Motley Fool Hidden Gems Investing - Investing in 2026: A Plan You Can Stick With
Episode Date: January 1, 2026Another profitable year is in the books for investors. Whether you invested in 2025 or are looking to get started, this episode is for you! Our hosts discuss some of the reasons why people struggle to... make those New Year's resolutions work, and share tips on how they've built frameworks that can help you build a plan that works for you. Never made a resolution? Neither has one of today's hosts! Companies discussed: LMND, NVDA, AMD, CELH, SHOP, DG Host: Jason Hall, Jon Quast, Dan Caplinger Producer: Anand Chokkavelu Engineer: Dan Boyd Disclosure: Advertisements are sponsored content and provided for informational purposes only. The Motley Fool and its affiliates (collectively, “TMF”) do not endorse, recommend, or verify the accuracy or completeness of the statements made within advertisements. TMF is not involved in the offer, sale, or solicitation of any securities advertised herein and makes no representations regarding the suitability, or risks associated with any investment opportunity presented. Investors should conduct their own due diligence and consult with legal, tax, and financial advisors before making any investment decisions. TMF assumes no responsibility for any losses or damages arising from this advertisement. We’re committed to transparency: All personal opinions in advertisements from Fools are their own. The product advertised in this episode was loaned to TMF and was returned after a test period or the product advertised in this episode was purchased by TMF. Advertiser has paid for the sponsorship of this episode. Learn more about your ad choices. Visit megaphone.fm/adchoices Learn more about your ad choices. Visit megaphone.fm/adchoices
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Jason Hall. It's a new year and for millions of people around the world, that means turning
over a new leaf. A lot of them, maybe you, have resolved to make 2026 the year they commit
to and stick to an investing plan. Today is Thursday, January 1st. Welcome to Motley Fool
Money. I'm your host, Jason Hall. Today, I'm joined by Fool analyst, Dan Kaplinger, and
the aforementioned John Kost. We're going to share our own investing struggles, successes,
and how we've been able to keep investing once the shiny new wears off and the reality of investing
is hard has set in. Okay, guys, the dirty little secret of the fitness industry is that it depends
on January for all those new customers to join, and then February for them to stop coming but
keep paying for those memberships. Now, I'm being cynical here, but the reality is that we all have
stories of a big commitment that we've made in the past and then failed to see through.
We're not going to talk about our favorite fitness stocks either. We're going to talk about
how we've gone through these mistakes and learned from them and then built investing
habits that we can stick to. But first, let's have a little bit of fun, mainly going to be
at your expense, John. What's an experience of a failed resolution that you want to share,
maybe that you've learned from? Yeah. Well, it's not going to be hard to poke fun at me.
this is an easy thing to do. Listen, I don't do New Year's resolutions. I don't. It's not my thing.
I hate the idea of waiting for a new year to make an important change. If there's something that I
need to do, let's do it now. So I try to regularly take stock of life and course correct as needed.
This includes, of course, course correcting when it comes to how I'm investing my money.
And in the past, early days, I really despised the idea of investing a small sum in a risky company.
I wanted it to be a rock-solid thing, and I wanted it to be a large position.
I've learned maybe that's not the best approach, maybe a little bit more of a barbell approach,
where I'm investing a lot of my money in safer things, but some of my money in riskier things.
Right, Jason? Yeah, John. A barbell strategy is
something that I've learned to use myself for exactly the reasons you talked about.
Let's get to the mistake. Come on. Okay. Well, if you're going to invest in a
riskier company, at least have an investment thesis explanation of why you think that this
could be a good stock, and then reinvest into the company as the investment thesis is playing out.
As you see the improvements that you need to see as it's moving from riskier to safer,
then invest more money. I tried to safeguard myself from that. Then many companies I invested
especially in 2021, as my investment thesis is breaking and the stock is falling, then I start
ignoring my own rule and investing more money into it because it was just so darn cheap.
Yeah. The famed investor, Michael Tyson, is famous for saying,
everybody has a plan until the market punches them in the face.
Yeah. And the market punched me in the face and I said, yes, please, can I have another?
So, I put more money into a losing idea. Now, it did work out in one case. With Lemonade,
I was waiting to see improvements in the loss ratio before I invested more money.
I didn't actually do that. I invested more money before I saw that. Now, that has worked out okay
here recently, but some of the companies that I doubled down on in that 2022-2023 timeframe,
Some of them are actually zeros. I do this for a living and I invested in a company that went to
zero. So this is a perfect opportunity to roast you, but I've got a couple of those zeros to
match here. So I don't know how much I can really poke you about that. Yeah, but how many of those
did I recommend to you? Well, now you're giving me ammunition to work with here, but I'm not going
to. I think the point is, and the big thing that take away from me is, you have to adapt. And when
you fail to adapt, that's when you struggle. So, Dan, talk a little bit about that. Why it's so
important in light of when people decide to get better about something like investing,
a big stumbling block they run into that John managed to avoid.
You know, Jason, you might notice when John was talking about those zeros, I was being very quiet
because I have plenty of those zeros of my own. And it's embarrassing, but it's just something
that you have to get past. And, you know, I think that John's got a great philosophy when it comes
to the lack of new year's resolution, just constantly being in a state of trying to
self-improve because with resolutions, too many people are focused on the time element
with new years, you know, it's coming. And so like the end of December is like this great time to
sort of like slack off and do like exactly the opposite of whatever it is you're going to resolve
and it's like you're waiting for the apple to drop and then suddenly everything's going to be easier
and you're going to stick to the plan and everything is going to be perfect well it rarely
works out that way sure you start out strong you've got some discipline you've had plenty of
fun beforehand but now once it gets difficult inevitably something's going to go wrong
And at that point, if you tied so much to this idea of, I'm going to start on January 1st,
and it's going to last throughout the year, something went wrong. It's so easy just to say,
okay, well, that failed. I quit. I'm going back to my old behavior. There's no point in even
trying to stick to this plan. I think the real thing that you have to learn is you're just not
going to get to perfection. But the good news with investing is you don't have to. Just being right
more often than not, is such a huge driver for investing success. But the one thing you do have
to do, you have to be resilient. You have to accept you're not going to bat 1,000. You have
to accept that you're going to make mistakes. You're going to have embarrassing losses.
Don't let that make you give up entirely. Just start over, put it behind you, move on to the
next investment idea, and just keep going. Don't wait until 2027. Don't wait until the next New
year's resolution phase. Just get up off the mat and move forward. That's the best thing you can do.
Dan, one of the things that I've struggled with in the past, and the gym example is a good one,
is we don't say, I'm going to go to the gym three times a week. We say, I'm going to get in shape.
I'm going to lose 30 pounds. I'm going to make some money. I'm going to invest. I'm going to do
well. And we focus on the goal and then we stumble and we see the goal get further away and we give
up versus focusing on the process and the habits that we need to build. And I think to me, that's
really the common theme of, of, of all of this. I won't tell you guys how much money I gave to a
gym that I went to five times. That's another show. We'll talk about that one. I think it's
smart to have measurable goals, but at the same time, I also think that it's important to accept
that you're learning something from the process that you're going through,
even if it doesn't yield immediate success, it's going to be valuable experience somewhere down
the road. You quoted the investor, Mike Tyson, but let me quote the investor, Rocky Balboa.
It's not about how hard you hit. It's about how hard you get hit and keep moving forward.
Fantastic. Up next, we're going to move beyond those mistakes. We're going to talk about the
lessons that we've learned that have made us better and more consistent investors.
Unlike some of those resolutions, we hope you stay with us.
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Welcome back to Motley Fool Money. Dan, we had a little fun there at each other's expense,
but let's talk about more of those lessons that we've learned and how we can apply them to
investing in a way that it's something we can stick to. I think one lesson that I've learned
is that one of the hardest things for me to do with investing is buying a stock when I feel like
I'm a little late, too late. I've missed the trend on something and that it doesn't make
sense for me to try to get on board. Too often, I just say, to heck with it, I missed it. And then
the stock keeps going up. And then I'm just like, well, why did you give up on that? But I find
myself, you just have to work on it. Recently, I took a step in the right direction. I bought
shares of Dollar General, which is ticker DG. I found myself inside their stores more often than
ever expected to, because it's proving to be a good go-to for discounts on some items like
soft drinks at grocery stores. They're just really using pricing pressure. They're maintaining
ridiculous margins on them. Dollar General, much more attractive there. Dollar General stock has
not done well until recently. It did well during the 2022 bear market, but then it tanked.
2023 2024 wasn't able to sustain the growth targets that it had set but since late 2024
it's doubled off of its lows and i'm ticked that i didn't hone in on the turnaround more quickly
in the past that would have totally dissuaded me from buying but i'm going in the other direction
i'm giving it a shot this time recently bought some shares so this is almost like a couple weeks
ago the three of us were on together and we talked about alphabet and this is one that you saw the
opportunity to buy in the past at a time that it was down. And this is a lesson that I've learned
too. Um, and the thing is with dollar general, you know, that's a real turnaround. The business
was really, really struggling. And what I've learned is sometimes it's better being late to
the turnaround than rushing too quickly when the business is still struggling. Uh, John, what's,
what's a trick that you figured out that's helped you keep at it? Yeah, I've started to prioritize
investing in companies that I really love the brand or the business. I really just love the
company. I'm not exactly sure when it was. It was a couple of years ago. I just looked at my
portfolio and all of the companies, of course, that I'm invested in, I believe can go up,
but it wasn't necessarily a group of companies that I was in love with, not a group of companies
that I was excited about. And look, it's not a mathematical thing, but it is a psychological
thing. Let me frame this for a second. Of companies that are worth more than $10 billion,
four of the top five over the past 10 years are Nvidia, AMD, Celsius, and Shopify. Each one has
been down 30% or more multiple times. Three of them have been down 70% during their time of being
four of the top five best-performing stocks. Here's the thing. If you don't love that company,
if you don't love that business, when it drops that much, you start saying,
do I really want to own this? Is this something I really want to hold? And then you sell at
precisely the worst time. And so I've been prioritizing investing in companies that I
do believe have good upside, but that I also love and building my portfolio around brands that I
really want to hang on to through thick and thin. So it's not mathematical, it's psychological,
but there is a huge psychological component to investing.
It's such a great point, John, because when you believe in the business,
there are all these naysayers who are pushing the share price down. You just tell those naysayers
they're wrong, no matter how far the downturn goes. Now, obviously, it doesn't mean that you're
going to be right every time, but in the times when it doesn't work out, at least you don't
have the double head of saying, well, gee, I always hated that company. Why did I ever buy
shares in the first place. When it does rebound, like those stocks that you mentioned, it just
feels so much better, even better, to get those big gains after having endured such a long period
of hardship. One of the interesting things about this to me is that if you're starting with a
business first, it certainly helps, especially with something like regret minimization, which
is really hard. If you start with, I really like the business, like you said, it certainly helps
holding through the downturns. But my one caution is there's a thin line between really being
compelled and attracted to a business and then letting that become bias that makes it harder
for you to be objective when there are real struggles with the business. Yeah, that's
certainly, it's certainly a double-edged sword. We do need to maintain a sober assessment of the
company and its outlook, its ability to create value over the long term. If you are in love with
the company, it may be a little bit harder, but it does carry the benefit that we are talking about.
You're going to hold it and holding onto potential winners is so crucial for a long-term success in
a portfolio. Okay. So we've talked about a few things that we've done, but up next, I want each
of us to share a habit that we formed that's made a big difference in our own investing and personal
financial success. So stick with us for that.
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Whatever lies ahead, don't change your morning, let your morning change you.
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Welcome back to Motley Fool Money. To wrap up today's show, let's each share something
that we have figured out that really helps us stick to it over the long term. I'll go first,
guys. The one thing that's made a big difference for me is delaying my earnings reviews for my
core holdings. I have a lot of professional obligations to The Fool and its members
for a number of companies that I follow. But in general, I don't really dive deep into earnings
for most of my personal holdings until we're weeks on the other side of earnings season.
Now, the reason that I do this is I want to be completely on the other side of how the market
reacts and also what the talking heads are shouting so I can be a little bit more objective.
And also, here's a funny little part of it that is a big part of it psychologically for me.
It also helps me reduce how much importance I put on a single 90-day-ish period of results
for companies that I intend to hopefully own for multiple decades in many cases.
Jason, I just can't tell you how many times I've seen a stock.
It makes a big move after hours, after it releases its earnings.
Everybody talks about the reason why it's making the big move.
Then overnight happens and regular trading starts. Suddenly, the stock moves in completely
the other direction. It's zagged back. Everybody who was talking the previous night is scurrying
to try to figure out, okay, do I just change the headline from down to up? What explanation am I
going to find for why it's up when I gave such a great explanation for why it was down last night?
And it's just one of those things that your approach, it helps to avoid that whipsaw.
All that short-term madness plays out, and then you have the actual story in a longer-term
context, which is exactly what you want in the first place.
So, Jason, I'm curious.
For me, time just rushes by, and I think there's such value in your strategy of waiting to
review the report.
But I saw a company report this morning.
I could have sworn they just reported last week.
It turns out it's already been three months. How do you remember what's your prompt to go back
and how often do you do it? Okay. I'm probably not supposed to admit this, but I don't.
And what I've learned 15 years of actively researching and buying stocks, if I miss a
quarter, there's probably nothing that I missed is, is the hard cold reality. Part of my check
for that though, is I always read the 10 case. I read the annual report every year. If you know
what to look for, you don't have to read all two or 300 pages. There's maybe 25 pages that are
important to read in a company's annual report. And if you're doing that, you're probably not
going to miss anything important more than if you see the stock is up or down a lot since the last
time you really checked in. And then that's the signal to go pop the hood on the business, do
some research and find out what's going on. Wow. I love that. There's probably a lot more
value in what you just said than what I'm about to say, but a little habit that I've developed
is just being willing to dollar cost average. And so this means buying very small stakes over
a period of time rather than buying it all at once. Now there are studies out there. Mathematically,
it makes sense. If you're going to invest in a company, just invest, just invest what you're
going to invest. Dollar cost averaging doesn't necessarily make the most mathematical sense,
but sometimes I have a huge psychological hurdle, kind of going back to what Dan was saying with
Dollar General. Sometimes I have a hard time just moving from the sideline into buying a stock.
And I found that being willing to dollar cost average that first purchase just gets me in the
game. And now I've overcome that psychological hurdle. And now I'm ready to invest maybe that
fuller stake much sooner than I would have if I didn't have that first small little buy.
Yeah. Ansel Adams is famous for having said the best camera to use is the one that you have with
you. And when it comes to investing strategies, it doesn't matter what the perfect strategy is
if it doesn't fit. And this is a perfect example of that. The research says one thing,
but then there's what works in the real world. And being willing to, for me, both average up
and buy the dip, it works because if your focus is on the business first and last,
then you're going to have a better outcome most of the time. Dan?
So my turn to share, I am married and my wife and I, we largely keep our finances separate,
especially with our investments. But we do have one significant joint stock account that I mostly
manage. One interesting thing I have found is I do a much better job of leaving that account alone
than I do my own individual accounts. And that joint account has performed better as well.
It's good, I have found, to have kind of my own separate avenues for taking flyers on some
interesting trends, on some more speculative stocks. But that joint account has been really
the core portfolio. And I found that having that portfolio be more balanced, be less sensitive to
short-term moves, it's been a godsend, not just because it's done really well, but because it has
also been sort of that core that gives me the freedom to take a little bit more risk elsewhere
in the portfolio. As a married man, I can say that the judgment of my spouse is a wonderful
incentive to behave more appropriately as an investor. It's funny that you mentioned that.
In my personal experience, we have a taxable brokerage that I certainly meddle in less,
and that's carried over to the education investments for our son. The same thing
has applied. And it's funny how those accounts have done quite well just because of the incentives to
maybe behave a little bit more. In the same way, I'm really grateful for the Motley Fool's
disclosure policy. All three of us have to disclose our positions. And so everything we do
is happening somewhat publicly. And so that has been a huge booster for my own investment returns
is knowing that if I do something that's not capital F foolish, it's going to show. And if,
so if I make a trader move or a boneheaded mistake, yeah, it's going to be out there
publicly. And so it does just keep you a little bit more on focus, uh, hanging onto the good
investment principles. And so I like what you're saying, Dan, Dan, John, I really appreciate you
guys coming on, being willing to share your mistakes and how they've led to successes.
This has been a great show. Thank you, Jason. Have a great New Year.
Happy New Year to both of you and all of our listeners. Hopefully, you have a very successful
2026 and well, well beyond. Just remember, as always, people on the program may have interest
in the stocks they talk about, and The Motley Fool may have formal recommendations for or against,
so don't buy or sell stocks based solely on what you hear. All personal finance content follows
Motley Fool editorial standards and is not approved by advertisers. Advertisers are sponsored
content and provided for informational purposes only. To see our full advertising disclosure,
please check out our show notes. For Jon Quast, Dan Kaplinger,
the entire Motley Fool Money team, I'm Jason Hall. We'll see you tomorrow.
