I lost! No- I won! What I Learned About Business From Playing Poker PART TWO

If you haven’t read my PART ONE blog on this subject, please do so now so this second part makes sense (it’s good- well worth the read):

Business Lessons Learned from Poker



Last time we were “together” I discussed with you how I had recently read a book on how to play Texas Hold Em poker.  I wanted to update you on my experiences since.  I thought that I had learned what I was to learn when I wrote that post, but thankfully my learnings had only just begun.

I read this great little book on how to become a better poker player.  I practiced with my kids and was beating the six I was playing with handily (I have 8 kids but the 3 year old and 5 year old can’t seem to get the game down yet).  So I was actually pretty confident going into my next poker game with my buddies.  I even decided I was going to take this more seriously to ensure my victory.  And here’s what happened:


  1. I got serious about it (i.e. didn’t really drink more than a beer or two over the 5 hours of play so as to keep my wits about me, I didn’t laugh much because I needed to focus on the game, and I didn’t have much fun at all).
  2. I was so confident in my newfound superiority that I broke my own rules. I didn’t play tight (if you remember, that was rule 1).  I kept deciding to just bend my rules here and there.  I’d pull a king/six for pocket cards and say to myself “ah, I’ll just give this king a whirl.  I can maybe beat them with my superior knowledge and skills”.  Deep down I was really arrogant.
  3. I lost. Big time.  I normally finish in the top two or three.  This time I was fourth.  I really was not good at all.
  4. Did I mention I didn’t have any fun either because I needed to be “Mr. Serious Poker Stud”?


So, how’d it pan out for me overall my first time out? Terrible.  I went home that night thinking, “What’s the deal? I read the book, I know more than all of them, and I sucked”.  It was very aggravating.  The next day I was still annoyed by it.  I really did expect to go in there and dominate.  Instead I was worse.


Does any of this sound familiar?  How about in business?  If you’ve owned a business for any length of time at all, you’ve likely had similar experiences.  I know I have.  You think you have what it takes to do something and the next thing you know you get your ass kicked.  It’s disheartening.  So the question becomes: What do we do from there?


I decided in the following days that I had put too much emphasis on immediate results and I needed to be much more patient.  Maybe I wouldn’t win for a few more months or even longer.  And I decided to look at it like I needed to practice.  So that’s what I did.


We played again exactly a month later.  I decided two things: first, it wasn’t worth being overly serious about it and not having any fun, so my priority was to have fun and enjoy this great group of fun, Christian men I got to hang out with for the night.  Second, I was going to follow the rules I had decided that I wanted to follow the first time, and let the chips fall where they may (pun very much intended).  And this is what happened:


  1. I had a blast! I drank a little (not too much of course- I’m Irish after all so that’s impossible anyway :).  We laughed harder than we had in a long time- every one of us had a great time with the exception of one buddy who apparently was unaware of the sneak-attack-like quality of gin!
  2. I was humble and followed my rules even when I didn’t want to. I mostly just let the cards I was dealt play the game for me.  It actually was pretty easy since all I had to do, for the most part, was just follow my rules and not second guess myself.  At one point my evil brother in law (who also happens to be a great friend of mine) got cocky and loud about the “hurricane winds” that were about to blow all my chips back his way.  He declared that right after looking at his pocket cards.  When I looked down you can’t imagine my delight when I realized I had pulled pocket aces-honestly- I know it sounds too good to be true but that’s exactly what I was thinking that very moment when I looked down at them (I think the odds are 85% of winning with pocket aces).  I immediately upped the bet knowing my confident opponent with go with it.  I ended that hand with a lot of his chips and the other players chips.  That was the beginning of the end of things. Interestingly, I was playing humbly the entire time, knowing how quickly fortunes can change in poker.
  3. I won!  Not only did I win but there was never a point where I was in any danger at all of not winning.  I had lots of chips because I avoided losing them.  I beat everyone in the group, but most importantly I beat the guy that’s been taking our money month after month (made especially fun after the “hurricane winds” declaration!).
  4. Did I mention I had fun? Granted winning is more fun than losing, especially when you’re competitive like me, but regardless of that I would have had a great time because I decided I was going to have fun in advance.


poker.071312So, what did I learn about business?  Some GREAT lessons:

  • Perseverance: I failed the first time after working to win. I could have just given up and said “Ah forget it.  I just stink at poker.”  But I didn’t.  I decided to keep going and stick to a game plan, and it paid off.
  • Fun: I decided that I was going to focus less on the end result and more on enjoying and appreciating the moment. I believe when we do this we tend to get better results in the end.  People, clients, employees, vendors, everyone is more attracted to people who are having fun.  People focusing on enjoying the process have more fun.  People thinking that they’ll have fun when they “get there” are not very attractive.  I think it’s similar to those people who “go out to find themselves and find happiness”- my wife and I always talk about how they never seem to find it.  Happiness happens when we’re not selfishly seeking it, it happens as a result of living a good life by serving God and others.  Similarly having fun and enjoying business happens in the process of working to build or do something worth doing.  It’s not the end results that make us happy, it’s deciding to have fun in the process!
  • Humility: The only times I can remember really losing in business is when I lacked humility. There is a BIG difference between lack of confidence and humility.  Humility is a great virtue in business and in life.  Lack of confidence is a burden and no virtue at all.  Humility is saying “I believe that I can do this and I’m going to work hard for it, but I know things can go wrong too, and there are probably things I don’t know, ”  Hubris or over-confidence is saying “I’m going to do this because I’m so good/smart/add your adjective here. I have nothing to worry about.”  Humility has saved lots of business owners financial lives.  Hubris/over-confidence has cost countless business owners not only financially but often, sadly, in more important areas of their lives- marriages, kids, friends, etc.
  • Game Plan: This one ties into “Perseverance”. How tempted are we in business to change our game plan every time it doesn’t work out the first time we try something?  I had a good game plan that I decided to use going into that first game that I lost in dismal fashion.  But the problem wasn’t with the game plan, it was with the execution (and even if I had executed perfectly, poker-as well as business- are not sciences, sometimes we’re just going to lose).  I could have scrapped the game plan and gone back to trying to win using just my wits, but that would have been throwing out the baby with the bath water.  It was far better to go back to my plan, stick to it, and be more disciplined about following my rules.  This also makes me think of how few small businesses even have a game plan.  How many are just “shooting from the hip” like I was before studying the game of poker a little.  So many small businesses don’t have any game plan at all, and they’re no better off than I was flying blind at the game of poker.
  • Perspective: I probably won’t win next month. Just because I now won after following my plan doesn’t mean I’m going to win every time. I’m not going to.  I do hope to use my plan to win more often, and hopefully even a lot more often, but I’m not going to get discouraged again if I have a bad game.  Even if I screw up and am undisciplined in my game plan.  I’m not going to do anything but re-commit to getting back to my plan.  How about in business?  I think some of the scariest businesses are those run by people who think that their success in the past guarantees their success in the future.  Business is always changing.  If we’re not constantly moving and shaking and working to improve, our competition is going to come up with ways to beat us, come up with something that will make us unnecessary, do something to reduce our margins, take our sales, etc.  We must keep perspective and realize that just because we’ve done something (done well, done poorly, whatever), the past doesn’t equal the future.  We’ve got to keep our heads, keep humble, and keep working to improve.


So, let’s all go out there and do these things: have FUN building our businesses and serving others, PERSEVERING in what we’re aiming to achieve, remaining HUMBLE in the process, following our GAME PLAN, and keeping PERSPECTIVE.  If we do these things I believe we will not only benefit personally, but those around us will benefit also.  And what could be better than doing things that we all win from, maybe with the exception of my evil brother in law!


  1. Bobbi Stanley

    Great story Jon! Thank you for the inspiration to start my week off!

    • Jon O'Malley

      Thanks Bobbi. Have a great week!

Leave a Reply

Your email address will not be published. Required fields are marked *

clear formSubmit

This site uses Akismet to reduce spam. Learn how your comment data is processed.