Gambling and My Financial Decisions


I’m starting to really like Mondays everyone! I’ve been reaching out to bloggers I follow to see if they’d like to write a guest post. I think guests give my blog a little more flavor. Today, I’ve got a little treat from Even Steven. I hope you all enjoy it as much as I did!

Have you ever gone to the casino or participated in a NCAA March Madness Pool guessing who’s going to win it all or even playing Fantasy Football with friends or co-workers and putting up $20 or $50 to put a little money on it.  Everyone gambles in some way and I’m no different, let me share some of my story and how gambling influences my financial decisions.

Growing up I felt like gambling was always around me, only in what most would consider rather normal circumstances.  People buying raffle tickets from me for my little league baseball team, seeing my family buy scratch off lottery tickets and Powerball lottery tickets, and even winning a Nascar pool at a local bar.  When you’re a kid you don’t really understand how gambling is involved in every day life.

In high school I played a little cards with my friends, learning a few games along the way; but we only played for change. So, I didn’t really think much of it other than having a good time with some buddies.  Off to college. While I was there the big “Poker Boom” happened.  Chris Moneymaker, the movie Rounders, and Online Poker were part of almost every college kid’s curriculum.  Online poker and tournament games with my college friends were more common than having a happy hour drink or heading off to a house party.  So to say my college life was filled with gambling is just the beginning of my gamble.

I played a ton of online poker in college, always on the computer for late nights and once I was 21 I was off to the brick and mortar casino’s, even stopping in Vegas for my 21st birthday party.  During the summers, while I was in college I caddied at a prestigious golf course and received cash for my work.  Since we had a lot of down time we played a lot of poker and when people weren’t playing poker they were gambling on Tiger Woods and who was better.  Gambling was all around me.  I didn’t think twice about taking on a student loan or paying for spring break with a credit card, I could win it back or earn it back on the golf course.  Gambling was influencing my decisions.

I successfully graduated from college and for a number of reasons I was not ready to begin working full-time.  I decided to gamble full-time instead.  For the next 3-4 months I went to the casino every day, usually 6 days a week, I made money, I paid off some debt, but money was of no object to me, I could lose $1000 or win $1000; it didn’t affect me either way.  I decided that playing poker every day was really a grind and I could do something else.

I ended up in the 9-5 day job and started to realize I didn’t want my entire life to be a gamble.  Although I did pick up all of my belongings to move to Miami for a girl, but love stories aside this was a huge gamble, I had some savings, but nowhere near enough, I didn’t think twice about putting it on a credit card, I even played online poker trying to earn my way through my decisions, since I didn’t have much of a bank roll that didn’t last long.

That gamble changed my life; it made me realize I wasn’t going to be able to gamble my way through life.  I moved back to Chicago and even asked that girl to marry me. Now this is not intended to be love story, but that gamble was the best one I have ever made.  My wife makes me not want to gamble, I talk out some of my decisions that I would have made years ago.

Even still the gamble is still there.  I wanted to buy stocks, rather than pay off debt.  I still get in the NCAA March Madness pool, play Fantasy Football, and get the urge to take a trip to the casino.  I love seeing IPO’s in the stock market, well-known companies that lose 20% in a day for buying opportunity. I bought Groupon without asking my wife, it’s a gamble even if it’s legal and in the stock market.

I have found other outlets to keep my energy focused on the good.  I blog over at as I work to pay back all my mistakes(debt), I run an eBay business where I buy and sell clothing, but most of all I listen to my wife, she has almost no gamble in her.  I have the risk tolerance of a man who prints money and she has the tolerance of an angry prison guard talking with an inmate (I hope I’m not the inmate in this scenario).

Maybe the gamble will never leave; maybe everyone has a little gamble in them, you know what maybe having a little gamble in them isn’t so bad.   Let me leave you with this and it’s something I’m sure I heard along the way.  Ever notice how the biggest and most expensive looking buildings are usually those at a casino and a bank?  Yeah, that’s because they make so much money off of you and me…….



  1. Everywhere in life there is risk. Life is risk. To live is to risk (you can substitute in the word gamble for risk if you like, they are the same thing). It is learning to manage risk and to have an appropriate return for your risk that is important. Poker and the stock market are not the same risks. At poker you have a chance of winning. Better to play where you can win than to gamble where your expected return is negative.

    • I agree learning to manage risk can be one of the most important financial choices you make. Gambling and playing poker made my risk meter almost turn off entirely, so now that my risk meter is back things are getting much better for me.

  2. Thank you Josh for giving me the opportunity to guest post on your site, it’s always great when other bloggers reach out and interact, makes you feel like part of the neighborhood.

  3. Hey Even Steven, thanks for sharing this personal story. It can be challenging dealing with the gambling bug – it gives such instant gratification, whether $5 at the casino or a $2000 quick trade on a stock. Paying off debt and investing in quality businesses for the long term certainly doesn’t provide the same short term buzz, but the payoff in the long run is unbelievable.

    Sounds like you hit the jackpot meeting your wife though! It helps to have something else in your life to pour your energy in to, to help steer you away from the ‘hit’ of gambling. Great stuff Even Steven, keep it up!

    • Thanks Jason, I will make sure to show Mrs. Even Steven the jackpot comment, I’m sure she will love it.

      Yeah it’s funny how I used to get excited about winning a hand of poker and now I get more excited from seeing an ebay sale or comment on my blog!

    • Life is full of risks, it’s tough to go from clicking “bet” on online poker, “pay” on a website, and then get your mind back to the reality of money and debt.

  4. I certainly do get excited to play the lotto – even if it’s only a $20 win! But I know that gambling can be dangerous – in the same way that many financial decisions can be dangerous. In either case, it’s important to be well-informed about the risk: know all consequences, be comfortable with them, and have a back-up plan in case you’re unlucky! Bottom-line with gambling: ALWAYS have a safety in place. Personally, I only gamble with amounts of money that I can afford to lose.

    • Katie it’s definetly a risk to gamble and I brought this up in the end, there is a reason banks and casino’s are the nicest buildings on the block, it’s because we are ok with losing a certain amount. It’s interesting, I’m sure there is studies out there, but seeing some of the people that come into the casino certainly tells a story.

  5. I don’t think any kind of gambling is necessarily bad as long as it’s controlled. Gambling problems are sort of ingrained in my husband’s family genes, so we try to really control any sort of triggers. I’m glad you’ve found a way to funnel your gambling tendency into a positive.

    • Thanks for sharing Kim, at that point when it’s ingrained in your family genes, I think it would be great to change the family tree and see if you can get that to a positive.

      Triggers are really important and knowing what they are is half the battle, for example I don’t go anywhere near a casino especially by myself.

  6. I used to play a lot of poker in high school and college. I went to the brick and mortar casinos almost every weekend in college (you can go when you’re 18 here). I had a friend who dropped out of college and grinded $100 and $200 sngs, maybe 8-12 tables at a time, and he did this during the golden age of online poker, when it was just starting to get popular. He even won one of the party poker tuesday $300 rebuy tourneys for something like $350k. It’s a bit insane to think about, especially since he got in at the right time and got out at the right time. He just became a lawyer and has been married for a few years now, couple kids. Really level-headed guy. If I had been in his grade (he was a couple years ahead of me) who knows how my life would have been different. I would have considered dropping out for sure.

    Needless to say, I didn’t make a whole lot playing poker and since “Black Friday” in the US I’ve barely played at all. I’ll definitely get back into it tho if it becomes legalized and there are favorable games with new players.

    • Thanks for sharing DC, it’s great when you someone who has a win, my close friend won the “bad beat” in college and walked away with 50K, certainly made college a little easier and probably a little more fun. But like you said we all kinda grow up and grow out of it for the most part.

      I rarely play poker now unless it’s with friends at a local game it’s just not where I want to be. I tell my friend I gamble every day, it’s just with a business on ebay, that’s my gamble.

  7. I used to play lots of cards with friends. Now when we do play it’s usually for bragging rights. I never had desire to gamble but I have in the past. I had a certain amount of cash I’d have with me and once that was gone. I would be done. I never thought of it as having potential for return rather an expense.

    I had someone in high school whose parents lost their home gambling. It was really unfortunate and the idea (luck) is so appealing to most.

  8. Thanks for sharing this personal story Even Steven. In the past I’ve had a little flutter myself here and there on the horses or greyhounds usually though, nothing too risky. I think it’s great that your wife is able to bring a little balance to your gambling and that you can now use your experience in a positive way.

    • Yeah when you are getting “free” lunches every day from the casino for playing evry day you are probably playing too much. I probably won’t be using that as a great idea for casino rewards and free lunches.

  9. I was never a big gambler – or so I thought – but I used to play the lotto at least every month along with a few scratch off tickets. There’s always that little rush you get when you think you have the winning ticket and then you find out that you lost your $5-$10 again.

    I also went to Atlantic City a few years ago with $200 to play blackjack and I was quickly up $250 – I should have stopped there because I lost the $250 + my original $200 + an extra $100 that I took out from the ATM trying to get my original $200 back. Never again!

    I don’t really play the lotto anymore either, especially the scratch off, but I am investing in the stock market – which is also a gamble, a less risky gamble but a gamble nonetheless.

    I’m glad you were able to find other outlets to focus your energy and money.

  10. I didn’t even get into buying lottery tickets and scratch offs, that’s a whole different story. There has been many studies showing how the lower income classes tend to buy this type of all or nothing gamble, it’s very interesting at least to me it is. I buy about 2 or 3 lottery tickets a year and for me it’s money well spent as I day dream about my 300 million dollar jackpot, not expecting any money to come of it. I suppose I could just day dream and save $10 for the year, but that doesn’t sound like any fun.

    Taking additional money from the ATM is ultimate “leak” at a casino and I have been there more times than I care to admit. Thanks for sharing it’s sometimes tough to admit blunders at the casino. But I sure do like the “Never Again”.

  11. I have done my fair share of gambling as well. Like you, I have learned that the house usually wins, so that is why I like to play Texas Hold em. You get to play the players instead of the house. I don’t do it often, but when I do, I never risk much money at all.

    • There are many truths in your statement about taking on the players when playing Texas Hold’em, but let’s not forget the “rake” which is like interest on a credit card, potential losses from bad cards/poor play, and the common practice of tipping the dealer when winning a hand. When you win these factors are certainly less but it’s interesting how a game we think of as playing against the “players”.

      I agree with you though I’d rather play against the guy next me than the house and now in my case not at all.

  12. Great article! I have learned to mold my money habits for the positive. For example, I am the spender and my wife is the saver, but I have learned to spend and bargain shop for stocks and investments, as opposed to trivial things that depreciate in value. Thanks for sharing your story!


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