This is episode 4 of the Gambling Still Sucks podcast. In this episode, I’ll be sharing how I went from being someone who absolutely hated gambling to becoming a compulsive gambler myself.
Hey there, and welcome to the Gambling Still Sucks podcast. I am Jamie. I’m a compulsive gambler, and I’m also the host of this show. The last day I gambled was July 15th of 2010.
In the last episode, I shared my story about running off the riverboat—the last day that I gambled. That was July 15th, 2010, which I like to call the riverboat episode. In this episode, I wanted to give you the backstory. We started with the last day I gambled, but how did I get to that point? Especially considering my background—growing up, I absolutely hated gambling. How did I make that transition?
Let’s start way back at the beginning. I remember the very first time I walked into a casino. It was in Atlantic City. I was there for a golf tournament with my mom, and we were just doing touristy things. We had a day to spend, so we were walking around Atlantic City, and we went into one of the casinos. I remember looking around and thinking, “Wow, this is really sort of cool.” It was one of those things where, because it was restricted, it made it more appealing. I wasn’t old enough to gamble, but the idea of it was exciting.
My mom is not a gambler at all. She’s the original couponer—before there ever was couponing, that was her. So the thought of putting money into a casino was definitely not something she was interested in, but we were just taking in the sights. For me, as an 18-year-old, my eyes lit up. I remember thinking, “I’m excited to come back here someday.”
Fast forward a year or so—my sister was living in Buffalo, and they had casinos nearby. I remember right after I turned 19, we went up to Canada, where you could drink and gamble at 19. We went out to celebrate my birthday, and then we ended up at the casino. It was more about going out to the bar than going to the casino, but it was super exciting for me because, like I said, I had seen a casino, and I thought, “When I’m old enough, I’m definitely going to come back.” So we went to the casino, played some slot machines—nothing big, just lost maybe $20 or $30.
After that, I didn’t really have many opportunities to go to casinos. They weren’t legal where I lived, and you had to be 21. From the time I was 19 until later, I didn’t go to casinos because I couldn’t. At that point, I understood the entertainment aspect of it—it was a cool night out, but I wasn’t trying to sneak off to find casinos. A lot of that was because there wasn’t an easy opportunity for me to do so without driving a long distance.
I started college, and I wasn’t involved in gambling at all. But then I found out that one of my close friends had a gambling problem. They were reaching out to me to help them with their finances because they were struggling to pay bills. Eventually, I found out that the reason was they were going to the casino and losing their money on slot machines. Here I am—a college kid—helping out my friend because they were one of my best friends. I started helping them get on a budget.
As we gamblers do, we all have the best intentions. I do believe my friend genuinely wanted to stop, but the addiction was so strong that it overcame them. It was repeated trips to the casino—losing more money, and me helping again. It became more and more frustrating for me because I wasn’t a compulsive gambler, and I just didn’t understand it. I thought, “Just stop going. If you stop, all the problems will go away.” I helped get them set up on a budget and knew all the details of their finances. If they just stopped going to the casino, they wouldn’t have any trouble.
But as we know, it’s never that simple. Over time, it became clear that my friend couldn’t stop, no matter how much they wanted to. I saw their struggles first-hand. It frustrated me, and I started to hate gambling. I hated it because I saw how destructive it was—not just for my friend but also for me, dealing with the consequences. If you had told me at that time that I’d eventually become a compulsive gambler, I would have laughed. I would have said, “There’s no way—that’ll never be me.” I could see how tough it was for my friend to quit, so why would I ever put myself in that situation?
But here I am today. How did I get here?
The summer after my sophomore year of college, I was hanging out with friends from school. One afternoon, we had probably played golf in the morning, and afterward, we went to a friend’s house where they were playing cards—poker. I had never played poker before. My family didn’t play cards, so I had no clue how the game worked. I knew the basics—that it was a card game, and there were different hands—but I didn’t know many of the hand rankings or rules.
I watched them play for about 45 minutes, then eventually joined in. I bought in for maybe $10 or $20—nothing big—but I was terrible. I didn’t even know what the hands were. Still, I’m a quick learner, and I started to pick it up. That was my first time playing poker, specifically Texas Hold’em.
This was during the summer of 2003. For anyone who was into poker back then, you’ll know that this was the year the World Series of Poker went mainstream on ESPN. ESPN started showing poker just like any other sport—like NBA or NFL games. It was a weekly series, and it built up to the end where Chris Moneymaker—this average accountant from Kentucky—beat all the pros and won the World Series of Poker. As early twenty-somethings, my roommates and I watched everything on ESPN, so we were all watching this. We started playing more and more, inspired by the show.
It became something we did as a house. It was just one of those things—get together, play a game of Texas Hold’em, and then go out. I started really digging into the game and realized, “This is all about math.” I was always good at math growing up—it was my easiest subject. I even won our county’s mental math competition in sixth and seventh grade. Math came naturally to me. So as I started getting into Texas Hold’em, I saw it was all just probability and statistics.
Unlike slot machines, which I had promised myself I’d never do because you can’t beat them, poker seemed different. I knew I couldn’t beat games like blackjack long-term, but poker was a game where you played against other people, not the house. For me, that seemed less like gambling and more like a game of skill. I started diving in even deeper.
With the poker boom and ESPN coverage came online poker. I remember when Party Poker came out. One of my roommates mentioned it to me, and I thought it was cool. I never wanted our home games to end—I would have played every night if we could. I was having so much fun—it was competitive, and it filled that gap that quitting competitive golf had left. Poker became my new competitive outlet.
When we weren’t playing as a house, I could play online in my room, and I started playing more often. At this point, I was still very conservative. The memory of my friend’s struggle was fresh, and I didn’t want to go down that road. I set strict limits for myself—only depositing a small amount of money and cashing out if I won over a certain threshold. Back then, cashing out online was easy and quick, so it fit well with my plan.
I did that for a while, probably breaking even overall. But like most gamblers, my stakes started to rise. Instead of playing the $10 or $25 tables, I moved up to $50, then $100. Eventually, I was playing two tables at once. Then, at my worst, I bought a second monitor so I could play eight tables at once, with buy-ins ranging from $100 to $200 per table. I had anywhere from $800 to $1600 in play at a time—absolute insanity.
This is when my gambling started becoming a real problem. I was losing more than I could afford, and my addictive personality was kicking in. I started playing more and more and going to class less and less. It all started with the idea that poker was different from other forms of gambling—it was a game of skill. The availability of online poker and my competitiveness all combined to create the perfect storm.
As much as I warned myself early on, seeing my friend’s struggles, I slowly worked my way into a big gambling problem. It didn’t happen overnight—it was gradual. I had some big wins, which hooked me. I remember one month when I won more money than I’d make in a year after graduating. I thought, “Why get a normal job when I can do this?” It made sense at the time, but now, looking back, I realize there was never going to be an amount of winning that would satisfy me. My competitiveness and desire to keep getting better would always get me in trouble.
So, that’s how I went from someone who hated gambling to someone playing eight tables at once, beyond my means, deep in addiction. I wanted to share this story not just to tell you about my journey, but to raise awareness that gambling can hit anyone. It can be very easy to rationalize that you’re different
and that it won’t happen to you. I did that, and I ended up exactly where I never thought I’d be.
In future episodes, I’ll continue my story, but for now, I want to shift gears a little bit and focus on other topics. I want to share my thoughts, experiences, and the things that have worked for me in recovery, as well as what I’ve seen work for others.
As a disclaimer, this podcast does not provide legal or medical advice. I’m not a doctor, an attorney, or a therapist. I’m just a guy who had a gambling problem. While we’ll discuss many topics, and I’ll provide insight into what worked for me, please seek the help of a professional. Go visit a lawyer, doctor, or therapist to help you deal with your gambling problem. The information we discuss is for informational purposes and should not be taken as professional legal or medical advice. Reliance on the information appearing on this podcast is solely at your own risk.
The music for this podcast is “Something Elated” by Broke For Free, and it is licensed under Creative Commons.
