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Tax Loss Harvesting Myths Debunked: What You Need to Know Now | AMA #4 with Jesse - E95

December 04, 2024 / 59:45

This episode of the Best Interest Podcast features an AMA session where host Jesse Kramer answers listener questions on personal finance topics. Key discussions include portfolio rebalancing, bond performance, Social Security strategies, and considerations for taxable brokerage accounts.

The first question from Kate focuses on portfolio rebalancing. She has a significant amount of her investments in tech stocks and is concerned about the risks involved. Jesse advises her on the importance of diversification and suggests rebalancing strategies, emphasizing the tax advantages of doing so within IRA accounts.

Dan C asks about the performance of bonds and why experts recommend them despite low returns. Jesse explains the relationship between bond prices and interest rates, highlighting the importance of total returns over just price appreciation. He also discusses the impact of inflation on bonds.

Peter G inquires about the benefits of taking Social Security early versus waiting for maximum benefits. Jesse emphasizes the importance of considering risk alongside potential returns, suggesting that guaranteed benefits from Social Security should not be disregarded.

Lastly, Lucas seeks advice on managing a taxable brokerage account. Jesse discusses the importance of tax planning, dividend reinvestment, and the potential need for estimated tax payments as income grows. He also touches on the significance of having a conservative approach to investments in taxable accounts.

TL;DR

Jesse answers listener questions on rebalancing portfolios, bond performance, Social Security strategies, and managing taxable brokerage accounts.

Video

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welcome to the best interest podcast
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where we believe Benjamin Franklin's
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advice that an investment in knowledge
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pays the best interest both in finances
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and in your life every episode teaches
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you personal finance and investing in
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simple terms now here's your host Jesse
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Kramer hello and welcome to episode 95
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of the best interest podcast my name is
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Jesse Kramer and today we are bringing
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you another AMA episode uh if you want
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to you can go listen to the Past AMA
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episodes which I believe were all very
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well received uh which were episodes 90
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86 and 81 and before we get into
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question one today we are going to start
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with our customary review of the week
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this one comes from nirak
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111 and nirak wrote in and said
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straightforward clear concise language I
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stumbled upon this podcast after hearing
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about it on another podcast I've
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listened to more than five episodes
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already I really like Jesse's
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presentation style and I will be
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listening more well NRA thank you very
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much for those kind words if you're
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listening to this right now you can
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email me Jesse bestter interest. blog
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and we will get you hooked up with a
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super soft bestest t-shirt okay let's
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dive into the AMA first question one
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Kate wrote in and Kate's got a a semi
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long question but it's pretty good
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pretty detailed so we're going to take
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our time and work our way through it
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Kate's question is about portfolio
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rebalancing Kate's in her early 40s she
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plans to work another 25 years years she
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has
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$650,000 in Ira 250,000 is in a S&T 500
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ETF the remaining 400,000 is in
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individual stocks with a very heavy
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concentration in tech stocks like Amazon
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Apple and Google and when Kate was
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younger she followed the maxim of buying
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what she knew which is something if
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you're familiar with Peter Lynch
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listeners he's a famous proponent of buy
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what you know and Kate says that those
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stocks the stocks that she knew they've
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done incredibly well for her over the
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last 15 years years but now she's
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getting nervous about having that much
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money in individual stocks especially
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all in the same industry the tech
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industry it's hard to sell those stocks
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in Kate's words when they've done so
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well for her over the past years but I
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know that I need to rebalance or risk
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tremendous loss so Jesse can you tell me
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how you would look at this which is a
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very good but ultimately still a problem
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a good problem to have how much of these
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tech stocks would you recommend selling
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and should Kate just keep pouring that
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money into an S&P 500 fund or diversify
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into another category how often would
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you consider rebalancing so Apple Google
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and Amazon they initially started out at
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only about 20% of Kate's portfolio but
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they've grown significantly over the
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last decade do you consider rebalancing
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on a regular schedule is there a point
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in time when the more conservative
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portion of your investment account is
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high enough that you just let the
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individual stocks ride Kate also
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included that she's a government
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employee and she's on track to retire
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with a pension that will be north of
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$75,000 a year here so she can afford to
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be a little bit more risky in her IRAs
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fantastic question Kate so first
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rebalancing inside of Ira accounts and
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other qualified accounts like a 401k or
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an HSA or something like that has no tax
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consequence and that's wonderful that's
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a great thing for you you don't have to
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fret about capital gains taxes in this
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case even though the stocks that you've
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picked have increased so much yes there
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are capital gains there but you don't
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have to pay capital gains taxes on any
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inside of a qualified account uh so that
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would be different if the Investments
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were in a taxable brokerage account I
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know later in today's episode we have a
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question about taxable brokerage
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accounts I I'll address that idea in a
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minute quite simply Kate the easiest
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diversification method would be to sell
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those individual stocks completely and
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then buy a total market index ETF that's
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the simple answer but okay you mentioned
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Apple Amazon and Google so I'll think
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about those I'll use those three
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companies in this example let's look at
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vti that's vanguard's total stock market
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index ETF that fund uh is composed of
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obviously many many many different
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companies but 6% of it is Apple 3.3% of
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it is Google 3.4% of it is Amazon in
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other words you'll still have plenty of
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exposure to those same exact tech
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companies inside of vti you won't
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necessarily feel the daily ups and downs
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of those individual names I would say
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many of us listening right now my own an
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index fun or just some sort of sort of
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Diversified mutual fund and we're
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blissfully unaware of the fact that on
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any given day some of the stocks that we
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have ownership of inside that fund
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they're losing money they're down on the
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day we don't know it because maybe the
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fund on the whole is up but anyway so
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that's just part and parcel of investing
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in a diversified fund or divers
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investing in a mutual fund like vti now
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Kate if you feel a particular emotional
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connection to those companies to Amazon
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and Apple and Google and you don't want
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to abandon them completely I get it
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that's very very common and in that case
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I would recommend you carve out a small
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portion of your investable dollars and
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make that small portion your sandbox
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that you get to play in how big is that
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portion it might be 3% it might be 5%
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maybe it can get all the way up to 10%
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of your investing dollars that's
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probably where I would cap it is at 10%
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of your investing dollars that can be
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your sandbox and within that sandbox if
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you want to own just Apple Amazon and
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Google so be it that's fine that's fine
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so 90% of your investing dollars will
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end up in a diversified lowcost
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portfolio the other 10% that can be your
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sandbox where you maybe you take more
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risks you hold single stocks you have a
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little bit of fun you own individual
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companies that you know companies that
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maybe you don't understand their balance
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sheets maybe you don't understand the
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true uh intricacies of their business
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but you're familiar with the brands and
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there's something interesting fun about
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owning brands that you're familiar with
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okay let's go to the other part of your
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question I recommend you create a
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rebalancing rule that works for you that
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you can stick with through thick and
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thin and there are a couple ways to
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approach the rebalancing rule one of
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them is very much time based where
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someone says I rebalance every 3 months
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or every 6 months or every 12 months no
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matter what there's a reminder on my
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calendar and it's time based it's
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date-based that on certain times of the
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year whether the Market's gone up or
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gone down I am going to rebalance or
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there's another type of rule where
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someone might say it's not time based
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but it's allocation based they might say
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if my allocation gets more than 5% out
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of whack then I rebalance so let's say
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you start at a 8020 allocation well in
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that case you're going to rebalance if
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you get to 7525 because you're 5% out of
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whack or if you get up to 8515 then
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you're going to rebalance and that
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Target 8020 right is like this
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gravitational pull or like this bungee
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cord that's going to pull you back in as
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soon as you get too far out of whack you
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go back to your target allocation so the
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first type requires you to bake in
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rebalancing into your calendar the
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second type requ Ires you to keep tabs
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on the portfolio itself so is one of
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those two rebalancing strategies better
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than the other not necessarily I mean I
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I suppose when it actually comes down to
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brass taxs and numbers yes I'm sure
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someone out there has done research and
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there are differences between the two in
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fact I I do remember reading something
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that the allocation based rebalancing
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tends to be better than the time-based
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rebalancing although in my opinion I
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think just from the human behavior point
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of view I would think that the
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time-based rebalancing is just easy
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easier right it's easy to say yeah on
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June 31st and December 31st every 6
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months I rebalance my portfolio and for
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what it's worth I think the differences
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between the two rebalancing strategies
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are slim and small enough you know very
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small differences and small benefits
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that either one you choose is going to
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be helpful and is going to be better
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than doing nothing at all so that
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listeners and K I I would leave that one
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up to you yourself best what works for
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you best but Kate had another part of
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her question is there a point in time
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time when the more conservative portion
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of your investment account is high
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enough that you just let your stocks
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ride and and yes there is I'm going to
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link an article in the show notes that I
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called the title of the article is when
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not to rebalance and in short it goes
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back to a couple fundamental ways to
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construct a portfolio one way to
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construct a portfolio is to measure
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strictly in percentages based on your
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ability to take on risk based on your
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willingness to take risk and your need
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for the returns that come from risk
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let's say you settle on a 60/40
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portfolio great that's your target
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you're measuring in percentages and
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whenever the portfolio Strays too far
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from those percentages you're going to
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rebalance right or whenever their six
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months or 12 months date comes up you're
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going to rebalance back to in that
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example 6040 but the second way to
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construct a portfolio is more about
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timelines and goals and building a
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certain amount of buffer into your
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portfolio that kind of investor might
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think to themselves you know what I I
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always want to have 10 years worth of
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spending sitting in lowrisk US bonds
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inside my portfolio I'm not thinking
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about 40% of my portfolio I'm thinking
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about 10 years worth of spending in
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bonds right it's not a percentage it's a
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dollar amount and so for that investor
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they will probably reach a point in
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their investing career where the bonds
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in their portfolio continue to cover
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their 10year need and their stocks are
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continuing to grow far beyond their
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original investment so what might have
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started as 6040 just because 40%
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happened to be 10 years worth of
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spending for them maybe it now becomes
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7030 because well their portfolio has
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grown and now only 30% of it is needed
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in bonds to cover 10 years worth of
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spending it's not that the bonds have
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shrunk in fact it'd probably be that the
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bonds are just the same exact size that
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they were when they started it's just
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that the stock growth is far outpacing
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the bond growth now I'd argue that as
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long as that investor is still
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comfortable in their financial plan with
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the idea of holding 10 years of bonds
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then yeah I I don't think they need to
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rebalance in that case so it's important
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for each of us to understand the reasons
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the rationale behind our chosen asset
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allocation your need to rebalance to
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that allocation will depend on the
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reasons that you chose it in the first
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place and the current state of your
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portfolio and in some cases it means a
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change in your portfolio will lead to
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rebalancing right the natural forces of
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the market will lead you to rebalance
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your portfolio but in other cases maybe
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your portfolio can be changing beneath
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your feet and that's perfectly fine
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because it's still doing the thing that
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you need it to do in this case you know
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you might still have the right amount of
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bonds that you need to reach your
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long-term goals and in that case you can
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let your portfolio ride at least you
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don't always have to rebalance it so
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thank you for the great question Kate
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question two Dan C wrote in and asked
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Jesse I'm hoping to get some
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clear-headed Jesse thinking here you and
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another financial planner encouraged me
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to buy bonds I'm involved with Vanguard
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and Fidelity so I looked at vanguard's
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vbtlx total Bond Market indexed Admiral
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shares it states that the average return
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after taxes on distributions was low
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single digits or even negative
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performance over 135 and 10year
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timelines since October 2001 that fund
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the Vanguard Total Bond market index
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fund has returned an average of
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1.8% per year I also looked at
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vanguard's long-term corporate bond
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Index Fund recommended by Morning Star
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and after taxes on distributions that
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one's returns are even worse over the
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past 135 and 10 years and since
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Inception it has returned 2.8% per year
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I'd like to see that performance laid
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out against inflation and as a hedge
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against falling markets I don't see how
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choosing bonds or a bond fund can help
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it looks like there would be a large
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loss so I haven't moved forward with
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bonds until I can figure out why the
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experts are recommending them in the
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first place what am I missing what am I
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not understanding am I reading the wrong
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chart or in the wrong way Dan what a
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phenomenal question another great
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question and there are two big big
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issues that I want to address here in
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the answer the first one is part of your
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question why the negative performance in
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bonds or just why the bad performance in
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bonds especially compared to stocks and
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then the second part of your question
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are bonds good against inflation or how
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should we think about bonds and and
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compare them to inflation so as far as
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the negative performance goes so
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listeners you you might be familiar with
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this already that bonds are quite
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sensitive to interest rates and the
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longer the bond you know a 30-year Bond
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versus a one-year Bond generally the
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more sensitive that bond is to interest
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rates that goes into uh this term called
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duration if you hear the word duration
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with bonds it doesn't quite mean what's
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the length of the bond you know 30 year
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versus one year so it is a bit confusing
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but it's related in a way duration
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really is a synonym for interest rate
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sensitivity now okay but why does this
00:12:46
matter why are longer bonds more
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sensitive to interest rates or or simply
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why are bonds sensitive to interest
00:12:53
rates in the first place so let's say
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you own a 30-year Bond or any year bond
00:12:57
we we'll just use 30-year Bond and it's
00:12:59
yielding 2% per year well right now you
00:13:03
can go to the US Treasury and buy a bond
00:13:06
at probably four four and a half%
00:13:08
something like that I'm not sure what
00:13:09
the 30-year yield is off the top of my
00:13:11
head but the idea is if you own a 2%
00:13:13
Bond and you're trying to sell it on the
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open market but I can go to the treasury
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and buy a bond at 4% why the heck would
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I want your 2% right so the only way you
00:13:23
could entice me to buy your 2% bond is
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if you lower the price so much
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that rather than buying spending $1,000
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at the US Treasury to buy a 4% Bond I'm
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going to pay you much much less to buy
00:13:37
your 2% Bond so much so that the
00:13:39
effective rate of return in the long run
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would be the same for me right because
00:13:43
at the end of the day when you when a
00:13:45
bond expires at the end of the day you
00:13:46
you get all the money back that was
00:13:48
originally used to purchase the bond so
00:13:50
in that way it is a little confusing I I
00:13:54
do admit that but bond prices are very
00:13:56
mathematical right cuz your 30-year 2%
00:13:59
Bond and my 30-year call it 4% Bond we
00:14:02
each spent $1,000 upfront but if I'm
00:14:05
getting all this extra return 4% versus
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2% well I'm certainly not going to pay
00:14:10
you $1,000 for yours when I can go buy a
00:14:13
new one for $1,000 at at the treasury so
00:14:15
I I hope that makes sense and the
00:14:17
interest rate hikes that we saw in 2022
00:14:20
and 2023 essentially what that did was
00:14:23
it took all these people out there who
00:14:25
owned bonds that they maybe bought in
00:14:27
the 2010s or the early 2020s that were
00:14:30
paying 1 or 2% and now all of a sudden
00:14:33
the treasury is selling bonds at 4 and
00:14:35
5% and what did we just go over well the
00:14:38
price of your existing bonds would have
00:14:40
dropped quite suddenly and that's why
00:14:43
Dan when you see those bond funds that
00:14:45
you're looking at on Vanguard or Morning
00:14:46
Star wherever you're looking that
00:14:48
explains the negative performance if we
00:14:50
zoom out further we do see that the 2022
00:14:53
and 2023 interest rate hikes and the
00:14:55
bond performance in those years is
00:14:56
fairly anomalous and that generally
00:14:59
bonds do provide a slow and steady
00:15:01
long-term return and there's another
00:15:03
note here another very important note
00:15:05
for what it's worth cuz this is a
00:15:06
mistake that I see all the time I see it
00:15:09
you know sometimes I'll see it when a
00:15:11
client asks me a question but way more
00:15:12
often than that I see it online right I
00:15:15
see it in the Facebook groups the Reddit
00:15:17
groups the places where DIY investors
00:15:19
and DIY financial planners talk with one
00:15:21
another and the mistake is that we need
00:15:23
to be very careful with bonds and bond
00:15:25
funds about looking at their prices
00:15:27
versus looking at their total returns we
00:15:30
need to be very careful here because a
00:15:31
bond by its very design is supposed to
00:15:33
be relatively stable in price while
00:15:36
providing a a coupon or an interest
00:15:38
payment to the bond owner so for example
00:15:41
if you pull up the chart for one of the
00:15:43
funds that Dan mentioned the Vanguard
00:15:45
Total Bond market index fund or
00:15:47
vltx you can see that the price was $10
00:15:50
per share in 2001 and it's about $9.60
00:15:54
per share today that's 23 years and the
00:15:57
price has actually gone down right it's
00:15:59
basically flat but it's even a little
00:16:01
bit negative over 23 years and to those
00:16:04
of us who understand say what the stock
00:16:05
market has done over the last 23 years
00:16:07
we think what a travesty and well the
00:16:10
thing is price alone simply doesn't
00:16:12
suffice here that's the fundamental
00:16:14
error and as fundamental an error as can
00:16:17
occur for someone who's looking into
00:16:18
their own Investments so make sure you
00:16:19
don't do this and the reason why is
00:16:21
because that price data it doesn't show
00:16:24
the coupons or the interest payments
00:16:26
that vbtx has been providing to it
00:16:29
owners over the last 23 years and that's
00:16:31
where all the return on bonds come from
00:16:34
so I went and pulled data on a couple
00:16:36
total Market bond funds for what it's
00:16:38
worth couldn't find the data on vbtx as
00:16:40
it's a mutual fund and the site I was
00:16:42
looking at had very very detailed data
00:16:44
on ETFs not on mutual funds so that's
00:16:46
what I'm using here but essentially the
00:16:48
two ETFs I'm looking at are proxies for
00:16:52
vbl TX one of them is called BND as in
00:16:55
bond without the O and that's vanguard's
00:16:57
Total Bond ET F and the other one is
00:17:00
called a ag which is the ey shares
00:17:03
version of the Bloomberg aggregate index
00:17:06
uh so they're both Index Fund ETFs with
00:17:09
mission statements of tracking the
00:17:11
Bloomberg a which you can kind of think
00:17:12
of as the total bond market so if I look
00:17:14
at Price alone right I'm only looking at
00:17:17
Price not Total return I'm making the
00:17:19
mistake here I would see that the a is
00:17:21
down 4.8% over the last 21 years 4.8% in
00:17:25
total over the last 21 years but if I
00:17:28
include interest payments from a which
00:17:30
again that's the whole point of owning a
00:17:31
bond in the first place we see that the
00:17:33
a is actually up 2.9% per year or 83% in
00:17:37
total over the past 21 years a very
00:17:39
similar story for BN B andd was created
00:17:42
in 2008 it's also down about 4% on price
00:17:46
over the last 16 years but if we look at
00:17:48
Total return it's up 57% or about 2.7%
00:17:52
per year over those 16 years granted if
00:17:55
we held those Bonds in a taxable account
00:17:57
then the interest we receive is is
00:17:59
taxable and those taxes do eat away at
00:18:01
our long-term returns so I think that's
00:18:03
probably where Dan is getting some of
00:18:05
the after tax numbers that he quoted in
00:18:07
his question they they sound quite
00:18:08
accurate I did some back of the napkin
00:18:10
math assuming a 25% marginal tax rate
00:18:12
blah blah blah and yeah it drops the
00:18:14
annualized returns from roughly 2.7% per
00:18:17
year down to about 1.8% per year that's
00:18:19
a big difference and for what it's worth
00:18:22
that gets into a a nuanced topic called
00:18:24
asset location some of you might be
00:18:26
familiar with that it's another way of
00:18:27
saying not only what are you investing
00:18:30
in you know stocks bonds blah blah blah
00:18:32
but which accounts are housing those
00:18:35
assets your IRA your 401k your taxable
00:18:38
account now personally I'm not a huge
00:18:41
proponent of allowing the tax tail to
00:18:44
wag the investment dog because sometimes
00:18:46
paying taxes on positive returns it's
00:18:48
simply part of this investing process
00:18:51
and it's a sign that your Investments
00:18:52
are performing pretty well for you but
00:18:54
all else being equal Why Pay More tax
00:18:56
than you have to so asset Loc a is a
00:18:59
good concept to know there but getting
00:19:01
back to the main point of this little
00:19:03
diet tribe price when it comes to bonds
00:19:06
price is not the metric of Merit and
00:19:08
even when it comes to stocks price is
00:19:10
not the metric of Merit right because
00:19:13
stock prices don't include dividends the
00:19:15
dividend is gone the price has gone down
00:19:17
well it's still part of Total return and
00:19:19
that's why Total return is the metric of
00:19:22
Merit which by the way it includes both
00:19:25
the price return and it includes the
00:19:27
interest or the dividends that are being
00:19:29
paid as a side note longtime listeners
00:19:31
will have heard me rail against the
00:19:33
baloney reasons why some people cling to
00:19:36
the idea of dividend investing yes
00:19:38
Dividends are a great thing and they are
00:19:40
part of the reason why we invest in
00:19:42
stocks in the first place but some
00:19:44
people would rather own say a 7%
00:19:47
dividend paying company whose price
00:19:48
never changes instead of owning perhaps
00:19:51
a non-dividend payer that grows by 10%
00:19:53
per year it's just terrible logic
00:19:55
there's nothing magic about dividend
00:19:57
payments any one who tries to claim or
00:19:59
or sell you otherwise they have a
00:20:01
fundamental misunderstanding of the math
00:20:03
or they simply don't understand how
00:20:04
businesses are run they don't understand
00:20:06
how the stock market works it might be
00:20:08
all three if you're listening right now
00:20:11
and you've been sold this idea that
00:20:13
dividend investing is Magic or some sort
00:20:15
of superior way of investing in stocks I
00:20:18
highly recommend you you dig into some
00:20:21
research or just dig into some just some
00:20:23
common articles that have been written
00:20:24
I'm happy to link mine in the show notes
00:20:27
I think you need to Avail yourself of
00:20:28
that misconception all right now for the
00:20:30
second part of Dan's question which is
00:20:32
about inflation and specifically Dan had
00:20:34
a question about whether bonds can or
00:20:35
should be acting as some sort of
00:20:37
inflation hedge where Dan was asking you
00:20:39
know why would I hold long-term bonds if
00:20:42
bonds lose value to inflation over time
00:20:44
and and the answer quite simply Dan is
00:20:46
that bonds are not a hedge against
00:20:48
inflation in fact quite the opposite
00:20:50
bonds are heavily affected uh heavily
00:20:53
subject to the forces of inflation with
00:20:56
a bond you are lending money to someone
00:20:58
today
00:20:59
in exchange for a fixed amount of money
00:21:01
in the future and what does inflation do
00:21:03
well it reduces the value of fixed
00:21:05
amounts of money in the future yikes so
00:21:07
it can be very risky to say okay here's
00:21:10
$1,000 today please give me $1,000 back
00:21:13
in 2034 that's a risky proposition
00:21:16
because who knows how much $1,000 will
00:21:18
be worth in 2034 so yes it is nice to
00:21:22
receive the coupon interest payments
00:21:24
along the way right that's the whole
00:21:25
point or that's the whole value
00:21:27
proposition of a bond in the first place
00:21:29
is that we get this Dependable interest
00:21:31
stream as long as we hold the bond but
00:21:33
who knows if those interest payments
00:21:35
will be worthwhile as we wait for our
00:21:38
principal payment to come back to us so
00:21:40
again inflation is the enemy of bonds
00:21:43
and that's why for most individuals and
00:21:45
families planning for their investment
00:21:47
lifetimes we don't want to give
00:21:49
inflation the opportunity to eat away at
00:21:51
our bond returns and that means bonds
00:21:53
should be thought of as a shorter term
00:21:55
asset than for example stocks so what
00:21:58
are bonds good for instead well bonds
00:22:00
provide a much higher guarantee over
00:22:02
short periods of time as compared to
00:22:05
stocks and they provide a slightly
00:22:07
higher return than straight up cash so
00:22:09
if you need money in the next two or
00:22:11
four or 6 years bonds likely make more
00:22:14
sense than stocks or cash in that
00:22:16
scenario once maybe you get out to eight
00:22:18
or 10 years down the line and we can
00:22:20
look at historical back tests and we can
00:22:22
see that the probability of stocks
00:22:25
exceeding Bond performance over that
00:22:26
kind of a time period really starts to
00:22:28
slant in our favor then those are the
00:22:30
time periods where stocks really start
00:22:32
to make more sense than bonds what else
00:22:34
are bonds good for well bonds provide
00:22:35
ballast which can be important and
00:22:37
appropriate for more risk averse
00:22:39
investors from experience it can be
00:22:41
scary for people when 90% of their
00:22:43
assets are in a 30% draw down if you
00:22:46
have like a 9010 portfolio and that 90
00:22:48
represents your stock allocation if the
00:22:50
stock market drops 30% well that that's
00:22:52
pretty scary that means your portfolio
00:22:54
is really feeling it if instead only 60%
00:22:57
of your assets are in draw down and the
00:22:59
other 40% which are in bonds are
00:23:01
actually up well that can lead to a much
00:23:03
better investing feeling and even if the
00:23:07
long-term numbers would push you toward
00:23:09
more and more stocks a big risk possibly
00:23:12
one of the biggest risks that any
00:23:14
investor faces and I'm glad I I don't
00:23:16
think I'm alone in saying this it's the
00:23:18
risk that along your long-term investing
00:23:21
Journey something is going to Buck you
00:23:23
off the horse something is going to make
00:23:24
you feel so upset frustrated scared
00:23:27
stressed that you are going to abandon
00:23:29
your investment plan that's one of the
00:23:31
biggest risks that we all face and one
00:23:34
of the ways we fight against that risk
00:23:36
is by making sure there's enough
00:23:37
conservatism in our plan and enough
00:23:39
conservatism in our portfolio that we
00:23:42
don't subject ourselves to those kind of
00:23:44
negative feelings that that would Buck
00:23:46
us off that horse so the idea there is
00:23:49
designing a portfolio that you can stick
00:23:50
with through thick and through thin
00:23:52
that's of ultimate importance and we
00:23:54
need to ask ourselves on on a personal
00:23:55
level what is that portfolio what is
00:23:57
that asset alloc that we can stick with
00:23:59
through thick and thin bonds often play
00:24:01
an important role in that conversation
00:24:03
another way uh of thinking about the
00:24:05
point that I just made is I can go to
00:24:07
some of my clients who who like to think
00:24:08
of things this way and I can say hey
00:24:10
Bobby you have eight years of future
00:24:13
spending safely allocated in bonds and
00:24:15
yes it stinks that here in the current
00:24:17
moment let's say the stock market
00:24:18
happens to be down and your stock
00:24:20
portfolio lost $100,000 from where it
00:24:23
just was a month ago that stinks but we
00:24:26
got to zoom out you still have eight
00:24:28
years worth of spending in bonds which
00:24:30
which means you have eight years before
00:24:32
you have to worry one little bit about
00:24:34
selling your stocks so do you believe
00:24:36
that 8 years is enough time for the
00:24:37
market to rebound from this current uh
00:24:40
draw down that that it's in some worried
00:24:42
investors they need that kind of cushion
00:24:44
in their portfolio to stick it out and
00:24:46
for some investors it just really helps
00:24:47
them to think about the amount of time
00:24:49
that their bonds are buying them where
00:24:52
they can stick it out they can wait for
00:24:54
the stock portion of their portfolio to
00:24:55
recover Dan thank you for the great
00:24:57
question again the topic of bond returns
00:25:00
to making sure we're looking at Total
00:25:01
return which includes interest payments
00:25:03
and possibly includes taxes that you've
00:25:04
paid not just looking at the price of
00:25:07
the bond or the bond funds alone and
00:25:09
yeah bonds should not be thought of as a
00:25:11
hedge for inflation in fact probably the
00:25:13
biggest risk to owning bonds is the
00:25:14
inflation risk so if anything I mean
00:25:16
it's just a reminder of why bonds are
00:25:19
generally a shorter term stable asset a
00:25:21
ballast of the portfolio you aren't
00:25:23
looking for long-term growth from bonds
00:25:26
from Bond ownership so thank you thank
00:25:28
you Dan here's a quick ad and then we'll
00:25:30
get back to the show did you know my
00:25:32
written Blog the best interest was
00:25:35
nominated for 2022 personal finance blog
00:25:38
of the year and it's been highlighted in
00:25:39
the Wall Street Journal Yahoo finance
00:25:41
and on CNBC I love writing especially
00:25:44
when that writing is to share financial
00:25:46
education and I usually write one or two
00:25:48
articles per week you can read them all
00:25:51
at bestter interest. blog again the web
00:25:54
address is bestter interest. blog check
00:25:58
out question number three comes from
00:26:01
Peter G Peter says I hope all is well I
00:26:03
appreciate all the great content you
00:26:04
provide I know the conventional wisdom
00:26:06
on Social Security is to wait for the
00:26:08
maximum lifetime benefit however doing
00:26:11
the calculations on online calculators
00:26:13
when I enter my information I get much
00:26:15
better long-term outcomes by taking
00:26:17
social security earlier and reducing my
00:26:19
portfolio withdrawal percentage using
00:26:22
the open Social Security app I come out
00:26:24
$60,000 ahead on the social security
00:26:27
access by waiting until age 70 rather
00:26:29
than taking it early but if I claim
00:26:32
Social Security earlier then my
00:26:33
Investment Portfolio would end up $1
00:26:35
million higher than if I claim at age 70
00:26:38
in other words would I rather receive
00:26:40
$60,000 extra in Social Security or have
00:26:43
one million extra in my portfolio it's a
00:26:46
no-brainer for this analysis I was using
00:26:48
a 40% stock 40% Bond 20% cash portfolio
00:26:52
with various withdrawal rates and
00:26:54
different amounts saved early claiming
00:26:56
of Social Security one each and every
00:26:58
time time I'd like to know your thoughts
00:26:59
on this Jesse and if I'm missing
00:27:01
something thank you so very cool
00:27:02
question Peter that's an awesome
00:27:04
question and here's the first thing
00:27:05
Peter's question inspired me to put some
00:27:07
of this down in writing because
00:27:09
sometimes it's just easier to show the
00:27:10
numbers in writing right than it is to
00:27:12
talk through a microphone so I think you
00:27:14
listeners should go read an article I
00:27:15
wrote we'll link it in the show notes
00:27:17
it's called why can't I take Social
00:27:19
Security early and invest it so again
00:27:21
the link will be in the show notes the
00:27:23
heart of the question is that an
00:27:24
Investment Portfolio might be able to
00:27:27
return seven or eight or 9 or 10% plus
00:27:30
per year who knows right it it can vary
00:27:31
over time but uh an Investment Portfolio
00:27:34
might be able to provide a really strong
00:27:36
return over a long period of time and
00:27:38
meanwhile the benefits of waiting on
00:27:39
Social Security especially in the early
00:27:41
years only increase in individuals
00:27:43
monthly payments by five or six or 7% or
00:27:46
if we look at the internal rate of
00:27:48
return on waiting for to claim our
00:27:50
social security that irr might only be
00:27:53
you know four 5 6% something like that
00:27:55
and so just from that kind of zoomed out
00:27:57
point of view the math does scream at us
00:28:00
and it says well duh you know if you can
00:28:03
get a 9% return on a 60/40 portfolio
00:28:06
over a sufficiently long period of Time
00:28:08
Versus a 5 or 6% irr from the Social
00:28:11
Security Administration by waiting well
00:28:13
then you'd be a fool to choose 6% just
00:28:15
take your Social Security as early as
00:28:17
possible invest it in your portfolio and
00:28:20
get the higher return and if we zoom out
00:28:22
on Peter's question today and the
00:28:24
question that inspired the the article I
00:28:25
just mentioned well of course that Math
00:28:27
Makes sense with sufficiently high
00:28:29
investment returns you should always
00:28:31
invest as early as possible even if the
00:28:34
benefit of delaying Social Security was
00:28:35
20% per year but I had an investment
00:28:38
that was paying me 40% per year well I'd
00:28:40
rather start collecting as soon as
00:28:41
possible and get the money invested in
00:28:43
the higher yielding investment so given
00:28:45
sufficiently High returns you always
00:28:47
want to start compound growth as soon as
00:28:49
possible but there is an all important
00:28:52
flaw in this line of thinking and it's
00:28:55
not subject only to Peter because this
00:28:57
is a flaw I think every time this
00:28:58
question comes up because I see this
00:29:00
question I saw this question come up
00:29:01
last week on Reddit and I chimed in with
00:29:03
an answer every time this question comes
00:29:05
up it's coming up because of this flaw
00:29:09
the flaw is that we need to return to
00:29:11
the foundational pillar of investing and
00:29:13
something we repeat pretty often here on
00:29:15
the best interest that risk and return
00:29:18
are intrinsically connected that returns
00:29:21
are not free but instead that returns
00:29:23
are compensation for taking on
00:29:25
investment risk so whenever an investor
00:29:28
Compares returns alone without also
00:29:30
comparing the risks involved they've
00:29:33
conducted an incomplete and an incorrect
00:29:35
and a flawed analysis Peter's question
00:29:37
today it's a great question but it only
00:29:40
looks at returns it doesn't consider
00:29:43
risk this is the reason for this concept
00:29:45
in the investing world of risk adjusted
00:29:47
returns because comparing only the
00:29:49
returns of two Investments without
00:29:52
dividing in some way by the risk that
00:29:53
we've taken it's not an Apples to Apples
00:29:55
comparison you know we just spent we
00:29:57
just answered Dan's question question
00:29:58
about bonds we talked about bonds and
00:29:59
stocks well if you look at the long-term
00:30:01
returns of stocks and you look at the
00:30:03
long-term returns of bonds why would you
00:30:05
ever ever own bonds stocks always
00:30:09
outperform Bonds in the long run well
00:30:11
the the reason why bonds make sense is
00:30:13
when we think about it through a risk
00:30:14
adjusted lens and we think about
00:30:16
especially over short periods of time
00:30:18
the probability the odds that stocks
00:30:20
actually lose US money versus the odds
00:30:23
that bonds lose US money and if we're
00:30:24
planning for some short-term goal can we
00:30:27
afford to take on that kind of risk so
00:30:29
anyway that gets us back to that idea of
00:30:30
risk adjusted returns so in order to
00:30:32
make a sensible comparison here in
00:30:34
Peter's question about social security
00:30:37
we need to level the playing field in
00:30:38
terms of risk the benefits of delaying
00:30:41
Social Security they are guaranteed by
00:30:43
the US government that's a very low risk
00:30:46
you we can get into a debate if you want
00:30:47
about how low of a risk it is with the
00:30:49
state of the US government fiscally and
00:30:51
all that but we need to ask ourselves
00:30:53
what kind of investment risk do we
00:30:54
compare uh the risk of the US government
00:30:56
to I see two VI options the first one
00:31:00
why does Warren Buffett invest all of
00:31:01
Burkshire Hathway's extra cash into US
00:31:04
Treasury short-term us treasury notes
00:31:06
instead of into say an S&P 500 Index
00:31:09
Fund doesn't he know that the S&P has a
00:31:11
much better long-term return blah blah
00:31:12
blah well the answer is US treasuries
00:31:15
are as risk-free as anything in the
00:31:17
investing Universe backed by the full
00:31:19
faith and credit of the US government so
00:31:21
as long as Uncle Sam pays his debts us
00:31:24
treasuries are risk-free the S&P is far
00:31:26
from risk-free and and Warren Buffett
00:31:28
knows that he wants his cash to be safe
00:31:30
and ready for deployment at a moment's
00:31:32
notice the S&P 500 cannot fulfill that
00:31:35
need so the first logical comparison
00:31:37
today then is to use a true risk-free
00:31:39
rate as our investment return something
00:31:42
like a high yield bank account or a
00:31:44
short-term us treasury note is
00:31:45
appropriate for that conveniently we did
00:31:47
that analysis in the linked article in
00:31:49
the show notes where a conclusion ends
00:31:51
up being no different than traditional
00:31:53
social security advice uh which is to
00:31:56
say that the break even point
00:31:58
which is the point at which uh
00:32:00
collecting late makes more sense than
00:32:02
collecting early or the point at which
00:32:03
the different ages that you can collect
00:32:05
Social Security they kind of converge at
00:32:07
a single age that occurs in the late 70s
00:32:10
and and what I mean by that is uh if
00:32:12
someone lives beyond their late 70s they
00:32:16
will have wished they collected later in
00:32:18
life if someone passes away before their
00:32:21
late '70s they would have wished that
00:32:23
they started collecting Social Security
00:32:24
as early as possible that's the break
00:32:26
even point and even when throw this
00:32:28
investing question into the analysis
00:32:30
like we're doing today if our investment
00:32:32
return is the risk-free rate of return
00:32:35
that you can get from a high yield
00:32:36
savings account or from a US Treasury
00:32:38
well then the break even Point still
00:32:40
occurs in the late '70s which is the
00:32:42
same as all traditional social security
00:32:45
advice that tends to be given now the
00:32:47
second option the second way to approach
00:32:48
Peter's question is to show the
00:32:50
potential downsides of Peter's analysis
00:32:53
so that is it's to show how higher
00:32:55
returns from a stock portfolio yeah if
00:32:57
they work in your favor I'm sure and and
00:32:59
the math shows it clearly that if stock
00:33:02
market returns work in your favor you
00:33:04
will have wished that you started
00:33:05
collecting Social Security as early as
00:33:07
possible so you could either put that
00:33:09
money to work in your portfolio or you
00:33:11
could reduce your withdrawals and
00:33:13
therefore keep more money in your
00:33:15
portfolio right the math is exactly the
00:33:17
same if we think of it that way the
00:33:18
point being if you start withdrawals
00:33:20
earlier more of your money is at work in
00:33:22
your portfolio compounding at a higher
00:33:24
rate of return and that ends up being
00:33:26
better but the the second thing we're
00:33:28
going to do right now is to show the
00:33:29
downside of that type of analysis which
00:33:31
is to show how higher returns from a
00:33:33
stock-based portfolio they're far from a
00:33:35
guarantee more specifically we can show
00:33:37
how the downside risk of a portfolio
00:33:39
could actually turn this result on its
00:33:41
head what happens if we suffer a bad
00:33:43
Market if we have bad Market timing if
00:33:45
we have a bad sequence of returns during
00:33:48
our early Social Security period so in
00:33:51
the linked article we looked at a
00:33:52
traditional 6040 portfolio looked at all
00:33:55
the historical returns of that 60/40
00:33:57
port pfolio as in you know the actual
00:34:00
returns that portfolio would have given
00:34:01
an investor since 1950 it had multiple
00:34:04
10-year periods with returns below 2%
00:34:07
per year what if we started our social
00:34:10
security timeline with that kind of low
00:34:11
return and then even if we said let's be
00:34:14
holistic here let's make up for that
00:34:15
return at the end of the analysis so
00:34:17
let's start with a pretty bad return and
00:34:19
then later on in life let's assume we
00:34:21
had pretty good Returns what does that
00:34:22
do to the idea of collecting Social
00:34:24
Security earlier the results are that
00:34:26
the 6040 solution if you will or just
00:34:28
the idea of collecting early and
00:34:30
investing it that solution comes with
00:34:33
very large risks our early Social
00:34:35
Security hack only worked in this
00:34:37
particular case if our retiree died
00:34:39
before age 75 that's not a good outcome
00:34:43
doubly so if Social Security ends up
00:34:45
being a safety net or a back stop in
00:34:46
your financial plan if something like
00:34:48
this were to work we would want to see
00:34:50
data that shows that yeah we can start
00:34:52
collecting Social Security at 62 and
00:34:55
even if we live till 85 90 95 that still
00:34:59
ends up being the smarter Choice than
00:35:01
waiting until age 70 to start collecting
00:35:03
that's how Social Security analysis
00:35:05
that's kind of the metric of Merit here
00:35:07
is what age would you have died at for
00:35:09
this particular choice to have made
00:35:11
sense so maybe I didn't explain that
00:35:13
perfectly clearly before but that's the
00:35:14
helpful way to think of it and all
00:35:16
traditional social security advice shows
00:35:18
the break even points occurring you know
00:35:20
in the late '70s what Peter's proposing
00:35:22
here are just the idea of collecting
00:35:24
Social Security early to invest it if
00:35:26
markets go through
00:35:28
a very realistic somewhat negative
00:35:30
sequence of returns that we've seen
00:35:32
before here in this world that we live
00:35:34
in what we see is that the break even
00:35:36
Point drops down to age 75 and that's a
00:35:38
bad thing that's a negative that's a
00:35:40
very much a negative uh result so if
00:35:43
Social Security is play money if it's
00:35:46
just for fun money in your financial
00:35:48
plan and you're okay with risking a loss
00:35:51
I can see the Merit and the appeal of
00:35:53
Peter's question today you can apply for
00:35:55
Social Security early you can invest it
00:35:56
reasonably and as long as markets
00:35:58
cooperate which to be fair they tend to
00:36:01
do that's the whole reason why we invest
00:36:03
in the first place as long as markets
00:36:05
cooperate you will be better off for it
00:36:07
but it's no guarantee and that's the
00:36:09
entire point of the Social Security
00:36:11
System it's to provide a guaranteed
00:36:13
benefit to retirees so if Social
00:36:16
Security and the guarantee that it
00:36:17
provides is playing even a minor role in
00:36:20
your financial plan I would strongly
00:36:22
discourage putting that money at
00:36:24
investment risk simply to eek out extra
00:36:26
investment returns ears when we make a
00:36:29
Level Playing Field comparison by using
00:36:31
a risk-free rate like we did today
00:36:33
whether it was the short-term treasury
00:36:35
note or the high yield savings account
00:36:38
kind of returns we see that there is no
00:36:40
net benefit to taking social security
00:36:42
early and investing it the only possible
00:36:44
benefit comes when we put our social
00:36:46
security dollars at risk and of course
00:36:48
if we're going to take on such a risk we
00:36:50
better have better looking numbers at
00:36:52
the end of the day right that's the only
00:36:54
logical result that would make us feel
00:36:56
good about taking net investment risk in
00:36:58
the first place so Peter for your
00:37:01
specific scenario I would ask yourself
00:37:03
how vital are social security dollars to
00:37:06
your long-term financial plan if it's
00:37:08
the kind of thing where you know you're
00:37:10
going to be okay without it even if
00:37:12
Social Security disappeared you'd be
00:37:13
fine without it then I could understand
00:37:15
your desire to take it early and
00:37:17
therefore decrease your withdrawal rate
00:37:19
from your portfolio but if you're
00:37:21
listening right now and you know Social
00:37:22
Security is going to be important for
00:37:23
your financial future I would highly
00:37:26
recommend hesitating double-checking
00:37:28
your numbers looking really deeply at
00:37:30
your plan asking your financial planner
00:37:32
whatever it may be before you make a
00:37:34
decision like collecting early just to
00:37:37
make extra Investments question number
00:37:39
four today comes from Lucas hey Jesse I
00:37:41
hope you're well I just recently found
00:37:43
you after you a guest on stacking
00:37:44
Benjamin's podcast and I've been
00:37:46
listening to your AMA episodes which I
00:37:47
find enjoyable and helpful I've got a
00:37:49
question I was hoping you could answer
00:37:51
here on your show my wife and I are in
00:37:53
our early 30s and we're shifting our
00:37:54
Focus to filling out our taxable
00:37:56
brokerage with all our extra funds
00:37:57
because we have our house paid off we
00:37:59
maximize our 401ks and backdoor Roth IRA
00:38:02
contributions throughout the year and we
00:38:03
usually have anywhere between 4, 6,000
00:38:06
left over each month to put into a
00:38:08
taxable brokerage which we just started
00:38:09
this year what are some things I should
00:38:11
be on the lookout for or take into
00:38:13
consideration we do reinvest dividends
00:38:15
and I know we'll need to pay taxes on
00:38:17
those and any distributions but is there
00:38:19
anything else I need to account for
00:38:20
thanks and keep up the good work Lucas
00:38:23
Lucas thank you for tuning in and
00:38:25
congratulations on what sounds like a
00:38:26
fantastic situ ation you find yourself
00:38:28
in you've got a paid off house you're
00:38:30
maxing out your retirement accounts and
00:38:32
you still have another 4 or $6,000 per
00:38:35
month to save and invest I believe
00:38:37
that's what they call a not to brag
00:38:38
moment but seriously kudos to you okay
00:38:41
here's some food for thought for you on
00:38:43
those taxable accounts to answer your
00:38:45
direct questions yes you'll want to have
00:38:47
a plan for reinvesting dividend payments
00:38:49
good for you it sounds like you have
00:38:51
that which is true for just about any
00:38:52
other account you own usually that means
00:38:55
a simple dividend reinvestment plan or
00:38:57
or drip it's usually like a toggle or an
00:38:59
option for those of you listening who
00:39:00
are unsure what I'm talking about it's a
00:39:02
a toggle or an option on the account
00:39:04
itself so when you log into Fidelity or
00:39:06
Vanguard or wherever and you can just
00:39:08
toggle this on to automatically reinvest
00:39:11
any dividends that are paid for you that
00:39:12
is almost always a good idea and yes
00:39:14
Lucas you'll need to pay annual taxes on
00:39:17
any interest or dividends you receive in
00:39:19
this account so that might be the first
00:39:21
thing to be aware of Lucas as your
00:39:23
taxable account grows in size and as
00:39:25
your interest and dividends also grow in
00:39:27
size there might come a point actually
00:39:29
where you're earning so much interest in
00:39:31
dividend income that it's actually going
00:39:32
to be a reasonably sizable portion of
00:39:35
your overall income pi and you're going
00:39:37
to have to do one of two things you'll
00:39:39
either have to increase the amount of
00:39:40
tax withholding at your day job or
00:39:43
you'll have to make quarterly estimated
00:39:44
tax payments so let's spend a couple
00:39:46
minutes on that quick aside what are
00:39:48
quarterly estimated tax payments and why
00:39:50
do we need to pay them first it's
00:39:51
important to uh establish that the US
00:39:53
tax code expects us the taxpayers to pay
00:39:56
in throughout the year it's a pay as you
00:39:59
go system it's not a pay the whole bill
00:40:02
next April system and for most of us
00:40:04
that means we pay into the tax system
00:40:07
every single time we receive a paycheck
00:40:09
that's called your withholding you can
00:40:10
see it right there on your pay stub uh
00:40:12
we've all seen it or felt it in our own
00:40:14
lives but now we need to ask ourselves
00:40:17
what happens when we receive income that
00:40:19
does not have that kind of withholding
00:40:22
set up that's exactly what Lucas or any
00:40:24
of us with a taxable brokerage account
00:40:26
that's what ends up happening to us
00:40:27
we're receiving dividend or interest
00:40:29
income we don't necessarily have tax
00:40:31
withholdings set up in those uh taxable
00:40:33
brokerage accounts well the answer is
00:40:35
that the IRS still expects us to pay as
00:40:38
we go and we can't get away with waiting
00:40:41
until next April to pay that tax bill so
00:40:43
for situations like that the IRS has
00:40:46
four quarterly deadlines where they
00:40:49
establish that deadline to receive an
00:40:51
estimated tax payment from us the
00:40:53
taxpayer typically you would work with
00:40:55
your accountant to calculate and admit
00:40:57
your estimated tax payment now the IRS
00:41:00
understands that nobody is perfect and
00:41:02
some taxpayers will end up owing a
00:41:04
little bit of money when they file taxes
00:41:06
in April and that's not because you
00:41:08
avoided the pay as you go system it's
00:41:10
just that you didn't quite pay enough as
00:41:12
you went as it were however so that's
00:41:14
why the the IRS does have a a 90%
00:41:17
Threshold at which they draw the line as
00:41:19
long as you paid as you went a total of
00:41:22
90% or more of the taxes you owed you
00:41:25
are safe or the alternate is as long as
00:41:29
you paid as you went the full amount of
00:41:32
taxes you owed in the previous year then
00:41:34
you're safe and and a quick example just
00:41:37
to make sure we're on the same side here
00:41:38
because taxes are confusing and this
00:41:40
logic is confusing here we are recording
00:41:42
in November of 20124 so let's say last
00:41:45
year 2023 let's say I my total federal
00:41:48
tax bill ended up being
00:41:50
$20,000 and this year 2024 well I don't
00:41:54
know what my tax bill is going to be
00:41:56
maybe my total tax bill is going to be
00:41:58
$30,000 for whatever reason so I I kind
00:42:01
of have two choices there either way I
00:42:03
need to pay as I go throughout the year
00:42:05
I need to make sure I'm paying into the
00:42:06
system and the IRS really has two
00:42:09
different benchmarks that they're going
00:42:10
to compare me against the first one is I
00:42:13
either need to make sure that I pay as I
00:42:14
go the full amount of whatever I I owed
00:42:17
them last year which was $20,000 so
00:42:19
that's the first barrier that I I can
00:42:21
try to get over or I can think about the
00:42:25
year as it goes along I can try to
00:42:26
estimate what my total tax bill will be
00:42:28
by the end of the year and I need to
00:42:29
make sure I pay in at least 90% of that
00:42:32
now in this hypothetical I just set up I
00:42:34
was saying that my tax bill this year is
00:42:37
$30,000 90% of that is 27 Grand it's
00:42:40
going to be easier for me in this case
00:42:42
just to make sure that I put in the full
00:42:44
amount that I owed last year so the IRS
00:42:47
will expect me come the end of 2024 that
00:42:50
I paid as I went $20,000 throughout this
00:42:54
2024 year that's how that system works
00:42:57
if you pay less than one of those two uh
00:43:00
thresholds that we just described you
00:43:02
will be subject to a small fine for lack
00:43:04
of timely payment it's an annoying thing
00:43:06
that you don't want to have to deal with
00:43:07
so Lucas as you're just starting out
00:43:09
this is probably going to be a non-issue
00:43:11
for you because your income your
00:43:13
interest income your dividend income is
00:43:15
going to be so small compared to uh your
00:43:18
W2 income and and the amount of
00:43:20
withholding that you're already taking
00:43:21
but if you eventually reach a point
00:43:23
where your taxable account is shutting
00:43:24
off lots of interest in dividends enough
00:43:27
so that it's a good percentage of your
00:43:28
total take-home income then you'll
00:43:29
definitely want to ensure that you're
00:43:31
either making estimated tax payments or
00:43:34
what might be easier is adjusting your
00:43:36
workplace withholding from your normal
00:43:38
paycheck adjusting that higher so that
00:43:41
you pay as you go more throughout the
00:43:43
year let's talk about your investment
00:43:44
strategy Lucas first I'd ask if you have
00:43:46
any specific goals for your money are
00:43:48
you saving for a boat for a lake house
00:43:50
are you investing just because you know
00:43:52
you just want to put that money to work
00:43:54
as always if you have specific goals
00:43:56
with specific timelines you can and
00:43:57
should construct your portfolio based on
00:43:59
the dollar amounts of those goals and
00:44:01
the asset classes that make sense for
00:44:03
your timelines but what if you don't
00:44:05
really have any specific goals what then
00:44:08
well I'd maintain that your tax bill
00:44:09
account should be slightly more
00:44:11
conservative than your retirement
00:44:12
accounts and again it comes down to
00:44:14
timelines because even though you might
00:44:16
not have a goal set for your tax
00:44:18
Investments right now and you might be
00:44:20
thinking in your head well there's an
00:44:21
infinite indefinite timeline there it's
00:44:23
a super long timeline I'm going to go
00:44:25
high risk there's always a chance that
00:44:27
that changes in the future I can say
00:44:29
from experience of working with clients
00:44:31
who on day one said yep we're just
00:44:33
investing for the long run just put it
00:44:34
to work long-term assets then a couple
00:44:36
years later they came back to me and
00:44:37
said well actually we're going to give
00:44:39
$30,000 to our kid for a home down
00:44:41
payment with a taxable account you can
00:44:43
pull the money out at any time for 90%
00:44:45
of people including me perhaps including
00:44:47
you I think it helps to look yourself in
00:44:49
the mirror and say you know what life
00:44:51
changes curveballs happen my goals for
00:44:53
this money today might change in the
00:44:55
future and I might have a sudden
00:44:57
timeline shift that I wasn't quite
00:44:58
expecting allocating this taxable
00:45:01
account in a slightly more conservative
00:45:03
manner as compared to retirement
00:45:04
accounts is acknowledging that very
00:45:06
human truth about ourselves so I would
00:45:08
consider that Lucas the next topic
00:45:10
capital gains if and when you eventually
00:45:13
sell Assets in this account Lucas you
00:45:14
will be subject to capital gains and
00:45:16
capital losses well hopefully more gains
00:45:18
and the subsequent taxes that come with
00:45:20
that capital gains tax planning it's a
00:45:22
very fun financial planning topic timing
00:45:25
is everything here if you end up
00:45:26
realizing capital gains while you're
00:45:28
still earning lots of income like from
00:45:30
your normal W2 job well you're
00:45:32
definitely going to pay taxes on those
00:45:33
gains if you can wait until low earning
00:45:36
years such as Retirement or just
00:45:38
something else that happens in life when
00:45:39
you have a low earning year I don't know
00:45:41
maybe you'll have a sabatical something
00:45:42
like that you can probably avoid quite a
00:45:45
bit of capital gains tax if you're
00:45:47
charitably inclined you can avoid quite
00:45:49
a bit of capital gains tax you can also
00:45:51
look into tax loss harvesting which
00:45:53
coincidentally is a common endof year
00:45:55
topic here we are in November 2024 even
00:45:58
though it shouldn't really be an endof
00:45:59
year topic it shouldn't be based on the
00:46:01
time of year at all tax loss harvesting
00:46:03
should only be based on market
00:46:05
performance that's an aside for another
00:46:06
day anyway there might not be uh many
00:46:09
tax losses for you to harvest here in
00:46:11
2024 Lucas or anyone listening uh in
00:46:14
general assets have performed very well
00:46:16
this year but on that topic tax loss
00:46:18
harvesting it's an okay but certainly
00:46:21
not an outstanding tool in the toolbx
00:46:24
I'll share my thoughts via an article I
00:46:26
wrote the link is in the show notes is
00:46:28
tax loss harvesting worthwhile for those
00:46:30
curious the short answer is the way most
00:46:33
people use tax loss harvesting results
00:46:35
in zero net change in their portfolio
00:46:38
construction right they're they're
00:46:39
selling one stock or One Fund to buy a
00:46:43
very similar stock or a very similar
00:46:44
fund so it's not like they're achieving
00:46:46
a better asset allocation or better
00:46:49
diversification there's no change there
00:46:51
but also the way people at least the way
00:46:53
most people use tax loss harvesting also
00:46:55
results in no net change in the cost
00:46:58
basis of their portfolio they realized
00:47:00
some losses today and they reinvest the
00:47:03
money which that that lowers your cost
00:47:05
basis right you're selling an asset that
00:47:07
had a higher cost basis you're selling
00:47:09
it for a loss you're buying back in a
00:47:11
different asset which presumably has a
00:47:13
lower cost basis so on that side of the
00:47:15
equation you're lowering the cost basis
00:47:17
of your portfolio and then you're
00:47:18
offsetting that by realizing some gains
00:47:21
and reinvesting that money too which
00:47:23
raises the cost basis on on that side of
00:47:25
your portfolio the losses offset the
00:47:27
gains resulting in no net tax this year
00:47:30
great that's fine that's kind of the
00:47:32
idea of tax loss harvesting but what did
00:47:34
we actually accomplish the cost basis of
00:47:36
your portfolio is exactly the same as it
00:47:38
was before you lowered it on one side
00:47:41
you raised it on the other side all we
00:47:43
did in this case was kick the capital
00:47:45
gains taxes down the road which has a
00:47:47
small minor benefit of doing that but
00:47:50
it's not nearly as good as as most
00:47:52
people think now there are some
00:47:53
interesting cases where tax loss
00:47:55
harvesting uh is extremely worth while
00:47:57
but usually it has to do with offsetting
00:47:58
the tax gains from some other type of
00:48:01
investment usually it might have to do
00:48:03
with a real diversification play that
00:48:05
also provides tax benefits so here's an
00:48:09
example let's say a retiree is
00:48:11
downsizing their house and the home sale
00:48:13
results in a large amount of taxable
00:48:15
gains now many of those gains are
00:48:17
actually going to be tax exempt as it
00:48:18
was their primary home but let's say
00:48:20
there's still another $100,000 in gains
00:48:23
resulting in about $24,000 in federal
00:48:25
taxes for them well if that individual
00:48:28
has a taxable account with any sort of
00:48:29
losses in it I would definitely
00:48:31
recommend running the math on if those
00:48:33
losses can be realized to offset some or
00:48:36
all of the gains from their home sale
00:48:38
that's a great use of tax loss
00:48:40
harvesting because the gains from the
00:48:41
home sale are there they didn't sell
00:48:43
their home to to adjust their asset
00:48:45
allocation they sold their home because
00:48:46
of just life in general and yeah those
00:48:50
gains all occurring in one year might
00:48:51
not be a very good thing for them and if
00:48:54
they can offset those gains with some
00:48:55
losses then might be a great net benefit
00:48:58
in the long run so anyway that's my
00:49:00
quick little aside and rant on tax loss
00:49:03
harvesting and just taxes and general
00:49:05
capital gains in in a taxable account
00:49:07
Lucas uh lastly I would think from an
00:49:09
estate planning point of view Lucas you
00:49:11
should understand what would happen with
00:49:13
your taxable account in the event of
00:49:15
your untimely death if for example you
00:49:17
know the assets would pass to your
00:49:19
spouse it might make sense to put a to
00:49:21
transfer on death designation on that
00:49:24
account if it's already a joint account
00:49:26
between you you and your spouse you
00:49:27
might want to put a uh with rights of
00:49:29
survivorship wos designation on the
00:49:32
account or if you'd want to pass those
00:49:35
assets onto another family member or a
00:49:38
friend you might want to detail that in
00:49:40
your will so thank you for the good
00:49:42
question Lucas and happy investing to
00:49:44
you here's a quick ad and then we'll get
00:49:47
back to the show serious question why do
00:49:50
podcasters constantly ask for ratings
00:49:52
and reviews yes they do help highlight
00:49:55
our shows to new listeners they help
00:49:56
strangers find us on Apple podcast and
00:49:59
Spotify it's totally true and a good
00:50:01
reason to ask for ratings and reviews
00:50:03
but I have something more important at
00:50:05
least more important to me I want to
00:50:07
know if you like this stuff I want to
00:50:09
know if you like my podcast episodes my
00:50:11
monologues my guests the information I
00:50:13
share with you and the stories I tell I
00:50:15
want to improve and make your listening
00:50:17
more enjoyable in the process so yeah I
00:50:20
would love to read your reviews and sure
00:50:22
if you throw a rating in there too
00:50:24
that's great if you like what I'm doing
00:50:26
please share it with me it's such a
00:50:28
great feeling to read your feedback I'd
00:50:30
love to read your review or see a rating
00:50:33
on Apple podcasts or Spotify thank you
00:50:36
and here's the last question today
00:50:37
listeners question number five comes
00:50:39
from Chris Jesse thanks for the work you
00:50:41
do there are a few local financial
00:50:42
planning firms who I know and trust and
00:50:44
I'm interested in working with them I've
00:50:46
asked them many questions thank you for
00:50:48
guiding Us in what questions to ask your
00:50:50
article was very helpful side note
00:50:52
listeners the article that Chris is
00:50:53
referring to we will link it into the
00:50:54
show notes it's the questions that I
00:50:56
would recommend that any of you go and
00:50:57
ask a financial adviser when you're
00:50:59
interviewing them now back to Chris but
00:51:02
my question Jesse is this I want to
00:51:03
potentially give a third of my portfolio
00:51:05
to each of the three advisers I know and
00:51:07
trust and get financial planning advice
00:51:09
from each and then depending on
00:51:11
performance and the quality of the
00:51:12
advice and just how I feel about the
00:51:14
relationship I'll Whittle two of the
00:51:16
three of them away over time what are
00:51:18
your thoughts on that Chris that's a
00:51:21
cool question and you're certainly not
00:51:22
the first person who's had that thought
00:51:24
or thought that question to themselves
00:51:26
and I get it you want to test drive a
00:51:28
little bit before you commit this is a a
00:51:30
very hopefully a long-term relationship
00:51:32
that you're entering into and there is
00:51:35
that question of do I know enough as an
00:51:37
outsider do I know enough between these
00:51:39
three different financial planners to
00:51:41
really make the decision on which one I
00:51:43
should go forward with or does it just
00:51:45
make more sense to spend a few years
00:51:47
getting to know each of the three better
00:51:49
and better and better before then
00:51:51
committing to to the long-term aspect of
00:51:53
the relationship I totally understand
00:51:55
that but I do think think what you
00:51:57
propose has way more negative downside
00:52:01
than positive upside way more cons than
00:52:03
pros and I I would caution you against
00:52:05
it and to be honest if I was one of
00:52:07
those three advisers and I knew that's
00:52:09
what you were doing I wouldn't agree to
00:52:11
sign up for it in the first place I
00:52:12
wouldn't partake in your experiment cuz
00:52:14
Not only would it be probably a bit of a
00:52:16
conflict of interest for me to
00:52:18
participate for myself but I I also know
00:52:21
for a fact that it would be bad for you
00:52:23
you're setting up a situation that's
00:52:25
going to be bad for you and there a few
00:52:26
reasons why that's what we'll get into
00:52:28
here with the meat of the question you
00:52:29
know the King Solomon baby story right
00:52:31
the Judgment of Solomon from the Hebrew
00:52:33
Bible in which Solomon ruled between two
00:52:35
women who' both claimed to be the mother
00:52:37
of a child Solomon orders the baby to be
00:52:39
cut in half pretty barbaric and each
00:52:42
woman receives one half the first woman
00:52:44
accepts the compromise as fair but then
00:52:46
the second woman begs Solomon to give
00:52:48
the baby to her rival preferring the
00:52:50
baby to live even without her and of
00:52:52
course that was a sign that the second
00:52:53
woman is the true mother blah blah blah
00:52:55
Solomon ch es it decree and gives the
00:52:57
baby to her that that's kind of what's
00:52:59
going on here is I I think the dividing
00:53:02
your portfolio and dividing your
00:53:03
financial plan into three different
00:53:05
parts it's a bit of a judgment test as
00:53:07
to to whether the folks who you're
00:53:09
planning to work with are are thinking
00:53:11
it through and thinking your best
00:53:12
interests getting back to Chris's
00:53:14
question let's just say I was one of
00:53:16
Chris's three advisers first it's going
00:53:18
to be challenging to invest Chris's
00:53:21
third of the the pie when there's a lack
00:53:24
of knowledge about what's going on in
00:53:25
the other 2/3
00:53:26
we've talked here on the podcast before
00:53:28
about the puzzle piece metaphor building
00:53:30
a plan building a financial plan is like
00:53:32
putting together a puzzle it comprises a
00:53:34
lot of different puzzle pieces from all
00:53:36
different aspects of your financial life
00:53:38
and it really does help having all the
00:53:39
puzzle pieces in order to successfully
00:53:41
and efficiently solve the puzzle I mean
00:53:43
just imagine solving a puzzle without
00:53:44
all the pieces it just doesn't work if
00:53:47
2third of Chris's assets are being
00:53:48
invested elsewhere and I don't really
00:53:50
know what's going on there I don't know
00:53:52
how they're approaching the investment
00:53:54
problem I don't know what kind of
00:53:55
decisions they're making what kind of
00:53:56
asset allocation is going on I'm not
00:53:58
sure I can do as good a job for Chris as
00:54:01
otherwise I could so that that's a
00:54:03
negative that's a pretty big negative
00:54:04
downside second for Chris I'm a little
00:54:07
curious what You' end up doing with the
00:54:10
three parallel sets of financial
00:54:11
planning advice three different
00:54:14
retirement dates three different Roth
00:54:16
conversion plans three different
00:54:17
everything and the question is are you
00:54:20
Chris going to be the knowledgeable
00:54:22
Arbiter who determines which of those
00:54:24
three sets of plans is best because it
00:54:27
does kind of beg a question if you're
00:54:29
smart enough to rank order those three
00:54:31
Financial plans I wonder why in your
00:54:34
interview process you haven't already
00:54:36
been able to separate the wheat from the
00:54:37
chaff of these three advisers why can't
00:54:40
you already tell which adviser or
00:54:42
planner is smartest order the question
00:54:44
is if you're smart enough to tell which
00:54:46
of those three is good why aren't you
00:54:48
just doing more of it yourself why are
00:54:50
you offloading it to them in the first
00:54:52
place and I think I might know the
00:54:54
answer to my own question there and the
00:54:56
answer there is the stuff can be pretty
00:54:57
complex and you might not be able to
00:54:59
tell which planner or plan is truly the
00:55:02
best you'll probably sit there for a few
00:55:04
years during this experiment you'll
00:55:06
stress out over a question that you're
00:55:09
probably unable to truly answer that's a
00:55:11
big challenge instead and and so what
00:55:13
I've done there is I presented you with
00:55:14
a problem that you don't really have an
00:55:15
answer to and that's harsh of me to do
00:55:18
but here's the answer here's my
00:55:20
recommendation I would ask yourself do
00:55:22
you believe that this person is an
00:55:24
expert and their value will be in excess
00:55:27
of the fees that you pay so that's a yes
00:55:29
or no question that you can answer for
00:55:31
all three advisers you're not
00:55:33
necessarily ranking them one two and
00:55:35
three it's just a yes or no black or
00:55:37
white question are they an expert and
00:55:39
will their value be in excess of their
00:55:41
fees so it sounds like maybe you said
00:55:44
you you know them you trust them maybe
00:55:46
the answer is yes for all three of them
00:55:48
you know they'd be a good adviser for
00:55:49
you you just don't know which one's
00:55:51
going to be the best okay well take all
00:55:53
the ones that you answered yes to that
00:55:55
they're an expert their value will be in
00:55:57
excess of their fees and then you can
00:55:59
ask some softer questions as tiebreakers
00:56:01
such as yeah which one do I trust the
00:56:03
most which one do I want to see the most
00:56:06
right which one do I want to see once or
00:56:07
twice or three times a year for the next
00:56:09
few decades um which one has the
00:56:11
smartest contingency plan in place if
00:56:13
they get hit by a bus uh which one's
00:56:16
investment philosophy just makes the
00:56:18
most sense to me and my understanding of
00:56:20
the investment World etc etc etc these
00:56:22
are some of the questions Chris that we
00:56:24
talked about in the article that you
00:56:25
mentioned in your question that I've
00:56:27
Linked In the show notes the 16
00:56:28
questions that you should be asking a
00:56:30
financial adviser so here's another
00:56:32
thought for you though Chris and a
00:56:33
thought that I think should give you
00:56:34
some hesitation if I'm one of these
00:56:37
three advisers and I know I'm being
00:56:39
judged on investment performance
00:56:41
especially over a short period of time
00:56:44
which in the investing world might mean
00:56:45
a year or two or three or five then I'm
00:56:48
going to think okay I've got a one in
00:56:50
three chance of winning the odds are not
00:56:52
really in my favor if I invest in a
00:56:55
simple or boring or mostly index or
00:56:58
highly Diversified way then I'm going to
00:57:00
expect my performance to be pretty
00:57:02
average right I mean that's the whole
00:57:03
idea of simple boring index Diversified
00:57:06
investing we get average Market type
00:57:08
performance but in a competition with
00:57:11
many different players average is never
00:57:13
going to win so doing the right thing
00:57:15
from a certified financial planner
00:57:17
fiduciary point of view doing the right
00:57:19
thing for you Chris is actually going to
00:57:22
lose in this competition that you've set
00:57:24
up so from a game theory point point of
00:57:26
view it's your competition is going to
00:57:28
incentivize me to do what exactly well
00:57:31
to take extra risk with your money Chris
00:57:33
in order to achieve extra returns that's
00:57:35
the only way I can expect to outperform
00:57:38
my competitors I I have to take more
00:57:40
risks than them and if they're smart
00:57:42
they're thinking the exact same thing
00:57:45
and then if I'm smart I know they're
00:57:47
thinking the exact same thing so now it
00:57:49
really becomes an arms race as to who's
00:57:51
going to take the most risk that's the
00:57:53
nature of the competition that you've
00:57:55
set up and it's clearly something that
00:57:57
is not in your best interest so one of
00:57:59
my friends listener of the show Craig he
00:58:01
likes to say imagine you did the keto
00:58:03
diet for breakfast a vegan diet for
00:58:06
lunch and the Mediterranean diet for
00:58:07
dinner would you expect good results
00:58:09
from that assuming you even achieved
00:58:11
some of your health or weight goals
00:58:14
you'd have no way of knowing which of
00:58:16
those three diets was actually
00:58:17
beneficial for you or which one was the
00:58:19
most beneficial for you in conclusion
00:58:22
Chris I would recommend you not pursue
00:58:24
that idea I understand the reasoning
00:58:26
behind it it's just a a fantastic and
00:58:28
beneficial question for everyone
00:58:29
listening to hear the thought process
00:58:31
there cuz I know for a fact you're not
00:58:32
the only person who's thought that but I
00:58:35
would caution you Chris against going
00:58:36
down that path and with that thank you
00:58:38
all for listening if you enjoyed this
00:58:40
AMA go back and listen to past amas
00:58:42
which were episodes 90 86 and 81 as
00:58:46
always thank you for all those who leave
00:58:47
ratings and reviews on Apple podcast and
00:58:49
Spotify I really appreciate it if you
00:58:51
haven't yet please go leave a rating and
00:58:53
review so that others can find this
00:58:55
helpful content and as always thank you
00:58:57
for listening to the best interest
00:58:59
[Music]
00:59:01
podcast thanks for tuning in to this
00:59:03
episode of the best interest podcast if
00:59:06
you have a question for Jesse to answer
00:59:07
on a future episode send him an email at
00:59:10
Jesse best bestin interest. blog again
00:59:13
that's Jesse attin interest. blog did
00:59:17
you enjoy the show subscribe rate and
00:59:19
review the podcast wherever you listen
00:59:21
this helps others find the show and
00:59:23
invest in knowledge themselves and we
00:59:26
really appreciate it we'll catch you on
00:59:27
the next episode of the best interest
00:59:30
[Music]
00:59:33
podcast the best interest podcast is a
00:59:35
personal podcast meant for education and
00:59:37
entertainment it should not be taken as
00:59:40
Financial advice and is not prescriptive
00:59:42
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