March Madness: Final Four Investing Bracket 2023 

Dear Mr. Market:

March Madness is back!  

And so are we… The world stopped pretty much everything at one point during the pandemic and sports were of course no exception. For true sports fans there was nothing more depressing than watching cornhole tournaments or empty arenas void of fans, sounds, and energy. Even if you don’t like or follow college basketball, we think you’ll enjoy what we pioneered and have put together. 

We’re proud to say that My Portfolio Guide, LLC was the first investment firm to publish a March Madness investing bracket where we share our picks and match them up against each other. We break down and assign each of the four “regions” with an asset class and then pick teams (stocks) that we think have the best chance at doing well relative to others.  

Not only is this “exercise” a way for us to share our ideas from a macro perspective, but it offers a fun platform to dig into a couple specific investments and themes we are following or excited about in the year ahead. 

Click here or below to enlarge and see the entire bracket for 2023.  

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Top 10 Dividend Growth Portfolio

Dear Mr. Market:

Dividends!

Journalists write about you daily. Investors constantly think and talk about you. Analysts and economists spend their entire careers trying to figure you out. You’re a complex yet simple character, Mr. Market! All that said, today we want to share with our readers a substantial part of you that doesn’t get enough appreciation (pun intended). Let’s talk dividends!

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Bear Market

Dear Mr. Market:

Simple title.

Simple reality.

That’s exactly where we’re at right now. We’re not going to wait for the financial media to announce it or tell us that it’s only a bear market if we officially drop -20% or more. The intent of this article is to explain not only what a real bear market is, and how this one has behaved differently, but also what to do next.

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The Stock Market Indicator that you won’t hear about…

Dear Mr. Market:

We’ll open this letter to our friend “Mr. Market” by stating one thing that will be very obvious in six to 12 months. 90% of people reading this article will have gotten it wrong. It’s not your fault though…it’s the way our minds are wired and the content we’re constantly being fed.

Regardless of your current market strategy it’s times like this that will test the most patient of long-term investors. We’ve written about this countless times but no matter what the sage counsel or stock market adage is, you should be rattled right now. We could be like most “perma-bull” financial advisors and try to data mine for all the reasons to stay calm or share positive anecdotes to convince you that now is the time to invest; it won’t matter though. Putting “lipstick on a pig” won’t help you nor the current market environment. Bad news and reasons to panic will be the headline for the weeks to come and there will seemingly be no safe place to hide.

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Sell in May and Go Away?

Dear Mr. Market:

Does the old stock market adage of “sell in May and go away” make sense? We’ve actually written about this one spring about nine years ago where we actually advocated taking some chips off the table, however it had less to do with a cute stock market rhyme and more due to profit taking. Where are we at now going into May and is this allegedly poor seasonal time of year appropriate to sell or perhaps not?

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Stock Market Correction: Finally!

Dear Mr. Market:

Finally. It’s here….a bonafide stock market correction. What’s also almost here is Groundhog Day…but more on that in a minute. For those of us with short memories we’ll have to do the necessary preamble and small talk refresher on what this is. For those of you who remember what you did (or were supposed to do/not do) during the last correction, here we go again. Do you remember the fantastic Bill Murray movie “Ground Hog Day”? Click here for the last time we wrote about it but again….people seem to forget what they ate for breakfast so you may not remember what happened in 2018.

Oh… but “it’s different this time“, right? Those are indeed the four most dangerous words in investing. Are there problems to worry about? YES!!!! (but there always has been and always will be)

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Jim Cramer and Stock Picking Performance… Booyah?

Dear Mr. Market:

It’s that time of year. Everyone has some stinkers in their portfolio and in a taxable account it’s a great time to evaluate whether one should offset that loss by taking some gains on your winners. If you followed any of Jim Cramer’s advice this past year you have some serious evaluating to do! The aim of this article is not a hit piece of Mr. Cramer but simply a word of caution and a reminder that (1) stock picking is often a futile endeavor and (2) If you are indeed going to follow someone’s picks it’s important to track them prior to blindly buying the next set of recommendations.

We begin by refreshing you on an “oldie but goodie” from the Dear Mr. Market archives. Please click here for some background on Jim Cramer and an article we wrote in 2013.

Below you will see a sample of his picks from the beginning of 2021 and how those picks have fared since. Yikes!

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Buy the Rumor and Sell the News

Dear Mr. Market:

The stock market has provided many sayings and memorable catchphrases that people tend to regurgitate ; some have merit and some are just garbage.

If you’re a regular reader of Dear Mr. Market, or a client of My Portfolio Guide, LLC, you’ll know that our all-time favorite is “The four most dangerous words in investing are …This time it’s different” -Sir John Templeton. Here are some other all-time adages that you’ve undoubtedly heard:

Buy low sell high” Uh…yeah, but easier said than done.

“The trend is your friend” Sure….until it’s not!

“If you have trouble imagining a 20% loss in the stock market, you shouldn’t be in stocks” -John Bogle

“Markets can stay irrational longer than you can stay solvent” -John Maynard Keynes

So…what does “buy the rumor and sell the news” mean? You probably know that the stock market is full of speculation, great stories, and chock-full of hidden nuggets as well as potential land mines. Even if you’re not an experienced investor or trader, at some point you’ll figure out that by the time your neighbor (you know the guy who never loses and is always up) tells you about a stock tip…the ink on the newspaper is already dry and that idea is likely stale.

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I got in at the top of the market…Now What?!?

Dear Mr. Market:

It’s over.

The “fat lady is singing”, the alarm bells are ringing, and you are literally the last dunce in the room who decided to get into the market at the all-time high. Now Mr. Market shows you what real pain looks like and sells off like nobody has ever imagined.

Let us preface this article by stating it’s worth bookmarking and revisiting for those times when you may be rethinking your investment time horizon or just how much risk you truly are able to take on.

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All-Time Favorite Stock Chart

Dear Mr. Market:

It’s been a while since we’ve had to talk about you. The world has been focused on many changes which sometimes leaves you to quietly do your thing while we catch our breath. We’ve ushered in a new year, the United States has a new President and administration, and we’re finally seeing some light at the end of the tunnel with regards to the most surreal pandemic one could imagine.

How have you been… Mr. Market?

Up, down, sideways, and all over the place…That’s how.

Today we write you a quick note to share our all-time favorite chart as well as a reminder to all those investors who may fall prey to short-term memory lapses. The recent stock market sell-off is a great wake up call to the fact that markets obviously don’t just go up in a straight line. It’s a bit more than that though…

Below is our all-time favorite stock chart and we’re going to share why it’s important to look at this every so often.

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