I had never gambled before and knew nothing about it, but I'd gotten too many e-mails like it. I was at my parents house for winter break during my first year at UT, and I was bored.

"Free $50 just for downloading our casino!"

Hmm. That doesn't seem very risky. I might as well download to see what it's all about.

I downloaded, and sure enough they added $50 to my account, which I quickly lost. Even though I lost it, there was a moment where I was up to $75. What if I had cashed out? Would they have actually given it to me? (actually the answer is no... later in my career I found out that that was a particularly sketchy casino)

Then I took a chance. I found another casino that promised to give me $200 if I deposited $200 at their casino. It was a lot of money - but that just made the free $200 more appealing. I was scared when I deposited, and my heart jumped when I saw my balance double to $400 instantly.

Blackjack.

I played a few hands and was actually winning. I managed to get up to $500 and I cashed out. Was I going to get paid? I was skeptical, and felt like an idiot for trusting the site. There was no way they were about to give me $300 for fifteen minutes of playing a game at their site.

A few days later a strange envelope came for me in the mail. It was a check for the $500 I had won. Wow.

When I returned to school I found myself in the cafeteria eating with some friends. Also in attendance was a guy named Adam, who was a friend of a friend. I mentioned something about my gambling experience, and his ears perked up. He was interested in gambling too.

At that point I was playing cautiously, maybe winning or losing $20 a day. I didn't have a ton of money, and I was just testing the ropes - I felt like there just HAD to be some way to make money doing it.

After lunch I invited Adam to join me and gamble on my computer. He brought along a computer blackjack game and the manual that came with it. We played a few hands and then the "blackjack strategies" section of the manual caught our attention.

The Double Martingale System.

It sounded exotic. We read the description of it and it seemed pretty legitimate :

Bet $1. If you win, you've just won a dollar and you're done with this cycle. Start over.

If you lose, then you bet $3. If you win that you have won 3, lost 1, for a grand total of winning $2. That's $1 per hand played.

If you lose again you bet $7. If you win that you've won 7, lost 4, for a grand total of winning $3. Still $1 per hand played.

In fact, as the progression escalated to 15, 31, 63, 127, 255 and beyond, you would always end up winning $1 per hand played. And you had to win eventually, right? It was genius.

We decided that we ought to go into business together and try this strategy out. Being the prudent business men we were, we played about five minutes on his simulation and declared the strategy a clear winner.

I had some money in one of my casino accounts, so we used that. At first it worked - we made maybe $30 or so. But then all of a sudden the progression had doubled and we had to bet over $500. We didn't have that much money in our account. But that wasn't the strategy's fault - we just didn't have enough money.

At this point it was about 7am. In our excitement we had stayed up all night playing and planning what to do with our massive winnings. That's when we made an important decision - we would empty my bank account which contained the $1000 that constituted my life savings, and use that. We'd split the winnings or losses down the middle.

Excited, we went downstairs to the bank and wired the money. A few minutes later, it was all there. We placed our $500 bet and held our breath. 16 vs. 10. Not good. We hit, got a 2, and the dealer busted. We won! It felt great -we knew the strategy was good and that we had made the right decision.

The big bet scared us, though. I don't remember exactly how we modified our strategy, but we somehow changed it so that after some point we would cut our losses and start the progression over.

But then something happened... instead of steady winning, we started losing. Soon we were down to only $800, but our resolve remained. We WOULD make this work. I was exhausted from staying up so late so I went to sleep while Adam continued to play.

When I woke up, it was like a kid on Christmas. l couldn't wait to see the small fortune he had surely amassed. I logged in and checked the balance :

$310

What? I expected an extra zero on the end - at least. I called Adam and woke him up.

"We need to get to playing. We need to make our money back."

Equally foolishly, he agreed. By the time he got to my room we were down to $150. Soon that $150 had turned to $77. Our hopes had been dashed. We failed, and all of my money was gone.

But then something strange happened. It was as if fate didn't wanted to avoid the imminent promises to never gamble again, and we started winning.

And winning. And winning. Soon we had recovered all of our money and then some! Our balance hit $2000. Every time we'd lose money we'd reevaluate the bizarre flowchart that described our strategy and add another branch to it.

Soon our friends were recruited, and a 24 hour playing schedule was implemented. We had a high score sheet where we'd write down our hourly profit and try to outdo each other.

We kept our lips shut about our winnings, but everyone in our dorm knew that we were gambling. More importantly, they knew that we had serious gambling problems. Random aquaintances would come up and try to explain the dangers of gambling. I'd keep a straight face, but inside I was dancing. I was going to be rich, and I wasn't going to work for it.

Soon we were up to $5000 or so and felt invincible. But the rumors around the dorm were increasing - everyone thought we were pouring all of our money down the drain like idiots. We had to change their minds.

We declared that we were big winners and offered a chance to invest with us. Give us your money on friday and on monday we would return it, reflecting our win. So cocky we were, that we guaranteed against losses. No one wanted to take it. Finally we found one person and took his $100.

On monday we proudly returned $200. Everyone was amazed, and we were happy because we'd just topped $10,000. The money went to our heads and we started spending it. We spent some in real life and even more future profits in our heads. We'd buy boats, an island, planes, or whatever else we wanted. I never had a cell phone before, but I went and bought the most expensive one available at the time that only high powered executives could afford.

Soon we split into two teams and kept playing. We'd go to the business building at UT and play side by side, smirking at the business students who were cranking out their term papers. Within a few more days we reached $15,000.

I thought we were unstoppable. But Hayden, eternally more cautious than I, managed to unravel our strategy and do the math. We were getting lucky... the odds weren't in our favor - they were just temporarily skewed and would catch up with us. As if on cue, Adam called to report a $5000 loss.

My whole world was crashing around me. The past couple weeks had me completely convinced I was on the fast track to wealth, and I didn't want to let go of that dream. Reluctantly we cashed out and split the profits.

Adam spent his $5000 on cello camp that year, leaving him broke again the next.

My $5000 sat in the bank for a while until I decided to try again. More thorough this time I worked and worked to try to come up with a winning strategy. By some fate, one hit me. It couldn't be that easy, could it?

Sure enough, the next few months proved that it could be that easy. I wasn't making much, but $100 per day for just an hour or two of work became my routine. Some of the casinos would pay me like that first one did, others would stiff me. Some seemed to have the games rigged and I couldn't win no matter what. As time passed I figured out which to trust and which to avoid.

I took my first job the next year. I wanted a car, but didn't want to spend all my money on one, so I decided to get a job and pay myself back before quitting. Using most of the money I didn't have in casinos I bought a 1985 Mercedes 380SE. It was my first Mercedes, and I was loved it.

My job was delivering pizzas, and I only needed to work for two months to recover the money spent on the car. Every day delivering in my Mercedes I would make $100, and then I would go home and make about that much gambling in just a few minutes. As pizza delivering became more boring, the gambling thing looked more attractive.

In a fit of irony my car actually broke on the way home when I was one day away from earning enough to pay myself back for it. The timing chain was broken and the car was totalled.

So much for a real job. I needed to focus on gambling and buy another Mercedes.

Shortly after, I decided to drop out of school. Class was getting in the way of gambling and thanks to Papa Johns Pizza, I knew I would never get a real job again - the money isn't good enough to justify giving up my precious time. With gambling I could play whenever I wanted, take time off when I wanted, and play from anywhere in the world.

I gleefully marched into the UT counselor's office.

"What can I help you with today?"
"I'd like to drop out"
"Oh... ok. Well.. why would you want to do that?"
"Because I don't like doing this, so I'm not going to"
"I'll just mark it as a semester off so that you can come back"
"No. I'm done."

And I was done. It felt surprisingly good.

Calling my mother didn't feel quite as good. In her life priority list, school is a clear number one. And possibly numbers two and three too. The conversation ended when she hung up on me :

"... Fine Tynan. Go play some poker. *click* "

It seemed like a good enough idea to me. She was convinced for a long time that I wasn't making any money. I'll never forget the quote : "Tynan, if you took a second and actually added up how much you won and lost, you'd find out that you were actually losing."

She was wrong, though. My monthly income doubled within a few months of dropping out. After a few months she began speaking with me again, and eventually gave me some of the money they had saved up for college to use in my gambling business. After that my income hit six figures and stayed there.

The next six years, peppered with a few stressful disasters, was pretty smooth sailing. I never worked more than 20 hours a week, and often less than 10. I hired employees, got an office, and had custom accounting software written. I even paid my taxes.

Finally I burnt out, though. It occured to me that although it was easy enough to make a huge salary every year, I was never going to become a multi millionaire from gambling. It has a limit. Also, after playing millions of dollars of hands every year, I just got sick of seeing casinos.

Yesterday after a business partner reneged on a deal that we made, I decided it's finally time to quit and move on to bigger and better things. I'll still deal with my existing cashouts, but within a month or two I'll probably be done with gambling for life. It's a bittersweet goodbye, since gambling was so incredibly profitable and fun for me.

It seems like a dumb idea to forfeit so much easy money, but the fact is that I don't enjoy it anymore. I really believe that it's important to enjoy what one does, so I'm going to work on becoming a rapper.

[Deleted affiliate link]

Two gambling related books that I love are : Bringing Down the House: The Inside Story of Six M.I.T. Students Who Took Vegas for Millions and
Busting Vegas : The MIT Whiz Kid Who Brought the Casinos to Their Knees.

Good luck!

EDIT: Someone has told me that Casino On Net is no longer 100% reputable. The incident he mentioned had to do with marketing and not player relations, but it's now been more than two years since posting this and I no longer know which casino is the best.

EDIT 2 (12/25/2009): This post is now four years old and gets a lot of people angry. Let me clear a few things up:

1. Yes, I was really a professional gambler for seven years. The idea that I would lie about this to make up a blog post (which all of my real life friends and family have read) is insane.

2. I will NOT tell how I made money. I will not tell you why. If you want to make money gambling, I suggest you play poker.

3. The links to Casino-On-Net are affiliate links. I don't know if I still get paid for them, since this was posted almost four years ago. I don't know if they're still a good casino. Back when I played they were easily the most reputable casino. They might not be anymore. Either way, I would NOT recommend gambling with them or anyone else.

4. I thought this was clear in the post, but I wasn't a very good writer back then: you are not at an advantage over the casino if you do the Martingale system. I got lucky.