When it comes to picking companies that can do great things for your portfolio, there are any number of criteria you can choose. Are they temporarily undervalued? Do they have a massive opportunity ahead? Are they Rule Breakers that are changing their industries, or the whole world? Well, Motley Fool co-founder David Gardner takes many things into account when he weighs investments, but in this Rule Breaker Investing podcast, he's picking a five-stock sampler of companies that are poised for gains because they are riding massive trends.

Special thanks to listener Paul Knaapen, who asked Gardner to choose the five Rule Breakers with the strongest tailwinds -- and you'll get to hear the investing story that led him to make the request, too. But then, you'll find out why Gardner thinks that NextEra Energy (NYSE:NEE), Roku (NASDAQ:ROKU), Teladoc (NYSE:TDOC), The Trade Desk (NASDAQ:TTD), and Waste Management (NYSE:WM) could power your portfolio upward over the long term.

To catch full episodes of all The Motley Fool's free podcasts, check out our podcast center. To get started investing, check out our quick-start guide to investing in stocks. A full transcript follows the video.

This video was recorded on Sept. 3, 2019.

David Gardner: One of my favorite assertions about the stock market and investing is that most people are confused about how to earn success. They believe it's about buying low and selling high. They think you need to have a target price; that the most important trait you can exhibit is sell discipline so that you can ensure you limit your losses. In a world too focused on the when of investing, I prefer the what of investing. I think what you buy matters most. It's hard to make 10 times your money on a stock if what you're buying never goes up 10 times in value, and many stocks on the market never do. If you get your what right, your when starts to matter less and less. 

This week on Rule Breaker Investing, I'm back to picking stocks again. We're focused on what. Particularly this time around, we're working to ensure our what, the five stocks I'll be picking up operates with big tailwinds. Big tailwinds, and thereby hangs a tail wind. On this week's Rule Breaker Investing

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Welcome back to Rule Breaker Investing! I don't know if it's the start of fall. In fact, I'm pretty sure it's not the start of fall. I think the autumnal equinox is somewhere on or around September 21st each year. But many of us here in the United States anyway think of it as Labor Day weekend, first weekend in September, last few days of August, seems like it's like that every year, and we all come back, school starts, and it feels like the first day of fall. We are taping on Tuesday, September 3rd. We always tape a day before we publish on Wednesdays. Here I am saying happy autumn! I hope many of you enjoyed our special Rule Breaker mailbag weekend extra. Yep, I insist on doing a mailbag every month. I insist on hearing from you and having a chance to have a conversation with you. My thanks again to my producer Rick Engdahl for taking some extra time out before a very busy holiday weekend and doing a whole extra podcast as a mailbag. 

I get many good stories and questions, and we can't possibly use them all any given month. Sometimes, I pin one up and I say, "I'm going to get back to that one." That happened a couple of months ago when the note that I'm about to share with you this week was sent. And I read it and I was like, "That's too long for a mailbag." Arguably, each month, our mailbags are quite long on their own every time anyway. They usually clock in somewhere right around an hour. This note on its own was a little bit too long for a mailbag, but darn, it sure did look like a great way to pick stocks, and a good theme for a five-stock sampler. That's why this week, I'm presenting to you Five Stocks With A Tailwind Blow

But as I said at the top, before we go into the stocks themselves, we have to do a little storytelling to see how we ended up with this tailwind theme. I like the play on words, because thereby hangs a tail, wind. Let's start it. 

The note came -- and, Paul, I apologize if I'm about to butcher your last name -- from Paul Knaapen. Paul, you dropped this note for a mailbag a couple of months ago. You said, "Hi, David. On Motley Fool Stock Advisor, team David's rule No. 2 is 'choose companies that will benefit from undeniable long-term trends.' I call these tailwinds. I request that you do a podcast picking your top five stocks with the strongest tailwinds." Now, that's the short of it, and that's what we're doing this week. But I liked the backstory, so here we go. He said, "This write-up of my story got so long, pitch it if you don't care." Well, I liked it, so here he goes. 

"My tailwind fetish came about over a 10-plus-year period where I was the president and CEO of a company whose revenues historically came predominantly from ad-sponsored weekly Catholic Church bulletins. Unless you're familiar with them, your first reaction is probably, 'What?' Rest assured, we are a real company with 4,000 print customers and between $50 million and $100 million of revenue. Not huge, but not miniature. Over those 10 years, the church bulletin business experienced some very special strong headwinds -- the priest scandal, decreasing allegiance of the next generation to religious institutions, the Great Recession, and decreasing affinity of small business to church bulletin advertising, on top of the general decline of ads on print. 

"Now, taking off my humility cap for a second, let me say that we had an excellent management team. Clearly, the tallest pygmy in our business, we outgrew all others over several decades. However, given the headwinds, about seven years ago, we started a fintech product," that would be financial technology, "to solicit and process church donations online. This business was a revelation to us as we pursued a business model that had tailwinds. First, we leveraged our large customer network to sign up churches. Then, lo and behold, after the first year, we signed a church. The revenues and margin grew annually as more church members participated online. And after year one, we had virtually no sales costs and no incremental software costs. Since subscribing to The Fool, I see that we were fortunate in this business model to touch on several of the aspects you are searching for. 

"Now, in the bulletin business, we were clearly the best and worked very hard to achieve a modest single-digit growth rate. In the online transaction world, we were mediocre among tougher competition, yet our existing customers grew 10% a year, and we were adding new customers constantly. What I learned is that in terms of creating shareholder value, an excellent management team facing strong headwinds can easily be outperformed by a mediocre team with strong tailwinds. 

"Then, about three years ago, I signed up for Stock Advisor and Rule Breakers in attempt to make my foolish investing habits more capital Foolish. Initially, I set out to do my own five-stock sampler, putting down $10,000 on each with an investing mantra of 'Stock Advisor and Rule Breakers will do the hard work of vetting the companies and management teams and I'll cherry pick companies with strong tailwinds. Thus, my choices will all be excellent management teams with strong tailwinds.'"

Now, here comes some of the math and some of what happened. "As with all novice learners, I was easily distracted and did not fully execute my mantra with these results. I picked Match Group, ticker MTCH, because I saw strong growth tailwinds from the next generation adding social media as a place to meet someone special to the classics from my day of bars and classrooms. I picked MercadoLibre, ticker MELI, because they had strong tailwinds from executing in a large developing market, something that Amazon, eBay, and PayPal proved in a developed market. I can justify Apple, ticker AAPL, having some tailwinds for moving into health-related wearables and other products; but the fact is, I was starting to falter from the mantra because I really picked Apple because it was trading back then at a ridiculously low 10X earnings per share. Then I picked Clean Energy, ticker CLNE, because I'm supportive of clean energy. I wanted to pick a small-cap. I thought oil prices going back to $100 a barrel would create tailwinds. So now, instead of looking for tailwinds, I'm making them up, deeming myself to be a prescient prognosticator of oil prices. Wrong! And, finally, despite that I hate retail stocks because I don't know who wins and why, I chose Under Armour, ticker UA, in part because The Fool pitched it as a retail and apps combo tech play. By looking at Nike and Adidas, I might have questioned whether there were any tailwinds at all.

"How did it all turn out? Well, three years later, Match Group was worth $50,000, a five-bagger. MercadoLibre was $36,000, and Apple was $21,000." You'll recall that each of these was a $10,000 investment. "Now, David, you really are hard on yourself when you pick a loser and sell something within three years because you take it like a man and just fess up to the loss. I was a little less manly and thought I should get credit for reinvesting my sale proceeds. So, when Clean Energy and Under Armour each lost about half their value, and I lost confidence in those companies and the reasons I picked them, I harvested my losses and reinvested that $10,000 of proceeds in Nvidia, ticker NVDA, seeing strong tailwinds there as fast, smart, well-interfaced chips become part of everything and need to be upgraded frequently. Nvidia was worth $13,000 on my measurement date. 

"To make it simple, we'll just add up the values. 50 + 36 + 21 + 13 = $120,000 on a $50,000 investment. I more than doubled my money in three years for about a 34% annualized return, which blew away the S&P 500. My main takeaways were these. One, David's mantra that while you will have losers, multi-baggers will more than offset a loss that is limited to the amount invested, rings true. Two, what if I had stuck to my tailwind guns and picked Nvidia and some other strong tailwind stock three years ago? Undoubtedly, I would have done much better. Three, I need to do more of this, so I've picked a few other stocks on my own and joined Supernova

"In conclusion, thanks for helping me have a fun time learning. You have met your mission in my case, as you have made me a smarter, happier, and richer investor. Thanks, Paul."

Also known as, I believe this would be, Paul, your screen name in our community, you chose TailwindBlow. That's why this week, I'm honored and enthusiastic to share Five Stocks With A Tailwind Blow. As I said earlier, thereby hangs a tale. You've now heard the tale. So, here comes the tailwind. 

Alright, stock No. 1 this week. We're going to do this alphabetically by company name, as is our habit. We're going to go all the way down to the letter N. Now, that doesn't mean I can't find any companies, any stocks A through M, with tailwinds. In fact, Paul just gave a few pretty good ones. Match Group I easily could have included on this list. It has a massive tailwind. That in part explains the tremendous performance of that stock. I still like it today. I've recommended it in a number of our past five-stock samplers. But I feel like that's too easy. So, let's be a little less obvious. Let's look a little harder. Maybe find a few companies on this list of five that not as many people know. 

Here at the letter N, we find ourselves with NextEra Energy, ticker NEE. Now, on the face of it, we all should know NextEra Energy. Don't you? Wait, I'm sorry! You don't? Well, in this age of clean energy, NextEra is literally the world leader in generating electricity from wind and solar. You didn't know NextEra Energy, which has a market cap of over $100 billion and has been a wonderful out-performer, and you'd never heard of this Rule Breaker. Well, I know some of you have. I'm having some fun there. 

NextEra Energy has put together an initial base business, Florida Power and Light, which is one of the largest utilities in the country, occupying a big part of Florida. But it used that base in order then to launch its NextEra Energy Group, which is all the renewables. It's invested tens of billions of dollars in recent years in order to become the worldwide leader. 

Now, for each of these stocks, I'll mention where the stock is, where it's been, and a few things about what I like about the company, including, of course, its tailwind. NextEra Energy trades right now as we talk at about $224 a share. That's a $106 billion market cap. I first picked it in Motley Fool Rule Breakers on January 24th of this year, so just eight months ago now. It was at about $177 then, so it's up about 25% in these eight months. Not bad vs. the stock market's 12%. We're ahead of the market. So, there are a few stats on NextEra Energy. If you're a Rule Breakers member, you've probably been holding this stock for months. But for my listeners here, you might be hearing about it for the first time. I think everybody should know this company. This is one of the best companies in America. It's routinely lauded as one of America's top employers. 

What do we like about this company? Why do I like it for the next three-plus years? That's how we'll be scoring the sampler, per normal. Over the next three years, we'll be looking back and see how we do with these five stocks. Yes, clean energy is the tailwind. It is a massive tailwind. While it's still a minority of the energy that we get on this earth, which still comes from things like oil, although natural gas is creeping up, and NextEra Energy plays well with natural gas as well, this is a company that has been investing tens of billions of dollars to build its capacity in the following three things: solar, which is a much bigger performer than wind, which is still a meaningful performer, but the third capacity they're building is storage, because, of course, part of this form of energy is, you need to be good at storing it. So, it's still early days, isn't it? For solar and wind. Solar feels to me like the ultimate form of energy we'll be using on this planet for as long as we're around. It's taken us a long time to get there and there's still a lot of technological improvements that we need in things like storage to make it work for everybody. But it seems blindingly obvious, I guess, pun intended, don't stare at the sun. It seems blindingly obvious to me that, looking backwards from the future, we'll say the sun made so much sense that it would be the biggest form of energy generation for us on Earth. And right now, you have an opportunity to buy the company that is the worldwide leader in that, and it's still early days. 

One other thing I'll point out before we move on to stock No. 2 is that this is a company that is a quote "dividend champion." That's a precious list of a small number of companies that have raised their dividend every single one of the past 25 years. A lot of people who are looking for income these days will be happy to note that the company pays about a 2.5% dividend yield. If you buy the stock over the succeeding year, you'll be paid back about 2.5% of whatever you invested in it in the form of dividends. Now, that can float up and down a little bit. Of course, the main reason I'm excited about this company is not just for the dividends, but for the capital appreciation. This has been a market-beating performer for meaningful amounts of time, and I'm counting on it to beat the market over the next three years, too. 

So, there we go. Five Stocks With A Tailwind Blow, stock No. 1, NextEra Energy.

Alright, stock No. 2. Now, before I present this company name, which starts with the letter R, I just want to speak about the tailwind. Have you noticed that a fair number of streaming services exist today with even more coming online for your entertainment needs? Have you noticed that? There's been a little company called Netflix you might have heard of which has been one of the best stocks you could have owned over the last 15 years and remains a big holding and one that we like a lot even though it's down some in recent months. In part, it's down because of the perception that Disney with its new streaming service Disney+ coming online in November, that Disney pulls content off of Netflix and weakens Netflix's offering and creates more competition. Of course, I like them all. They're all pretty affordable, especially relative to where my cable bill was about five or six years ago. But it's not just about Netflix, HBO, Amazon Prime and Disney+ and Hulu, oh, and also NBC Universal, CBS is coming out with -- you know, The Motley Fool should probably come out with our own streaming content and have a budget. I don't know if we'll actually go there or not. But the point is, everybody and his pal Joey are coming out these days with a streaming service. This company that starts with the letter R, I hope you know of it -- if you're a regular listener or a Rule Breakers member, you may even love this company. 

The next one, stock No. 2, is Roku, ticker ROKU, the company name. As we tape, the stock's at about $156 a share. That gives Roku a $17 billion market cap. Now, that market cap is way higher than just a year ago. I picked this stock first for Rule Breakers March 14th of this year, so this is another 2019 pick that I'm sharing with you in this five-stock sampler. The stock was at $61.82 that day. You may have heard me mention just a few seconds ago that it's at $156 today. So, yeah, it's up 145% since March. The market up only 5%. It's rocked the world, Roku, as a stock. 

You might be wondering, "You'd buy it now at a $17 billion market cap after it's more than tripled from where it was a year ago?" The answer is yes. When we find winners, we usually hold on to them and we like to add to them when possible. We've been doing so very well. We're looking at the future, not the past. Not where the stock was. We're looking at the future powered by a big tailwind blow. Because the entire entertainment world is in the process of moving to the internet to offer its content. Roku, that little $30 box, is beautifully positioned as an agnostic player, ready to host all of these companies' streaming services. The beauty of the Roku business model is that they make a little bit of money when you buy a Roku box. They could probably even reduce that further and spread the world with even cheaper Roku boxes. But what they've already done has millions of people using Roku as their on-ramp to streaming. Really, this is an advertising play, far more than a $30 hardware purchase. Lots of collecting of data, seeing what you're clicking on, what other people are, serving you up ads that would make sense for you, and, by the way, getting a cut of subscriptions. When people buy something like a subscription, or a one-off purchase off their Roku, they get a sliver of that revenue from the content provider. This is a brilliantly positioned company. There are few bigger tailwinds that I see looking around. That in part explains why Roku has so dramatically appreciated in just the last year. And yet, we're never about one year with our investing at The Motley Fool. I certainly don't spend much time looking backwards with Rule Breaker Investing. It's a volatile stock. I don't know, maybe it'll sell off here and lose a third of its value by January. I have no idea in the short term. But I know one thing: we're going to do well when we find these kinds of companies with big tailwinds, Paul. Buy and hold them. Roku is stock No. 2. 

Alright, stock No. 3, and it is Teladoc, ticker TDOC. Teladoc's stock as we speak is trading around $56 a share. It's a $4 billion market cap. By the way, market cap, yeah, the game show, coming later this month. I first picked Teladoc for Rule Breakers members on November 22nd, 2017. That sounds like it was right around Thanksgiving. Well, let's give thanks, because ever since then, Teladoc is up 70%; the market up 17%. So, from $34 to $56. It's been a wonderful, still under two-year run for this emergent company. 

Now, what's the tailwind that you or I might have identified that seems to me sits behind and powers Teladoc and many other companies? Well, trick question because I think I see two tailwinds that I want to identify. The first is cheaper healthcare. There is so much attention being paid, especially in the U.S. today, on how to make healthcare cheaper. Anybody who can bring something that would make it cheaper and easier seems to me very well positioned. That's tailwind No. 1 that's going to benefit and is benefiting Teladoc. No. 2, of course, is video conferencing. If you think about a recent IPO like Zoom, a very successful though still emergent, early company. You might be Zooming yourself these days. I do it quite a lot. There are other companies out there, too. BlueJeans or just Skype. There are a lot of different apps that we're all using to video conference. We're all increasingly getting familiar and comfortable with -- well, when it just works, anyway -- video conferencing. So, when you put video conferencing together with cheaper healthcare, that sounds a little bit like telemedicine to me. So, I guess it's not a big surprise that Teladoc in its most recent quarter had grown at sales 38% higher over the year before. It's been growing strongly and steadily. By the way, a good sign that you've found a stock with a tailwind blow is that kind of sales growth. After all, tailwinds should lead to well above average sales growth. Now, not every company can turn sales growth into profits. You should always be suspect of companies that haven't done it. By the way, Teladoc is one of them. Teladoc is not making money, yet. At present, it is a money-losing operation. But it is the Rule Breaker. It is the company that got out first at scale with a brand that we recognize. For a lot of you, you might have Teladoc as one of your corporate benefits today. Increasingly, that's how people are finding telemedicine, through their corporate employer, who might make it a benefit for you. By the way, if you don't have that benefit at work, I would suggest that you go talk to your benefits person or the CEO of the company, or maybe that's you, and consider giving that as a benefit to your employees. It certainly would help our stock, TDOC. But I think it'll also help your employees. We don't always have the time to take Junior down to the doctor. Sometimes we don't even need to do that. We could get a quick, easy answer via video conferencing. By the way, you can do it over the desktop or the phone. Teladoc is working increasingly to make this as accessible as possible for as many people as possible. I should mention, by the way, that the stock took a hit in December when it was revealed that at the time, its chief operating officer was having an affair with a woman 24 years his junior, which may or may not have included some stock tips about when she should sell shares of the company. That didn't go down very well. I didn't like to hear that. I know the market didn't, either. That gentlemen resigned effective January 1st, 2019, so, starting the year off right for shareholders. Teladoc has been bouncing up and down a little bit since. But, of course, we're not about what already happened. We're about what's going to happen next. This looks like, to me, a stock with a tailwind blow. 

Alright, stock No. 4, one of our stellar, truly stellar performers over the last couple of years. If you like the performance you've heard from Roku, or from Teladoc, or even NextEra Energy, up 25% just this year, you're going to love The Trade Desk, ticker TTD. This is a stock I first picked on February 22nd, 2017. That's about two and a half years ago. It was at $34.30 then. Today, it's risen from $34 to $236. It's up 617%. The market's been pretty good, up 30% since then, but we have absolutely destroyed the market, and on its own, it would have pulled any other group of four stocks up and beaten the market over that time. I'm really happy that not only did we recommend it to Rule Breakers members, but we then rerecommended it and added it, even though it was higher, and we're all doing pretty well in this company. But that was then. This is now. This is a company whose tailwind should continue to propel The Trade Desk forward for the foreseeable future. The stock, by the way, I already mentioned, is $236 as we record. That's a market cap of about $11.25 billion. 

So, what's the tailwind behind The Trade Desk? Well, in a way, it's an industry that you and I can recognize even if we don't know that much about it. It's the advertising industry. Specifically, it's the growth of digital advertising. Earlier, I thanked NetSuite, our sponsor. Somebody placed that ad. Now, we are a seller in this buyer and seller marketplace here at The Motley Fool Rule Breaker Investing or Motley Fool Money, our various podcasts. We're sellers. We have content. You come for it. We hope as many people will come as possible. Tell your friends about Motley Fool podcasts. Thank you very much! The buyers are the people who want to pay dollars to be featured. The buyer in this case is NetSuite. Now, in an earlier era of technology here in America, probably your country, too, wherever you live, the world of advertising was simpler. A ton of print, some TV and radio. You probably would hire an ad agency if you were a bigger scale thing. So, you'd have a middleman who was working with you to place you in the right magazine or the right Super Bowl ad, or whatever it is. It was a simpler world. These days, the world has gotten a lot more complicated. You might have noticed there's this thing called the internets. The internets has a lot of ad space. There is huge complexity to figuring out which page should have an ad, who's reading that page, and what the ad should be. If you're trying to manage ad campaigns these days, it's incredibly complex to figure out where you should place your ads. Should it be right there in a Facebook page? Or should it be a bus wrap in Buffalo? Or both? Well, what I really appreciate about The Trade Desk is, it has a leadership position creating a platform where buyers meet sellers more directly, as opposed to traditionally just going through an ad firm. 

These days, every day, even as I speak, people are bidding for ad placements using this online platform. It's a brilliant business model. Started by two co-founders, the CTO and the CEO, a wonderful partnership, the CEO being Jeff Green today, 10 years ago. And here they are with an $11 billion market cap and a big, winning stock. But as I look forward, I see that they're beautifully positioned for more and more advertising to happen in more and more places all around the internet and offline, too, and for people in some cases to make it cheaper, cut out the middleman, and bid directly for ads. By the way, that platform really helps buyers, the advertisers, reduce their costs by making suggestions and helping them make smarter decisions for their ad campaigns. No surprise then, that in its most recent quarter, The Trade Desk had top line growth of 43%. By the way, the company has $200 billion of cash and no debt. And for 23 straight quarters, it's announced its customer retention rate at 95% or higher. They don't lose customers who are using this platform. A very evident tailwind and another one of those companies -- we find them here at Rule Breaker Investing and Motley Fool Rule Breakers, we're focused on finding the top dogs and first movers in important emerging industries. That's trait No. 1 of our approach that we've practiced for 20-plus years now. Trade Desk is just the most recent great example of that. So, that's stock No. 4. 

And finally this week, stock No. 5. After companies like Roku and Teladoc and The Trade Desk, this company is going to sound awfully humdrum. The ticker symbol is WM. The company name is Waste Management. You probably can picture that yellow and green W and M logo. If you're in the United States of America or Canada, it's probably driving around your neighborhood from time to time, picking up trash, distributing it to their centers. This company has the largest network of landfills in the U.S. A great competitive moat for the business. 252 landfills, the No. 1 player. Also, hundreds of transfer stations. The business of Waste Management is critically important to a growing society, especially one increasingly conscious about recycling and making the best decisions about the things that we throw away. I love that this company is the leader. We're finding, again, the leader doing something really important in this world. What's the tailwind? The growth of excess. More stuff every year. More stuff to throw away. A growing population in the U.S. and Canada with global potential. Waste Management, also a company paying a nice dividend. 

What you have here is a company that stabilizes this five-stock sampler. We're taking some big risks with some stocks that have already run up a lot, even though they're still smaller companies. But with my two bookends -- NextEra Energy, the $100 billion-plus company, and then Waste Management, which, by the way, tips the scales at a $50 market cap -- I really like this five-stock sampler. I should mention, Waste Management is also a recent pick of mine for Stock Advisor. I picked it on June 20th of this year at $116.06. Well, it's up to $119 right now. It's up about 3%. That is against a market down 1%. It's been a market-beater. Of course, don't expect a company like NextEra Energy or Waste Management to ring up triple digits for us in the three years ahead, but do expect them to be stable companies. If, in fact, it's a weak market at points the next few years, we might be particularly grateful that we added these companies to our five-stock sampler. 

So, there you have it. Five Stocks With A Tailwind Blow: NextEra Energy, Roku, Teladoc, The Trade Desk, and Waste Management. Yep, we'll be typing this into the little spreadsheet we keep here at Fool HQ and checking back with these companies one, two, and three years hence. 

Speaking of checking back, next week on Rule Breaker Investing, it will be one of our Reviewapalooza shows, so I will be looking back at stocks picked in these samplers one, two, or three years ago. We'll be doing a few of them. That's why it's Reviewapalooza. Not just one. I think we'll be doing three. It's always an exciting show for me to do because we get to get a lot of different company names in play, see how the performance has been, and what we can learn. 

In the meantime, whether fall started yesterday or on September 21st, I hope it starts well for you. Fool on!

As always, people on this 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. Learn more about Rule Breaker Investing at rbi.fool.com.