Sept. 29, 2025

Concentrated Stock & Capital Gains: Strategies to Manage Risk and Taxes

Concentrated Stock & Capital Gains: Strategies to Manage Risk and Taxes

In this episode of Something More with Chris Boyd, Jeff Perry, and Russ Ball join Chris
to tackle the challenges of concentrated stock positions and embedded capital gains.
Whether it is legacy shares, inherited assets, or long-held business equity, these situations
can create significant tax and portfolio risk. The team explores smart strategies to manage
exposure, reduce volatility, and navigate tax implications without necessarily selling.
This episode is a must-listen for investors facing concentrated positions or advisors
helping clients preserve wealth while minimizing tax burdens.
For more information or to reach TEAM AMR, click the following link:
https://www.wealthenhancement.com/s/advisor-teams/amr
#CapitalGains #ConcentratedStock #TaxPlanning #InvestmentStrategy #PortfolioRisk
#WealthManagement #FinancialPlanning #EstateStrategy #OptionsHedging
#AssetAllocation

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Welcome to Something More with Chris Boyd.

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Chris Boyd is a Certified Financial Planner Practitioner

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and Senior Vice President and Financial Advisor at

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Wealth Enhancement Group, one of the nation's largest

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registered investment advisors.

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We call it Something More because we'd like

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to talk not only about those important dollar

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and cents issues, but also the quality of

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life issues that make the money matters matter.

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Here he is, your fulfillment facilitator, your partner

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in prosperity, advising clients on Cape Cod and

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across the country.

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Here's your host, Jay Christopher Boyd.

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Welcome to Something More with Chris Boyd.

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I'm here with Jeff Perry and Russ Ball.

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We are all of the AMR team at

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Wealth Enhancement and glad to have you with

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us.

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Today, we are talking about concentrated stock or

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actually, I think we could even extend this

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to circumstances where you have embedded capital gains,

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high capital gains concerns, and how do you

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navigate those?

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And what are some techniques that we can

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try to help you think about that?

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We tend to see this often when people

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have a long-term legacy position in a

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stock.

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Maybe they inherited it and have had it

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for years.

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Maybe they worked in an industry and had

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a stock in that instance.

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It could be, and in other instances, we've

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even seen like real estate or other types

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of assets that have a lot of embedded,

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a business or whatever, they have a lot

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of embedded capital gain.

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And so how do you navigate trying to

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reduce that capital gains exposure or limit the

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risks when you have a concentrated stock?

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So there's different types of approaches and different

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ways we can navigate that.

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So let's talk about these a little bit.

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I was thinking, Russ, we've seemed like we

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keep running into this recently.

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What are some of the techniques that come

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to mind?

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Yeah.

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Well, I think when people start off with

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either concentrated in one position, like you said,

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or just legacy stocks that have been held

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over a long period of time since the

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90s or whatever, the question is, what do

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you do?

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How do you manage around that?

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And I think that's probably the most conservative

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option.

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We've been talking about concentrated stock recently.

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The most conservative option would be to manage

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what you can around those positions.

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But I don't want to sell them.

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I don't want to pay taxes.

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Yeah, that's a great point.

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So if I don't want to sell this

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position, well, first off, it's important to recognize,

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depending on the amount of scale, like how

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much we're in a particular position, this can

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add a magnitude of risk.

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So we generally think in terms of guidance

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for people to think around 5% of

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your investment portfolio in any one name, you

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get beyond that, you're starting to get to

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a point where you have more risk.

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Even if it's maybe 10%, it might depend

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on the stock, the kind of company it

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is, but how diversified within the company.

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You might have multiple companies, different areas of

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business within it.

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Berkshire Hathaway.

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Berkshire Hathaway is a good example.

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Procter & Gamble, something like that.

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It's many companies all in one stock.

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So that kind of thing, that's a good

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example.

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But even so, we typically would say if

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it's getting beyond that 5% range, we're

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getting extra magnitude of risk built into the

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portfolio.

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And so that's where we start to get

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nervous.

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So the one way we can try to

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manage the risk is by looking at the

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asset allocation.

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What's our overall allocation?

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And if we can, maybe there's places that

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we can reduce our overall exposure to risk,

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volatility, stock in this case.

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So we have had occasion where we talked

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about asset location.

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If we make those changes in our taxable

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accounts, well, there might be some tax consequences.

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But if we have non-taxable accounts or

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tax deferred, let's say, IRAs, 401ks, certainly Roth

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IRA too, but we tend to like to

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keep that for growth if we can.

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But these might be places where we could

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make a change, or if you had annuity

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assets.

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These might be places where you could rearrange

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the allocation of what kind of investments you

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own without a tax consequence.

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And you might be able to scale up

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the lower risk investments as a starting point

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without any tax consequence.

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So that's maybe step one.

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That's what you're driving at?

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Yeah, exactly.

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To take a look at everything else.

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And if you're, for whatever reason, locked into

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that position, either you have a lot of

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conviction, you're extremely attached to that position because

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that does happen.

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It's not always the best.

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That's probably not what we would prefer to

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have a sentimental attachment to specific positions, but

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it does happen.

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And I think another piece is, yes, on

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the asset allocation side to try to reduce

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risk in other areas, but also reducing risk

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away from that specific sector.

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So if it's a tech stock that this

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individual might have or whatever it may be,

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you can- Well, we have an example

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of an older gentleman who has telecom stocks.

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They've had- Acquired them through a ESOP,

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an employee.

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Or inherited or whatever.

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Either way, they got them.

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I was talking with a client recently where

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they went through the breakup and now come

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back together.

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They've been round trip on their telecom stocks.

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So the basis on these is nil.

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And on the one hand, you'd say, well,

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maybe I'd rather just hold onto it until

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I pass away because there's a step up

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in basis for my heirs.

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But there's also this, we're missing out on

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opportunity because the performance of these stocks isn't

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as good.

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The dividend is nice, but the overall performance

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has been subpar.

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So maybe how old I am is part

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of this equation, right?

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We have a case where we're dealing with

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a family who has the owner is in

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his 90s, I want to say, and some

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legacy stocks.

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Well, I get why.

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So how do we, in that case, maybe

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it's more about how do we mitigate risk?

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In some cases, it might be, where can

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we make some changes?

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There might be some low hanging fruit.

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Some of these stocks may actually be worth

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less than what they have as basis.

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And there can be opportunities to do some

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offsetting of capital gains with capital losses.

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But for example, if you owned, just as

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an example, if you own GE in the

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90s or the early 2000s, and it's seen

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drastic changes in the way GE is structured

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and priced and so forth, you might actually

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have a capital loss in your mix to

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draw from.

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And that could work against something else that

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you have as a big long-term capital

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gain, as an example.

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So in any case, but if we've got

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instances where we might have something we would

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like to try to hold on to because

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we'd rather have the step up in basis,

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what's a way we might be able to

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navigate the risks?

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Perhaps an option strategy could be a consideration.

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You want to talk about that, Russ?

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Yeah.

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So especially if you have one stock or

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a concentrated group of stocks, but really it

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works best, I think, if we're talking about

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one specific stock.

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A single position that's concentrated.

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Yep.

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If you say, this stock has done really

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well, I'm worried about how it's going to

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affect my overall portfolio if that stock plummets

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tomorrow.

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Because I've got such a large concentration in

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this one company.

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Yeah.

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So yeah.

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Go ahead.

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Yeah.

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Just that there are ways we can use

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an option strategy to hedge against that downside

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risk.

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So you'd basically be buying a put and

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I'll let you...

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Yeah.

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So I'll take on this.

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So I think we don't need to get

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too into the weeds on this.

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I think most people would say, options?

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I don't want to have risk.

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I'm trying to reduce my risk.

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And options sounds like, because of what we

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hear from people, oftentimes options are used for

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leverage to give me enhanced risk, but to

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try to get more juice in a portfolio.

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That's not what we're talking about here.

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Well, one of the ways options can be

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used is to mitigate downside risk.

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Think like an insurance policy.

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I can pay a premium, buy an insurance

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policy to mitigate my downside.

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And essentially, I might still have some downside,

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but I might be able to say, I

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want to put a floor on that downside.

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And usually when we do these approaches, so

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we're buying, we're paying a premium for that

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to protect that downside, but we might also

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sell an option to cap our upside so

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that it will help to pay for this

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insurance.

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And when we use a team that does

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this exclusively, oftentimes they can manage this in

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a way where we can try to avoid

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having an actual transaction occur.

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They can get rid of the contracts, roll

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the contracts and just keep moving the expiration

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date further down the line to avoid any

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kind of experience where we have to sell

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the security that we really don't want to

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sell for a tax purpose.

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So that's one possible way is this involved,

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but sophisticated way of mitigating risk through the

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use of options as a way to limit

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downside exposure.

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And it's important to recognize when you buy

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insurance, there's usually a premium involved.

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So there is some cost oftentimes when you're

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doing this.

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You can mitigate some of that cost and

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make it more manageable and not so painful

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in the process.

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But I think we probably overlooked the first

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and most obvious choice of when you have

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this issue.

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If you've got concentrated stock, you don't really

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want to pay the tax.

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But in some cases, we've had clients and

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friends who've had a concentrated position, had a

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huge run up, felt great, made a lot

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of money, but I don't want to pay

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that tax.

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And they chose not to.

267
00:11:56,480 --> 00:12:00,100
Well, and the good news is the stock

268
00:12:00,100 --> 00:12:01,840
has changed in price and they don't have

269
00:12:01,840 --> 00:12:06,520
a capital gains tax anymore, but that's not

270
00:12:06,520 --> 00:12:07,380
always the good news.

271
00:12:07,500 --> 00:12:10,280
That's bad news too, that the price has

272
00:12:10,280 --> 00:12:10,560
changed.

273
00:12:11,020 --> 00:12:15,220
So sometimes it's worth biting the bullet, just

274
00:12:15,220 --> 00:12:17,860
recognizing you don't own all the value of

275
00:12:17,860 --> 00:12:18,400
that stock.

276
00:12:18,520 --> 00:12:20,380
Uncle Sam's got a claim on some of

277
00:12:20,380 --> 00:12:20,740
the gain.

278
00:12:21,300 --> 00:12:26,200
And so many people put the primary decision

279
00:12:26,200 --> 00:12:29,980
as the tax consequence of whether or not

280
00:12:29,980 --> 00:12:31,480
to sell an investment.

281
00:12:31,620 --> 00:12:35,900
And that's a factor, but it's really not

282
00:12:35,900 --> 00:12:37,020
the most important factor.

283
00:12:37,020 --> 00:12:39,820
The most important factor from my perspective is

284
00:12:39,820 --> 00:12:42,140
what's the outlook for the stock?

285
00:12:43,440 --> 00:12:45,480
Is it in a growing industry?

286
00:12:45,760 --> 00:12:47,380
Are their earnings good?

287
00:12:47,440 --> 00:12:49,080
Is the company being managed right?

288
00:12:49,080 --> 00:12:50,460
Is it in the right sector?

289
00:12:50,840 --> 00:12:52,320
Where are we in the business cycle?

290
00:12:52,340 --> 00:12:54,720
All these things that Brian and you do,

291
00:12:55,080 --> 00:12:57,820
Chris, when you're analyzing a stock, either fundamentally

292
00:12:57,820 --> 00:13:01,280
or technically, but that should be question one.

293
00:13:01,460 --> 00:13:02,680
I own this stock.

294
00:13:03,100 --> 00:13:04,720
Is the future of the stock positive?

295
00:13:06,000 --> 00:13:08,880
That's a whole different analysis than holding some

296
00:13:08,880 --> 00:13:13,100
old industrial company because you've got a large

297
00:13:13,100 --> 00:13:15,540
capital gain that's in a business that is

298
00:13:15,540 --> 00:13:16,960
questionable for the future.

299
00:13:17,680 --> 00:13:19,820
We had a conversation with someone who thinks

300
00:13:19,820 --> 00:13:21,280
the company is great that they have a

301
00:13:21,280 --> 00:13:23,680
concentrated position in, but they think it's kind

302
00:13:23,680 --> 00:13:25,040
of had a good run and maybe it's

303
00:13:25,040 --> 00:13:26,360
a little overpriced right now.

304
00:13:26,740 --> 00:13:30,180
What if you're someone else who says, well,

305
00:13:30,320 --> 00:13:31,900
it's not the stock I don't like.

306
00:13:32,100 --> 00:13:34,820
I think we're poised for a downturn with

307
00:13:34,820 --> 00:13:36,680
the markets or the economy.

308
00:13:36,940 --> 00:13:39,580
We're in a position where the outlook isn't

309
00:13:39,580 --> 00:13:40,200
as good.

310
00:13:40,460 --> 00:13:41,520
Or even the sector, right?

311
00:13:41,800 --> 00:13:42,780
Or the sector, right?

312
00:13:42,840 --> 00:13:45,620
So those are all variables that make it

313
00:13:45,620 --> 00:13:47,040
more difficult to navigate.

314
00:13:48,100 --> 00:13:49,960
On the one hand, I want to say,

315
00:13:50,060 --> 00:13:53,020
one of the options is you could sell.

316
00:13:55,420 --> 00:13:56,320
It's painful.

317
00:13:56,600 --> 00:14:02,240
Nobody likes taxes, but on some level, historically,

318
00:14:02,620 --> 00:14:05,420
taxes are relatively inexpensive today.

319
00:14:05,900 --> 00:14:07,120
That's a good point too, right?

320
00:14:07,180 --> 00:14:09,620
It may not be a bad thing to

321
00:14:09,620 --> 00:14:10,100
consider.

322
00:14:10,380 --> 00:14:10,500
All right.

323
00:14:10,600 --> 00:14:11,400
So that's one option.

324
00:14:11,440 --> 00:14:13,600
And not an all or nothing proposition too.

325
00:14:13,600 --> 00:14:14,340
Absolutely right.

326
00:14:14,560 --> 00:14:14,700
All right.

327
00:14:14,860 --> 00:14:16,200
So that's one option.

328
00:14:16,300 --> 00:14:19,040
We have a gentleman who has capital gains

329
00:14:19,040 --> 00:14:21,420
from real estate that they're dealing with.

330
00:14:22,300 --> 00:14:24,400
And we're trying to navigate that.

331
00:14:24,560 --> 00:14:27,600
Let's talk about the idea of how do

332
00:14:27,600 --> 00:14:33,660
we try to manage capital gains through the

333
00:14:33,660 --> 00:14:36,820
try to create a mechanism where we can

334
00:14:36,820 --> 00:14:41,200
generate intentionally, generate capital losses.

335
00:14:42,640 --> 00:14:44,360
So this is another possibility.

336
00:14:44,540 --> 00:14:45,800
You want to start and I'll jump in?

337
00:14:45,980 --> 00:14:46,080
Yeah.

338
00:14:46,080 --> 00:14:48,060
Well, I think it's important to remember that

339
00:14:48,060 --> 00:14:51,580
capital gains and losses are not just in

340
00:14:51,580 --> 00:14:53,220
your stock portfolio.

341
00:14:53,560 --> 00:14:55,620
They're also, like you said, if you're selling

342
00:14:55,620 --> 00:14:57,800
a business, if you're selling a home, capital

343
00:14:57,800 --> 00:15:00,740
gains- Like a rental property or like

344
00:15:00,740 --> 00:15:02,620
an investment property type of- Yeah.

345
00:15:02,740 --> 00:15:03,560
I mean, or your own property.

346
00:15:03,560 --> 00:15:03,660
Yeah.

347
00:15:03,780 --> 00:15:05,380
I guess it's after a certain amount of

348
00:15:05,380 --> 00:15:05,680
gain.

349
00:15:05,940 --> 00:15:06,100
Right.

350
00:15:06,180 --> 00:15:07,280
Depending on the value, right?

351
00:15:07,440 --> 00:15:07,660
Yeah.

352
00:15:08,360 --> 00:15:11,500
So those gains, they're still capital gains when

353
00:15:11,500 --> 00:15:13,060
you sell a house and they could be

354
00:15:13,060 --> 00:15:16,540
offset by losses in your stock portfolio because

355
00:15:16,540 --> 00:15:17,720
those are capital losses.

356
00:15:18,720 --> 00:15:24,100
So one option is, it can get a

357
00:15:24,100 --> 00:15:25,880
little bit into the weeds to go into

358
00:15:25,880 --> 00:15:28,900
the details, but it's based on a direct

359
00:15:28,900 --> 00:15:30,700
indexing sort of approach.

360
00:15:31,160 --> 00:15:34,680
And direct indexing basically is you look at

361
00:15:34,680 --> 00:15:37,220
a portfolio like the S&P 500 and

362
00:15:37,220 --> 00:15:39,860
rather than buying a mutual fund or ETF

363
00:15:39,860 --> 00:15:43,380
that contains all of it in one security,

364
00:15:44,020 --> 00:15:45,160
you're saying, I'm going to break that up.

365
00:15:45,280 --> 00:15:47,600
I'm going to buy a number, a hundreds

366
00:15:47,600 --> 00:15:50,100
sometimes of those stocks in the portfolio.

367
00:15:50,440 --> 00:15:50,940
Yeah.

368
00:15:50,940 --> 00:15:52,700
So it moves in a way that's similar

369
00:15:52,700 --> 00:15:53,700
to that index.

370
00:15:54,840 --> 00:15:57,400
But in the midst of that, with all

371
00:15:57,400 --> 00:16:00,960
these individual positions, some of them go down.

372
00:16:01,740 --> 00:16:06,940
And we could replace those positions that went

373
00:16:06,940 --> 00:16:10,880
down with something that's very similar.

374
00:16:11,140 --> 00:16:13,620
So we'll stay invested in a way that

375
00:16:13,620 --> 00:16:16,160
it still continues to look like the index,

376
00:16:16,620 --> 00:16:19,660
but I can capture all these little moves

377
00:16:19,660 --> 00:16:25,780
on the downside to benefit from that capital

378
00:16:25,780 --> 00:16:29,540
loss, that decline in value for a small

379
00:16:29,540 --> 00:16:32,940
piece of the mix and harvest that to

380
00:16:32,940 --> 00:16:35,780
help me manage gains that I have to

381
00:16:35,780 --> 00:16:36,520
deal with elsewhere.

382
00:16:38,200 --> 00:16:41,540
And in some instances, we might even leverage

383
00:16:41,540 --> 00:16:45,440
that where we have a long short strategy

384
00:16:45,440 --> 00:16:48,860
paired with that, where we're going to put

385
00:16:48,860 --> 00:16:53,420
a little bit more exposure on top and

386
00:16:53,420 --> 00:16:56,920
below, where if we're buying long and selling

387
00:16:56,920 --> 00:17:01,440
short, and if the market goes up, well,

388
00:17:01,580 --> 00:17:03,339
one portion of that is going to make

389
00:17:03,339 --> 00:17:05,000
money, but another portion of that is going

390
00:17:05,000 --> 00:17:05,520
to lose money.

391
00:17:05,680 --> 00:17:09,240
The short portion would have losses.

392
00:17:09,920 --> 00:17:13,839
If we see the market go down, well,

393
00:17:14,060 --> 00:17:17,700
the long portion has losses, but the short

394
00:17:17,700 --> 00:17:18,760
portion will have made money.

395
00:17:18,900 --> 00:17:22,060
So we're neutral to what happens in the

396
00:17:22,060 --> 00:17:26,339
market because we've got long and short, but

397
00:17:26,339 --> 00:17:29,120
invariably, some portion of that will give us

398
00:17:29,120 --> 00:17:32,060
an opportunity to harvest losses.

399
00:17:33,300 --> 00:17:36,200
And we can use that in a way

400
00:17:36,200 --> 00:17:43,700
to try to capture some tax benefit now

401
00:17:44,580 --> 00:17:46,760
and use that as a way to help

402
00:17:46,760 --> 00:17:49,200
to offset that gain.

403
00:17:49,280 --> 00:17:50,800
We might be dealing with that real estate,

404
00:17:50,800 --> 00:17:53,180
or in the case of the concentrated position,

405
00:17:53,400 --> 00:17:55,740
we might be able to sell some holdings

406
00:17:55,740 --> 00:17:59,780
to help mitigate that risk, that tax, and

407
00:17:59,780 --> 00:18:02,460
to diversify from the risk that we have

408
00:18:02,460 --> 00:18:03,600
in the concentrated stock.

409
00:18:04,220 --> 00:18:06,500
And one additional benefit is that when you

410
00:18:06,500 --> 00:18:09,900
generate those losses, let's say you get into

411
00:18:09,900 --> 00:18:12,800
one of these strategies and the market starts

412
00:18:12,800 --> 00:18:15,840
going down right away, you start racking up

413
00:18:15,840 --> 00:18:18,700
losses, it's not going to feel great because

414
00:18:18,700 --> 00:18:20,640
you're kind of going along the ride with

415
00:18:20,640 --> 00:18:22,800
the market, but you're also generating losses that

416
00:18:22,800 --> 00:18:25,660
you can carry forward year after year, as

417
00:18:25,660 --> 00:18:27,520
long as you live, really.

418
00:18:27,740 --> 00:18:30,740
Yeah, we have someone who has this kind

419
00:18:30,740 --> 00:18:34,260
of a circumstance with a future sale of

420
00:18:34,260 --> 00:18:35,640
an appreciated asset.

421
00:18:35,880 --> 00:18:38,980
It's not today, but they know they're thinking

422
00:18:38,980 --> 00:18:44,360
of selling this appreciated asset and want to

423
00:18:44,360 --> 00:18:48,440
be prepared for the future gains.

424
00:18:49,020 --> 00:18:51,220
So they're locking in losses to sort of

425
00:18:51,220 --> 00:18:53,760
capture those so that then they just stay.

426
00:18:54,400 --> 00:18:57,840
You get to deduct $3,000 a year,

427
00:18:58,280 --> 00:19:00,260
so they might diminish a little bit over

428
00:19:00,260 --> 00:19:02,920
time, but you've banked those losses so you

429
00:19:02,920 --> 00:19:04,920
can use them against future gains, and it's

430
00:19:04,920 --> 00:19:06,440
another date down the road.

431
00:19:07,300 --> 00:19:10,120
So that can also be, with some forethought,

432
00:19:10,240 --> 00:19:13,280
some time to prepare, you can be better

433
00:19:13,280 --> 00:19:15,820
situated for when you have that.

434
00:19:16,860 --> 00:19:19,080
So it's an unusual thought process.

435
00:19:19,240 --> 00:19:24,340
I think sometimes we talk about capturing losses

436
00:19:24,340 --> 00:19:28,280
and harvesting losses, and people think, why would

437
00:19:28,280 --> 00:19:29,440
you want to have losses?

438
00:19:29,760 --> 00:19:31,900
You don't necessarily want to have losses.

439
00:19:32,100 --> 00:19:37,340
But in this case, we can intentionally set

440
00:19:37,340 --> 00:19:40,380
out to manipulate the structure of things so

441
00:19:40,380 --> 00:19:42,700
that we can gather those losses to help

442
00:19:42,700 --> 00:19:43,880
offset taxes.

443
00:19:44,580 --> 00:19:47,080
And that is another form of return.

444
00:19:47,260 --> 00:19:49,440
It's not what you make, it's what you

445
00:19:49,440 --> 00:19:49,820
keep.

446
00:19:50,540 --> 00:19:53,020
So this helps us to have what they

447
00:19:53,020 --> 00:19:54,000
call tax alpha.

448
00:19:54,400 --> 00:19:57,080
We're going to have some added benefit and

449
00:19:57,080 --> 00:20:02,040
have a better effective outcome because of trying

450
00:20:02,040 --> 00:20:03,760
to mitigate some of that tax burden.

451
00:20:03,840 --> 00:20:05,820
And it may be that we still have

452
00:20:05,820 --> 00:20:08,520
some tax burden down the road, but in

453
00:20:08,520 --> 00:20:11,600
the case of, say, the concentrated position or

454
00:20:11,600 --> 00:20:16,540
the instance of the real estate that we're

455
00:20:16,540 --> 00:20:19,540
trying to avoid a tax on, this gives

456
00:20:19,540 --> 00:20:23,320
us the opportunity to push that problem down

457
00:20:23,320 --> 00:20:24,380
the road a little bit.

458
00:20:24,480 --> 00:20:26,900
And in the case of some of these,

459
00:20:27,000 --> 00:20:29,080
it gives us more opportunity for more diversification,

460
00:20:29,440 --> 00:20:30,240
which may be...

461
00:20:30,240 --> 00:20:31,980
That's what I was going to comment on,

462
00:20:32,080 --> 00:20:34,460
that you're doing that strategy in the context

463
00:20:34,460 --> 00:20:37,740
of a broad-based index situation.

464
00:20:38,220 --> 00:20:41,720
So you're, in essence, have that diversification, not

465
00:20:41,720 --> 00:20:44,080
only by company, but also by sector and

466
00:20:44,080 --> 00:20:45,060
so forth.

467
00:20:45,700 --> 00:20:48,480
So you're not trying to pick winners and

468
00:20:48,480 --> 00:20:48,760
losers.

469
00:20:49,200 --> 00:20:51,300
You're doing it in a context of what

470
00:20:51,300 --> 00:20:52,480
a lot of people like to do is

471
00:20:52,480 --> 00:20:53,360
invest in index.

472
00:20:53,360 --> 00:20:54,040
Yeah.

473
00:20:55,020 --> 00:20:57,100
And there's a certain efficiency there.

474
00:20:57,460 --> 00:20:59,180
But in our case, what we're really just

475
00:20:59,180 --> 00:21:01,080
trying to do is diminish risk.

476
00:21:01,920 --> 00:21:04,520
And that can give us a way to

477
00:21:04,520 --> 00:21:06,180
effectively accomplish that.

478
00:21:07,060 --> 00:21:10,000
So there are other techniques that are even

479
00:21:10,000 --> 00:21:14,560
more involved and sophisticated that maybe go beyond

480
00:21:14,560 --> 00:21:17,260
the scope of a program like this.

481
00:21:17,540 --> 00:21:20,500
But I think it's important to just recognize

482
00:21:20,500 --> 00:21:23,520
that this is a challenge that people...

483
00:21:23,520 --> 00:21:27,520
It's not unique to have this difficulty of

484
00:21:27,520 --> 00:21:33,820
either a long-held stock position, even if

485
00:21:33,820 --> 00:21:37,520
it's inherited, maybe inherited from a parent or

486
00:21:37,520 --> 00:21:37,820
something.

487
00:21:38,140 --> 00:21:39,140
And this is very common.

488
00:21:39,260 --> 00:21:41,500
People have stuff, they just hold onto it

489
00:21:41,500 --> 00:21:42,340
and never change it.

490
00:21:43,060 --> 00:21:45,600
And then now, 20 years later or whatever

491
00:21:45,600 --> 00:21:49,180
it might be, you're faced with, oh, maybe

492
00:21:49,180 --> 00:21:51,720
I should think about my investments in a

493
00:21:51,720 --> 00:21:54,280
strategy that's appropriate for me.

494
00:21:54,960 --> 00:21:56,080
What should I do?

495
00:21:56,500 --> 00:22:00,260
And there's all this embedded tax concern.

496
00:22:01,420 --> 00:22:03,100
So that's not unusual.

497
00:22:03,500 --> 00:22:06,700
It's not unusual for people to have stock

498
00:22:06,700 --> 00:22:11,260
maybe from an employer, maybe to have real

499
00:22:11,260 --> 00:22:15,280
estate that's appreciated, a business that's appreciated.

500
00:22:16,240 --> 00:22:18,560
And having the reality that we've got a

501
00:22:18,560 --> 00:22:20,800
gain that we're going to be faced with,

502
00:22:21,040 --> 00:22:25,440
how do we manage that gain and try

503
00:22:25,440 --> 00:22:29,300
to offset some of that gain through the

504
00:22:29,300 --> 00:22:31,440
use of a technique like this to help

505
00:22:31,440 --> 00:22:37,900
diminish capital gains exposure by capturing losses along

506
00:22:37,900 --> 00:22:41,180
the way or by mitigating the risk through

507
00:22:41,180 --> 00:22:43,320
the use of options as a way to

508
00:22:43,320 --> 00:22:44,720
navigate that.

509
00:22:46,300 --> 00:22:49,060
Or just looking at your overall portfolio and

510
00:22:49,060 --> 00:22:50,880
looking at where there are places where we

511
00:22:50,880 --> 00:22:53,540
can do some changes without some tax burden

512
00:22:53,540 --> 00:22:55,800
to help manage risk.

513
00:22:56,460 --> 00:22:57,900
There's a variety of things to look at.

514
00:22:58,160 --> 00:22:59,640
It's best done in the context of a

515
00:22:59,640 --> 00:23:00,200
financial plan.

516
00:23:00,640 --> 00:23:01,120
Is that where you're going?

517
00:23:01,300 --> 00:23:01,400
Absolutely.

518
00:23:01,460 --> 00:23:03,040
No, I was just going to say that

519
00:23:03,040 --> 00:23:06,200
it's also not like you have to choose

520
00:23:06,200 --> 00:23:08,560
one solution and go with that.

521
00:23:09,260 --> 00:23:10,860
We try to take a look at it

522
00:23:10,860 --> 00:23:13,760
all within that financial plan context as well.

523
00:23:14,180 --> 00:23:15,920
But we look at the whole picture and

524
00:23:15,920 --> 00:23:17,580
we decide, all right, here's what we're going

525
00:23:17,580 --> 00:23:18,420
to do with this piece.

526
00:23:18,520 --> 00:23:19,820
Here's what we would do with this piece.

527
00:23:20,720 --> 00:23:24,640
And maybe some hedging, some tax loss harvesting,

528
00:23:25,220 --> 00:23:27,580
rather than it all being in one specific

529
00:23:27,580 --> 00:23:28,620
strategy.

530
00:23:29,000 --> 00:23:30,580
I remember a couple of clients we've worked

531
00:23:30,580 --> 00:23:34,360
with years past where we had this issue,

532
00:23:34,780 --> 00:23:38,560
appreciated assets, but we also had the desire

533
00:23:38,560 --> 00:23:41,520
for income over a lifetime.

534
00:23:43,200 --> 00:23:48,500
And in some instances, some charitable intentions.

535
00:23:49,200 --> 00:23:54,900
Sometimes people prioritize charitable intent and other times

536
00:23:54,900 --> 00:23:58,400
people just prioritize mitigating, avoiding capital gains.

537
00:23:59,140 --> 00:24:02,820
We talk about a charitable remainder trust, also

538
00:24:02,820 --> 00:24:05,420
known as a capital gains avoidance trust.

539
00:24:06,100 --> 00:24:08,740
It's really more of a, it's not avoidance,

540
00:24:08,920 --> 00:24:12,620
but you're not getting hit with it all

541
00:24:12,620 --> 00:24:13,020
at once.

542
00:24:13,220 --> 00:24:15,000
It's a graduate, you can push it off.

543
00:24:15,920 --> 00:24:19,060
But the idea of taking some position that's

544
00:24:19,060 --> 00:24:22,600
concentrated with a lot of capital gains in

545
00:24:22,600 --> 00:24:25,340
it, we've done this a number of times

546
00:24:25,340 --> 00:24:32,500
where people have donated that stock to this

547
00:24:32,500 --> 00:24:38,480
charitable intention eventually, but get a charitable deduction

548
00:24:38,480 --> 00:24:39,300
right up front.

549
00:24:39,460 --> 00:24:42,860
So some immediate tax benefit and the ability

550
00:24:42,860 --> 00:24:44,820
to then derive income.

551
00:24:44,980 --> 00:24:47,360
We can reposition in the trust that stock

552
00:24:47,360 --> 00:24:50,660
into something that's more diversified and more balanced

553
00:24:50,660 --> 00:24:53,460
and structure it where they can generate a

554
00:24:53,460 --> 00:24:58,960
cashflow from this for themselves, for themselves and

555
00:24:58,960 --> 00:24:59,420
a spouse.

556
00:24:59,560 --> 00:25:01,200
We have one woman who did it with

557
00:25:01,200 --> 00:25:04,020
herself, her spouse, and her sibling.

558
00:25:04,760 --> 00:25:06,300
So as long as any one of them

559
00:25:06,300 --> 00:25:09,940
is alive and their assets remain in the

560
00:25:09,940 --> 00:25:13,540
trust that there's still presumably going to outlive

561
00:25:13,540 --> 00:25:18,880
them all, there's income stream provided to them.

562
00:25:19,380 --> 00:25:21,700
And there's different ways to structure a charitable

563
00:25:21,700 --> 00:25:22,760
remainder trust.

564
00:25:22,940 --> 00:25:25,700
One that's geared to try to maximize income

565
00:25:25,700 --> 00:25:31,880
to the family, the donors, the beneficiaries, but

566
00:25:31,880 --> 00:25:36,020
there's also some that are more regimented, but

567
00:25:36,020 --> 00:25:38,060
can have more growth so that there's more

568
00:25:38,060 --> 00:25:41,460
for the charitable intentions later on.

569
00:25:41,460 --> 00:25:42,800
So depending on what we're trying to do,

570
00:25:42,880 --> 00:25:44,340
there's ways to structure that.

571
00:25:45,260 --> 00:25:48,580
There are other techniques as well that are

572
00:25:48,580 --> 00:25:49,980
state planning techniques.

573
00:25:50,880 --> 00:25:52,440
I think I mentioned one to you.

574
00:25:52,500 --> 00:25:54,440
I didn't even remember now what it was.

575
00:25:54,520 --> 00:25:56,220
Do you remember what my brother mentioned something

576
00:25:56,220 --> 00:25:58,140
to me just today?

577
00:26:00,100 --> 00:26:01,480
I'll look it up.

578
00:26:03,560 --> 00:26:05,860
And that may be something we want to

579
00:26:05,860 --> 00:26:07,960
look into for people as well in their

580
00:26:07,960 --> 00:26:10,660
estate planning, but a deferred sales trust is

581
00:26:10,660 --> 00:26:12,540
another technique he was talking about.

582
00:26:12,980 --> 00:26:16,120
So the estate planning can provide some interesting

583
00:26:16,120 --> 00:26:19,020
opportunities as well that we can try to

584
00:26:19,020 --> 00:26:21,820
collaborate with all these various ways of trying

585
00:26:21,820 --> 00:26:26,920
to manage how best to handle these appreciated

586
00:26:26,920 --> 00:26:27,580
assets.

587
00:26:27,940 --> 00:26:31,480
And the time horizon involved is certainly relevant.

588
00:26:31,480 --> 00:26:32,900
It might be.

589
00:26:33,200 --> 00:26:35,820
The solution or the mitigation of these taxes

590
00:26:35,820 --> 00:26:37,460
may be a multi-year approach.

591
00:26:38,100 --> 00:26:39,760
Yeah, yeah, exactly.

592
00:26:39,980 --> 00:26:40,480
Good point.

593
00:26:41,180 --> 00:26:45,040
And so let's just kind of wind it

594
00:26:45,040 --> 00:26:47,860
down to say that this is all best

595
00:26:47,860 --> 00:26:50,180
done in the context of a financial plan.

596
00:26:50,320 --> 00:26:52,580
So we know how all the pieces fit

597
00:26:52,580 --> 00:26:53,060
together.

598
00:26:53,660 --> 00:26:58,300
We can think about estate planning considerations and

599
00:26:58,300 --> 00:27:00,240
charitable giving considerations.

600
00:27:00,860 --> 00:27:03,080
Think about some of these techniques we've just

601
00:27:03,080 --> 00:27:06,220
elaborated on and the context of the portfolio,

602
00:27:06,400 --> 00:27:08,300
how the rest of all those pieces fit

603
00:27:08,300 --> 00:27:08,700
together.

604
00:27:09,000 --> 00:27:10,980
If you're faced with some of these kinds

605
00:27:10,980 --> 00:27:13,240
of issues, you're not alone.

606
00:27:13,560 --> 00:27:16,040
There's lots of people who have similar kind

607
00:27:16,040 --> 00:27:18,340
of challenges and a little bit of planning

608
00:27:18,340 --> 00:27:21,100
can go a long way and helping you

609
00:27:21,100 --> 00:27:23,020
to navigate that tax cost.

610
00:27:23,460 --> 00:27:25,060
Russ and I were just talking last night

611
00:27:25,060 --> 00:27:28,940
and saying, it seems like tax priorities, tax

612
00:27:28,940 --> 00:27:32,460
issues, it's more on people's minds today than

613
00:27:32,460 --> 00:27:33,180
ever before.

614
00:27:33,400 --> 00:27:38,900
How do I navigate and manage my expenses

615
00:27:38,900 --> 00:27:41,700
when it comes to tax costs as part

616
00:27:41,700 --> 00:27:43,180
of my investment strategies?

617
00:27:44,240 --> 00:27:48,280
It's probably more than ever on people's minds.

618
00:27:48,280 --> 00:27:51,660
There are some great resources and techniques.

619
00:27:52,440 --> 00:27:55,000
And if you need help navigating how that

620
00:27:55,000 --> 00:27:57,820
works for you, give us a call, reach

621
00:27:57,820 --> 00:27:58,080
out.

622
00:27:58,240 --> 00:28:00,060
Don't hesitate to try to see if we

623
00:28:00,060 --> 00:28:01,980
can be a resource in helping you figure

624
00:28:01,980 --> 00:28:05,380
out what's the best path forward, not only

625
00:28:05,380 --> 00:28:08,400
for your portfolio, but for your overall life

626
00:28:08,400 --> 00:28:10,520
circumstances for your financial plan.

627
00:28:10,780 --> 00:28:13,660
So with that, thanks for being with us.

628
00:28:13,980 --> 00:28:15,440
And if any way we can be of

629
00:28:15,440 --> 00:28:16,340
help, reach out.

630
00:28:16,540 --> 00:28:18,920
Until next time, keep striving for something more.

631
00:28:45,800 --> 00:28:48,780
AMR-info at wealthenhancement.com.

632
00:28:49,160 --> 00:28:50,900
You're listening to something more with Chris Boyd

633
00:28:50,900 --> 00:28:51,740
Financial Talk Show.

634
00:28:51,900 --> 00:28:54,340
Wealth Enhancement Advisory Services and Jay Christopher Boyd

635
00:28:54,340 --> 00:28:56,660
provide investment advice on an individual basis to

636
00:28:56,660 --> 00:28:57,220
clients only.

637
00:28:57,360 --> 00:28:59,360
Proper advice depends on a complete analysis of

638
00:28:59,360 --> 00:29:00,520
all facts and circumstances.

639
00:29:00,780 --> 00:29:02,640
The information given on this program is general

640
00:29:02,640 --> 00:29:04,680
financial comments and cannot be relied upon as

641
00:29:04,680 --> 00:29:06,240
pertaining to your specific situation.

642
00:29:06,440 --> 00:29:08,420
Wealth Enhancement Group cannot guarantee that using the

643
00:29:08,420 --> 00:29:10,440
information from this show will generate profits or

644
00:29:10,440 --> 00:29:11,600
ensure freedom from loss.

645
00:29:11,740 --> 00:29:13,900
Listeners should consult their own financial advisors or

646
00:29:13,900 --> 00:29:16,020
conduct their own due diligence before making any

647
00:29:16,020 --> 00:29:16,780
financial decisions.