Will Barton on High Dividend Opportunities

23 Feb 2026 · 49 min · 17 chapters

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Podcast Episode Notes: Will Barton on High Dividend Opportunities

Podcast Title

Investing Experts Podcast Description Seeking Alpha's deep dive stock analysis and topical takes on the market with top analysts and industry experts.

Episode Title

Will Barton on High Dividend Opportunities Episode Description Will Barton from High Dividend Opportunities shares insights on income investing strategies, focusing on high dividend stocks, fixed income, and various investment vehicles.

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Key Topics Discussed

  1. High Dividend Strategies (0:20)
  2. Focus on replacing lost income after retirement with high-yield investments (8% to 10% yield).
  3. Goal: Provide monthly cash flow without needing to sell shares.
  1. Personal Investment Journey (7:15)
  2. Will's transition from a traditional job to managing personal investments led him to join High Dividend Opportunities in 2018.
  3. Emphasizes the importance of building a dividend income portfolio to cover living expenses.
  1. Income Method Explained (12:00)
  2. Income Method involves constructing a portfolio focused on generating consistent cash flow.
  3. Importance of reinvesting cash flow to combat inflation and provide living expenses.
  1. Fixed Income vs. Equity Portfolios (15:00)
  2. Discussion on the differences and balance between fixed income (bonds, preferred stocks) and equities (REITs, stocks).
  3. Emphasis on maintaining a diversified portfolio to mitigate risks.
  1. ETFs vs. CEFs (15:30)
  2. Closed-End Funds (CEFs) provide opportunities to buy at discounts during market panic, unlike ETFs which trade close to net asset value (NAV).
  1. AGNC Preferred Stock (17:30)
  2. Overview of AGNC's preferred stock and its performance.
  3. Discussion of risk factors and stable income generation.
  1. Earnings and Cash Flow Statements (21:30)
  2. Importance of analyzing company earnings and cash flow to assess dividend sustainability.
  1. Understanding Dividend Cuts (24:40)
  2. Risks of unexpected dividend cuts and the necessity of diversification to mitigate impact.
  1. Retirement Planning Essentials (28:00)
  2. Key considerations for retirement planning, including lifestyle and financial flexibility.
  3. Importance of planning for both financial and personal time management post-retirement.
  1. Challenges in Income Investing (41:00)
  2. Yield chasing can be detrimental; maintaining focus on sustainable income is crucial.
  3. Need for a robust tracking system to monitor performance and income generation.

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Key Takeaways

  • Income Stability: Building a portfolio that provides reliable cash flow is essential, particularly for retirees.
  • Diversification: Maintaining a diversified portfolio across different sectors minimizes risk from unexpected events.
  • Education: Investors should understand their investments deeply and avoid panic selling during market downturns.
  • Planning: Have a clear retirement plan that includes both financial and personal time management considerations.

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Investment Philosophy

  • Focus on dividends as a primary source of return rather than share price movements.
  • Stay disciplined and consistent with the income method strategy, regardless of market conditions.

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Final Thoughts from Will Barton

  • Emphasizes the importance of ongoing education in investing and the goal of achieving financial independence for individuals.
  • Encourages listeners to engage with the High Dividend Opportunities community for resources and support.

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Additional Resources

  • For more insights on income investing, listeners can check out High Dividend Opportunities and consider joining for further support and resources.

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Disclaimer: The information presented in this episode is intended for educational purposes only and should not be considered investment advice. Always consult a licensed professional before making any investment decisions.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

Tap a time to open that second in VO

The Income Investing Strategy

0:45 to 3:20

Will shares insights on replacing monthly income through high-yield investments.

“But where this really comes from is a foundational belief in investing.”

Personal Investing Journey

3:20 to 6:40

Will discusses his career change and journey towards dividend income investment.

“He brought me on at HDL and I've been working for them ever since.”

Formulating the Income Method

6:40 to 10:00

An explanation of how the income method was developed and its principles.

“And everything we do is approached with that broad plan of, okay, this is the income method.”

Market Dynamics and Investment Strategies

10:00 to 13:20

Will elaborates on adapting to market conditions and identifying investment opportunities.

“We have to work a little bit harder to find them, but there are still good opportunities there.”

Portfolio Management Techniques

13:20 to 14:00

Discussion on how to balance different investments within a portfolio.

“And so, you know, we put all those in our core two bucket.”

Understanding Preferred Portfolios and CEFs

14:00 to 16:40

Learn the advantages of preferred portfolios and closed-end funds (CEFs) over traditional ETFs.

“And then on our preferred portfolio, we keep that separate because like I said, we have 50 holdings in it now.”

Evaluating Investment Opportunities in 2023

16:40 to 19:00

Discover insights on tangible assets and investment strategies for the current year.

“And we're kind of opportunistic in that respect.”

The Importance of Fundamentals in Investing

19:00 to 23:40

Understand why focusing on company fundamentals is crucial for long-term investment success.

“You know, investors are starting to realize that valuation does matter.”

Dealing with Dividend Cuts: A Case Study

23:40 to 27:40

Examine how to handle unexpected dividend cuts and learn from specific investment experiences.

“And that diminishes to the point where you get down to 10, 15, 20 % of your total return is explained by whatever the price did and everything else is the dividend that you received.”

Retirement Planning Insights

27:40 to 28:00

Gain valuable tips on planning for retirement and ensuring financial security during retirement.

“Sometimes you're looking back at it in history going, you shouldn't be surprised.”
Show all 17 chapters

Preparing for Retirement: Beyond the Nest Egg

28:00 to 29:28

Learn the importance of planning your time and activities for retirement beyond just financial savings.

“Would you say that there are some mistakes that you see pretty often?”

Flexibility in Budgeting and Investing

29:28 to 31:46

Discover strategies for flexible budgeting that can help you navigate financial uncertainties.

“There are certainly a lot of people find pleasure in managing their portfolios.”

Understanding Dividend Investing

31:46 to 36:07

Get insights into the challenges of tracking dividend investments and the importance of long-term focus.

“flexibility in your finances is, in my opinion, always the best possible thing that you can have.”

The Value of Consistent Investment Strategies

36:07 to 40:53

Learn why maintaining a consistent investment strategy is crucial during market volatility.

“And so I think there's a moment that clicks for people.”

Reacting to Market Changes: The Tariff Tantrum

40:53 to 42:00

Explore how different investment strategies perform during market changes and the importance of patience.

“And that's one of the reasons why we've really focused on the education side.”

Investment Strategies and Market Reactions

42:00 to 45:28

Explore how different crises impact investment strategies and the importance of a steady approach to dividend investing.

“And that's kind of a long time to come over to us.”

Financial Independence through Education

47:21 to 49:10

Understand the philosophy of treating your investment portfolio like a business and the focus on educational resources.

“And so that helps get you a really good idea of, you know, how much income your portfolio is producing.”
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Transcript

Automatic transcript. May contain errors.

0:10Will Barton:Will Barton from High Dividend Opportunities. It's great to have you back on Investing Experts. Welcome back. Oh, well, thank you for having me. Share with our audience what you guys focus on at High Dividend Opportunities. Obviously, dividends are a part of the picture, but specifically how you approach that part of the income investing strategy and market. And then share your own, if you would, investing experience or what brought you together with the other analysts at High Dividend Opportunities. That'd be awesome. Well, our focus at High Dividend Opportunities is obviously the high dividends, right?

0:46But where this really comes from is a foundational belief in investing. When you reach retirement, you don't need to have a million dollars, two million dollars. You know, obviously we'd all love to have a billion dollars, but what you're losing when you retire is a monthly income. You're missing that paycheck that was coming in every other week, once a month or whatever it was. And our goal is to replace that income with the nest egg that you've built up over the years. And so our focus is on investments that are providing you with a high yield right now and are going to produce enough cash flow into your portfolio so that you can withdraw the income from it every month without having to sell a single share.

1:35We all know about the dot-com crash, the great financial crisis. The stock market goes through large swings. If you're in your investing years and you're just adding money in, that's no big deal. You shrug it off, you move on, you know it's going to recover eventually, you buy more when you can. If you're retired and you're taking money out every single month, it can be a very big issue for you. And so our goal is what we call the income method, where you have a portfolio that's yielding 8 % to 10%, which is consistent with the market's long-term returns. and you're getting most of your total return in cash flow every single month.

2:19You can then reinvest a portion of that cash flow to keep your income growing, keeping pace with inflation, and you can withdraw what you need and take it out and use it for your living expenses. And you never have to sell a single share. I started getting involved with HDO back in 2018. 2018. And I was at a point in my life where I left a job. I had left my nice cubicle career that was paying me a decent salary. And I jumped into the wild unknown of saying, you know, I don't want to do this anymore. I have enough money. I'm going to be able to take care of my bills. And I was just managing my own investments.

3:08And I was kind of following along this trend of, let me build up my dividend income. Let me get it enough that it's covering my bills so that I don't have to sell shares. And that's when I met Rita. He brought me on at HDL and I've been working for them ever since. My investing career started like most people. I had a few thousand dollars. I put it in an account. It was a lot of money to me at the time. And I'd put it in and I'd get scared and I'd, you know, oh no, let me sell, take my wins before I go. Or I'd see something fall a lot and it was, you know, very stressful for me. Well, me being me, I kind of got the idea early on of, well, why don't I just get these dividends?

3:55Let me try out these stocks. Back throughout the early 2000s, it was let's buy something that's going to pay me. Then life started happening. I started working. I had a career. I wasn't watching my investments like a hawk. I was just like everybody else, just let's throw the money in. And I let it build up and I kind of really trended towards this idea of, hey, I don't have to sell. For me, a very foundational moment was the great financial crisis. I was a real estate guy. I worked in real estate. I lost my job like many other people who worked in real estate. I was going through a divorce at the time.

4:37I totally ignored my investment portfolio. And it went through a huge swing because I was invested in REITs. I was invested in utilities. I was invested in all sorts of companies that were very dependent on land assets and using debt. But life was happening. And so I didn't pay attention to my investment account. And when it came up the other side, it's probably a good thing that I wasn't paying attention to it because if I had, I might've done something stupid and I might've sold everything. I learned that lesson that, hey, it's going to come back. Your dividends are going to keep coming in. Stuff goes through hard times.

5:16It comes out. Usually when it comes out, the other side is stronger than it was before. And so for me personally, that was really a transformational moment of where I realized, you know, you don't have to be watching over the stock market every minute. You don't have to be trying to sell high and catch the waves and try to predict what's going to happen in the world tomorrow because none of us do. You know, we can't predict what's happening in our personal lives tomorrow, let alone what's happening in the rest of the world. And so, you know, over the years, I've worked very closely with Rita and we worked on really formalizing the income method, which is kind of a combination of everybody on the team.

6:02Um, you know, everybody's experience all combined. We started laying it out with a set of rules, you know, things that you do want to do, things that you don't want to do. The arena is a big fan of diversification, having no more than two to 3 % in any one particular investment. Uh, a lesson that I learned the hard way. He was right. We created a very comprehensive plan so that we're not just out there investing willy nilly. We know what we're investing in. We know why this stock is good for our portfolio. We know what it's doing for us right now and what we hope it's going to do in the future.

6:42And everything we do is approached with that broad plan of, okay, this is the income method. Our goal is 8 % to 10 % current yield and to make sure that we keep our income growing every single year. Now, how do we go in the market and achieve those goals?

6:58Will Barton:I should say at the outset, by the way, for those that are familiar with Seeking Alpha, you're probably very familiar with High Dividend Opportunities and Will Barton and Rita Morwa. It's our number one income investing group. So a lot to benefit from that service and from the strategy. When you are talking about the yield that you're concentrating on, what would you say in terms of contextualizing that? Like in terms of, let's say, with the rate cuts going up or down, are there things that you're paying more attention to or that you have more in focus? When you're looking at REITs, is there something that you're doing something slightly differently than you would a regular stock?

7:43Will Barton:Maybe if you could offer us some context vis-a-vis the yield conversation, I think that might be helpful. Yeah. And when we say, you know, 8 % to 10 % average yields, you know, that number is derived because we believe that's a reasonable amount of return that you can expect to get out of the stock market over the long term. you know within any particular individual investment we're going to have some more variety you know we a yield means nothing if the company isn't going to be able to continue paying it and so we construct our portfolio and we adapt with the times you know based on what's happening with overall market you know for example interest rates have gone up a lot and we started seeing a lot of fixed income opportunities that were in that 8 % to 10 % range.

8:33Fixed income like bonds, preferred equity, which pays a predetermined amount every single quarter. And so we've been loading up on those because A, they're safer, right? Preferred has to be paid before the common stock gets paid. Bonds have to be paid. Otherwise, the company's going bankrupt. And so you have a very stable and secure amount of cash flow that's coming from it, which suits our needs and our goals that we discussed before. And so with interest rates going higher, it has the effect of making everything that is based on cash flow cheaper. Because if you can go invest, if you can go buy U.S.

9:17Treasuries for, you know, 4%, well, you need you want your fixed income to be yielding more than that. Otherwise, just buy treasuries. They're more direct competitors in terms of what they do for your portfolio. And over the last two, three years, we've really focused on the preferred equities in particular. We built up a portfolio of over 50 preferreds. And that was in part driven by our overall goal of making sure our income is stable. And also because it was just a great opportunity to lock these yields in before interest rates come back down. And we've kind of seen that, you know, the opportunities are less today than they were last year.

10:00We have to work a little bit harder to find them, but there are still good opportunities there. And turning to the second part of your question, when we're looking at company to company, like if we're looking at a REIT compared to like Verizon is a company that we bought late last year. With something like a REIT, you're looking at an investment where a very large portion of the total return is going to come from the dividends. Price upside is going to be limited because they're required by tax law to distribute 90 % of their taxable income. As a consequence of that, they're not retaining the capital.

10:39They're giving it to you. So when you're looking at those investments, you're really looking at what's the income? Is it sustainable? Is it going to be variable? example, when we talk about mortgage REITs like AGNC, for example, where they're buying agency mortgage-backed securities, we know that business model is going to have quite a bit of variation in the income, right? They're making an investment. They're sending you the profits. The investment isn't going to have the same return every single year. There will be periods where it's really good, periods where it's a little bit lower, it will generally always be high in terms of yield.

11:23It'll always be in that used to be 8 % to 10 % range. Recently, they've been in that 13 % to 15 % range. So we're always looking to balance out those opportunities with the opportunities like a Verizon where the market just panicked, the yield is high because the market thinks, oh, no, something's going wrong. And you just have a good deal with a company that is going to have the capability of growing their price consistently over time. And so that provides you a nice little balance where you're getting your income, but you also have those holdings in the portfolio that are also going up in price and providing you a little bit more capital to work with in the future.

12:02Will Barton:How do you allocate or are there different portfolios for different time horizons. How do you think about the portfolio and the allocation factors, questions? Our portfolio really has four parts to it. We have two parts that are more on the equity side and two parts that are on the fixed income side. On the equity side, we have our core one portfolio, which is funds. We have a strong bias towards closed-end funds, although we do have a couple of ETFs in there. And those are our source of diversification. Funds allow us to invest in sectors where you don't have a lot of dividends. For example, sectors like commodities or the oil majors, and also some that are just correlated with the S &P 500.

12:52So we get exposure to that upside and the closed end funds will convert it into cashflow for us. And then we have our core two, which is our individual picks, you know, those are going to be stocks that are more like REITs, MLPs, usually they're companies that are going to be producing high amounts of cash flow consistently. Every once in a while we have, you know, the Verizons of the world where we can go out and we can buy a corporation that is just, is paying a high yield because the price is low. And so, you know, we put all those in our core two bucket. And then on the fixed income side, we have our maturity ladder, which is mostly baby bonds.

13:35We do have some traditional bonds and some term preferred. And the idea behind that is we set it up in a maturity ladder structure so that every year you have some that are scheduled to mature. and that provides your portfolio with lump sums of income as those securities mature consistently over time, helps protect against interest rate risk because you're getting that capital back on a schedule and being able to redeploy it at whatever the current market rate is. And then on our preferred portfolio, we keep that separate because like I said, we have 50 holdings in it now. When HGO first started, there was four.

14:14We've grown it up over time because preferred equity takes on a little bit more risk than bonds, but you get that fixed, you know, predictable return or not return, but rather cashflow that's coming into your portfolio on a regular basis. And so it really provides a good base of income for you to start from when you're making the more, you know, the higher yielding, the more speculative investments, where you're swinging for the fences and you're dealing with the risks of the stock market could crash, the economy could crash, things can go downhill.

14:51Will Barton:What else would you say why you favor CEFs over ETFs? Like when and why? The great thing about CEFs is that they trade based on the market forces. Rita loves to talk about one of the annual letters that Warren Buffett wrote for Berkshire. I can't remember exactly what year it was, but in a letter he talks about how the liquidity of the market should always be a benefit to a patient investor. Because it's like your neighbor. If your neighbor is shouting at you every single day, hey, I'll sell you my farm for X dollars, you can decide to sell it. If you think he shouted a good price, you could decide to hold your farm.

15:38If he shouts a bad price, you can decide to buy his farm if he shouts a price low enough for you. And that's kind of how CEFs are, right? Their shares trade freely in the market, but their net asset value is based on their actual underlying performance. That's what the managers are managing. And so there's a lot of opportunities when the market gets very pessimistic, when people get panicked, they'll be selling it at large discounts. And if you can buy cheaper, you're going to have a higher total return. And so there's a lot of opportunities among CEFs to buy into the fear and be able to take advantage of that neighbor who is just shouting prices at you.

16:29You know, when they shout a good price, go buy it. If it gets expensive, back off a little bit, hold on to it, sell it if it gets high enough. You know, we had one this year that we exited last month because it just got too expensive for us. And we're kind of opportunistic in that respect. You know, the yield starts getting down to 5-6%. It's not achieving our goals anymore. And, okay, if you guys want it for that, it's yours. And that's kind of how we approach that. And CES provide that opportunity more than ETFs do. ETFs always trade very close to now, usually within pennies, which has its benefits.

17:13But it also means that you're always paying what is currently a fair price. We like to buy things for unfair prices.

17:20Will Barton:And what would you say or would you be willing to share an example of a preferred from last year that looked really good, that's done really well, and maybe one that you've looked at this year, like to your point that they don't look as good this year, that you looked at and was like, no thanks. It's not unfair enough of us. Yeah, I would say one of the things that we jumped on was AGNC. They came out with a new preferred last year. AGNC is a company that is just flush with cash, right? They're in a business where they're buying assets that are, you know, banks buy for liquidity purposes. Agency MBS is super liquid.

17:58They can sell it at any time. You know, AGNC themselves routinely has billions of dollars of cash on hand. All right. When they had AGNCZ that they issued at an 8.75 % coupon, that's just a coupon that is way high, you know, for what they should be for considering the risk that they're taking. You know, we consider the preferred of these companies to be very low risk, you know, relative to other opportunities in the market. And so we snapped it up. It's trading above par right now. It's still not a horrible buy. The market's figured it out.

18:30Will Barton:Any more context to share about this year in particular when it comes to income investing or different vehicles or things that you're particularly noticing about this year specifically? This year, much of our focus this year is on tangible assets. We've seen what we call a rotation to value that's been kind of occurring early in the year here. Investors, even with some of the large cap stocks that are performing very well objectively, even with the meeting expectations, they're seeing their prices sell off. You know, investors are starting to realize that valuation does matter. And so our focus this year is really on tangible.

19:22On investments that have tangible assets, real estate is something that we're really looking forward to right now. And we haven't really pulled the trigger on a lot of REITs where they're kind of on our watch list because we want to buy them. We're just waiting for the best opportunities. We think that energy is, we have a few energy holdings in our portfolio that have been doing extraordinarily well. We just had an announcement that they're going to raise the dividend for an MLP Western WES. And so we're focusing on energy, utilities, real estate, those kinds of companies that have large amounts of physical assets.

20:06that they are benefiting not only from the rotation into value, but also interest rates have been really high. And all of these companies, the basic business model when you zoom out is we're going to buy assets, we're going to take out debt to fund it, and that's going to enhance our dividend stream. And so what happens when interest rates go up, they're paying more to borrow, their profits get reduced a little bit. For the high quality ones, we've seen a lack of growth. For some of the ones that were a little bit pushing the edge a little bit, we've actually seen them pulling back a little bit.

20:44And so our focus this year is really going to be on taking advantage of those opportunities. As interest rates come down, they're going to be able to refinance at lower rates. And they're going to be able to buy assets where the prices have already adjusted to what interest rates are. And that's our main focus for 2026 right now, what we're watching for and the types of holdings that we're going to be adding throughout the year.

21:12Will Barton:Do you guys use like anything in our quant system, like the dividend scorecard? Is that something, or do you focus on any of the factors that our quant system focuses on? Is that something that you evaluate yourselves to or it's not really a part of your strategy? We really don't. I'm a stats nerd. I dive into the 10Qs and the 10K and go through the cash flow statements line by line. It's one of the things that I think really sets us apart from the other services that are available out there is during earnings season, we don't sleep. companies are reporting and we're diving into the numbers and looking at the numbers, trying to determine what it means for our cashflow, which is ultimately what protects our dividends.

22:03And so I think it's the best way for us to do that is to sit down and grant your way through the paperwork. I've experimented with having AI try to read me a 10Q and stuff. And the problem is, I don't know when it's giving me an incorrect answer until I dive in and read it myself. And if I have to read it myself, I might as well have just read it myself. So that's my approach. You know, for me, fundamentals is everything. I have gotten to the point where I simply don't care what happens to the share price. It's one of those things that when I started working for Rita, I kind of had to curve myself and learn a little bit that, you know, for a lot of people, share price is still everything.

22:48We'll publish an article and if the stock price is down 5 % the next week, people are in the comments laughing at us. Oh, you just lost. And it's like, well, the price is down. So what? That's not where our returns come from. Over the long term, substantially, all of our returns are going to come from dividends. And so, you know, when you start looking at an investment that you've held for, you know, three, five, 10 years, the price becomes a diminishing portion of whatever the total return is. You know, whether the price went up or down, it goes from being 100 % of your total return within the first month is going to be the price going up or down.

23:29but then you get that first dividend. Well, now you're going to have 99 % of your price is going to be explained by the price moving up and down. And then you get another dividend and now you're down to 97 % of your price is explained by the price moving up and down. And that diminishes to the point where you get down to 10, 15, 20 % of your total return is explained by whatever the price did and everything else is the dividend that you received. So for me, the fundamentals are everything. Is the company going to do well? Are they going to continue producing cash flow? Is that going to continue to translate into a dividend?

24:09And as long as it is, I'm willing to hold through that 50 % downswing or 60 % downswing or whatever scary number the market wants to deliver. The question is, how much money is the company producing? Is it going to continue you're producing that. And if it is, the rest is just noise. At the end of the day, two prices matter. The price you paid when you bought it, the price you paid when you sold it, everything else in between is just noise and doesn't matter to your total return.

24:39Will Barton:When you're following this strategy or as you're following this strategy, have you been recently surprised by a dividend cut that despite your certainty, there's been a dividend cut or some other nefarious factor coming at you that you weren't anticipating? Absolutely. You know, we have a portfolio, you know, where usually we have around 50 holdings in our common and our funds. And, you know, you're going to have surprise dividend cuts. That's one of the reasons why we always emphasize diversification. You know, keep your holdings within two to three percent of your portfolio because then it's not a huge life-changing impact when you are surprised.

25:24We were recently surprised by a sector where I didn't think they were going to cut their dividends as much as they did. Oxford Lane Capital, everybody loves to talk about it because when things get dramatic, they love to talk about it. We did have a situation here where they cut their dividend by 50%. I wouldn't have been surprised to We've seen a 10 or 15 % cut because we knew that their cash flow was getting squeezed a little bit by spread tightening. But they decided to get very aggressive with it. You know, they cut their dividend by 50%. They were yielding. They were one of those nosebleed yields for us, right?

26:01They were, they've been yielding 20 to 30 % for the past year. You know, so it was a very high dividend to start with. Call you shocked when it gets cut. That's what everybody says, right? But when you look at why they cut, it comes down to the company was paying out all of their cash flow. So they weren't retaining anything that they could keep back to grow. Everything was going into the hands of shareholders. All the value was disappearing into our pockets. And they made the decision that with the prices declining and their NAB declining so much that they wanted to retain some capital. And so they cut the dividends enough so that they can retain capital, so that they can rebuild NAV, and so that they can be active in the market fine while prices are low.

26:48It's hard logic to argue against. Obviously, with our focus on the dividends, we like to get as much cash up front as soon as possible. But it was a remarkable strategy change for them compared to what they've done in the past. and, you know, when management changes their strategy, then you have to make a decision. Is it something I still want to stick with? Is it something I want to exit? In the case of Oxford Lake Capital, we've decided to stick with it because, you know, the yield is still very good. And, you know, we believe that, you know, their strategy of let's go ahead and rebuild NAV, the price is going to come back.

Read the full transcript

27:35We'll probably see dividends have to be raised somewhat in the upcoming years as their taxable income goes up. So those situations happen. Sometimes you're surprised. Sometimes you're looking back at it in history going, you shouldn't be surprised. You roll with the punches.

27:52Will Barton:Life is what happens when we're not planning for dividend cuts. What would you say in terms of retirement if investors are focused on retirement? Would you say that there are some mistakes that you see pretty often? The biggest mistake I made when I decided that I was going to quit my job was make sure you plan what you're going to do with your time. You don't really appreciate how much time you spend working until you're not doing it anymore. and it's not directly related to investing, but it is because for most of us, we're either making money or we're spending money.

28:36It's, you don't want to be sitting around doing nothing because you don't have enough money to do anything. And so when you're making your retirement plan, you really want to have a good concept of the types of things you want to be doing with your time and, you know, whether or not, your nest egg is going to be large enough to support the types of things that you want to do. Obviously, if you want to live a life where you're jet setting and living on yachts, you're going to have to have a much larger nest egg. If you enjoy gardening and going fishing, maybe you don't need as much of a nest egg, although fishing can get pretty darn expensive.

29:15And so I think a lot of people focus so much on the money that they forget to account for the sheer amount of time that they're going to have on their hands and figure out what they're going to do with it. And I think it's very important to make sure that you're doing things that stimulate your mind, that keep you busy, and that'll help you avoid issues like depression and obviously going broke if you're spending money that you don't have. There are certainly a lot of people find pleasure in managing their portfolios. In our live chat, there's guys who hang out there almost every single day and they just love to talk about investing.

29:55For them, it's that intellectual stimulation. It's giving them that camaraderie talking to other people who are doing the same thing that they're doing. And so, you know, we have a good live community on our chat that's active every single day talking about investing. And after hours, who knows what they're talking about? They're talking about their cars. They're talking about their music, you know, whatever they want. And so I think that's something that investors really need to when you're approaching retirement. Yes, worry about the money, but start with the idea of what's my plan going to be?

30:30What am I going to do with myself? work up your budget with both the absolute essentials, which obviously you want to make sure that you have a house over your head. You want to make sure you have food and healthcare and all that stuff you can't live without, but make sure you have a flexible budget that, you know, okay, you know, these are the hobbies that I'm going to want to engage in. You know, this is the portion of my income that's going to be a little bit flexible that I can tighten my bell if the market crashes. In 2020, March 2020 came around. I looked right at Hope and I said, hon, we're eating mac and cheese.

31:09We're going on the college diet. And every penny that I had available to me was being plowed into the market because I recognized this is an opportunity to buy. Now, I don't know how long it's going to stick around. Being the good woman that she is, She humored me. And we ate macaroni and cheese. We didn't spend any extra money on anything, which became a little bit easier once I shut everything down. But having that flexibility in your budget where you're only living on a portion of your income and you have an amount that you can make that choice of, yes, I think this is what I want to do. And really having flexibility in your finances is, in my opinion, always the best possible thing that you can have.

31:54I think it's much better for investing. You can make wiser decisions when you're not dealing with, I need this money to feed myself. You can make decisions with more clear head based on what you really think the investment is going to do. and having that stress of worrying about your daily bills out of the picture is going to be probably the best thing that you can do for yourself, whether you're retired, whether you're 20 years old, just going to college, right? And that's one of the reasons why we kind of focus on having a large fixed income portfolio. You know, we recommend having 35 to 50 % of your allocation in fixed income because it provides you that base of cash flow coming into your portfolio that isn't going to be as variable.

32:46And then that removes the stress from the portion of your portfolio that might come up with unpleasant surprises. The riskier assets like Oxford Lane Capital investing in CLOs, which is they're taking the risky portion of risky loans and giving you that super high juice deal. And so you can have that balance where you have the base to fall back on, allowing you to make the bigger swings on the other side.

33:18Will Barton:Would you say the challenge that is most prominent in income investing is yield chasing or would you put something else there? The biggest challenge is actually in tracking it. When you buy a dividend paying stock, Look, there's no easy way in your brokerage to know whether you're up, down, or in between. Because the cost basis that your broker reports is going to be the amount that you paid. If you are dripping your dividends, it's going to be the amount that the dividends would grip that. They're not counting all the cash that you're taking out of it because your broker doesn't care about the cash that you took out.

34:00They're tracking it for tax purposes primarily. And so it's very easy to get lost and not even know whether you are up in an investment or whether you're down in an investment. You know, and really track how an investment is doing unless you actually go through your records and you start tracking every dividend that you were paid. And I think what happens with a lot of people is they get wrapped up in, you know, what the price has changed. You know, over the last four years, we saw interest rates go up a lot. The result of that is basically every dividend paying investment in the stock market went down at price.

34:43You know, rather the valuations went down. If they're growing fast enough, maybe they managed to maintain their price a little bit. But, you know, it's just a macro factor that you can't get away from. Right. We're not dividend investors because we believe dividend stocks are going to be the best stocks this year. We're going to be dividend investors this year, next year, the following year, the year after. Some of those will be the best year. Some of them, dividend stocks won't be the best year. And that's just reality. The market comes and goes in waves. Interest rates come up and down. And our strategy is centered on the cash flow, centered on the dividends coming in.

35:24And so we're not trying to identify, oh, well, this is going to be a good year for dividend stocks because the rotation to value is happening. And on the other hand, in 2021, we weren't sitting there going, oh, well, dividend stocks are all very expensive. We should sell them all and go buy Amazon. We're never going to do that. It doesn't matter what direction we think the stock market is going. We're never going to be buying crypto. So, you know, we're never going to be diving into some other asset class that doesn't provide dividends just because it might be better. And the reality is, is there's years where it will be better.

36:07And so I think there's a moment that clicks for people. And it's great to see, you know, because sometimes you have a member who just comes in the chat and it's just one day it clicks for them like, oh, wow. You know, and usually it's when you have one of those holdings that went for a roller coaster ride, right? It went down a lot. You know, maybe you had a dividend cut. You know, it was ugly. Things weren't great. But then you look at your portfolio in the aftermath and you're looking at the income that you're getting next month and you're like, oh, okay. I mean, it didn't change my life whatsoever.

36:44I'm okay. You know, I survived. it's kind of what happened to me back during the great financial crisis. You know, I looked at my portfolio and I'm like, it's fine. Yeah, it was scary. And, you know, the members who stuck with us through COVID, you know, a very large number of them have stuck around and they'll probably stick around with us for life because they went through that terror, that uncertainty, that, you know, the world's falling apart, dividends are being cut, companies, you know, The EPR properties, one of our companies that we invest in, you know, they had over 80 percent of their tenants stop paying rent.

37:26That's that's serious for every company. Right. No, no company can sit there with an 80 percent drop in revenue and, you know, just be fine with it. Right. You know, but they managed to navigate that. And, you know, they've come up the other side and they've come up an even stronger company. And so I think when people see, yes, you can go through these hard times, you can go through the unexpected, and it doesn't impact your lifestyle, that's when it clicks. For people that it doesn't click it, and they sell everything. You know, it's one of the most personally challenging things for me since I started doing this was in March 2020.

38:16People lost confidence. And they sent me direct messages telling me that, you know, I'm selling, you know, and it was that second and third week of March when everything was down. You know, everything was down a lot. And they're just like, you know, you lost me all this money. I'm selling. You're horrible. And it was very emotionally hard to read. And obviously, there's nothing I can say to you at that point. Right. You've lost confidence. You don't believe that word I say. You're going to go. You're going to do what you do. I can't control your money. and it was very hard. And, you know, both me and Rita back then, we had a talk and we're like, we need to work on educating people more about why we're doing this.

39:11You know, focus more on the education side so that people understand what we're doing, why we're doing it. Because the worst thing you can do, and this goes for any investment strategy, is to switch horses in the midst of a crisis. If you're a growth investor, when growth stocks are collapsing, it's not the time that you suddenly want to be like, oh, hey, yeah, I want to learn about this dividend investing now. It's whatever style of investing you are going to do, you want to enter into it with a plan. You want to enter into it with a plan of what you're going to do when it breaks down because it will.

39:55There's no investing style that's always the best every single year. It doesn't exist. It never will exist. And the worst thing you could do is sell at the bottom and then go chase into the next investment style that's at the top right now. If you're selling all of your dividend stocks to buy growth stocks when they're expensive and then you're selling all your growth stocks in 2022 when they crash to go buy dividend stocks, which are on their way back down in 2023 and 2024. I see a lot of people jumping from the frying pan into the fire. And you need to find the investment strategy that works for you, that makes sense to you, and that you can internalize and execute even when things get tough.

40:46And I think that's probably the worst thing that any investor can do is to be investing in a strategy that they don't have confidence in. And that's one of the reasons why we've really focused on the education side. And if you're going to panic and sell everything, you know, because things fall apart and prices crash, then don't listen to me. I don't want it to be my fault.

41:13Will Barton:And there's categories of black swans. I mean, there's a black there's a great financial crisis, which is very scary. There's a pandemic, which is a bit scarier. And what did you find a lot of fear? I mean, I'm sure you found fear, but did you find that same kind of fear or response around the tariff tantrum last year? Well, for us, the tariff tantrum was shrugging, right? Our stocks weren't really heavily impacted. We had a handful of fringe holdings that kind of went down a lot, but a lot of our investments barely blinked. So, that's kind of one of those cases where people who were invested in other companies that were more directly impacted, then suddenly they're starting to talk about changing strategies.

42:02And that's kind of a long time to come over to us. Wait it out. Let your holdings rebound. Then sell when they're expensive. You know, because if you were selling, you know, the stocks that crashed in April 2025, well, I mean, pretty much all of those are way higher today. Right. And that's that's kind of what I'm talking about is people want to switch horses and they'll look at the look at a sector that's not being hit hard. And, you know, our portfolio wasn't being hit hard at all. Our drawdown that month was not particularly large compared to the overall market. um you know and yeah people like to cheer it on and you know for me it's just like okay shrug your shoulders yeah we're not falling a lot more means we don't have the bargain opportunities to buy um and you can tell when somebody has been has uh has drank the kool-aid completely and they've converted to the income method when they're sitting there going oh man it's going up in price why isn't stuff falling give me something cheaper i want to invest that higher yield and that's the stock market is the only market in the world where the buyers go to and they get grumpy because things are too cheap and yeah so that it's there are different types of crises they're going to impact different investment strategies you know differently our portfolio is naturally going to be exposed more to yeah interest rate risk higher interest rates are going to put a strain on us.

43:33When you start having credit risk, because we have a lot of assets that are either borrowers or lenders. And so when credit risk spikes up, that's going to be a more difficult time for our holdings. So a dot-com bust, I would expect our portfolio to basically shrug it off kind of like it did the tariff tantrum. You start getting into a great financial crisis, it's a totally different story because that was entirely credit-based. And the people who were invested in the mega growth stocks, they basically shrugged their shoulders through it, relatively speaking, at least. And so that's kind of one of the things to keep in perspective is, what are the macro movements doing?

44:21And I know some people like to move in and out. Based on those macro movements, we don't do that because like I said, our stock picks come from our overall strategy, which is really a lifestyle strategy of we want to have that cashflow coming into our accounts. We're never going to be growth investors. We're going to be dividend investors. And some years, dividend investments are going to be better than others. Some years, they'll be the best investments in the market. Some years, they'll be the worst investments in the market. Most years, they'll be somewhere in between. And that's really the perspective that we come from is this.

45:02This is our plan, and we're going to pursue it. We're not going to change. It's in our name. It's high dividend opportunities.

45:09Will Barton:Faith and context, supremely important. Will, I really appreciate this conversation. I appreciate you diving so deep. I know there's so much interest in our audience and in general around income investing, around dividend investing. There's a lot of really quality nuggets to chew on here. So very appreciative. And High Dividend Opportunities, once again, is your investing group. You are right now having a deal on that. I'd love for you to share more about what that entails for our listeners. And if you would care to leave any final words of wisdom for our audience, I would greatly appreciate it.

45:45Will Barton:But thanks again for coming on. Open invitation to come back. Well, thank you for having me, Rita. It's been great. Yeah, we're having a sale right now. It's our 10-year anniversary sale. Rita started High Dividend Opportunities back in 2016, and we reached 10 years, which is quite an achievement for an investment service to make. Congratulations. It's huge. Yeah. I've been fortunate to have been along for a large chunk of it. And we're offering kind of a throwback pricing. It's the largest discount that Seeking Alpha would let us have. And we're probably never going to have a discount this big yet.

46:22Yeah. So it's$255 off an annual membership and you pay for a year up front. Once you stick with us for a year, we work on earning your trust to make sure that you stay with us indefinitely. We offer a lot of resources beyond just PICS because, like I said, it's certainly for me teaching people how to invest and why we're doing what we're doing so that you can construct your own plan to either follow us diligently or just use our strategy for a portion of your portfolio. I really like to focus on the education side, teaching you about why we're picking what we're picking, what we expect from them, and how you can identify investments yourself.

47:07We offer a broad array of tools that are geared towards dividend investors, like a dividend tracker. Every holding that we pick, we track what the dividend is going to be. even for our variable dividend payers, we project what they're going to be in the next few quarters. And so that helps get you a really good idea of, you know, how much income your portfolio is producing. To me, your portfolio is a business. It produces cash flow for you and it should be managed like a business. Your goal is to increase that cash flow, you know, and keep it increasing every single year. Like a business, you're going to have setbacks.

47:46You know, you're going to have challenges, but you can keep it growing every single year. And that's the goal that we seek to do. And, you know, I am doing this because I truly fell in love with it. For me, it was, I have a lot of time on my hands. I'm just going to start writing about my portfolio on the internet and just to make sure I was staying engaged with it and make sure that I was, you know, when Rita sent me a message one day and said, Hey, I really like your work. Can you give me a call? I'd like to talk to you. And he invited me to join the team. It was, you know, he gave me much more than just a position to work in.

48:31It's, it's something that I absolutely love to do every single day. Um, and it gives me the intellectual stimulation and the opportunity to teach people how to gain their financial independence and gain confidence in their investment strategy. and ultimately to improve their retirements. So check out our sale and we look forward to seeing you in our group. Just a reminder, anything you hear on this podcast should not be considered investment advice. This is for entertainment purposes only and you should seek advice from a licensed professional before investing. If you enjoyed the episode, leave a rating or review on your favorite podcasting app and we'll see you soon with a new episode.

49:16We'll be right back.

From the publisher
Will Barton from High Dividend Opportunities shares their strategy (0:20) Contextualizing the yield conversation (7:15) Fixed income and equity portfolios (12:00) ETFs vs CEFs (15:00) AGNC preferred stock (17:30) Earnings, cash flow statements protect dividends (21:30) Dividend cuts can surprise you (24:40) Retirement essentials (28:00) Income investing challenges and benefits (41:00)

Episode transcripts

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