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Controversial Retirement Money Topics | AMA #14 - E132

March 04, 2026 / 54:51

This episode of Personal Finance for Long-Term Investors features Jesse Kramer answering listener questions about controversial topics in financial planning and investing. Key subjects include dividend investing, individual bonds versus bond funds, tax planning, and investment strategies like buying the dip.

Jesse addresses a question from Goran regarding dividends, explaining that while dividends provide income, they reduce the company's cash and thus its stock price. He uses a lemonade stand analogy to illustrate that dividend payments are not free for the business.

Another question from John prompts a discussion on individual bonds versus bond funds. Jesse explains that while individual bonds return to par value at maturity, bond funds do not mature and can fluctuate in value, making their management more complex.

Jennifer's question about tax planning leads to a conversation on fairness in tax payments, where Jesse emphasizes the importance of financial education in navigating tax strategies. He also discusses the implications of tax loss harvesting and the nuances of financial advice.

Finally, Jesse answers questions about market commentary and the psychology of investing, reinforcing the idea that understanding financial principles is crucial for long-term success.

TLDR

Jesse answers listener questions on dividends, bonds, tax planning, and investment strategies in this AMA episode.

Episode

54:51
00:00:00
Welcome to personal finance for long-term investors, where we believe Benjamin Franklin's advice that an
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investment in knowledge pays the best interest both in finances and in your life. Every episode teaches you personal
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finance and long-term investing in simple terms. Now, here's your host, Jesse Kramer. Hello and welcome to
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Personal Finance for Long-Term Investors, episode 132. My name is Jesse Kramer. By day, I work at a fiduciary
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wealth management firm helping clients nationwide. You can learn more at bestinterest.blog. blog/work. [music]
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The link is in the show notes. By night, I write the best interest blog and I host this podcast. I also put out a
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weekly [music] email newsletter. And all those projects help busy professionals and retirees avoid mistakes and grow
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wealth by simplifying their investing, their taxes, and their retirement planning. Today is our 14th Ask Me
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Anything episode, and this is going to be a fun one. As some of you know, I keep a a running list of possible AMA
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questions. The list is now long enough that for the most part, I'm going to try
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to weave some sort of underlying theme into each AMA episode. And today, this AMA episode is going to focus on
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controversial and misunderstood topics from the world of financial planning and investing. Some questions came from blog
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readers and podcast listeners just like you, who submitted them to my email, jesse at bestinterest.blog. Other
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questions came from a LinkedIn post I made where I kind of uh previewed that I'd be recording this episode and a
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bunch of people chimed in with their ideas. But we'll cover topics today like
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dividend investing, individual bonds versus bond funds, tax planning versus tax avoidance, kind of the gray area
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there, buying the dip as it's called as an investment strategy, and a few more.
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But first, before we get into the fun stuff, we'll do a quick review of the week. This one is from Carowind 21, who
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says, "A numbers-based approach, five stars. I love how Jesse goes beyond the
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basics and actually crunches the numbers. A great listen for DIYers and those who are data driven." Well,
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Carowwin, thank you very much for the five-star review and the kind words. You can shoot me an email to
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[email protected] and I'll get you hooked up with a supersoft podcast t-shirt. The first
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question today comes from Goran. And Goran says, Jesse, in episode 127, you explained the 4% rule and how dividends
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are part of it. But I got puzzled when you said that dividends are not free. What do you mean by that? I've heard
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that when a company pays out a dividend on that day, allegedly the stock price drops by the dividend percentage. But
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why? For example, if Apple makes uh $1 billion in a quarter, pays out $100 million in dividends, and stashes 900
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million under a mattress, shouldn't that trigger the price to go up as the investors would reinvest dividends and
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create a demand for a stock? Not that any of it matters as much as what Tim Cook will say during the investors
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conference. Maybe you can provide some insights on one of your future episodes. Well, Goran, yeah, great question. And
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here we go. First, I'm going to explain kind of the myth around the way dividends work and and dividend
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investing as a practice and then I'll explain the truth once I explain the myth. So, let's say you own a share of
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Apple. Very good. It's currently trading at about $250 per share and it has a
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dividend yield of about.42%. And if you do some quick math,42% of $250 is just about precisely $1. So,
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every year you could expect that Apple will pay you about a dollar for being an owner. That's your dividend. and you
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still own the stock on top of receiving that $1 dividend. And next year you'll
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get another dollar, maybe even a little more. And the year after that, another dollar, maybe even a little more. So you
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still own the stock and you're getting this income stream in the form of dividends. And that dividend income
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stream is one of the main ways that stock owners receive their return on investment. Dividends are a wonderful
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thing. But here's the question at the heart of this myth. If instead of giving
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you that dollar in the form of a dividend, if Apple decided to hang on to that dollar instead, what would happen
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to Apple's stock price? Now, it might be a challenging question to conceptualize
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because Apple is such a huge company and it's so complex. So, let's do what every
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finance and economics lesson does starting in elementary school. Let's examine a lemonade stand. You know, you
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help your daughter open a lemonade stand and you're trying to understand how much
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her business is worth. She's got a table. She's got a picture of lemonade.
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She's got some signs. She's built this positive reputation in the neighborhood
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and that's worth something too. She's making sales every day and all those
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future sales are worth something too to the business. But then let's imagine she
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tells you, "Hey dad, I also have $10,000 sitting in cash here in my cash register
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from all the sales I've made." Well, that money is certainly going to go onto
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her business balance sheet, and it's definitely worth something. And I hope you all agree with me that we must
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somehow account for the $10,000 sitting in her cash register if we're taking an
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accurate snapshot of the business value. In fact, that's probably the easiest
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part of her business to value, right?$10,000 in cash is worth $10,000 to the business. But what if she said,
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you know, hey, Dad, rather than keeping this $10,000 in the cash register, I'm
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going to distribute these profits out to the owners. And that's you, my dad, and
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that's me, your daughter. So, so me and you, dad and daughter, are now going to
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receive the $10,000 into our personal accounts, and the the business cash register no longer has the $10,000
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inside of it anymore. Well, listeners, that is essentially a dividend distribution. The owners of the business
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just received profits in the form of money in their pocket. But is the business worth as much after the
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distribution as it was before? Well, the the booth is the same, the table is the
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same, the pitcher and the signs and the reputation and the future sales, they are all the same for this lemonade
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stand, but the cash register that once held $10,000 now holds nothing. So, pretty clearly the business is identical
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minus $10,000 in value. That dividend payment that your daughter made was not free for the business. This is such a a
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simple idea really. The owners received $10,000 because the business lost $10,000. It wasn't free. It wasn't magic
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money. It wasn't something for nothing. And there are some investors out there
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who don't quite grasp that. Now, now why? I would say because in their mind,
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they they do still own the booth. They own the picture. They own the signs. They own the reputation, all the future
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sales. They still own those things exactly like they owned them before. That's absolutely true. But the company
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valuation, including the stock price itself, absolutely incorporated the company's cash on hand. In corporate
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finance lingo, they might call it CCE, cash and cash equivalents. That is usually its own line item on a on a
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corporate balance sheet. And if you look at the CCE before and after a dividend payment is made, you will see the CCE
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drop by exactly the amount of that dividend payment. It's simple subtraction. There's nothing magical
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going on here. And if you are rationally evaluating that business, you will take
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that reduction in in cash and cash equivalents into account. But back to Goran's example, he said, "If Apple
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makes a billion dollars, puts $900 million under a mattress into its cash and cash equivalents, then pays out
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hund00 million in dividends." Goran was asking, "Shouldn't the stock price go up
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because, well, in Goran's mind, and he's and he's right to some extent, right?
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They now have more in CCE than before. They have more in cash than before because they took $900 million and and
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stuck it under the mattress. But we need to ask, where did the billion dollars in
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revenue come from?" And I would argue that the $1 billion arrived because uh
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future revenue or what was previously called future revenue was realized and became current revenue. And from an
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analysis perspective, that money didn't appear out of nowhere. Investors already
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had that future revenue incorporated into the stock price. Like Warren Buffett would say, he he would say, you
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need to discount all future revenue that a company might make. So that $1 billion, Goran, it was already
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incorporated into the stock price. And all that happened was the the $1 billion moved from it'll be here next quarter.
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So maybe it's worth a tiny bit less than1 billion because we need to discount it. So it moves from that state
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into a column that now says okay the $1 billion is literally in our hands and now it's worth a full $1 billion. And
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that's simply how it works. So I hope that to some extent explains why dividends aren't free, right? It's it's
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money moving from the cash register of the business into the pockets of the owners. But therefore, it's value that's
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disappearing from the balance sheet of the business. And therefore, the value of the business has to drop when a
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dividend payment is paid out. And then even if a company puts more money into cash after a good quarter, the question
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really is, well, was that good quarter already part of the of the stock valuation, right? Did the company
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predict it was going to have that good quarter? all the investors took that into account and then that's what ended
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up happening. That's what drives a stock price. Now, if the good quarter happened
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and nobody was expecting it, that's the kind of thing that could cause a stock
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price to actually go up. It's when those future expectations of a company are
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actually incorrect. And if they're incorrect to the upside, you're probably
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going to see a stock price that goes up. But anyway, excellent question, Goran. I
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hope I answered it sufficiently. Okay, the next question is going to be about individual bonds versus bond funds.
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Recently, a reader, John, wrote in and said, "Jesse, I'm not sure why people
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would buy traditional bonds if you can get a similar yield in an ETF, which is more liquid." But then again, lots of
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readers, lots of listeners will write in and say something like, "Well, Jesse, my
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bond funds, they took a beating in 2022, and some of them are still lower in value now than they were 3 or 4 years
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ago. Yet, individual government bonds, they will always return to par. I'm always going to get my full money back
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out of a government bond." So, why would you ever want to own a bond fund that
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can lose value and stay down when instead you can own a government bond that's always going to get back to its
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par value? So, it's an excellent question. I will link an article if you'd prefer to read through this and
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take your time, an article I just wrote. But anyway, this is a nuance topic, but
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since most retirees either own bonds right now or future retirees will own some bonds during their retirement, it's
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definitely a topic worth delving into. And when we peel back the onion over the next few minutes, I hope you realize
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that this question is equivalent to, or at least I would say it's equivalent to,
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would you rather buy your eggs one at a time or would you rather buy them by the
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dozen? It doesn't change the egg. It doesn't change the meals you could make
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with the egg. It doesn't change the space in your fridge. They are the same eggs. And so really, that's the question
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that we want to ask today. Think of it that way. And now we'll dive into the
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details about whether retirees should own individual bonds instead of bond funds or vice versa. The root of the
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issue is that individual bonds mature, eventually an individual bond will return its face value back to its owners
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plus interest along the way. And if interest rates go up and bond prices fall, the owners of those individual
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bonds, they tend to think, well, that's okay. My my bond price maybe it fell
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according to Bloomberg, but I'm just going to hold my bond to maturity and get the full value back. So the bond
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owners, they feel like they can ignore the current price. And I would argue that's borderline imaginary. They are
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choosing to ignore the current price because they know someday way out in the future, maybe in a few months, most
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likely in a few years, they can get their full value back. But bond funds, bond funds don't mature. They only
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return interest. To get your capital back out of a bond fund, you would need to sell shares of that fund, possibly at
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a loss. The same interest rate hike that the individual bond owners ignored. It feels much harder to ignore when it's a
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bond fund. Okay. Okay, well let's pause. What is a bond fund? What does a bond
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fund hold? Isn't it nothing more than the sum of many individual bonds? And if
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people have convinced themselves to ignore the price changes in individual bonds, why can't we do the same thing
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with a bond fund? Well, I think there's one vital difference between individual
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bonds and bond funds. And as far as I'm concerned, this is the only difference
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that actually matters in this conversation, right? This is the only difference that holds any water in this
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conversation. And the difference is that bond funds and those who run them, they
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tend to reset the funds duration regularly. Most individual investors on the other hand will only do so
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sporadically. Okay, now that is a very jargony statement I just made. But what exactly does it mean? Let's take for
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example BSV, the Vanguard short-term bond ETF. It holds a bunch of 1 to5year US Treasury bonds and currently it has
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an average duration of 2.6 years. Duration, as a reminder, is a measure of interest rate sensitivity. The higher
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the duration, the more sensitive an asset like a bond is to an interest rate change. Every day the the individual
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bonds inside of BSV because again BSV is a fund has a bunch of individual bonds in it. So every day the individual bonds
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get one day closer to maturity. Every day the overall duration of BSD ticks downward. Everything's getting one day
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closer to maturity. And if the managers over at Vanguard, right, if those fund managers stood by and did nothing, the
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fund would eventually completely mature and return all of its capital to its owners. But BSV has a job. And that job
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is not to reach maturity. Its job is to maintain a duration in that mid 2.x range. That's the purpose of this
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specific tool. And there are a bunch of investors out there who depend on it. who depend on BSV to maintain that
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predefined purpose. The reason why they hold BSV in their portfolio is because they want something with that duration
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of 2.x years. So to accomplish this, the fund managers over at Vanguard, they are
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going to regularly trim a little here, trim a little there, reinvest some of the fund income into probably longer
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duration bonds to offset the remaining bonds as they shimmy their way toward maturity. That's how bond funds like BSV
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work. They are on a very regular basis resetting their durations. But now let's
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compare that to Joe Retiree. You know the DIYer out there maybe like some of you Mr. DIY bond ladder. Joe might have
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$50,000 in each of one and two and three and four and 5year Treasury bonds. That's his bond ladder. And every day
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Joe's bond ladder gets one day closer to maturity. Every day the overall duration
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of Joe's bond exposure ticks downward. But unlike the fund managers at BSV, Joe
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really doesn't care about that. In fact, it's actually probably what Joe had in
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mind in the first place. To him, it is a feature. It's certainly not a bug. Joe
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wants his one-year treasury to mature soon. He wants that capital to fund his retirement. Then, he's going to
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rebalance his portfolio to free up 50,000 new dollars, and he's going to buy a new shiny 5-year bond with that.
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And that's the lading that he has in mind. That's how a bond ladder works.
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But now let's pause because did you kind of catch what just happened there? Joe
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retiree is doing exactly what the BSV fund manager is doing. He's resetting his duration, but Joe is only doing it
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once a year. He's taking the new $50,000 essentially that just matured from his
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one-year bond and he's circling back around and buying a 5-year bond with it,
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getting his ladder to exactly where it was before. Um, duration wise, the BSV manager is probably doing it like once a
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week, but Joe, Mr. DIY ladder, he's doing it once a year. That's the only
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difference is how frequently they're resetting their duration. Other than that, bond funds and individual bond
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ladders are essentially the same. Okay, real quick aside, and then we'll get
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back to the main show here. Would you rather purchase a 10-year bond that costs $1,000 and is yielding 2%. Or a
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10-year bond that costs $900 and is yielding 3%. I know it would probably help if you could write this down and do
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the math, but it is a trick question. They lead to the same result because 10 years from now, in both cases, you would
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have $1,200 in hand from either bond. And yes, that the specific cash flows might be different. And if we apply a
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discount rate, the end result might be slightly different. But please, you know, accept this example for what it
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is. My point here is that price and interest rate are these counterveiling forces. The the price of your bonds
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might be down, but that's because the yield has increased in an equal but opposite way. And if the price of your
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bonds rises, that's because the the yield of those bonds has decreased. And that's just cold mechanical math. Bond
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math is very cold mechanical math. And the reason why I'm saying all this is
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because I know some of you might be saying, Jesse, everything you've said makes sense to me, but my bond funds,
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their prices are still down from 2022. And that's totally true. If you look at
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a chart for Agg, A is a kind of this mid duration bond fund. It's the duration
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for what it's worth is about 6 years. A is still down 15% from 2022. It still
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hasn't recovered. Although I will say its owners have been receiving a nice income stream along the way. But a is a
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fund and the managers of that fund are consistently resetting its duration. If Joe Retiree had built something like a
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12-year bond ladder in 2022, its duration would also be about 6 years, the equivalent to agg. And if Joe
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Retiree had done that, where exactly would his bond ladder be right now? I can tell you his longer duration
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individual bonds would have taken a beating in 2022 and they would still be underwater. And Joe could make himself
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feel better by saying, "Well, they don't feel underwater to me because I'll just
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wait 6 7 8 more years until they mature." And that's fine if it makes Joe
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feel better. But mathematically, Joe's revolving bond ladder has matched a in
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this case step for step along the way. Joe rebalances his ladder once a year, whereas the A rebalances much more
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frequently. That's the only difference. Other than that, the cash flows are the
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same. The portfolio values are the same. The yields are the same. Everything is the same. Bond funds are collections of
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individual bonds. A retirees bond ladder is exactly the same. Aside from any tracking error due to rebalancing
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frequency or aside from any, you know, discrepancies due to maybe the fund just holding different types of bonds. You
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know, maybe it has some corporates instead of all treasuries or something like that. But other than those things,
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we shouldn't expect any significant differences between individual bond ladders and bond funds. So, excellent
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question, John. Thank you for writing in. I hope that answered your question. Here's a quick ad and then we'll get
00:17:58
back to the show. I love getting your questions and some of you ask me questions about the wealth management
00:18:03
firm I work for in Rochester, New York. Others ask about the best interest blog and this podcast, Personal Finance for
00:18:08
Long-Term Investors, which operate without advertising, without pushy sales, and with no payw walls. How can
00:18:13
the blog and podcast stay afloat without me dumping my own money into it? Well, to answer both those questions, I want
00:18:18
to point you to episode 78 of Personal Finance for Long-Term Investors. I intentionally recorded episode 78 to
00:18:24
shine light on those topics and inform you how you are actually helping and can continue helping these projects carry
00:18:29
forward. So, if you've ever been curious about the business of my blog and podcast, or if you're curious about my
00:18:35
day job in wealth management, please check out episode 78 and let me know what you think. On to the next question
00:18:40
here. Jennifer wrote in and said, "Jesse, my husband and I have saved and invested about $3 million over the past
00:18:45
35 years. Or more accurately, we've saved about 1 million of that and the rest is due to market growth.
00:18:51
Compounding is an amazing thing. But here's our struggle. Is tax planning just a way for well-off people to not
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pay their fair share?" Jennifer, very good question, and here's the way I see
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it deep down. Everybody pays taxes for the most part. I think if you're not paying taxes, you're either very low
00:19:07
income or you're probably doing something illegal. I know there are stories out there and you maybe you can
00:19:13
hear the hesitation in my voice. I know there are stories out there about kind of ridiculously rich people not paying
00:19:19
any taxes due to interesting corporate accounting. And that very well might take place. In my personal experience,
00:19:27
I'm not working with anybody who's the CEO of of a Fortune 500 company or or
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anyone who's making, you know, tripledigit millions a year, but somehow it's all not technically income and
00:19:38
therefore they don't pay any tax. I mean, that stuff might be going on, but for the most part, everybody pays taxes.
00:19:43
99% plus of people work hard for decades of their lives and working people pay income taxes. Now, most of us pay other
00:19:50
kinds of taxes, too. And while everybody I don't think anybody likes to see their
00:19:55
tax dollars used on things that they perceive as bad or stupid or just inefficient, I would also argue that
00:20:01
many of us are happy with paved roads and firefighters and after school programs for atrisisk youth. But you're
00:20:08
right in one way, Jennifer. You have presumably built up this nice little account out there of pre-tax retirement
00:20:14
dollars. I'm making an assumption. I'm assuming that some of your $3 million
00:20:17
are pre-tax. And you're hearing a lot of people like me offer up ways that you
00:20:22
could pay 0% or 10% or 12% taxes on those dollars instead of 24 or 32 or 35% taxes on those dollars. And now part of
00:20:32
the question might be, is it fair that you might be paying less tax when working people are paying more tax? Now
00:20:39
I'm going to lean toward no because you already went through the period of your
00:20:44
life where you were paying more tax during your working years. like you already went through that phase. So from
00:20:49
that point of view, I don't see necessarily any sort of, you know, moral or ethical quandry as far as maybe you
00:20:55
are paying less tax than the people who are actively working. But then you could
00:20:59
say, well, what about the poor sap who who never listens to this podcast? He might be stuck paying more than you
00:21:05
simply because he didn't know any better. And I mean, on that front, I'd
00:21:09
say I'd love to educate that poor sap. But until he finds that education, until
00:21:13
he educates himself on these topics, he's going to be paying somewhat of an ignorance tax. And that idea of an
00:21:19
ignorance tax, it exists everywhere, not just in the world of retirement planning. In fact, we're probably all
00:21:25
paying various forms of ignorance taxes every day. It's just that we don't know
00:21:29
any better. Part of the problem with being ignorant is you're not even aware
00:21:32
you're ignorant in the first place. You know, in your question, Jennifer, you
00:21:35
mentioned the idea of compounding. And you know, is it fair? In the same way, we could ask, "Is it fair that you and
00:21:40
your husband discovered and seized upon the magic of compounding 35 years ago while other people never realize it in
00:21:45
the first place?" I would argue that you're receiving the reward of having
00:21:49
discovered something very valuable long ago and maybe other people are paying some form of ignorance tax for not
00:21:55
realizing that in the first place. So, is it a moral issue? Is an ethical issue? I don't think so. It's probably
00:22:01
just an education issue. I think it's one of the reasons why I think to myself
00:22:04
that an investment in knowledge pays the best interest is that by kind of learning these things and applying them
00:22:09
in our own lives and maybe doing a little part here or there to make sure that other people know them too, we can
00:22:14
all benefit from some form of of better financial education. And the important thing here too when it comes to taxes,
00:22:21
tax planning versus tax avoidance, there are certain things you can do in the tax
00:22:26
world that are either very gray. Like maybe uh someone at the IRS could find them illegal or just are straight up
00:22:33
black and white. That is an illegal thing. And nothing we talk about here on this podcast at least is even close to
00:22:39
the gray part. We are always on the good side of the fence and by a long shot. So, I'm sure there are certain tax quote
00:22:47
unquote tax planning ideas out there that flirt with some form of gray illegality. I wouldn't recommend doing
00:22:54
that. I would get uh good tax planning ideas from a CFP and then I'd run them
00:22:59
by your CPA. As long as it's legal and as long as it's kind of, you know, on
00:23:03
the legal side by a good margin, I think you have absolutely nothing to worry about. That's my two cents. Thank you
00:23:08
for that question, Jennifer. And now we're going to go to a question from Kyle. Kyle says, "Jesse, I see market
00:23:13
crashes as opportunities. I contribute to my 401k on a regular basis and that gets invested, but then I take about
00:23:19
$500 a month and that $500 it sounds like has gone up over time. So maybe at one point it was a couple hundred a
00:23:25
month. Now it's $500 a month." Kyle takes $500 a month and it goes into his
00:23:30
opportunity fund, which sounds to me like a like a bank account. Then whenever the market takes a sharp drop,
00:23:36
I dip into that opportunity fund to invest. I guess I'm smart enough to realize that people like you think I'm
00:23:42
wrong for doing this, but I'm not smart enough to understand why. That's okay.
00:23:47
Kyle says he's smart enough to realize that some people think he's wrong, but
00:23:50
he doesn't understand why he's wrong. So, he's asking, "Could you please
00:23:53
explain it in a way I'd understand?" Kyle, thank you for the question, and
00:23:56
that's a great question. It comes up pretty often, and I think the explanation here is pretty
00:24:00
straightforward. So, you take $500 a month, you put it into your opportunity fund, and presumably that opportunity
00:24:07
fund is something like a high yield savings account earning 3% per year right now. Excellent. And then what is
00:24:13
the rest of the market doing in the meantime? Is it growing at 3% like your bank account? Is it growing at more than
00:24:18
3% or is it growing at less than 3%. And I hope you would agree with me that on average the market and your portfolio
00:24:26
will grow at a rate faster than the 3% in your opportunity fund. So at least up front your opportunity fund seems to be
00:24:33
kind of losing ground to the market. But wait, you say, you know, because you are
00:24:38
waiting for a period of time when the market drops sharply, 10%, 20%, 30% or more. And we know that during that
00:24:45
specific period, you'll be very happy that your opportunity fund was earning
00:24:49
3% while the rest of the market dropped 20%. So you're losing on the front end
00:24:55
because we know the market will tend to outperform your opportunity fund over time. But then you've got to be winning
00:25:01
on the back end because when the market drops, you're really glad you've had
00:25:05
money sitting there in the bank account. And so really the question comes down to
00:25:09
does the winning portion that we just described more than make up for the losing portion that we just described?
00:25:15
And it's actually pretty easy to find that out because if we were to back test
00:25:19
that strategy over historical markets, if we were to look at, you know, S&P 500
00:25:24
price history or NASDAQ price history or the Russell 3000 price history and just
00:25:29
try to back test one of these strategies, we could find out if you were losing more than you were winning
00:25:35
or vice versa. Now, what would you find out? Well, you would see pretty clearly that this strategy that the losing would
00:25:41
be not only more frequent, but would be more consequential than the winning. Or in other words, that those short periods
00:25:47
of winning, the times where buying the dip actually seems to work out, they wouldn't be consequential enough to make
00:25:54
up for all the losing you would be doing on the front end. Now whether your opportunity fund is some tiny fraction
00:26:00
of your investing dollars or a huge fraction of your investing dollars, those dollars will over history have
00:26:06
been losing dollars instead of winning dollars. And and we don't really want
00:26:09
that. Now, could you create some sort of specific niche rules to improve your odds or some some rules to maybe win
00:26:18
during a historical back test? I'm sure you could. I've heard some things before
00:26:21
where, you know, maybe you would change the opportunity fund depending on the PE
00:26:25
ratio of the market. The theory there being if the market is overpriced or underpriced, maybe uh your your
00:26:30
opportunity fund strategy would be more or less effective. Maybe you could make your decisions based on the Buffet
00:26:36
indicator, which is a fraction of the total stock market value against the gross domestic product of the US. You
00:26:42
could whatever. You could look at rates of inflation. You know, you could put more money in during the odd months or
00:26:46
the even months, something quacky like that. You could look at the astrology signs on and on and on and on. And I'm
00:26:51
sure some of those rules might improve your odds. Some of those rules might even prove to be effective when examined
00:26:58
in hindsight. And if you want to pursue those rules, more power to you. I personally don't uh in my portfolio or
00:27:05
in my practice use any rules like that. And I think buying the dip on net is just a losing game. So I don't uh I
00:27:11
don't partake in it. But thank you for the excellent question, Kyle, because I
00:27:14
think it's always good to review that question and use it as a uh as a learning opportunity. And the next
00:27:19
question is from Derek. Derek says, "Is tax loss harvesting just a thing that
00:27:23
advisers say when they're trying to get somebody to sell out of a bad stock position and make it sound like a
00:27:28
strategy?" Derek goes on to say, "Here's my logic. If I have a target asset
00:27:33
allocation, presumably over the long term, all of the components will be profitable. But in the intermediate
00:27:38
term, if one fund, say bonds, is showing a loss, the act of rebalancing would have me sell some of my stock fund and
00:27:46
invest the proceeds into the bond fund to reestablish my desired asset allocation. That sounds like the
00:27:51
opposite of tax loss harvesting to me. Of course, when the time comes to enjoy the fruits of my investments, I see
00:27:57
there's definitely an advantage to considering the tax basis of whatever funds I'm selling. It just sounds to me
00:28:02
like there's a lot more discussion than necessary on the loss harvesting topic.
00:28:05
Yeah, Derek, you make a really good point and if I can summarize what you're
00:28:08
saying, you're basically saying that smart rebalancing is often the opposite
00:28:12
of tax loss harvesting. Rather than selling your losing positions at a loss, you buy more of your losing positions. I
00:28:19
mean, that's what rebalancing is. And you are absolutely correct on that front. However, I will say I don't think
00:28:24
that's necessarily how most financial planners position tax loss harvesting.
00:28:28
Instead, they say this. If Dererick invests $1,000 a month into his taxable brokerage account and he is dollar cost
00:28:34
averaged into say VTI into that ETF for years and years and years and then one year the markets drop pretty
00:28:41
significantly. While many of Dererick's individual past purchases are still definitely going to be at a profit
00:28:46
because he's been investing for years and years and years, some of his most recent purchases of VTI, they will be
00:28:52
sitting at a loss. The monthly purchase he made 3 months ago, well that's going
00:28:55
to be at a loss now because the market just dropped. So the idea is can we harvest those losses and then
00:29:01
immediately reinvest those dollars into something similar like a VO. That is how
00:29:06
I think tax loss harvesting is usually positioned Derek. So it's not rebalancing. It's just that we're we're
00:29:12
selling some assets that are at a losing position in order to use those losses somewhere in the portfolio. But the
00:29:18
question is how are we going to use those losses? Now that to me is the the allimportant question and I would wager
00:29:25
that that many advisers, many content creators in this financial planning, retirement planning space, they don't
00:29:31
realize just the minimal impact, the very very small impact that these losses have except in a few corner cases. And
00:29:39
what are those corner cases? Well, the main one, the big one is a corner case where you would be or should be tweaking
00:29:46
your allocation anyway. So here are some examples. You inherited a lake home from
00:29:50
your uncle. Nice. Good for you. We're sorry your uncle passed away. And since
00:29:54
you've inherited it, it's appreciated in value and but it's a nuisance. You've
00:29:58
had it for a few summers. You don't use it. It's kind of just a nuisance and
00:30:02
you're looking to sell the lake home. And you sell it, but it's appreciated in
00:30:05
value. So, it's going to trigger some capital gains for you. Well, if you have
00:30:09
losses sitting in your portfolio, you can tax loss harvest in your brokerage account and use those losses to offset
00:30:16
the gains from the lakehouse. So again, going back to the corner case that I described, it happens in a place where
00:30:21
you would be or should be tweaking your allocation anyway. And in this particular scenario, we're saying, well,
00:30:27
you want to sell the lakehouse anyway. So, if you're going to sell it anyway,
00:30:31
you might as well see if there's an opportunity to do some tax loss harvesting somewhere else and use those
00:30:36
losses to offset the gains. Or here's another one. You work for Google and you've been wanting to sell some of your
00:30:41
concentrated Google position for the good of your portfolio. you know, you own too much Google, so you would be and
00:30:47
you should be tweaking your asset allocation anyway, you need to deconentrate from Google. So great, if
00:30:54
you can tax loss harvest and use some of those losses to offset the gains, that's
00:30:58
a wonderful thing. So in other words, if your financial plan suggests that you ought to be making a change anyway, then
00:31:04
you can look into tax loss harvesting and it'll likely be a terrific net positive for you. But if your financial
00:31:11
plan or your portfolio suggests that you ought to be staying the course and you decide to tax loss harvest, all you're
00:31:17
going to be doing is reassigning your cost basis from one good asset to another good asset and postponing your
00:31:24
capital gains tax bill to a later date. Now, technically speaking, postponing your capital gains bill to a later date
00:31:30
is worth something positive, but it's not worth very much and it's usually not
00:31:34
worth the hassle. The juice in this case is not worth the squeeze. So again, tax
00:31:38
loss harvesting can be good. I I do think it's probably oversold in your defense, Derek. The real, if we want to
00:31:44
call it like a metric of merit or the real question we ought to be asking ourselves is, would I be making some big
00:31:50
change in my financial plan or in my portfolio anyway? And if the answer is yes, then you can say, oh well, do I
00:31:56
have an opportunity to also tax loss harvest and use those losses to offset some gains? Thank you, Derek, for that
00:32:03
excellent question. And now the next question is a kind of a two-parter from Cody Garrett and Derek Tharp. Both of
00:32:08
whom are very much uh respected voices in the world of financial planning. And this came from my LinkedIn post that
00:32:14
they responded to. So Cody Garrett, he basically says that peace of mind is a bad reason for someone to pay down a
00:32:20
lowinterest mortgage. His argument basically is that the math is so clear that you should not pay down a
00:32:26
lowinterest mortgage. It's kind of a copout to say that peace of mind is the
00:32:30
reason why you're doing it. But then Derek Tharp kind of had a bit of a rebuttal and he said, you know, hey,
00:32:34
should we be telling clients or other people, should we be telling people what their goals ought to be? So, in other
00:32:40
words, you know, right, Cody is saying if you're a long-term investor and you
00:32:44
have a 3% mortgage, while it might feel good to pay down that mortgage, that's
00:32:47
still not a good enough reason to do so because more times than not, long-term investing is going to be financially
00:32:53
better. The spreadsheet will clearly say that that's a better thing. But then
00:32:55
Derek is saying, well, if a family has a goal of say being debtree or owning their house in full or or something
00:33:03
similar to that, should we be sitting here as outsiders or as their financial planner and saying like, "No, no, no.
00:33:09
Trust me, you don't want that to be your goal?" And to me, this begs an even
00:33:13
bigger question that I'll I'll sometimes laugh about with clients. And that
00:33:17
bigger question is just that it's not my job. I don't think it's any financial
00:33:21
planner's job to tell you whether owning a boat is good or bad. To tell you whether taking a trip to Thailand is
00:33:27
good or bad or whether spending $100,000 to to redo your kitchen is good or bad.
00:33:33
That's not my job. It's it's certainly not my job to layer my personal value
00:33:38
judgments onto your spending, onto your decisions, or onto your goal setting. It's just not my job to do that. My job
00:33:45
though is to educate you on the trade-offs, to explain to you the various opportunity costs of the options
00:33:51
in front of you, and quite often to explain to you that one choice might be mathematically better than the other.
00:33:56
And if I'm really good at my job, I will even instill in you how much better one
00:34:01
choice is than the other. Some choices are, you know, kind of like a 5149 split where there's really not that big of a
00:34:08
difference. Sure, maybe one is technically slightly better on paper, but let's be honest, 51.49 is pretty
00:34:13
darn close to 50/50, but other choices are it's going to be like someone who
00:34:17
wants to max out their credit card so that they can go gamble at the casino. It's just a very obvious bad choice or a
00:34:22
very, very obvious good choice. So, I think that's where I fall on this conversation where, you know what, I do
00:34:27
think that it's right for me to explain if someone does want to pay down their
00:34:31
low interest mortgage, I'll explain to them the pros and cons of doing so. And
00:34:36
I might explain to them that all us being equal, a spreadsheet might not agree with that choice. But I also want
00:34:41
to understand where they're coming from. And if they're the kind of person who
00:34:44
says, you know what, my entire life I've hated the idea of having debt. I never
00:34:48
want to have any debt on my balance sheet. No amount of spreadsheets are going to tell me that having debt is a
00:34:52
good thing. Well, for that person, I think paying down a low interest mortgage is the right thing to do. So
00:34:57
anyway, thank you Cody and Derek for that one. The next one is from Phil. Phil is a fellow uh financial adviser
00:35:02
and Phil said that his controversial take is uh don't hire an adviser just S&P and chill. And anyway, I like that
00:35:09
one, Phil. But listeners, I've already talked about that one pretty in-depth.
00:35:12
So, if you want to go back to episode 81, uh you can hear some specifics about the 100% S&P 500 portfolio. And then you
00:35:20
can go back to episode 124 for my kind of deep dive answer on whether DIY finance afficados should consider hiring
00:35:27
any sort of outside advisory help. Here's a quick ad and then we'll get back to the show. I send a free weekly
00:35:33
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That's right, a free weekly email that thousands of people like you are already
00:36:13
reading, a free white paper to help you plan for retirement. And you can sign up
00:36:17
for free at bestinterest.blog. This next one we actually will get into some detail here on the next one. John
00:36:23
wrote in and he said that his controversial take is that Roth conversions are oversold, that asset
00:36:29
location is oversold, and that tax planning in general is oversold. I really like this one, and in fact, I
00:36:35
think I've discussed it, you know, in before to some detail. I've had some
00:36:39
pretty serious conversations with serious people about the Roth conversion that they think they want to make and
00:36:45
I've told them, hey, I think this is a bad idea. You know, where did this idea
00:36:49
get into your head in the first place? And the answer they give me is usually, well, aren't Roth conversions just like
00:36:54
universally a good thing? Anyway, back on episode 127, I shared a story of a woman who sold the idea of buying a
00:37:00
fixed indexed annuity under the guys that doing so would open up doors for her to then execute Roth conversions. In
00:37:07
other words, Roth conversions were the sizzle that this particular insurance company was using to sell their stake,
00:37:13
the fixed index annuities, to this woman. Roth conversions are a great tool. Plenty of people at some time in
00:37:21
their long-term investing journey would benefit from using Roth conversions, but
00:37:25
Roth conversions are one of many things in financial planning that have a distinct Goldilock zone. And this is
00:37:31
actually a good idea that I think I'll turn into an article or a future podcast
00:37:34
topic at some point in more detail. The Goldilock zone, you know, not too hot, not too cold, just right. And one key
00:37:39
aspect of Roth conversions is not overdoing it because overdoing it can absolutely end up being worse than not
00:37:46
doing any Roth conversions at all. The idea of a Roth conversion is to intentionally move income from some
00:37:52
future highinccome year into a very low income year. But if you overdo it, if you overdo your Roth conversions, you
00:37:59
will accidentally turn your, you know, very low income year into a high income year because you've pulled in too much
00:38:06
income. So that is not what we want to do. Anyway, so yes, Roth conversions certainly can be overdone. I might agree
00:38:11
with John in terms of the fact that I think sometimes they are used as a selling point to take action and it's
00:38:17
not always the right thing. Like Roth conversions are not universally good in all in all scenarios. And John also
00:38:22
mentioned um asset location. This one is definitely oversold, at least in my opinion. I'm not sure I've ever seen
00:38:28
someone seriously try to sell asset location strategies while also providing a real number to describe the benefit of
00:38:35
doing so. So some quick definitions, right? Asset location refers to strategically placing your assets,
00:38:41
stocks, bonds, whatever into the quote unquote right account, the right location to achieve smart tax benefits.
00:38:48
The simplified logic is that bonds for example, which create lots of taxable income. Well, those should go into a
00:38:53
qualified account where that taxable income isn't actually counted against you. Isn't actually taxable, right? It's
00:38:59
a qualified tax-free account. Whereas a lower income producing asset like a growth stock, well, that should go into
00:39:07
your taxable account because even though the the income is counted against you there, we already defined this growth
00:39:12
stock as being a lowinccome asset. It's kind of matching up that the the lowinccome assets should go into taxable
00:39:18
accounts. The highinccome assets should go into qualified accounts. And I'll
00:39:22
just pause there, I guess, before I tell you the problem because on its face, don't get me wrong, that is a good idea.
00:39:27
It's a good thing to do. And and sure, you know, all else being equal, if you
00:39:31
got everything else done, all your ducks in a row, you might as well get asset location done, too. The problem is that
00:39:37
asset location just has a relatively low or small benefit. It's on the order of
00:39:42
like.1% to 2% per year. In other words, if you think of someone who initially has a equal waiting across all their
00:39:50
different accounts, you know, taxable, traditional, and Roth, and then you compare that to someone where the only
00:39:55
thing they are trying to do is optimize their tax location, and you compare their long-term investing results over
00:40:01
time, you would find that the tax location optimizer has a better after tax return of something like.1% to 2%
00:40:09
per year. And that's not nothing. It's certainly worth examining, but this is
00:40:13
not something that's going to alter your life. And and there are lots of things
00:40:16
in financial planning that can move the needle that much, if not much more. And the problem or the the important note is
00:40:22
that asset location has a lot of externalities attached to it. It can introduce liquidity and accessibility
00:40:29
and timeline issues into your financial plan because you're you're intentionally
00:40:33
kind of moving around assets into these very specific accounts. And for example,
00:40:37
one thing I'm a major proponent of is that your kind of shortest duration assets should be readily available for
00:40:43
you to spend. Usually meaning some sort of, you know, short-term bond. But here we are with asset location and we're
00:40:49
putting all of our short-term bonds into our qualified accounts, into our traditional accounts and Roth accounts.
00:40:54
I will say usually for most people it would be into their traditional account. But at the same time, an optimal
00:41:00
withdrawal strategy does not have you pulling on your traditional account first. has you pulling on your taxable
00:41:05
account first. So that right there, there's this kind of timeline mismatch with the rest of your financial plan.
00:41:11
Asset location can also introduce rebalancing problems for for some of the same reasons. How are you supposed to
00:41:16
rebalance across accounts if you only are supposed to hold bonds in your traditional account and you're only
00:41:21
supposed to hold stocks in your taxable account? It causes friction as I already
00:41:25
mentioned with optimal withdrawal strategies. Similar friction can be caused in estate planning due to the
00:41:30
different rules governing how taxable accounts and qualified accounts get passed down to heirs. So anyway, asset
00:41:35
location is a place where the juice might not be worth the squeeze. And I do think when I see people really pushing
00:41:41
hard on asset location, I question whether they've thought through kind of the full, you know, long-term
00:41:47
multi-deade ramifications of of optimizing your portfolio in that way. So John, thank you for your question on
00:41:52
that one, and I'd be interested to know what what you think about my answer. The
00:41:56
next one's from Wilson. Wilson says, "Once you have enough assets, why would
00:41:59
you still hire an AUM adviser, an assets under management adviser? Why wouldn't
00:42:03
you just hire a flat fee adviser?" Quick uh definitions for those who aren't
00:42:07
familiar. Assets under management, AUM, that's a type of adviser who might say,
00:42:11
"I charge you 1% of your assets or 75% of your assets." So, every year, their
00:42:16
annual fee is based on a percentage of the assets that the adviser is managing. Flat fee, as the name might imply,
00:42:23
usually just means a a price is quoted to you. I charge you $8,000 a year. I charge you $12,000 a year, regardless of
00:42:30
the assets I'm managing. That is my flat fee. Both of those fee arrangements can
00:42:35
still be fee only. It can be the only way that an adviser charges their fee. And I see that definition messed up
00:42:41
actually a lot online. Again, that that fee only word says uh an adviser, it's
00:42:46
the only way they charge fees. And usually and and still in in today's kind of financial services industry and
00:42:52
landscape, most feeonly advisers fall under the AUM model. It's the only way
00:42:56
they charge fees. They are fee only. It is an AUM fee. But yes, there is a growing tide of what might be called
00:43:03
adviceonly advisers who either charge hourly. They don't actually manage assets. They're advice only. And they
00:43:09
charge hourly or they charge flat fees. There's kind of a bit of a mix and a
00:43:13
match. And I totally understand. Let me say this too. totally understand from the consumer point of view why it's so
00:43:18
confusing because I even see other professionals messing up the verbiage and I can see some people right now the
00:43:24
way I just described it to you I could see some people coming back to me and saying Jesse I actually think you got
00:43:28
that one wrong I'm pretty sure I got it right but if you think I got something
00:43:31
wrong let me know so again Wilson is saying once you have enough assets why would you still hire an AUM adviser why
00:43:37
wouldn't you just hire a flat fee adviser and I think what Wilson's saying
00:43:40
here is I think it was Jennifer who asked us a question a few minutes ago and Jennifer's question had to do with
00:43:45
the difference between tax planning and tax avoidance. And her story was that she and her husband have saved up $3
00:43:50
million over their careers. They're retiring with $3 million. So, I think what Wilson is saying is, well, listen,
00:43:55
if a adviser is going to come in and charge Jennifer 1%, that's $30,000 a year and Jennifer could probably go find
00:44:02
a flat fee adviser for again 8 or 10 or 12 or maybe $15,000 a year. There's I
00:44:08
think Wilson's saying that she could probably save some money. So, great question. Fees are an incredibly
00:44:12
important topic. I have lots of thoughts on fees as you've probably already heard
00:44:16
and you know as long as they're not too too biased. I really enjoy hearing people share their thoughts on the
00:44:21
various fee structures in this industry whether it's an adviser and how they
00:44:24
charge fees or whether it's a a client and how they perceive or you know how
00:44:28
they pay fees or how they perceive the different fee structures that are out there. And I do think when it comes to
00:44:33
this whole fee debate because it is a debate and it's been to some extent beaten to death but I think of one of
00:44:39
Warren Buffett's famous apherisms. He said that price is what you pay and value is what you get. And of course, he
00:44:45
was talking about stocks. You know, price is what you pay, value is what you get with a stock. But I think that
00:44:49
applies here. And I I sit here and I think to myself, if I charged people 1.5%, 1% or.5%.
00:44:57
If I charged them a flat fee of 20K a year or 10K a year or less or more, or if I charged them, I don't know, $1,000
00:45:05
a month or $500 an hour. All those different ways of pricing, right? Those are all different prices. But I think to
00:45:11
myself, in all those different price scenarios, would the value I deliver be any different? You know, would my
00:45:17
knowledge be different? Would I care about people more or less? And the answer to those questions is I don't I
00:45:22
don't think so. I think the value I deliver would be the same. I could see in some situations maybe the time I have
00:45:28
to deliver advice might be different. If if I'm charging more, I get to work with
00:45:32
fewer clients and I get to devote more time and energy to them. If I'm charging
00:45:37
less, I might have to work with more clients to kind of make the business model work and I might have less time.
00:45:42
So, I think that's an important difference. But as far as, you know, my my knowledge, my desire to help, my
00:45:48
care, I think a lot of the value is the same for me personally, regardless of the price that I'm charging. So, then I
00:45:55
put myself in your shoes, Wilson, or the shoes of someone who's looking to work
00:45:58
with a financial adviser. And I think you need to really care about both the value and the price. Obviously, you
00:46:03
know, all else being equal, we all need to be very fee conscious. There's no
00:46:07
doubt about it. One of my friendly acquaintances, Wilson, he's this upper level executive at a publicly traded
00:46:12
company that you absolutely would have heard of. And I'd reckon this guy is probably making, you know, a million
00:46:18
dollars a year or more, a smart guy, nice guy, all the things. And he occasionally likes to pepper me with
00:46:24
financial planning questions. And I've asked him, well, hey, do you work with a
00:46:28
financial planner? and he told me he works with the same, you know, 70-year-old Northwest Mutual Insurance
00:46:34
guy that his uncle introduced him to 30 years ago when he got out of college. And to me, I hear that story and it's a
00:46:40
little bit blasphemous. You know, I'm not a huge fan of of Northwest Mutual and the whole life insurance products
00:46:47
and the annuity products. And at the same time though, going back to this high net worth executive who's kind of
00:46:52
the character in my story here, this this person I know, he told me in no uncertain terms, Jesse, I would trust
00:46:58
this guy with my life. So my point is there is some value there in the relationship itself. I think it's hard
00:47:05
to express that value on a spreadsheet. It's certainly not tangible. It's
00:47:08
intangible. Now, just because it's intangible doesn't mean we should be okay with a 2% AUM fee or a 10%
00:47:15
commission on an insurance product or a, you know, I would say I would argue a whole life insurance product in the
00:47:20
first place or all the other questionable ways that financial advice can be charged for. I don't think that
00:47:25
we have to make excuses for that. But I will say that I think there is a lot of value in the relationship and the trust
00:47:31
itself. And I guess just wrapping things up and and gathering my thoughts here, Wilson, it's to go back to what I said a
00:47:36
minute ago. I think it's really important for you to definitely think about both the price and the value. You
00:47:41
you have to think about both. And again, as investors, we all need to be conscious of fees. Absolutely. And we
00:47:47
all need to make sure that whatever fees we are paying, we're getting requisite
00:47:51
value out of paying those fees. So that's probably the hard part for you. I think I think understanding the price is
00:47:56
the easy part when you're determining if you want to go out and seek professional
00:48:01
financial advice, or at least it should be the easy part, right? If fees are ever confusing to you in some way, it
00:48:06
probably says more about the fees that are being charged and the people who are charging them than it says about your
00:48:12
math skills. Like fees should be very easy to understand conceptually. The value is probably the harder part
00:48:19
because I think there is a pretty wide spectrum of advice and advisors out there. That's your challenge is to make
00:48:25
sure that you're getting enough value for the price that you're paying. So,
00:48:28
thank you for that question, Wilson. And now we're going to pivot to Alex. Alex
00:48:31
had a great question. This is again a question or a controversial take. You could say a controversial question and
00:48:37
it is when you read balance, aren't you by definition selling what's good and
00:48:41
buying what's bad? And of course you kind of are and who in their right mind
00:48:45
would want to sell something that's good and buy something that's bad? You can
00:48:49
kind of hear me laughing to myself cuz there's this Homer Simpson quote where
00:48:52
Homer's son Bart says, "This is the worst day of my life." And then Homer
00:48:57
says, "Oh, this is the worst day of your life so far." And I think something
00:49:01
similar applies here to your portfolio because the funny Simpsons joke is that life can always get worse. But I think
00:49:06
the important takeaway for us is that your portfolio has done X and Y and Z so far. And when you rebalance, you're
00:49:14
selling what's been good so far and you're buying what's been bad so far.
00:49:18
Because if you do it right, and I think this we actually talked about this with one of the questions earlier today. If
00:49:23
you do it right, hopefully you're filling your portfolio with assets that you believe in over the long run. and
00:49:28
you understand that some of these assets will both over and underperform over different shorter periods of time. You
00:49:35
believe in the assets in the long run, but you know over the short run there's
00:49:38
going to be over and underperformance. And you understand that reversion to the mean is this strong undercurrent in
00:49:44
investing. You also understand that trees don't grow to the sky. As they say, nothing goes up forever. Everything
00:49:49
has an upper limit. And when you rebalance, you're taking all of those ideas into account. You're saying, I
00:49:54
like everything I own. Some things have done much better than others over this recent short period of time and my
00:50:00
belief is that such outperformance doesn't continue forever. I don't know
00:50:04
exactly when the outperformance will stop but eventually it will. And in order to account for that fact while
00:50:10
also accounting for my own ignorance about the specific timing. The smartest thing I can do right now is create
00:50:16
rules. Right? Rules about how to rebalance, how and when I'm going to rebalance and then follow those rules
00:50:21
really strictly in, you know, in 60 seconds. That is the theory behind rebalancing. Technically speaking,
00:50:27
you're selling what's good and you're buying what's bad. But you're only
00:50:31
selling what's been recently good and you're buying what's recently been bad
00:50:35
because deep down inside, if you've done it right, you you think that everything
00:50:39
you own is going to be good over a long enough period of time. You just don't
00:50:42
know exactly what those periods of time are going to look like. You're ignorant
00:50:45
to that fact. And so, you have to set up rules and then follow them. Thank you, Alex, for the excellent question. And
00:50:50
now, I think this is the final question today. It is. We're going to go to Crystal. And Crystal said, "Jesse,
00:50:57
market commentary. This is literally just one person's comments on the market." And I think Crystal is right.
00:51:02
It's kind of funny. You know, in a market full of millions of investors and trillions of dollars, we're going to put
00:51:07
a microphone in front of one person and allow them to share their opinions. Yes,
00:51:12
my own workplace has CNBC on in the break room. And well, I think it's much better than having on ESPN or The Price
00:51:19
is Right or the Golden Girls reruns. CNBC makes sense. But sometimes I'm walking in to get my morning coffee and
00:51:25
I watch the TV for a minute and I think this is just entertainment, right? This is not education. Going back a couple
00:51:31
months ago, one of the podcast reviews that a listener like you wrote for me, they included a line where they said,
00:51:36
"This is not an exciting podcast, but it is very educational." And I thought,
00:51:41
"Good. I don't want this to be like paint drying, you know? I don't want it
00:51:44
to be that boring, but I also don't want this podcast to be your dopamine fix."
00:51:49
Because I mean, here's a little tell or a little story. You know, next time you
00:51:52
have CNBC on, watch it all the way through the commercial break, right? Don't turn the channel at the commercial
00:51:57
break. And you'll see some advertisements for Vanguard and Schwab and stuff like that. And that's all
00:52:02
good, but you're going to see a lot of ads that are selling gold to senior citizens that are selling option
00:52:08
strategies to young gambler types. You'll see some lady named Diane who's
00:52:12
selling her husband Roger's stock picking service. I'm dead serious. because Roger is too busy in the back
00:52:17
picking winning stocks to appear in the commercial himself. So, he has his wife Diane come sell the service for him. I
00:52:23
mean, come on, right? Market commentary, in my view, is kind of part of this whole galaxy. And, you know, that the
00:52:30
CNBC, the investing galaxy. And I say galaxy intentionally because it's, you
00:52:35
know, a collection of many, many different things that all technically orbit around the same black hole. That's
00:52:40
what a galaxy is. And what's that black hole exactly? I guess I'm not sure in
00:52:44
this metaphor. It's probably some combination of the economy and the stock market or just money in general. You
00:52:50
know, that's the black hole. That's the big pull. That's the thing that's
00:52:52
sucking us all in. And when I see CNBC, when I hear the market commentary that Crystal's calling out here, they are
00:53:00
closeish to the center of the galaxy. And there's a lot of gravitational pull
00:53:05
on them. The pull of whatever is in that black hole is warping what CNBC and those market commentators decide to say.
00:53:12
And I'll certainly admit I am within that galaxy, too. And I think so are you
00:53:17
because you're here listening. But I very much want to be way on the outskirts of the galaxy. I want to be
00:53:22
really far away from the black hole. I want the effects of that gravity to be pretty minimally felt and not too
00:53:29
warping of what I have to say. And so you won't hear my market commentary about, you know, the prognostications
00:53:35
about the 2026 market returns because I think that the only rational answer ends
00:53:40
with I don't know. So, thank you for the excellent question, Crystal. And again,
00:53:44
all of you, thank you for the amazing AMA ask me anything questions. Please keep them coming. You can submit
00:53:49
questions by sending me an email. The email address is [email protected]. And while you're there on the blog, make
00:53:55
sure you sign up for the free weekly email newsletter. I think we're a little
00:53:59
bit north of 41 or 4,200 subscribers right now. And as always, thank you for listening to Personal Finance for
00:54:05
Long-Term Investors. >> Thanks for tuning in to this episode of Personal Finance for Long-Term
00:54:10
Investors. If you have a question for Jesse to answer on a future episode, send him an email over at his blog, The
00:54:17
Bestin Interest. His email address is [email protected]. Again, that's jessevestinterest.blog.
00:54:25
Did you enjoy the show? Subscribe, rate, and review the podcast wherever you listen. This helps others find the show
00:54:31
and invest in knowledge themselves. And we really appreciate it. We'll catch you
00:54:36
on the next episode of Personal Finance for Long-Term Investors. Personal Finance for Long-Term Investors is a
00:54:42
personal podcast meant for education and entertainment. It should not be taken as
00:54:47
financial advice and it's not prescriptive of your financial situation.

Episode Highlights

  • Understanding Dividends
    Jesse explains why dividends aren't free and how they affect stock prices.
    “Dividends are not free.”
    @ 02m 07s
    March 04, 2026
  • Individual Bonds vs. Bond Funds
    Explore the differences between owning individual bonds and bond funds.
    “Would you rather buy your eggs one at a time or by the dozen?”
    @ 08m 54s
    March 04, 2026
  • The Importance of Compounding
    Jennifer shares her experience of saving and investing over 35 years, highlighting the power of compounding.
    “Compounding is an amazing thing.”
    @ 18m 53s
    March 04, 2026
  • Understanding Tax Planning
    A deep dive into the ethics of tax planning and its implications for wealth management.
    “Is tax planning just a way for well-off people to not pay their fair share?”
    @ 18m 56s
    March 04, 2026
  • Opportunity Fund Strategy
    Kyle explains his strategy of using an opportunity fund to invest during market drops.
    “I see market crashes as opportunities.”
    @ 23m 13s
    March 04, 2026
  • Tax Loss Harvesting Debate
    Derek questions the effectiveness of tax loss harvesting versus smart rebalancing.
    “Is tax loss harvesting just a thing that advisers say?”
    @ 27m 21s
    March 04, 2026
  • Roth Conversions: The Goldilocks Zone
    Roth conversions can be beneficial, but they must be done carefully to avoid pitfalls.
    “Roth conversions are one of many things in financial planning that have a distinct Goldilock zone.”
    @ 37m 28s
    March 04, 2026
  • Understanding Financial Advisers
    The difference between AUM and flat fee advisers can save you money if you have enough assets.
    “Once you have enough assets, why would you still hire an AUM adviser?”
    @ 41m 59s
    March 04, 2026
  • The Theory Behind Rebalancing
    Understanding the importance of rebalancing your portfolio over time.
    “The smartest thing I can do right now is create rules.”
    @ 50m 14s
    March 04, 2026
  • Market Commentary as Entertainment
    A humorous take on market commentary and its role in investing.
    “In a market full of millions of investors, we’re going to put a microphone in front of one person.”
    @ 50m 57s
    March 04, 2026

Episode Quotes

  • The business is identical minus $10,000 in value.
    Controversial Retirement Money Topics | AMA #14 - E132
  • Bond math is very cold mechanical math.
    Controversial Retirement Money Topics | AMA #14 - E132
  • I’d love to educate that poor sap.
    Controversial Retirement Money Topics | AMA #14 - E132
  • The juice in this case is not worth the squeeze.
    Controversial Retirement Money Topics | AMA #14 - E132
  • Price is what you pay, value is what you get.
    Controversial Retirement Money Topics | AMA #14 - E132
  • Trees don’t grow to the sky.
    Controversial Retirement Money Topics | AMA #14 - E132

Key Moments

  • Ask Me Anything00:44
  • Dividends Explained02:07
  • Tax Planning Ethics18:56
  • Opportunity Fund Explained23:13
  • Tax Loss Harvesting Discussion27:21
  • Roth Conversion Debate36:35
  • Adviser Fees Discussion44:11
  • Value vs. Price44:46

Tension Over Time

Words per Minute Over Time

Vibes Breakdown