggle with. But if your process is, you're consistently beating the closing line, you know that your money is going in the right place. 10 bad bets in a row can win and 10 good bets in a row can lose in a large enough sample size. That's why tracking helps more than anything. 

11:15
From the moment I joined BetStamp, I started logging every pick, every price, every result. Over time, patterns started to show up. My closing line value was consistently positive. This means that I was beating the market. Even when that win-loss record went through some tough stretches, I was confident in my wagers. That's where you learn another big lesson in sports betting, which is patience and winning long-term. The goal is not to be right tonight, it's about being right over the course of a season or, better yet, over the course of many years. 

11:41
That shift in mindset completely changed how I bet. I stopped chasing losses, stopped forcing action and started waiting for real edges. Now I know that if I keep making good bets, the math will take care of itself, even if there's a bad run of variance. I know that my money is going in the right place. I can trust my process and trust that I know that I'm making winning wagers over a long-term sample size. Now we've arrived at the final lesson, and one that ties over everything. As much as I know about sports betting, I know that there is so much that I don't know about sports betting, and it's important to keep learning. 

12:18
Working with Rob taught me that betting is constant adaptation. Edges disappear, markets evolve and if you stay stagnant, you fall behind fast. You don't have to know everything, you just have to be curious enough to keep improving. Every bettor I know who's made it, whether it be through intuition or top-down betting or by making a model, they all have one thing in common they never stop trying to understand why something works. That's what separates the people who just bet and the people who get better. 

12:46
So, to wrap it up, here is what changed for me. I started tracking everything. I learned how markets actually work. I accepted that betting is math, not logic. I removed biases and stopped betting as a fan. I focused on process instead of results and I learned to stay patient. That's why I went from a losing better to a winning better. 

13:04
There's not some magic secret system out there that's automatically going to do it for you. You have to put in the work and gather the information necessary that is going to make those changes for you, and the resources are out there. Some of it's even right here on this channel. I can attribute a lot of my success and growth in the early stages to stuff I learned for free right here on Circles Off, and that's not me saying that. The proof is clearly there with my tracking. 

13:28
If you're early on in your betting journey, don't chase wins, chase understanding. And while you're chasing that understanding, learn from your mistakes. Bet amounts that you're able to lose, and as you learn and as you start to win, you can scale up and win more. Track your results, learn the math and think about prices, not picks. That's the real foundation for becoming a long term winner. If you enjoyed this, and especially if you learned something new from the video today, make sure you hit that like button and you're subscribed to the Circles Off channel. Drop a comment down below about what lesson helped you the most and what you're looking to learn next. 

 





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