I’ve mentioned before that I’ve been a professional gambler for many years. Some people may not understand exactly what I mean by this (though I’d expect almost everyone to at least have an inkling – who doesn’t watch movies, after all?), so I thought I’d write a post explaining what I mean by professional gambling and to summarize a bit of my story regarding that.

As for the gambling part, I mean online, and very occasionally live, poker, starting as an underage teenager around the mid-2000s and ending, I’d say, around two years ago. I also did sports betting starting around the mid-2010s, and to some extent, I’m still involved in it today, though presently not winning nearly enough to make a living.

As for the professional part, I estimate I’m up around half a million bucks over the past two decades, and it has constituted most of my livelihood during that time. (For those wondering: I don’t actually have half a million dollars, unfortunately, but we will get to that part shortly.)

As to how it all happened, I will try to give the full story without making this a mammoth post:

I was a kid when the poker boom happened (around 2003-2005), and I ended up getting hooked real hard on those WSOP and WPT poker tournament shows. I would play poker with my cousins, with my high school classmates, and I would religiously watch new episodes of any live poker show that would air on TV.

Before long, I found out you could play poker online for play money. Anyone could make an account, and no ID or credit card was needed. Soon enough, I found that those same sites would run huge freeroll tournaments several times each day, to which anybody could register for free. A very small percentage of people (say, the top 5%) would gain a ticket to a daily tournament where hundreds of people would play for a prize pool of around $50 (I think first place was like $5). The freerolls took about 4 hours to get to the top 5% winners, and people obviously didn’t take them very seriously. Most would just go all-in every hand, trying either to get a huge stack or to get it over with and not waste any more of their time. Eventually, I figured out that if I patiently waited for good hands and actually made an effort to play well—and did that for every freeroll I could manage to play every day—I would make the $50 prize pool tournament almost every day! I was probably profiting about $10-15 a week, hahaha. There was no way I could ever withdraw or spend that money on anything but I was in high school and felt like a baller, so it was all good.

(Devilfish Ulliot, one of my favorite players from the poker boom. The guy was a legit criminal and a complete degenerate but he made for great TV. He died in 2015.)

By my first year of college, I think I had about $300 between my PokerStars and WPT accounts. At that time, I think I was grinding $3 sit-n-go’s, which are unscheduled tournaments with about 9 people that start as soon as they fill up. I ran my money up to about $1,000 during that year, but eventually, I started running bad (having bad luck), and I ended up breaking even for a long time, even though the games were very soft. I remember I would play way too many SNGs at the same time and make all kinds of misclicks and mistakes. I remember breaking even for what felt like an entire year.

I think around my second year of college, I decided to switch to cash games. I had been playing SNGs and larger tournaments without much success, and most people in the know at that time were saying that cash games were where the money was. I didn’t do well at first: I wasn’t used to the different playstyle, table selection was a pain, and I was still playing way too many tables at once. I broke even for a good while and eventually decided to subscribe to one of those old instructional poker video sites (sort of a proto-Udemy for poker pros) where top pros would make videos for people to learn. I also got coaching from a couple of more experienced pros and greatly benefited from that. I eventually did a lot better, and by my third or fourth year of college, my bankroll was generally above $10,000, and I was playing cash for significantly higher stakes than before.

I took a bunch of shots at that time on bigger live tournaments. PokerStars would run live circuits in different countries, and I would occasionally travel to play at those. I played bigger tournaments than I could really afford, ran bad, and lost most of my money several times doing that. I suspect I was already burned out with poker at that point, having obsessed over it for the better part of a decade, and I was hoping to make a big score so I could move on to something else. Long story short, I lost most of my money playing live tournaments and spent a year or two after that playing lower stakes and making just enough to pay rent and afford groceries.

Back in those days, people were starting to solve the game theory part of No-Limit Hold'em (less complex games like Limit Hold'em had already been mathematically solved by then), and it was really fun to go along with that. The GTO software options weren’t too advanced back then and required a lot of input from the user, but I think they still greatly accelerated the process of the games getting a lot tougher very quickly. I got coaching from a guy who had a deep understanding of how to use software to solve some of the more complex mathematical aspects of poker, and it helped me a lot. I think that was the last time I put any real effort into the game.

(This is the type of software people were using back then to solve the game theory aspects of Hold'em. They could do some pretty advanced simulations, but the user still was expected to do the bulk of the modelling of whatever situation one was trying to figure out. Nowadays GTO solvers do all the work for you, almost instantly.)

I think around 2017, I moved back to my hometown and stayed with my parents for about a year. I ran really hot, soon rebuilt my bankroll, and eventually was playing some of my highest stakes so far.

At that time, I also started sports betting (mostly soccer) and did very well at first. I was pretty clueless, but didn’t know it, and I got super lucky at spots, but also didn’t realize that. Only later, when I hit some rough patches betting on sports, did I realize how good I had run at the start.

I haven't mentioned programming so far in this story, but I think this was the time when I studied coding a lot because I was doing very well gambling, and whenever that happens, I always play/bet much less volume, I suppose being unconsciously afraid of losing it all back (which can easily happen). The general pattern of my adult life probably has been: if I'm doing well gambling, I’m thinking about what I can do to move away from gambling; if I’m doing badly, then all I do is play/bet until I do well again.

I started dating my then-girlfriend (now wife), and we moved in together. I made good money gambling during that time and managed to buy a bunch of Bitcoin right after it crashed from its then-ATH in late 2017. Around then, I was learning full-stack JavaScript and was definitely giving a lot of thought to making a career switch; it would have been a great decision because I could have benefited from the spectacular web development job market of the COVID years. Unfortunately, I went on a very bad run in the first year of the pandemic, lost most of my money, and spent the next year and a half working to win it all back. Any thoughts of a career switch had to be put on hold.

(I obviously didn’t know how good it would have been to go into full-stack JavaScript back in 2020, else I would have done it. Now I’m trying to make the career switch five years later, and the junior job market is an absolute hellscape. Alas for imperfect information.)
I eventually did better, then at some point did worse again, then better again, and finally worse (are you starting to notice a pattern, dear reader?).

For the last 5-6 years, I've mostly focused on sports betting, playing poker ever less frequently. I've done the best betting on Chilean/South American soccer and Dota 2 (my favorite eSport forever), with mixed results in other sports like the NFL and basketball. I continued to play online poker for some time at diminishing stakes and profits (the games have gotten much tougher), mostly to supplement my sports betting income.

After a very stressful period of running bad about two years ago, I decided I wanted to stop and finally move on to something else. I had developed tendonitis in my right from so much multi-tabling and was in constant pain every day, but didn't have the option to stop grinding either because I was short on money due to my downswings. I stopped eventually playing poker almost completely and started a full-time job at a hotel I had worked at previously, mostly as a night auditor. The work isn’t very demanding and leaves me a fair bit of time to code, so I’m grateful for that. Obviously, I intend to do web development full time when the opportunity finally comes.

(this is a recent picture of me at my job on a regular night)

I think that's it for my story as a gambler. Overall, I'm grateful because it got me by for many years and managed to save a bit of money: at the end of everything I'm not rich, and I'm not destitute.

Next time I'll write about my transition into web development and my current search for employment.