The Highs and Low of My Gambling Story

Many of us search for it. The feeling of freedom that having enough money that it does not affect the way you life. “Fuck you money” John Goodman’s character in “The Gambler” describes to Mark Wahlberg. Having enough money to do or not do what you want, to not have to put up with your boss. That kind of money. I always liked the Idea. I don’t want to be rich. I want to be in control of my life. real control. I have always been searching ways to achieve this, most of which went horribly. Finally one day I found something. To say it changed my life feels like a bit of an exaggeration, but I do think it is appropriate.

I don’t remember exactly how it happened, but one day in January 2022 I found an account on Twitter giving out gambling picks, but not in the way you expect. So many people who claim to be gambling experts are exploiting people in some way. I also don’t remember why this one felt different at the time. The account was talking abut expected value or “EV”. For anyone familiar, this might be an eye roll, but I will assume no one knows what this means. The basic strategy was this. Different places to bet have slightly different prices. Figure out which ones are the closest to the true price and then find any other sportsbooks that aren’t priced correctly and bet those. I have always been very risk averse so I found a very basic strategy for sizing my bets. My “bankroll” was 400 dollars to start and most people in this community say you choose a unit size equal to around one percent of your bankroll. Four dollars. I know that sounds small, but it immediately took. I was hooked. By the end of February that year I had made over $600. More than doubled my bankroll. This was It I figured it out.

I should mention that the best this account was giving out were all based on promotions given out by different sites as marketing. 25% boost on a specific sport. Things like that. At the time I had accounts with three different sportsbook. Fanduel, Draftkings , and BetMGM. I took advantage of every single boost and promotion they offered. In March I made over $1600. We were moving. I was averaging around $1100$ per month this year and in July I finally decided to open a new account. I don’t know why I was so scared to expand, This was clearly working, but like I said I was very risk averse. Also keep in mind my take home pay at this point was probably less that $3000 per month so I had basically given myself a 33% raise. This was a lot of responsibility. The new account I opened was with BetRivers. The promos there were great. $250 turned into over $2000 by the end of the year. The rate of growth was unbelievable to me. Honestly it could have been much faster but the mentality of getting comfortable with betting $50 on a bet when that same year you were betting $4 was difficult. Regardless this was an incredible success. I couldn’t believe I finally found something that worked for me. The end of year one of this journey I had made over $13000.

These promotions were treating me very well, but they do have maximum bet sizes. I scaled my operation so that the math was telling me to bet more than I was allowed. At this point I started looking for other opportunities to find good bets. I now had the proof it was possible. I just had to find it. I started trying out different people selling picks. Some I found were good, others absolutely were not. Having an edge on typical bets is usually not nearly as large as the promotions I have been talking about so far. Having a 3% edge on normal, non boosted bets is an awesome return. I know it might not sound like it, but compounding that thousands of times is how the greatest gamblers do this for a living. Getting used to that compared to my 25% or more boosts was difficult. Truly realizing a 3% edge can also take hundreds if not thousands of bets. It is a real mental exercise.

This first chart shows 50 random bettors if every single one only bet an edge of 3% at -110 odds. That is a great process and as you can see even after 1000 bets many of them will still be negative.

This chart shows 50 more bettors betting with a 25% edge. I made the odds a bit longer because usually these boosts and promos require longer odds to make it more difficult to take advantage. Still every single bettor is positive and 49 are after only 200 bets. Much smoother.

January 2023 I learned a new lesson. I wanted to expand my list of accounts. More books, more promos, more profit. I opened an account at Pointsbet (now Fanatics in the U.S.) I deposited 400 dollars in January. I believe the signup bonus was bet 4 100 dollar bets, get 4 100 dollar free bets. Keep in mind 100 dollars per bet was still pretty nerve wracking for me at this time. I also happened to catch a string of bad luck on these. I lost 7 of the 8 bets. Even worse, I then experienced what gamblers call being “limited”. even though I lost most of my bets. I bet them at very advantageous prices. This can set of internal reviews at books. They will then limit the max amount you can bet on any one wager. I was livid. I had heard about these but never thought they would happen to me. It happened so fast. I never did get my 400 dollars back from Pointsbet. Regardless things kept moving along. I began hearing about different types of sites trying different business models. Fliff is a social sportsbook that tries to use laws of lottery instead of sportbooks. It’sa a grey area in the law, while Kutt is a book that did not take the bets. You can submit you own wager of any kind for any other user on the site to accept. I wanted to keep expanding trying new things. My thought was keep expanding for more opporunities and more diversification. In April I hit my new monthly high. $3525. I couldn’t believe it. This was more than my work paychecks for the month. I was flying high.

July and August were always the most frustrating months for me. Less sports going on at that time means less bets means each ones feels more important. August 2023 was my first losing month of my gambling story. Only -$100. I know it sounds silly, but I was crushed. I was having a lot of fun placing and tracking these bets but it really stings putting all of this time in and having nothing to show for it after the month. It also makes you doubt that whatever magic was working for you is still there. Trusting the system even after 17 months is still hard.

The end of this year was a rollercoaster. My most profitable month came on November when I made over $4000 followed by my largest loss of -$850 in December. By this point I had 10 accounts in total It was a wild ride but my final total of 2023 was a little over $17000.

January 2024 was even worse losing over $1200. I think at this point was one of my lowest confidence levels throughout the whole experience. They say don’t keep any money you will use in your life in your bankroll, but I did not follow that rule. Such a large chunk of my income was coming from gambling at this point I was spoiled and was not worried I would ever lose anything important. But around this time My now fiance and I were shopping for a house. As much as I hoped thing would turn around before the money was due, they did not. I pulled out $10000 to use towards the down payment on our new house. I am so happy this hobby gave me the opportunity to do this. Taking this out, on top of my January losses slowed my progress. It might have come at good time though. I was trying too many different Ideas, instead of focusing on what worked. I slowly built my confidence and bankroll back up through the year. In August I decided to start tracking every bet I placed instead of just account balances. i knew it would be tedious, but the information I could from the data would be worth it. December came around this year and i hit my new monthly high, $6000. Total for the year was $23000.

My first two months of 2025 I thought I finally figured it out. Draftkings started giving me larger and larger promotions so I tried to push myself to take full advantage of them even though they made me uncomfortable. $100 limits on pretty large parlays, then $250 limits. I’m not sure if this was smart, lucky or a mixture of both, but I hit multiple bets that paid over $3000. I thought I had finally made it. I was ready to quit my job. At some point in February, someone from Draftkings reached out to me and asked if I’d like to try out the DK VIP program. I had heard if you can get into VIP programs you can really take advantage so I jumped at the offer. I forget exactly what the offer was, but I had to bet certain amounts for free bets, so I took advantage of them as aggressively as I could. This is my biggest mistake in my journey. Shortly after, I realized I started trying to put in bets and they were getting declined with smaller and smaller limits until finally I couldn’t bet more than a few dollars on them. I think responding to this email put a spotlight on my account that I wish I could take back. I also received limits from other sportsbooks around the same time. I assume it was a coincidence but it made it hurt even more. I had one more than $23000 in just January and February, but by the end of February the limits were in full effect. For the rest of the year I flopped around trying to find my way to adapt and remain profitable, but I never really did. I only made about $1000 dollars the rest of the year. I even took some time off through the summer because the losing was really getting to me.

Now in 2026 a new hurdle has put a total halt to my gambling. Every year until now I have paid my taxes on these winning, but this year an awful law was put into place. Only %90 percent of your losing bets can counteract your winning bets. So hypothetically, if you won 100k and lost 100k you would owe taxes on $10000 even though you did not actually make any money. It is insanity. I have not placed a bet since December 31st 2025.

I still have hope this law will be fixed, and hopefully some normal order will prevail, but I have not been able to find any path forward with the current structure. It is incredibly disappointing, but I hope one day to return. Hopefully you found some of my story interesting and if you have any question or advice, leave them in the comments.