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Controversial Retirement Money Topics | AMA #14 - E132

March 04, 2026 / 54:51

This episode features Jesse Kramer answering listener questions on controversial and misunderstood topics in personal finance and investing. Key discussions include dividend investing, individual bonds versus bond funds, tax planning, and market strategies.

Jesse addresses a question from Goran about the nature of dividends, explaining that while dividends provide income, they also reduce the company's cash reserves, impacting stock price. He clarifies that dividends are not free and discusses how stock valuations account for cash on hand.

Another question from John raises the comparison between individual bonds and bond funds. Jesse explains that individual bonds return to par at maturity, while bond funds do not, leading to different investment strategies for retirees.

Jennifer's question about tax planning prompts Jesse to discuss the ethics of tax avoidance versus tax planning, emphasizing the importance of financial education. He argues that understanding tax implications can help individuals make informed decisions.

Finally, Jesse addresses Kyle's strategy of using an opportunity fund to buy during market dips, explaining the potential downsides of this approach and emphasizing the importance of long-term investment strategies.

TL;DR

Jesse answers listener questions on dividends, bonds, tax planning, and investment strategies in personal finance.

Video

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

Episode Highlights

  • Investment in Knowledge
    Benjamin Franklin's timeless advice reminds us that knowledge is the best investment.
    “An investment in knowledge pays the best interest.”
    @ 00m 04s
    March 04, 2026
  • Dividends Explained
    Understanding why dividends aren't free and their impact on stock prices.
    “Dividends are not free; they come at a cost.”
    @ 02m 09s
    March 04, 2026
  • Bond Funds vs. Individual Bonds
    Exploring the differences between owning individual bonds and bond funds for retirees.
    “Would you rather buy your eggs one at a time or by the dozen?”
    @ 09m 56s
    March 04, 2026
  • The Importance of Rebalancing
    Joe rebalances his ladder once a year, while others do it more frequently. The cash flows and portfolio values remain the same, emphasizing the importance of rebalancing in investment strategies.
    “That's the only difference.”
    @ 17m 18s
    March 04, 2026
  • Understanding Tax Planning
    Jennifer questions if tax planning is just a way for the wealthy to avoid taxes. The discussion highlights that most people pay taxes and emphasizes the importance of financial education.
    “I think if you’re not paying taxes, you’re probably doing something illegal.”
    @ 19m 04s
    March 04, 2026
  • Market Crashes as Opportunities
    Kyle views market crashes as opportunities to invest. However, Jesse explains why this strategy may not be effective in the long run.
    “Buying the dip on net is just a losing game.”
    @ 27m 09s
    March 04, 2026
  • The Role of Financial Advisers
    It's not my job to layer personal value judgments onto your financial decisions.
    “It's just not my job to do that.”
    @ 33m 43s
    March 04, 2026
  • Roth Conversions and Asset Location
    Roth conversions can be beneficial, but they are not universally good in all scenarios.
    “Roth conversions are one of many things in financial planning that have a distinct Goldilock zone.”
    @ 37m 28s
    March 04, 2026
  • Understanding Fees in Financial Advice
    Price is what you pay, but value is what you get from financial advice.
    “Price is what you pay, value is what you get.”
    @ 44m 41s
    March 04, 2026
  • The Importance of Rebalancing
    Rebalancing your portfolio is crucial to account for performance fluctuations over time.
    “The smartest thing I can do right now is create rules.”
    @ 50m 14s
    March 04, 2026
  • Market Commentary as Entertainment
    Market commentary often feels more like entertainment than education, according to Jesse.
    “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
  • A Personal Podcast
    This podcast is meant for education and entertainment, not as financial advice.
    “It should not be taken as financial advice.”
    @ 54m 45s
    March 04, 2026

Episode Quotes

Key Moments

  • Dividends Myth02:09
  • Tax Planning Debate18:56
  • Market Crash Opportunities23:13
  • Job of a Financial Adviser33:43
  • Value vs Price44:41
  • Rebalancing Rules50:14
  • Market Commentary50:57
  • Podcast Purpose54:45

Words per Minute Over Time

Vibes Breakdown

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