Title: How to Build a Dividend Income Portfolio (With Jenny Harrington) Show: Dividend Stockpile (YouTube channel; host Jeremy) Guest: Jenny Harrington — CEO & portfolio manager, Gilman Hill Asset Management (equity-income strategy) Date: 2026-09-21 (YouTube publish date, verified from the watch page) URL: https://youtu.be/d_SxEStst44 Length: 32:36 Note: YouTube auto-caption transcript pasted by Stephen. Fillers (um/uh, you know, like, stutters, false starts) removed and a few obvious caption misspellings fixed ("$512"/"$745" = $5.12/$7.45, "sacrosen" = sacrosanct, "death rows" = death throes, "assception" = inception, "fair" = fare); wording otherwise verbatim, including auto-caption mangles (e.g. "Newberger Burman" = Neuberger Berman; "Dowo"/"Dow like D" = Dow Inc.; "FDV" = likely the Fidelity High Dividend ETF FDVV; "Claudet Alman" = her joke name for an AI analyst; "notebook LLM" = Google NotebookLM; "David Swenson" = David Swensen; "principle" = principal). Speaker turns marked ">>" as in the caption; the host (Jeremy) and Jenny Harrington alternate.
Transcripts:
00:00 Hey everybody, welcome back to Dividend Stockpile. So today we're actually going to answer a listener question and expand on it on how to transition or how to start with dividend investing. And to help with this discussion, I'm excited to have Jenny Harrington from Gilman Hill Asset Management back on the channel.
00:18 Jenny is the CEO and portfolio manager of their equity income strategy where she runs a dividend income strategy for her clients. So she's the perfect person to help with this question. So Jenny, welcome back. >> Thanks for having me. It's always so nice to be with you. >> Absolutely. I love our conversations. You are, of course, a wealth of knowledge and a huge proponent of dividend investing.
00:38 So, when we got this question from a previous video, I knew I needed to have you come back on to talk directly about it because you've actually done this for your clients in a professional setting. You've transitioned people into becoming dividend investors. So, I couldn't think of anyone better to have this conversation with.
00:54 Obviously you've been on CNBC and a bunch of other places and here on the channel, but can you give everyone just a quick background of yourself just in case they've missed you before? >> Jeez, I always hate doing it for myself. Okay. So let's see. I was born in 1975. No, just kidding. [laughter] That's true, but I won't really go that far back.
01:15 So I started at Goldman Sachs and then I went to Newberger Burman. And when I was at Newberger Burman, I was on a team that managed a really large cap core US strategy. And I had one client call at the end of 2001, a guy named Craig, and he said, "Look, I'm mid-50s. I'm getting ready to retire. So I need income, but I'm only mid-50s, so I also need growth.
01:34 I'm too young to retire. What can you do for me?" And what I did was I transitioned his kind of plain vanilla S&P 500ish portfolio to a portfolio that would generate 5% or better dividend income. And because it was in stocks, it would have growth on top of that. So, fast forward all these years. I left Newberger. Now I'm at Gilman Hill.
01:53 Oh my gosh, Jeremy, this is my 20th year at Gilman Hill. I'm like a real grownup. And since I already said 1975, I'm 51, so I've been here for 20 years. And the strategy is still the same. The strategy still has the objective of generating a 5% or better dividend income yield. We also have an international income strategy here that my partner Greg manages.
02:13 because we have a discipline growth strategy, but we're focusing on the dividend one. And so what else about that? So, the strategy is the same. It's still diversified by type of stock. So, there's REITs, there's MLPs, there's utilities, but there's all sorts of common stocks in there, too. And the interesting thing for your listeners in particular is if you look at a really really long-term chart of the S&P 500, you see that the S&P 500's dividends have grown at about 5.
02:43 7% a year over the last 60 years or so. Totally coincidentally, the Gilman Hill dividend income strategy, the dividends have also grown at about 5.7% a year over that long term. So the nice thing about that in this funny world that we're in now is that the income growth outpaces inflation. >> You don't get that from bonds. And so that's a really unique element of the strategy. But that's about it.
03:05 We're in Connecticut. We have lovely clients. We manage all separately managed accounts. No funds, no mutual funds, no ETFs. All separately managed accounts. So there you go. There's my background. >> Awesome. I can't believe it's been 20 years. That's absolutely amazing. So many clients you've helped over the years.
03:23 And the other thing I wanted to talk about for people who are trying to get into dividend investing is you have an amazing dividend investing book. So, I'll just plug it right here. Everyone go check it out. Definitely order it at your local bookstore or wherever you get your books. But it's an excellent book on dividend investing.
03:38 And I heard that you have a new book coming out. Do you want to plug that real quick? >> Sure. So, it's called Investment Wisdom for Our Friends and Loved Ones. And I teamed up with my friend Rebecca Patterson and the two of us asked 23 of our friends to each write a chapter of the investment wisdom that they would share with a friend who is educated, sophisticated, smart, has enough money to care. It is not a financial literacy.
04:01 It's not like oh don't buy Starbucks and don't get your nails done. It is legitimately you are smart, sophisticated, everything. You just happen to not be a professional investor. Where do you start? I've found over the years that when my friends ask me that, I don't have a great place to start.
04:16 So, you have 23 chapters, 23 different perspectives. And it gets you started. And by reading this, you can start to suss out, am I a growth investor, am I a value investor, am I a fundamental investor, a technician, where do I skew? And then at the end, which I love too, we have a reading list. So, after you've read all of our chapters, then you can read what we suggest.
04:35 And you can really start your investment education journey. So, I think it's a great starting place. All of the authors' profits will go to the Council for Economic Education and Boys and Girls Clubs. So we're not making any money off of it. It was really created to be a gift for our friends and people that we love.
04:53 >> That's amazing. So, you can pre-order it now. I already have. It's already in my order book. But it comes out in November, I believe. >> Yes, November 17th. And on the pre-orders, I'll make one more plug. If you can order from your local bookstore, please support your local bookstores.
05:08 It just means the world to them. And it's good for society. [laughter] >> Absolutely. >> No judgments. No judgments. >> No, definitely a big fan. I'll definitely put a link to your books on the thing, everyone to go pre-order it. But it's actually a great transition because what you said about the new book is how do you begin investing? How do you learn your style? And some people have been raised to do index funds or ETFs and just a S&P 500 or NASDAQ and just grow over time.
05:35 But a whole another way of investing which obviously both you and I love to do is dividend investing. And so we got this question about how to be a dividend investor or how to transition a 60/40 portfolio into a dividend portfolio. And so that's the reason for this entire conversation. So the book ties in perfectly to what this discussion is.
05:56 So I guess with that so someone who wants to start off with dividend investing but has really no idea how to begin. What would your first step be for that person? What approach would you have them take? >> I'll just give one funny aside. So, I did a conference for CNBC and my talk of course was on dividend investing and one of the guys said, "I keep buying Kimberly Clark, but then I get too frustrated.
06:19 I give up on it and I go back to buying Nvidia." And he was basically trying to have me convince him that he should own Kimberly Clark. And I said, "Buddy, you've answered your own question. You want to be a dividend investor, but you are not a dividend investor. You can't handle that fear of, you can't handle the patience, you can't handle the fear of missing out on the growth." So, it was interesting.
06:39 So I think where you get started with being a dividend investor is frankly the same place you'd get started with anything else. You start figuring out, do I want to own individual stocks or funds? And actually oh you know what, in this new book one of the chapters written by my friend Nancy Mayor, the advice she gives, which I think is very very very good.
07:03 She basically concludes her chapter with the following. She says look if you're not sure go put 80% of it into an ETF. I think her thing is just put it in the S&P but then use the other 25% or 20% and buy a couple of stocks because that way your brain will be really tuned in, but you also won't be taking so much risk that you're uncomfortable, that you don't have the weight of all these stocks on you.
07:27 So, if you're really starting that's not a bad way to start, which is bifurcated, maybe find a couple funds and then a couple stocks. But whether you're buying funds or stocks, the process is the same. And whether you're buying growth funds and growth stocks or dividend growth or dividend income, it's the same.
07:45 You screen, right? So you get some list of all the funds that are available or all the stocks that are available. You research, you look at the valuations, you understand the fundamentals, you read everything you can, you think about the specific company, and you think about the macroeconomic environment. And that's where you start.
08:03 And that's frankly the hard part and in a way the boring part. It's so much easier just to tell a great story. And SpaceX is the ultimate great story. The actual research on SpaceX and trying to figure out what the valuation should be, that would be very hard and very boring work to do.
08:20 But I think if you want to be a good investor, you need to grit your teeth and do that hard work of researching, considering the valuation, really micro micro kind of bottom up work and then the macro top down work. >> So I definitely like that idea of starting off with the majority of the portfolio in ETF and there's plenty of really good dividend ETFs out there.
08:39 A couple of the most common ones are things like SCHD, FDV, even DIVO. There's a bunch of different ones out there. So, that's definitely a good place to start, especially if you're still just trying to figure out how to invest and what to look for. That's a good way to get started while you're doing your research and while you're learning.
08:56 But to your point, there's nothing like owning individual stocks to really get your mind going, really get in the process of building out your investing style and what you look for by having individual stocks you're digging into. So, I definitely agree with that. >> And you know what we have? We're living in a time where we all have an incredible advantage.
09:13 We all have our own $350,000 a year Columbia Business School analyst at our disposal. I call her Claudet Alman. [laughter] And you should go ask Claudet Alman either through ChatGPT or Claude. But if you're looking at dividend ETFs, you have to ask some very shrewd questions.
09:32 First you need to ask what the fees are >> and then you need to ask is leverage used, are derivatives used >> how is the income generated, and then you need to ask how would this security fare during something like the pandemic, during something like the great financial crisis, how would this fare in a rising rate environment, if there's leverage what kind of macroeconomic environment would derail that income stream. You can ask these questions and they're going to give you excellent plain English answers.
10:04 Jeremy, if we were having this conversation a year and a half ago, that would be extremely complicated to suss out and now you really can use Claude and Chat to answer and probably Gemini and just use those two, but you need to ask that because a lot of the dividend ETFs, they look a lot better than they really are.
10:26 And they've got these yields that make your eyes pop and there's a reason, there's a lot of risk in them. So you do need to be really careful. >> Absolutely. And there's different types of ETFs at this point in the income space. You have your traditional dividend payers are going to pay that 2 to 3% range, maybe even 4%.
10:42 But then you have some of these higher options based income ETFs. Those are the ones you can see these monster yields, anything from 10 to 100% yield. And so you really have to know what you're getting into. Don't just look at yield alone. Look through the details of the ETF to make sure you truly understand how they're generating that income and if it's sustainable.
10:59 So I definitely agree with that. And we're going to dig into that a little bit later on in the conversation, but it's really good to do your research even if you're doing ETFs just so you fully understand what you're actually buying. So using Claudette as you said or doing your own research, what kinds of things if you are looking for individual dividend paying companies do you think are most important to start your research with? >> So the first thing you want to look for is the ability to pay.
11:24 So you want to look for something like, you know what, let me look at Kimberly again. You want to look at something like Kimberly where the dividend is $5.12 a year and the expected earnings is $7.45. So you have plenty of coverage. You know that the earnings are going to more than cover the dividend. That's the first thing.
11:44 Second thing you want to look to that history and see how long have they been able to sustain this. We talk about dividend aristocrats a lot. Dividend aristocrats are great. That's a 25 year history of both paying a dividend and raising a dividend. The only trouble is they're such great quality companies that they trade at premium valuations and frequently the yields aren't very high.
12:05 But conceptually that's what you're looking for. You're looking for this long sustained history of paying a dividend every year and hopefully [clears throat] increasing it. So after you've figured out that part, which is frankly the easy part because you can just look to history and you can ask ChatGPT again. You need to proof it.
12:21 But it's frequently right. You can just say how many years have they paid, or show me the dividend history for the past 20 years, and then if you say it was interrupted, why was it interrupted, you can ask it those things. But then this is the harder part where it really needs your human brain to some degree, or you feed in the transcripts.
12:40 So after you see that the numbers work then you need to understand what the management and the board's commitment is to paying that dividend. And one of the things that we've been doing now is we've fed in like 10 years of transcripts and say, "Please tell me if the management's language around the dividend has changed at all.
12:58 " And what you might see is something like Dow, right? We own Dow like D, the stock, not the Dow Jones. But we own Dowo for a long time and for a long time the management said the dividend is our number one priority, sacrosanct, and then that language started to get squishy and as soon as you see the language start to get squishy you know that something might change and you don't want that.
13:22 So this used to be a day or two days or five days of reading 10-Ks to understand that; now you can just upload them into notebook LLM which is Google, or Chat or Claude and say tell me how it's changed and it'll tell you how that's changed. >> Absolutely. It's so important to understand what the management philosophy and willingness to continue to pay it.
13:43 You see some of these that are paying one cent increases just to keep their streak alive. But do they really believe in dividend investing and dividend growth investing? It's really important to understand where their management sits because at the end of the day, they're going to be the ones determining whether we continue to get raises in our dividends or they're going to cut them.
13:59 I've seen a couple what people used to consider very stable dividend payers have recently reduced their dividend or cut their dividend. But if you research what the management has been saying over the last couple years, you could probably forecast that being cut. So, it's really important to understand what the management is saying about that if you're going to be investing in individual stocks.
14:20 So, I know that you and your strategy, you focus on higher yielders. As you said, you're looking for an average of 5% yield. You also look for growth, but you want to have that 5% minimum. Other people are more of what they consider dividend growth where they're willing to accept a 2 to 3% yield but hopefully growing at say seven, eight or nine% a year.
14:38 Where do you kind of feel people should start when it comes to the dividend growth over dividend income type of mindset? >> I think they need to start with their own portfolio needs. >> So let's say you're about to retire, you have a million dollars and you need to replace 50,000 a year of income. >> You're going to be forced to buy dividend income stocks.
14:58 Let's say you're 35 years old and you've got 400,000 and you think you're going to retire in 20 years and you want to slowly start building that income stream. You can start with dividend growth, but it really starts with what you need. Not, hey, you should start here. >> Yeah. Yeah. Exactly. Definitely. >> Only simple answer of the day.
15:17 [laughter] >> Yep. You definitely have to know your own needs. To your point, if you need the income now, you're going to want to look for that higher yield while still being safe. But if you still have 20, 30, 40 years before you're going to need it, eventually that dividend growth is going to surpass the current yield you can get today and you'll be better off.
15:32 But it's something you're going to have to determine what your timeline is. For me, before I use my dividends, it's probably going to be another 10 to 15 years. So, I can take a little bit more growth path than if I needed the money today, I'd be looking at the five to six% like Jenny runs in her strategy.
15:48 So, it really all depends on where your timeline looks and what you need the money for. So, I definitely agree with that. And you can do a little bit of both. You don't have to pick all or one, but it really depends on what you need for your income needs. For sure. >> Yeah. And that leads into, let's indulge ourselves here.
16:06 Hopefully your listeners don't hate me for this, but this is a little wonky, but something that we think about a lot, Jeremy and I, because we're nerdy dividend investors, is yield on inception. Mhm. >> Let's say you buy a stock today with a 2% yield >> and let's say that that grows at 7%. The dividend grows at 7%.
16:26 That means in 10 years, or let's say it's paying a $2 dividend, right? $100 stock or whatever, it's paying a $2 dividend, 2% yield. The yield grows by 7%. That's what I said. That means in 10 years you now have a 4% yield on what you originally paid. So that's the yield on inception.
16:47 So it's an interesting thing that you can buy something with a lower yield now and then it can have a much higher yield based on your inception by the time you need the income. And sometimes when I look back to portfolios that have been with me for a long time, the yield on inception is like 20%. >> You're at 25%.
17:04 It's absolutely wild because the income based on the initial value has grown so much. >> Absolutely. And some other people and some media call it yield on cost but yield on inception is the same thing. Basically you buy it at a certain price and because the dividend is raised every year and if you're not using the dividend it can also be reinvested to grow even faster than just what the company's raising it.
17:25 So to your point over time that yield on cost or that yield on inception can be that 20, 25, even 50% if you have a really long time frame. And so just think about the power of that. When you do need the money, you're getting 20% of your investment every single year just in dividends or 25% or whatever the number ends up being.
17:42 So it's a really powerful part of dividend growth investing that a lot of people can't conceptualize, but it really does happen. And you've had clients for 20 plus years at this point. You've seen it happen. And I've been investing since 1999. I've definitely seen it happen in my own portfolio. So it is a real thing. So it's definitely one of the benefits of dividend growth investing.
18:00 >> Yeah. Yeah. And it's the real advantage of someone starting down this path when they're 35, not 55, because then they can let that grow and they frankly have access to a wider group of companies, a broader group of companies and frankly a higher quality group. >> Yeah, absolutely. And those will have some capital appreciation during those years as well in addition to the dividend growing.
18:20 So, it's a perfect package. It can really sustain you for a long time. It can build a lot of wealth over time plus give you that income you're looking for in the future. You don't have to sell off your stocks if you don't want to, >> right? >> So you strive for around a 5% yield. My personal investing is a little bit lower.
18:38 I'm probably in the fours myself between my dividend growth and my higher yielding companies, but what kind of warning signs should people look out for when the dividend might be too high? >> So, I was thinking about this and it's hard to quantify what to look for, but I think the bottom line is you need to make sure it passes the smell test.
19:00 And when I think about that, I think about Wendy's. Where Wendy's, when did they end up cutting? Like a year agoish. Before they cut, they had a big dividend, like an 8% or 7%. And they technically speaking had the earnings to cover it, but it didn't make sense, and you're like, I don't get it.
19:22 It's just Wendy's, right? It's clearly not that thriving a business. The earnings have been going down over and over and over. So, you see the earnings declining. It's not in some thriving industry. The yield's so high that you know that the company's not being rewarded for paying the high dividend.
19:40 And sure enough they cut the dividend. So I would really say that sometimes it even looks sustainable on paper but if it just doesn't logically make sense... You saw with the retailers, the retailers like Macy's and Gap and Nordstrom and all those and Kohl's, all those guys had huge yields five and 10 years ago but you knew that [clears throat] bricks and mortar retail was dying, they were in the death throes. Actually I think Macy's just had really good numbers which surprised me, but you knew that they were in the death throes, so
20:07 it didn't really make sense that they could keep growing their dividends if we all knew that bricks and mortar retail was dying and we saw their earnings going down every year. So really just say, does it make sense? [laughter] And I would say anything above, in the wrong industry, anything above 7% you just have to be skeptical of.
20:27 Now I have tons of 7% yielders in the portfolio but they're little unicorns. [laughter] And they took me a lot of work to get there. But really be skeptical >> frankly skeptical over five probably, right. [laughter] >> Yeah that certainly makes sense. Another thing obviously depending on the industry but also look at their peers.
20:43 If you know a thriving company in that sector, it only has a 3% yield, but this one has an 8% yield. Makes you wonder why the market's letting one have such a high yield and not the other one. >> Yeah. >> Just real quick on that, I stepped on a total landmine in 2023 with Advance Auto. >> So, it's Advance Auto, O'Reilly, and Autozone, and I kept thinking, oh well, now they have a new management team, now this, now that. No.
21:08 You know why? They were the worst. It totally blew up. It was a horrible investment. I should have just looked at it that simplistically and that straightforwardly and I would have avoided that landmine. So yeah, look at the peers for sure. [laughter] >> Yeah. Yeah. I don't want to focus too much on the negative side of dividend cuts and things like that.
21:25 But if you're going to be a dividend investor, you have to understand that it could happen and you need to find what to look out for to try and avoid it the best you can. >> You know what Charlie Ellis says? Charlie Ellis in his intro to David Swenson's Pioneering Portfolio Management says, "Avoid a few disasters and compounding will take care of the rest.
21:44 " So I think it is worth it to put a lot of focus on the negative because the positive is the easy part. >> Yeah, fair enough. Fair enough. All right, let's talk about another thing that I don't think you personally subscribe to, these higher yield options based income ETFs. I don't want to name names, but there's quite a few out there that are using derivatives and options and things like that >> to juice up their yields.
22:04 As said at the beginning, they're paying anywhere from 10 to 100% yield. I've had plenty of those people on the channel and I definitely recommend everyone really understand what they're doing. Make sure it fits what you're looking for in your risk tolerance. But what's your opinion on these high income ETFs right now, especially for a newer investor? >> Okay.
22:23 So, I know there's a whole group of them that have been labeled Boomer Candy, which I really like, and we did a little deep dive on the Boomer Candy, and they're kind of fine. You know what they really are? They're a structured product that limit your downside and limit your upside, and it's high fee, and that's fine.
22:38 I think you need to be very, very, very careful of it being return of principle where you put 100,000 in and it pays you 10% a year and that sounds great and you're left with zero at the end because they've returned your principal. So you must ask ChatGPT or Claude, whatever, you must ask is this returning, is this a return of principle >> it's a return of principle you need to understand not only is your income not going to grow, but your market value will be devalued or whatever, you're getting it all back. So I think that's
23:12 the problem for me is that people fundamentally don't understand a lot of them and they think it's really great, so be very very careful of what you're buying. That's it. I don't invest in them so I don't know them really well. I just kind of know what worries me, and then people get sour, and then they make stupid decisions and they take on too much risk to make up for it. So just be really careful.
23:34 >> Absolutely. And also if you invest one of these higher yielding ones and it does poorly for you, you might write off quote unquote dividend investing or income investing saying it's all a scam, but it's not necessarily obvious. Of course, every strategy is just might have been that particular strategy that that fund was using didn't work out.
23:50 Another thing to focus on is the stocks or the sectors that they invest in. If the whole sector goes down or the stock goes down that they're investing in, of course, your value is going to go down too, whether they pay out a yield or not. So, you have to understand what the underlying strategy is both on the underlying assets as well as the options or the income strategy that they have on top of it.
24:10 So, definitely keep that in mind. If you do your research, there's definitely some good ones out there, but don't get enticed by these 75% yields and 100% yields if you don't know what you should be doing. But now, I wanted to talk directly about the listener question. So, obviously, we kind of been building up to it talking about how to become a dividend investor and how to transition a portfolio into dividend investing, but this is the specific question that we got.
24:30 So, I'm going to read it off and I'll put it on the screen. How would you transition a balanced portfolio with significant long-term gains currently sitting in a 60% equity 40% bond portfolio and includes stock ETFs, individual bonds, and bond ETFs? How would you transition that to a dividend portfolio? >> Okay, so I love and hate this question at the same time because this is the definition of there's a million ways to skin a cat.
24:57 >> Okay. >> And there isn't a straightforward answer. And if this were my friend or my client asking me this, I would then have a thousand questions for them. So let's say they're in just a straight up, let's say they live in Florida, so there's no state tax, and let's say there's a 15%, everything's long-term, and there's a 15% capital gain.
25:21 And let's say there's a $100,000 gain on the whole portfolio. Then I would say, "Are you comfortable biting the bullet and just writing a check for $15,000 and you can just transition it overnight and make it what you want to be?" And they might say yes and they might say no. If they say yes, great, easy as pie.
25:38 You just sell everything off and you start fresh the next day and you just start building the positions back up. And then that goes to the beginning of do you do some funds and some stocks. That part's different. But there could be so much complexity in this. Maybe some are long-term, maybe some are short term.
25:57 Maybe they live in San Francisco, but they're moving to Wyoming in two years, in which case you'd say, ah, maybe hold off for two years and wait until your tax rate goes down because San Francisco is super high, California plus the city; Wyoming's lower. Maybe if they're just one of those people who really hates paying the government, maybe you do it over the course of three years. Mhm.
26:20 >> Maybe they don't need the income today. Maybe they are just starting to get used to... Oh, actually, you know what, Jeremy? Yesterday I had lunch with a client down in DC and the guy's 67 and it's all in a retirement account, so there's no capital gains.
26:36 And he said, "How do you propose I do this?" And I'm like, "Well, you could just leave it all in growth and then all on day one in three years we could transition it into dividend stocks, but psychologically he needs to see the income start. So, we're going to take half the portfolio now and we're going to transition it to income so he can start to see it build up and then he'll simply feel better.
26:55 So, that's part of this, too. If there isn't a rush, you could eke it out. Or if you hate taxes, but there is a rush for income, fine, [clears throat] do it halfway. Just sell some of those bonds when you need income because they probably don't have big capital gains and use that as your income, but you slowly transition the rest.
27:16 So, I imagine this is probably going to be the single wishy-washiest question you ever get on this show, but it kills me because I'm like, "Oh my gosh, I can't answer this question without really knowing their situation." And there's so much just emotional stuff behind it. And there's so much timing.
27:33 So, you need to figure out what your timing is, what your comfort with paying taxes is, what your emotional [clears throat] comfort is with an immediate transition versus a slow transition. >> It makes sense that to your point, there's a lot of nuance here and a lot of further questions that you would probably want if this was a client that you're working with.
27:53 I think just from my viewpoint on this one in particular, it really comes down to your mindset and your attitude towards it. If you're willing to make the transition, you've already made up your mind, then it really just depends on how quickly you want to do it. But you have to have that mindset because you might have been in a index portfolio or a growth portfolio for the last 30 years and now you're transitioning in a different style.
28:17 So you have to really feel comfortable with what you're moving into because you don't want to transition and then two years from now transition again back to growth. You want to really be sure that you're committing to it. And to your point, it might be more of a transition where you do a small percentage of your portfolio, transition over to income paying assets over time as opposed to doing just cut it and run type of thing. Yeah.
28:38 >> So different ways. >> Yeah. But I think, let's say it's someone who's 70 years old and it is only 100,000 of capital gains on a say million half dollar portfolio and they need the income to start. I'd be like, bite the bullet. Do it all now. Pay the taxes. >> Yep. Yeah. Because in most years the value will go up and you'll get that dividend income started right away; if you wait,
29:06 you're just delaying the income coming in. So, it certainly makes sense. All right. Well, thank you for that. And obviously hopefully for the listener who asked that direct question, hopefully that was sufficient enough and hopefully the rest of our discussion today kind of helped you have that mindset of how to approach it for yourself.
29:23 Obviously, go talk to an actual financial adviser if you want specific guidance. We're just here to have a discussion for educational purposes. All right. So, as we start wrapping up, I wanted to ask you one last thing. So, what advice would you give to someone who really is just trying to start off? Is there two or three things you would say really are the most important things to focus on? >> Yeah, I think it's just read, practice, and repeat.
29:47 >> And that's it. I get really annoyed with a lot of my friends where they're like, "Well, I don't want to turn the portfolio over to my kids because I gave them these books to read and they didn't do it." I'm like, "You can't just read and you can't just practice." And I think learning and being a student goes right along with reading.
30:08 So, I just think you read, you practice, you read, you practice, you read, you practice. Long haul to become a good investor. And it takes a long time. And it's great. You're always interested, you're always curious, you couldn't get bored if you tried, but it does not happen quickly. >> Absolutely.
30:24 I always say, and I think I've mentioned it to you before, I call it my investing practice. I'm practicing investing. I'm learning how to be an investor by reading, by watching YouTube videos, by listening to podcasts, by doing the research, doing the work. When I first started off transitioning to my dividend portfolio about 15 years ago, I only started with like $2,500 because I wanted to quote unquote test the waters.
30:43 I wanted to see if I really wanted to be a dividend investor. And so I started off small and once I started seeing those dividends come in, I was hooked. And now probably 99% of my portfolio pays some type of income to me out of my portfolio. So I've fully made the transition. Obviously that's why I talk about it here on the channel.
30:59 But even if you just need to start small and practice and see what it feels like and get experience like Jenny said, do it and repeat it and then over time you'll get comfortable with this type of investing. So >> I feel like we sound like yoga instructors right now, [laughter] >> right? Because we're practicing.
31:14 We're doing a little >> Yeah. It's called practice because you never get to perfection. It's just practicing. Welcome to my yoga practice. Welcome to my investment practice. You'll never be perfect. You'll just keep practicing. [laughter] >> Yep. Well, I think that's what all investing.
31:32 You've obviously been doing it for many years. I've been [clears throat] doing it personally for [laughter] many years and we still get things wrong. So, you'll never be perfect, but practice gets you towards perfect. So hopefully always keep studying, keep investigating new strategies and what works for you and hopefully you can continue to be a dividend growth investor or dividend income investor over time.
31:53 All right, Jenny, really appreciate your time today and your advice and recommendations on how to become a dividend investor. Really appreciate it. Where can people find you, your books, all that stuff? >> Okay, so books, you can go to your local bookstore. You can go to Amazon or Barnes & Noble. Well, I don't know if Amazon appreciates it, but I know Barnes & Noble appreciates it, and then you can always just check out our company website which is just gilmanhill.
32:16 com and I've got lots of clips and stuff up there. But thanks so much for having me on, Jeremy. It is always fun to be with you. >> Yeah, absolutely. I always enjoy it. Thank you so much and we'll chat again soon. Thanks for watching. While you're here, check out this next video to learn more about dividends, income investing, and options selling.
32:33 And while you're here, make sure you subscribe, click the like button. It really does help. Thank