All Reds: One man’s tale of repaying student loans with online gambling

By Jeremy Da Rosa on Jan 29th, 2013 | Daily Grind, Pay Yourself, Work

Phil could have used this.

Editor’s Note: Phil Goss, the author of this guest post, could have used the “Probability Calculator” pictured above. He currently lives in Guatemala and continues teaching and coaching gymnastics and has regularly beat me at poker.

As my student loans crept up on me and my income continued to decline, I knew working at a restaurant couldn’t be my best option. I needed to do something and fast. I was a recent graduate from University of Illinois at Chicago after rapidly graduating with a simple Spanish degree in 8 years. The sad part is of that is I didn’t even know Spanish well enough to get a job. Needless to say, I didn’t have a lot of prospects, and my student loans were very high. After a lot of thought, I did what any wise, normal, college graduate does when they need more money: I moved to Guatemala. With that, I left Chicago, my lax but well-paid jobs, my extremely cheap apartment ($167/month) and my poker buddies.

While I quickly found a job teaching English and coaching gymnastics (at the same time, HOLLAH!) in Guatemala for about $1k total a month, I knew, with my student loans, that this would not make ends meet–I had to do something. Once again, I chose to take the sane route of any mature adult: I turned to online gambling. No-Limit Texas Hold’em poker to be precise. I had played online poker before but only as a hobby. I needed to change my approach if I wanted to use poker to make payments on my student loans.

After trying a few different styles, I decided that Heads Up was the game for me. I started with only $50. My goal was to get to about $125 and then cash out $100. Since the site I used allows only one cash-out per month with no fee, I thought this would be the right amount to put a nice dent in my student loans. So I went to work. Every time I cashed out, the check went to my mother’s house where she deposited it in my bank account. From there, I was able to make easy payments to my student loans.

I started with $5 games. The competition was pretty bad, and I was surprised if I lost. At that level, there didn’t seem to be much skill. I would regularly win 5 games in a row. There was just something about my game back then that I still can’t put my figure on–it just seemed so easy. I played there for about 1 year, and got paid okay, but I wanted more. So I moved to $10 games. This seemed to be the perfect price for me. I was still winning, but now I was able to cash out up to $250 at times. I stayed at this level for about another year. I was cashing regularly and making good payments on my student loans.

One month, I got up to about $200 after I had already cashed out. I didn’t want to cash again and get charged the extra cash-out fee, so I just bumped up the stakes. I began to play $20 games, then $50, and then I was a regular at the $100 tables. I was up to $1,500 in winnings, and I only needed to wait about 10 more days until my biggest payout with online poker.
Sadly, I couldn’t wait those 10 days. I watched as my bankroll went from $1,500 to $0 in about one week. I was devastated. Every night during that span I would go to sleep anxious about I was going to win it back. I would wake up early and start playing in a lost effort to get back what was once mine. Not only did I lose all my money, but I didn’t have enough in my poker account to play even at the lowest limits!

Even today, the anxiety hasn’t gone away. I still dream of that money. The sad part is, I never got my mojo back. I haven’t made regular cash-outs with online poker since. I still play sometimes, but I rarely cash out. It’s back to how it all started…a fun hobby, but not a means of making student loans payments.

Picture from via cc.