How Successful Investors Get RICH

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Topic: How To Invest

What do playing the stock market and chess have in common?

stock market and chess

Successfully playing the stock market — like chess—is never about going for broke.

Many investors like to use analogies from sports or the military to describe their investment approach, so they’ll often use the phrase playing the stock market. But if I had to compare our investing approach to anything outside the investment business, I’d choose chess.

Good chess players never “go for broke,” as the saying goes. Instead, they try to position their pieces so they can profit from the mistakes they expect from opponents who are less talented, less experienced or less patient.

How Successful Investors Get RICH

Learn everything you need to know in 'The Canadian Guide on How to Invest in Stocks Successfully' for FREE from The Successful Investor.

How to Invest In Stocks Guide: Find 10 factors that make your investments safer and stronger.

Successful investors follow a comparable approach. But the crucial difference is that they have no opponent who can be relied upon to make mistakes.

Instead, successful investors try to arrange their portfolios so that they more-or-less automatically tap into the profit and long-term growth that inevitably come to well-established companies operating in relatively free economies in relatively prosperous times.

Four key points to sum up the basics of successfully playing the stock market

At the same time, it’s essential to diversify, as you do if you are investing your money with our three-pronged investment approach of targeting well-established companies, spreading your investments across most if not all of the five economic sectors, and avoiding stocks in the broker/media limelight.

In addition, successful investors need to limit their involvement in trouble-prone areas like new issues, start-up companies and illiquid investments.

They need to stay out of companies in which they have doubts of any sort about the integrity of insiders.

They also need to recognize the special risks of investing in fashionable or excessively popular minefields, such as Internet stocks in the late 1990s, or income trusts in the 2000s, or today’s social media stars.

In fact, you could sum up the basics of successful investing quite simply in four key points:

  1. Don’t depend on luck to make money for you or to prevent losses.
  2. Be skeptical of the claims and recommendations of brokers, promoters or anybody else with a vested interest in a particular investment.
  3. Don’t do anything stupid.
  4. Win by not losing.

How many stocks should you hold in your portfolio?

You’ll hear all kinds of advice pertaining to the number of stocks you should hold in your account when you start playing the stock market. We recommend that you invest initially in a minimum of four or five stocks—one from each of most, if not all, of the five main economic sectors (Resources & Commodities, Finance, Manufacturing & Industry, Utilities and Consumer).

You can buy them one at a time or over a period of months (or even years), rather than all at once. After that, you can gradually add new names to your portfolio as funds become available, taking care to spread your holdings out as we recommend.

When you get above $200,000 or so, you can gradually increase the number of stocks you hold. When your portfolio reaches the $500,000 to $1-million range, 25 to 30 stocks is a good number to aim for. For a mature portfolio, 40 stocks is a good upper limit.

Of course, you may fall a few stocks below that range, or go a few above it, particularly when you’re making changes to your holdings. That won’t matter if you follow our three-part prescription of mainly investing in well-established companies; spreading your money across the five main economic sectors; and downplaying stocks that are in the broker/media limelight.

There is a reason why our upper limit for any portfolio is around 40 stocks. Any more than that, and even your best choices will have little impact on your personal wealth.

Be smart while playing the stock market and avoid diluting your profits with mutual funds

Some investors prefer to hold stocks through mutual funds or ETFs. However, many fund investors routinely hold more than 40 stocks through their fund holdings. That’s because they often invest in 10 or more individual funds, any one of which may hold 50 to 100 stocks. There’s a lot of overlap in stocks between funds, of course, but this still represents far too much diversification.

When you hold too many stocks, you spread your money out too thinly and condemn yourself to mediocre results, at best. The best you can hope for is a long-term return that more or less equals the market, minus the average mutual fund MER (the yearly cost of investing in most funds) of 2.5% to 3%.

All of these points relate to our analogy of the intelligent chess player’s approach to investing. Successful investors playing the stock market will set up a portfolio that can tap into the best opportunities in the market, under all market conditions—instead of just reacting to events in the market and the economy and hoping you’ve made the right moves.

Are you a new investor who has just started playing the stock market? What other topics would you like to hear about? Share your thoughts with us in the comments.

This article was originally published in 2017 and is regularly updated.


  • Frank 

    Dear Pat :
    I enjoyed your comparison very much indeed , more so since i am a dedicated chess player since I was 4 years old , now 78 and I still play chess every day .

    Your analysis is bang on and to this day we have always lived & took care of our investments accordingly ….and we will never change !!!

    Keep it coming .

    regards ,


  • Trust. When I meet a person, I know very early on whether I like and trust that person. With a stock selection, I like to know as much as possible about the persons behind that stock.

  • Michael 

    Dear Pat
    Game theory states that the only way to win over the long haul in a multi-person game or competition (or by extension, if investing in the stock market), is to minimize the maximum loss that you could face. Logically therefore one should aim for no-risk investments, i.e. cash. However we know that such an extreme approach is not very rewarding. Certainly this line of argument supports your approach that slow-and-steady eventually does better than investing in speculative or high-beta stocks where success depends on luck as much as judgment. Maybe a world index fund is the best we can do ?

  • Gordon 

    Bragging is bad but maybe others can learn from my success.

    As the crash of ’08 was approaching there was a considerable debate on the net whether we would have inflation or deflation after the real estate bubble burst.

    No way I knew so I did what I call prepaying my expenses. I bought quality stocks which produce the things I need: energy, food & agriculture, telecommunications (i.e. entertainment) and insurance (health care).

    If my expenses went up (inflation), so would my dividends. If my dividends went down (deflation) so would the cost of my needs.

    It has worked well. Food, energy and health care have led price hikes. Other stuff, which I do not own, has gone down in price.

    After the initial panic I got out of cash. Excess income went into precious metals.

    Now I am redeploying that into the sectors that have lagged so far and require a broader recovery.

    And, of course, now like for the last 25 years, I rely almost exclusively on the stock picks of Mr McKeough.

  • Ronald 

    I seldom to never play the stock market. I have met friends who tell others that I play the stock market and I have to correct them and say I don’t play the market, I invest in it. Sometimes I feel like going off the board like Teck Resources in 2008 when it was down to $3.25 at one point but I didn’t pull the trigger.

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