Investing And Life Are More Like Poker Than Chess

“Success is nothing more than a few simple disciplines, practiced every day.” – Jim Rohn

Investing and life are more like poker than chess. I recently listened to an interview with Annie Duke. Ms. Duke’s book, Thinking in Bets along with the interview really resonate with me because her thinking is quite similar to mine.

In this quick video, I detail the parallels of investing and poker and why it is critical to keep a “poker face,” keeping your emotional composure during bad….and even good investment periods!

About Thinking in Bets: Making Smarter Decisions When You Don’t Have All the Facts

Thinking In Bets Book Cover

Annie Duke, a former World Series of Poker champion turned business consultant, draws on examples from business, sports, politics, and (of course) poker to share tools anyone can use to embrace uncertainty and make better decisions.

I like this book for many reasons, the greatest one being the statement, “Even the best decision doesn’t yield the best outcome every time.” In poker, like in investing, you can make the best decisions but there are still unknown elements at play.


Transcript of the video:

Hi there. Mike Brady with Generosity Wealth Management, a comprehensive, full service financial firm headquartered right here in Boulder, Colorado. 

Today I want to talk about how investing and life is more like poker than it is chess. I got a lot of these ideas I’m going to share with you today from an interview and a book that I read by Annie Duke. I’m going to put a link in the newsletter and in the transcript of this. ( Annie Duke, Thinking in Bets.

And when I heard her interview on this podcast it was like she was speaking right to me because that’s the way I think. And so of course I thought she was brilliant. If you watch my videos going back seven, eight, nine years you’ll hear that I talk in well let’s increase our probability of success. And I think the odds are because that’s really the way life and investing is. Let’s think about chess for a second. Chess there’s these pieces on the board and all of them are visible. You see it and so does your opponent. With all that visibility it’s a completely logical game. The person who is the more experienced, the person who is the better player should always win. And if that person doesn’t win then they can go back piece by piece or play by play and say oh, this is where I made a mistake.

That’s not the case with poker. Let’s talk about poker for a bit. You don’t get to see all the cards so there’s a hidden element there. It’s all a bunch of odds. You might have an 85 percent probability, 90 percent. But there’s still 10 percent that you could be wrong. And it doesn’t mean that you were wrong because the outcome went against you. But there were things that you didn’t know. There were unforeseen things and there is luck. I’m not going to ask you to raise your hand but if I was to say who has run a red light, most of us would raise our hand. Even if it’s only once in our life or if it’s once a day. Just because you run a red light doesn’t mean you automatically get hit although it dramatically increases your odds of getting hit. Just like if you’re following the rules and you go through a green light it doesn’t guarantee that you won’t get hit, T-boned by somebody else. So there are factors outside of our control that we have to understand.

When we’re looking at a poker game, a typical poker hand a professional might take two minutes. Therefore, you might have 30 hands in an hour. And a professional poker player is going to know the odds. They have to work really hard to know the odds, play the game, to be cool. Maybe there’s a string of bad luck that you have but you stick to your particular core knowing that you’re a really good player. You know the odds better than the people that you’re playing against and you just can’t get too emotional one way or the other. If you’ve ever seen a poker game nobody’s jumping up and down when they win or at two, three or four hands they’re getting super depressed. Maybe amateurs are but definitely not the professionals.

So investing is very similar. We can do the best that we can with all the different variables that are known to us we can come up with a strategy. We can say wow, I think the market is going to do this, I think the market is going to do that. And we could be wrong because there are going to be things that are unforeseen that are going to be in the future. Nobody knows the future. So that by definition is going to be a variable that we’re not able to account for fully. Therefore, what do we do? What we do is we, of course, look at a diversified portfolio. We say well how can I not stick my neck out so much that if that 10 percent or that 20 percent or whatever the number is that I’m wrong, I’m really stuck that I’ve lost so much. How much are you willing to risk? So a diversified portfolio is very, very important. Staying in it for the long term. If you find your strategy that works with your risk level, your tolerance, that allows you to stay emotionally cool it’s got to be a long term. If you were a poker player it might be many hours. If you are an investor it should be many years. And so you’ve got to keep that in mind as well.

Life is full of unknown variables so we try to increase our knowledge. We try to increase it so we can make the best decisions. We try to learn from those decisions as well. It is not a chess game. It’s not a guarantee. So if you’re looking for a guarantee then investing in life, you know, you’ve come to the wrong place so you’re never going to get that and you’re going to be continually disappointed.

Mike Brady, Generosity Wealth Management, 303-747-6455. You have a great day. Thanks. Bye bye.


2018 1st Quarter Review

“Twenty years from now you will be more disappointed by the things that you didn’t do than by the ones you did do, so throw off the bowlines, sail away from safe harbor, catch the trade winds in your sails. Explore, dream, discover.” – Mark Twain

The 1st quarter of 2018 is already over and it was an interesting 3 months to say the least. If we look at 2017, the fact that we had only a little bit of volatility is the exception. Most years there’s over ten percent declines at some point during the year. Which is something we’ve about hit already this year. That’s the normal and not anything to be freaked out about – listen to find out why.

Transcript of the video:

Hi there.  Mike Brady with Generosity Wealth Management, a comprehensive, full service financial firm headquartered right here in Boulder, Colorado. 

I’m here to talk about the first quarter review and the rest of the year preview.  Charles Dickens in a Tale of Two Cities started off by saying it was the best of times and it was the worst of times.  I suppose maybe we could start off that way with the first quarter as well.  January for the unmanaged stock market indexes was a continuation of a strong upward movement that we saw in 2017 with very little volatility.  That’s really one of the big stories as far as I’m concerned is that 2017 was so low volatile and that was the unique situation.  All the way up to about January 26 of this year when volatility decided to come back.  And so we definitely saw that in February.  March looked like it was starting to come back up again and then we gave it away in the third week of March.  And so the quarter ended a nine out of the eleven major S&P sectors, 9 of them were negative and two of them were positive.  And those two that were positive was actually information technology and consumer discretionary.  And so that’s kind of interesting. 

Of the indexes, pretty much all of them were negative except for emerging markets and actually the NASDAQ.  The NASDAQ unmanaged stock market index was positive.  But even those that were negative in the U.S. here, not counting – I mean when you look at Japan and you look at some of the others abroad they were actually down quite a lot at negative seven percent or so.  We were down one-and-a-half to two-and-a-half percent.  That’s really breakeven in my mind, particularly when you can make a one percent move in a day which we definitely had some more one percent moves this past quarter than we had in quite some time in the last couple of years.    

So it’s good to put this in perspective.  The way I look at investments is that it’s three steps forward, one step back and maybe sometimes it’s two steps back.  And if you focus so much on the negatives, on the steps back, then you’re never going to have the steps forward as well.  And so when all this volatility is happening and let’s look at that chart that I have up on the screen.  So you’re back to where you were three-and-a-half months ago. This is not that you’re back to where you were ten years ago.   

Let’s put everything in perspective.  As a matter of fact, it is normal for there to be volatility.  It is normal for there to be declines.  And with the number, the DOW being 25,000 and 26,000, 500 and 1,000 point movements are less significant as a percentage.  So we have to look at things in percentages.  I remember back in 1987, you know, I’m 49 years old right now and at that time I was a freshman in college when the October 1987 crash happened and that was 500 points.  Well that was 20 to 25 percent of the whole market.  Well, 500 points on 25,000 is not that statistically significant like it was 20 to 30 years ago.  So the numbers get magnified just like our portfolios.  The larger the numbers, of course, a percentage change one way or the other can be thousands, tens of thousands, maybe hundreds of thousands of dollars.  And so we have to keep it in perspective from a percentage point of view. 

I continue to be optimistic and that means not that I guarantee it, absolutely not.  There’s no guarantees in this world.  Life is not a guarantee.  Investments are not a guarantee.  I’m actually going to do a follow up video to this about how investing is like poker, not chess.   

Just to give you a little preview of that.  There are unforeseen things in poker and there is a certain amount of luck involved in poker whereas chess is all strategy.  The better person should always win whereas that’s not the case in poker and that’s not the case in investments and that’s not the case in life.  There are things that are unforeseen, things that we can do the best that we can.  We can increase our probabilities of success.  And so as I look towards the rest of the year I see lots of profitability with companies, I see lots of technical change continued.  I believe that the tax change that just happened was a very favorable thing, at least in the short run and the short run being the next one to three to four years or so as cash comes back I’m sure, and we reinvest some of that cash as well.  Other people might have a different point of view and that’s absolutely fine.  That’s what’s great about America is that we can have different points of view.   

You have to remember though that from a long term point of view which is the way we have to look at it, things are complicated.  There’s many different variables that determine this.  And so you might place a higher value on the variability of chaos as you might see it.  You might place a higher value on tariffs and say wow, this is a bad thing.  I don’t place that as high of a concern but maybe I’m wrong.  Maybe you’re right, maybe you’re wrong.  Maybe you get it.  I just read this morning how Elizabeth Warren is in favor of the tariffs in China just like President Trump.  I never thought the two of them would agree but there we go.   

So it’s very interesting that there’s all these different variables.  We have to remain long term investors because I can go back 25 years, I’ve been doing this 27 years, and go back my entire career and there’s always been a reason to be pessimistic.  There’s always reasons to be optimistic and so the question is over a longer term – three years, five years, ten years, et cetera, what’s in your best favor because it’s very hard to read the tea leaves on a shorter term basis.   

I’m optimistic.  I continue to be so.  I believe that there’s a greater than 50 percent probability that things are going to continue to work out fine.  Maybe there’s going to be some increased volatility which is normal.  The fact that we had only a little bit of volatility last year is the exception.  Most years there’s over ten percent declines at some point during the year.  And so we about hit that this year.  So that’s the normal and not anything to be freaked out about. 

Mike Brady, Generosity Wealth Management, 303-747-6455.  Give me a call at any time.  Thanks.  Bye bye. 



Recent Market Activity

“Our greatest glory is not in never failing, but in rising every time we fall”
– Confucius

The last few days have seen lots of headlines and news about the markets, and you may be wondering what this all means.

History has shown that investors are rewarded for steady nerves and long term vision.  If you’;re in your 60s and 70s, hopefully you still have many years in front of you, so your vision should be long term.


Volatility is normal, and the low volatility we’ve seen in the past few years is the exception, not the norm!


Click on the special video for my up to date thoughts.

2017 Review and 2018 Thoughts

Happy Families are all alike; every unhappy family is unhappy in its own way
– Leo Tolstoy in Anna Karenina


There is plenty to be happy about this year, as almost across the board the unmanaged stock and bond market indexes were up.  International markets as well.

I get asked all the time “when is the market going to crash?” and “how bad will it be?”.  They’re the wrong question.

And I use an analogy of a marriage and disagreements to make my point.

Below is my end of the year video, where I outline my thoughts on 2017, and also what current conditions might mean for 2018.

I highly recommend you watch it, and if you have any questions, please don’t hesitate to give me a call.  I’m here to help and serve.

2017 3rd Quarter Review

“To know what you know and what you do not know, 
that is true knowledge” – Confucius


The 3rd quarter of 2017 is over, and it was another good one.


Practically every non-managed stock market index was up, in almost every sector.  The markets perform in one of three ways — up, down, and sideways.  After a few years of a sideways market, since the election we’ve seen a fairly steady and consistent up market, reaching new highs almost daily.

In my video, I address the need to ignore negative naysayers, as there are always doomsday prophesiers willing to say “it’s at all time highs, this is why it will crash.”


Ups and downs are normal, but the successful people are those that have a plan and stick with it.


Check out my video above.