Can Your Portfolio Survive Market Timing?

Summary

Podcast Summary: Ask The Compound – "Can Your Portfolio Survive Market Timing?"

Episode Date: July 15, 2026
Hosts: Ben Carlson (A), Duncan Hill (B)
Guest: Taylor (C) – Estate Planning Specialist

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Episode Overview

This episode of Ask The Compound dives into some of the most common – and pressing – personal finance and investing questions from listeners. With a practical and approachable tone, Ben Carlson, Duncan Hill, and returning guest Taylor fielded topics including the dangers of market timing, managing overwhelming debt, the increasing importance of estate planning, how to talk to family about money, whether advisors need advisors, and ways to set up kids for financial success.

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Key Discussion Points & Insights

1. The Reality of Market Timing vs. Staying Invested

[03:51–08:39]

• Listener Question: How do two market "parables" intersect?

  • Bob, the “World’s Worst Market Timer” (invests at peaks but never sells, benefits from compounding).
  • The Tom Lee statistic: Missing the 10 best days devastates returns.

• Ben’s Key Points:

  • “I’m not even going to run the numbers for if Bob bought at the peak and then sold at the bottom, because obviously he’d be broke. That’s the worst strategy you could do.” (04:01)
  • The “best and worst days” in the market are clustered together—often right amid crashes and recoveries (examples: 2008, 2020).
  • Trying to avoid only the bad days is impossible because the best days usually arrive immediately after the worst.
  • The success of “Bob” wasn’t luck or tactical skill; it came from staying invested through bad and good alike.
  • “It’s not timing the market, it’s time in the market.” (04:36)
  • Takeaway: The best way to ensure you capture outsized returns is simply to stay in the market—even through volatile times.

• Duncan’s Perspective:

  • Observes that many new investors believe the market will always “revert” to old lower levels, which rarely happens over the long term.

• Highlighted Quote:

  • “If you buy the stock market today, is it going to be higher 10, 20, 30 years from now? The odds are pretty in your favor.” – Ben (08:10)

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2. Tackling $90,000 in Credit Card Debt

[08:41–13:34]

• Scenario: Listener’s “friend” has no assets, lives in a friend’s basement, and has $90k in credit card debt after failed business attempt. Should he seek bankruptcy, negotiate, or try something else?

• Ben’s Practical Advice:

  • Creditors have little leverage when the debtor has no assets: “What are they gonna take?” (10:21)
  • Contact creditors directly to negotiate a plan. Some may write off partial debt.
  • Nonprofit credit counseling is a better first resource than for-profit debt settlement companies, which charge high fees.
  • Filing for Chapter 7 bankruptcy might be the cleanest option when you have no assets, especially before a new business accrues value.

• Notable Moments:

  • Ben: “He has all the leverage here. He’s got nothing to lose.” (10:23)
  • “Google a nonprofit credit counselor…See what they can do in terms of lowering your rate.” (11:33)
  • On bankruptcy: “That’s probably the best option. I mean, start free and clear.” (12:40)
  • Duncan: “$90,000 to an individual sounds like a ton of debt. For a business that doesn’t sound insurmountable … if it ends up doing well.” (12:48)

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3. The Critical Role of Estate Planning in Financial Planning

[13:37–21:50]

• Expert Guest Taylor Joins:

  • “There’s going to be a lot of death in the years, which sounds very... it doesn’t sound great to talk [about], but it’s true.” – Ben (14:15)
  • Estate planning isn’t just for the wealthy; it’s increasingly urgent due to generational wealth transfer (baby boomers).

• Taylor’s Insights:

  • Avoiding estate planning means “you kind of leave it up to chance or to the courts or whatever.” (15:22)
  • Proactive estate and financial planning can make things much easier on heirs.
  • An advisor can help facilitate tough conversations with family.

• Memorable Quote:

  • “Mortality is hard to really think through, but if you’re not willing to do the work and have those conversations when you’re gone... you kind of leave it up to chance.” – Taylor (15:22)

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4. How to Talk to Relatives About Wills and Inheritance

[17:10–21:50]

• Listener Scenario: Married into a blended family, nominated executor for mother-in-law’s will, awkward family history around money.

• Panel’s Guidance:

  • Being asked to be executor grants you license to ask about wishes and details.
  • “It’s your responsibility to know. If I’m going to be the executor of this will, I should probably understand the basics of your financial plan.” – Ben (18:21)
  • Taylor: Approach the conversation as wanting to “help me help you,” focusing on fulfilling their intent, not personal gain.
  • Transparency and family meetings are key—even if it feels awkward.

• Fun Moment:

  • “As executor of the will, I’m cutting the turkey this year! I have the power seat.” – Ben, joking about family dynamics (20:24)

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5. Should Financial Advisors Have Their Own Advisor?

[21:50–25:30]

• Core Insight:

  • Even experts need an objective third party. Advisors, like everyone else, have blind spots and can benefit from external accountability.
  • “The cobbler without shoes” – many advisors are guilty of not tending to their own financial details (23:01)
  • Ben: “Why would you not lean on that expertise as an advisor?” (22:16)
  • “The best hitters still have hitting coaches.” – Duncan (25:24)

• Memorable Quote:

  • “Every advisor has that [blind spot]. The biggest blind spot is the blind spot you don’t see.” – Ben (25:16)

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6. Setting Up Children for Financial Success

[25:37–30:31]

• Listener Question: Best way to start 16- and 19-year-olds with investing.

• Panel Suggestions:

  • Focus first on intent: Is it about growing assets, teaching stewardship, or preparing for wealth transfer?
  • If kids have earned income, opening a Roth IRA is the “low-hanging fruit.” (27:45)
  • For younger kids: Engage them by buying stocks in brands they know and use (Apple, Disney, Starbucks).
  • Instill the importance of saving and compounding early. “Most people will say, ‘I wish I’d started earlier.’” – Ben (29:07)
  • Parent match incentives (“for every dollar you save, I’ll match 50 cents”) can help build habits.

• Quote:

  • “Assuming they have part-time jobs … help them put away some of their money even if it’s 20 bucks. Just right to start kind of teaching that discipline.” – Taylor (29:43)

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Notable Quotes & Memorable Moments

• On Market Timing:
  • “All the good days happen with the bad days…there’s not like a trick here. Bob had to eat the best day and the worst day still because he invested at the peak.” – Ben (07:13)
• On Credit Card Debt:
  • “Bankruptcy attorneys can tell you…it’s better to resolve this now before the business has any assets.” – Ben (11:52)
• On Estate Planning:
  • “If you’re not willing to do the work and have those conversations when you’re gone…you kind of leave it up to chance or to the courts.” – Taylor (15:22)
• On Family Money Conversations:
  • “Transparency. Always the best policy.” – Taylor (20:50)
• On Advisors Needing Advisors:
  • “The best hitters still have hitting coaches, right?” – Duncan (25:24)
• On Starting Kids Early:
  • “The compounding is going to be so massive in 20, 30, 40, 50 years…get them started out on the right foot.” – Ben (29:07)

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Timestamps for Key Segments

• Market Timing & Bob’s Story: 03:51–08:39
• Dealing with Credit Card Debt: 08:41–13:34
• Estate Planning’s Role in Financial Planning: 13:37–16:48
• Navigating Family Will Discussions: 17:10–21:50
• Should Advisors Have Advisors? 21:50–25:30
• Helping Kids Invest & Build Habits: 25:37–30:31

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Summary Takeaways

• Don’t try to time markets—you’ll likely miss the best days and harm your long-term returns. The key is to stay invested.
• If you’re overwhelmed by debt with few assets, bankruptcy may be the most pragmatic solution.
• Estate planning is essential regardless of wealth; don’t leave your family in the lurch.
• Transparency and communication about money is critical in families, especially around inheritance.
• Even financial advisors gain from outside, objective advice.
• Get kids started with saving and investing early—with Roth IRAs and teaching stewardship—compounding does the heavy lifting over decades.

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For more advice or to ask a question, contact: askthecompoundshowmail.com

Next Episode Preview: More live questions, practical investing wisdom, and (hopefully) more memorable stories—stay tuned!

Transcript

[A]

Welcome to Ask the Compound, the show where you ask the questions, we provide the answers. I am Ben Carlson. Let's say you decided to start a company. Lots of people are doing that these days, this decade. But it's not quite working out as you thought it would. Now you're sitting on $90,000 in credit card debt with no light at the end of the tunnel. What do you do? What do you do? I'm going to answer these questions and more straight from you, the audience on today's show. Let's go. Our email here is askthecompoundshowmail.com I always Duncan Crap for his investing prowess. He was telling us before we got on today that he sold IBM the day before it had what, a 23% crash?

[B]

Yeah, I mean that's about the luckiest I think I've ever been in the, in the market. I, I don't even really know why. Like I told you, I was just kind of like, I'm up big in this. I've owned it for like five years. Like what more can it do? I wanted to like allocate it to some other stocks, some riskier stocks. And, and yeah, got out the day before.

[A]

Of course he wanted to get into something riskier.

[B]

Well, yeah. IBM. I mean, yeah, come on.

[A]

Yeah, it's a boomer stock. All right. On today's show we're going to cover questions from our compound inbox about timing the market for long term investors paying off $90,000 in credit card debt. The role of estate planning or financial plan. How to talk to your in laws about money. Do financial advisors need their own advisor? And how to set up your children for financial success. Today's show is sponsored by Public. If you're actively involved in your portfolio, you probably catch yourself repeating the same actions. Buying the dip, manually sweeping idle cash, putting on a hedge on public. You can now create AI agents that'll handle all of these tasks on your behalf. Just describe what you want to do in plain English like if the Vix hits 25, buy a put option on the S&P 500. You approve the workflow and your agent handles the rest. Monitoring the market, watching your conditions and executing your trades exactly as defined. Public is the world's first agentic brokerage. An investing platform driven by your intent, not just your clicks. You can get full read and write access to your account via the public API. Go to public.comatc to get started. That's public.comatc paid for by Public Investing. Full disclosures in the podcast description all right, lots of good questions today. Last week, Dave in the chat asked for a particular guest. We got her. She's here. Dave, let's do it.

[B]

And say what you will about IBM, but they've got a nice logo. I can't remember if that's Saul Bass or who, but it's a nice logo.

[A]

All right. I mean, my last interaction with IBM was probably a computer I had in 1994.

[B]

They were the ones with the little red eraser in the middle of the

[A]

keyboard that you could navigate around Ms. Dos. That's about it.

[B]

I think I used to play Duke Nukemon on one, maybe.

[A]

Can't believe. I mean, you could type an IBM into your search and get a chart going back to like 1968 or something. It's crazy.

[B]

Yeah.

[A]

All right, let's do it.

[B]

Okay. Up first we got one from Rob. I have a question about reconciling two very famous market parables. Ben, your story of Bob the world's Worst Market Timer perfectly illustrates the power of compounding and the importance of never selling, even if your entry points are disastrously bad. On the other hand, we frequently hear of a statistic often championed by Tom Lee that if you miss the 10 best days in the market over a given decade, your overall returns are practically wiped out or even negative. My question is, how do these two concepts intersect? Is the secret to Bob's ultimate success entirely dependent on the fact that by never selling he accidentally captured Tom Lee's 10 best days, which usually happen right in the middle of the crashes Bob bought into? If we ran a simulation of a Bob who bought at the peaks but panic sold at the bottom and missed those 10 best bounce back days, exactly how catastrophic would the math look compared to the original Bob? I'd love to hear your thoughts on how the missing the best day statistic contextualizes Bob's survival. Thanks for the great content and chart on that was a tongue twister.

[A]

Yeah, I actually updated the number for Bob, the world's worst market timer and risk and reward. I showed, you know, if he bought at the bottom, if he dollar cost averaged. I'm not even going to run the numbers for if Bob bought at the peak and then sold at the bottom because obviously he'd be broken. That'd be the. That's the, that's the. Obviously the worst strategy you could do the. The parable. Bob, the world's worst Market Timer is actually one of the reasons I wrote my book in the first place. Because so many people pushed back on it, kept giving Me. Exception after exception after exception. That's where all the now show Japan mostly came from. So the 10 best and worst days thing is a bit misunderstood. So let's do a chart on this. This one's JP Morgan has this and every single financial institution has this one. Right? They show the long term. The stock market's up 10% per year. Miss the 10 best days, your return drops substantially. Miss the 20 best days, drops even more. Miss the 30 best days. So the point is it's just these handful of big days can have a huge impact on your overall return. It's, it's, this is the whole. It's not time in the market. No, it's not timing the market. It's time in the market. Advisors love to say that. Classic start off. Yeah, classic credit to me. I don't think I've ever said it before. I probably have. Let's be honest.

[B]

I mean, you've never even waved on a zoom call.

[A]

That's true. I don't wave on zoom calls. I refuse. Some people like to. You're a waiver. I can't remember. Do you wave on zoom calls?

[B]

If other people do it, I'll do it. I mean, I'm not gonna like lead the way with a wave, but.

[A]

Lemming. You're lemming. Duncan.

[B]

I'm just being respectful.

[A]

Here's the thing. So we have a chart on this. We show this to clients, actually. So let's do a chart on. This is. What if you avoided the best and worst day? So this shows $1 invested in the S&P 500 in 1990. If you missed the 25 worst days, $236 that turned into. If you missed the best 25 days, it turns into $8. So this shows a huge difference. If you could just miss the worst days, you're doing amazing. If you miss the best days, you're doing terribly. Right now look at the middle. If you invested in all days, you're doing pretty well. That's buy and hold. But what if you missed the 25 best, worst and best days, both of them? You end up doing like marginally better than the buy and hold. It's pretty much a buy and hold. So the question is why? Why is this chart off? It's because the best and worst days happen together. Chart on. Stole this one from exhibit A. This shows the best and worst days since 1990. You can see they cluster together. They all kind of happen at the, you know, 2008, of course, 2020. These things happen together. That's because when the market is in a downtrend, people panic. They panic buy and they panic sell chart off. So you see them both. Like it's great. Like, oh, I'll just miss the worst days. That's easy. You can't because they happen with the best days. So it's not like Bob took advantage by buying at the peak. He had all of them. So let's. I pulled this up. This is from one of my spreadsheets that shows February of 2020 to April of 2020 when we had the huge Covid crash. These are just the daily returns. I've color coded them because I'm good at Excel. Look at this. You have the negative 9% positive 9%, negative 12% positive 6% negative 5%. So all these, it's back and forth and back and forth. The Michael Scott snip snap. All the good days happen with the bad days. Because people are wondering, is this the end? No, this is not the end. And you have this panic back and forth. And that's what happens during volatile markets. So there's not like a trick here or a secret. It's just Bob stayed invested. Right. Remember, because he invested at the peak. So he had to eat the good with the bad, bad with the good. So his success really was putting his money into the peak but then keeping it invested for years and years and years. That was what the. That's where the compounding came from. There's no like trick to it. Bob had to eat the best day and the worst day still because he invested at the peak.

[B]

Yeah. I don't know what it is, but I've noticed a lot of young people and people new to the market in general, they seem to always think that the market is going to revert to some mean from like years ago, like it has to. So it's like, oh, the market topped. It's like, well, yeah, but that means, that doesn't mean the market's not going to be much higher years from now. Right? Like, yeah, it's a top right now. But people always, I do think it's going to go back down to some level from many years ago because it just has to.

[A]

You're right. I think there's some people who think that the market like it ends, like this is the end, the market's done, but it keeps going. You're right. And that's why long term investing is so important. Because you have to ask yourself, if I buy a stock today, I buy the stock market today. Maybe not a stock. Any individual stock could Possibly go to zero. If you buy the stock market today, is it going to be higher? 10, 20, 30 years from now? The odds are pretty in your favor, right? That's the point. You're right, Duncan.

[B]

Well, and your point is? Always buying an index when it's down is always pretty much a good idea. Whereas, like, individual stocks. Yeah, some individual stocks don't make it, you know?

[A]

Yeah. You never know.

[B]

Yeah.

[A]

All right, let's do another one.

[B]

Okay. Up next. We got one. Okay. Hey, guys. Most of your questions come from people with money. Well, I have a friend who is brilliant, but not brilliant with money. He's got no assets. I mean, nothing sounds a little harsh. Sold his car and is living in a friend's basement. He used to work in tech and has spent the last year developing his own business, and now it's ready to launch. But he has $90,000 in credit card debt. He's considering all of his options, including Chapter 7 bankruptcy and raising money from angel investors. I've heard you talk about negotiating credit card debt before. What resources should he look into regarding settling the debt for a lower amount so it isn't hanging over his head as he launches the new business? Do you think, is this the person? Who are they talking about themselves?

[A]

This feels to me like this is the friend that everyone texts about behind his back. Like, can you believe what Dave did?

[B]

Yeah.

[A]

Really? He tried to start his own business and now he lives in someone's basement. Maybe. Sometimes people say we do focus too much on wealthy people's questions on this show. So that, you know, I'd say kudos to your friend for taking a risk. Right. Starting your own business is hard. Maybe one day this will work out for him. And this will be like the garage. Like start of the business in the garage. This will be the Steve Jobs and Steve Wozniak started Apple in a garage. Probably not, because most small businesses fail. But maybe you never know.

[B]

If you gotta have debt, I guess credit card is better than student loan, right? Because you can file bankruptcy.

[A]

It's funny, there's the old saying. If you owe the bank $100, that's your problem. If you owe the bank $100 million, that's the bank's problem. Your friend has no assets to speak of. He lives in a friend's basement. He sold his car. He has a negative net worth.

[B]

What are they gonna take? I guess the business. Yes, right.

[A]

That's the thing. He has all the leverage here. Well, you're right. What are they gonna take? So he's Got nothing to lose. So the hard part is sometimes the credit card companies will wait. They prefer for you to miss a bunch of payments and effectively go into default until they get to the point of coming to the negotiating table. Now at that point your credit score might be shot, but I'm not sure that's the biggest worry right now. For the friend credit score, obviously that that's probably going to be shot either way. So you can Google like I would start with like a nonprofit credit counselor. They might reduce the rate, probably not the balance. The for profit debt settlement companies are going to charge you like so they sound appealing, but they're probably going to start charge some like upfront exorbitant fee that they kind of tack on even though they lower your rate. I'm not sure how many angel investors are going to be willing to sign up to pay off your credit card debts. Maybe this is a brilliant idea. Doesn't sound like it. I would probably do three things simultaneously to run the numbers. I'd call the credit card companies to see what they can do for you. They come up with a payment plan. They might write some of it off. If you just say, listen, I have zero assets, I have a negative net worth. I started a business, got away from me. What can you do for me? I'll pay you back a little. I'm not going to pay you back at all. It's worth a shot. Try a non profit credit counseling company. Just google them. There's a bunch of them out there. See what they can do in terms of lowering your rate. Again, I don't think they're going to lower the balance.

[B]

And finally, I'd use AI to ask too. I mean locally, wherever they live, there's probably resources.

[A]

Yeah, it's worth it.

[B]

Yeah.

[A]

Again, I would avoid the for profit ones. I think you're probably going to get taken and it's going to be more debt. And I would also talk to a bankruptcy attorney. Chapter seven, fully discharge the debt. Like it doesn't take all that long. From what I understand, it's probably the cleanest option. But I think you run all the numbers from there and see what makes the most sense. Bankruptcy attorneys can tell you. They'll probably tell you it's better to resolve this now before the business has any assets. Right. So I think you have to ask your friend how much confidence he has that this business is going to succeed. Doesn't sound like you have much confidence. Again, it's a great story. If it works out. It's a sad story. If it doesn't. I'm guessing bankruptcy is probably the cleanest option here, to be honest, especially if he's going to give this company a spin. Plus, at that point, you can do the Michael Scott thing and just walk in front of your friends and say, I declare bankruptcy. I declare it. Right. Classic bankruptcy. I think that's probably the best option. I mean, start free and clear.

[B]

Maybe, maybe I'm being too optimistic, but I would just say $90,000 to an individual sounds like a ton of debt. For a business that doesn't sound insurmountable. You know what I mean? Like, so if the business ends up doing well and is making profits, then it might not be as big of a deal, but, yeah, we have no idea.

[A]

Businesses, I'm guessing if you're trying to get angel investors, they're probably going to see cleaner books before giving money, but maybe it's a brilliant idea.

[B]

That's a good question. I mean, this is very niche, so you might not know. But would that deter angel investors if you file bankruptcy?

[A]

I mean, if they did, like a third party background check, it's possible, but I guess it's easy to explain, like, hey, I'm trying to build this business, so I don't think it's like the end of the world.

[B]

My bankruptcy is your alpha. There you go. Right?

[A]

Yep. All right, next question.

[B]

Okay, up next, we got one from Dave. A financial planning topic that I think has not been covered much at all in episodes of Ask the Compound is the role estate planning plays in financial planning With Bill and Bill. We know income tax planning is part of the real wealth advice services provided, but what about estate planning?

[A]

Yeah. This is a question from Dave, who's always in the live chat every week. And last week he said, hey, when's Taylor coming back on the show? Taylor was on maternity leave for a couple months, so let's bring her back. She's here.

[B]

Hey, Taylor. You're muted. Taylor.

[C]

Sorry. Hi. How could you forget? Right?

[A]

Yeah. Duncan waves on the zooms and Taylor mutes herself. Good to be back. So Taylor is one of our estate planning experts at the firm. I've been thinking about this a lot in recent years because there are so many baby boomers, right? 70 million plus. There's going to be a lot of death in the years, which sounds very. It doesn't sound great to talk. No one likes to talk about these things, but it's true. Dealing with my brother's estate, like he had all this stuff together and it was still kind of a pain in the Ass. This stuff is not easy to deal with. So I'm curious how you think. I think this estate planning topic is going to be just more important than ever. People are going to realize how important it is. So how do you see it fitting into our client relationships and the financial planning process?

[C]

I think I've definitely seen it pick up. I don't know if that's just a factor of. That's a lot of my background, so I kind of am biased towards it, but I think there's more of an emphasis on it. I think a lot of attention is paid to the work and the planning while someone's living. And to your point, Ben, people don't like to talk about death or taxes.

[A]

Yeah. It's a taboo subject. Like, let's just pretend like it's not going to happen.

[C]

Right. Mortality is hard to really think through, but if you're not willing to do the work and have those conversations when you're gone. Right. You kind of leave it up to chance or to the courts or whatever. So I think there should be a big emphasis on it. And obviously that goes for any range of wealth. Right. Especially with thinking of passing assets to your children or family members. Hopefully you want them to be as buttoned up as possible and want all that to go smoothly.

[A]

Yeah. You want to make that as clean as you possibly can. Right. So it's just preparing for that eventuality. There's plenty of things you can do to plan so you're not trying to scramble after the fact. Right. And this sounds like we're doing a commercial for financial advisors, but one of the things that a financial advisor can do is have those difficult conversations. If you don't want to have them amongst your family, the objective third party can come in and do the talking for you.

[C]

Yeah. And I think what maybe is also missed is thinking like, well, I have X amount of money today and I spend X and I'll probably run out. But that might not always be the case. And so I know here we do a lot of projections and looking at what portfolios may grow to over 20, 30 years, and you may be surprised to see what might actually be left Right. To your kids or to your family members. And that might kind of, you know, make it worth spending time on. You see those numbers?

[A]

Yeah. And there's obviously always unexpected things that can happen. It could be, you know, there's two spouses and one of the spouses passes away, and you want to make sure your spouse is taken care of or your kids or whatever. And it's sort of planning ahead. I know we have a good one next. I think that kind of can get more into the process. Duncan, why don't we go to the next question? I think this kind of gets into the more nitty gritty this too.

[B]

Okay, next we have one from Eric. Please help me with the following situation. I married and my mother in law asked me to be executor of their will. Her first husband died and she remarried when my wife was about 10. Each has kids of their own and they did not adopt the others. She has stated that they do not have a will and I don't know how they handle their finances. How do I bring this up? My dad asked his dad about a will when he was in his mid-70s and dad said my grandpa basically disowned him and left him nothing. My inclination is to avoid the situation altogether and do the best I can afterwards. But I know this isn't the best way. That sounds super harsh.

[A]

The story of yeah, grandpa was.

[B]

That's wild.

[A]

Money comes with a lot of baggage. Yeah, grandpa was trying to make your

[B]

life not miserable when I die. Wow. How dare you. That's.

[A]

I guess the good news is the mother in law trusts him. Right. She asked him to be the executor. Well, he obviously is a trustworthy person, but if they don't talk about it ahead of time, it's basically going to make his life impossible. The executor's job, Taylor, correct me if wrong, is to carry out the instructions of the will. That's the whole job, Right?

[C]

The whole job.

[A]

So it's not like you're curious about their finances. It's your responsibility to know if I'm going to be the executor of this will. I should probably understand the basics of your financial plan and what you want to get out of it. Now it obviously does make it more tricky that we've got a Brady Bunch situation here where we've got two spouses that came in together like that. Duncan. Both of their own kids. It's kind of separate. So like what advice would you give this guy as he tries to do this? Is it bringing an expert in? Like bringing a lawyer in? Like, how would you even start this since obviously he's very tentative about it.

[C]

Right, Right. And he probably feels a certain type of way about it because he's a biased party. Right. If he's a spouse of one of the heirs of the estate. Right. He probably doesn't want it to be perceived that way, especially among the siblings and yeah, it gets messy. I think, Ben, to your point, since the mother in law asked him, she already kind of opened that door. Right. Some people don't even know they're the executor until the person passes away. Right. And that's, like, really secretive. So the fact that she already opened that door, I think he has every right and would be wise to kind of say, you know, happy to serve in this role. You know, help me help you. I think approaching it from a standpoint of not trying, you know, not for his interest alone, but, like, I want to make sure that I do the best job I can for the family and for you. Right. Do right by you. With you nominating me in this role. And I think, too, asking for a copy of the will when it's done is prudent asking, you know, saying you need. You want to have that on file because heaven forbid, you can't find their copy. Right? So I think it's just good, prudent management, right, to ask some of these questions, and hopefully it goes a little better than it did with your grandfather.

[A]

It's funny, a bunch of people in the comments are saying, like, that it's a hard job, right? Because if his wife has siblings, they're gonna be looking at the. Hey, your husband is executing this. Are you, like, shady side deals?

[B]

They drop that at, like, Thanksgiving, Like. Well, as executor.

[A]

Yeah, as executor of the will, I'm cutting the turkey this year. Damn it. I have the power. I'm sitting at the head of the table.

[B]

Exactly.

[A]

I have the power seat. Yeah, but, yeah, you're right. It's. It's. It's. They opened the door. Even if you have these bad family, you know, she opened the door for you to say something and ask some questions. And I think that's perfectly reasonable. And it's kind of like, if you don't trust me to ask this stuff now, how can you trust me to execute the will after the fact?

[C]

Right. Transparency. Always the best policy. And I think, too, if something. Ben, you said maybe think of it. If he can say, like, I want to avoid future conflict when you're gone. I don't want my siblings to see me in a certain way. So if maybe a family meeting. I know that sounds, you know, not super fun.

[B]

Sounds very Brady Bunch.

[C]

Yep, it does.

[B]

It's true. Chris said, you will need a. You need a will, even if you are leaving zero to kids, otherwise kids will suffer. So.

[C]

Oh, yeah, you need a will completely Trying.

[A]

Yeah. Trying to sort it out and. Yeah, yeah, yeah.

[B]

Because it's not just about money, Right. It's about what you like, order of operations, everything that needs to be done.

[C]

Yeah.

[A]

Okay.

[C]

Good luck. Let us know how it goes.

[B]

Yeah, and congrats on being an executor. I mean, that's a nice sign. They. They definitely like you.

[A]

And listen, I'd also bring the wife in here, though, too. Like, you know, she's got to be part of the. She can help be the go between a little bit. Yeah, I'm sure there have been some arguments already. All right, let's do another question.

[B]

Okay. Up next, we got one. I think as anonymous, I'm a financial advisor, but I don't have a personal financial advisor of my own. I assume a lot of other advisors listen to your podcast and would be interested to hear your thoughts on this topic. Should financial advisors have their own personal finance financial advisor? And they are. Right. We have a lot of advisors listening to the show because they're kind of like, getting intel from Ben on how to talk with their clients about things, you know?

[A]

Yes, this is a great question. I think I remember first hearing Carl Richards talk about this, how he had his own financial advisor years ago, and people are like, what? Why would you. You know, you're an expert to the financial advisors. How could you have one? I think one of the cool things about interacting with all of our advisors and all the experts in the different areas and taxes and insurance and estate planning, all these things, is that advisors have dealt with a range of. A wide range of different clients and situations and scenarios and problems. And so my thing is, like, why would you not lean on that expertise as an advisor? Lean on the. Our advisors do that as it is, right? Hey, I got a client who's dealing with this. I'm not really familiar with this problem. Who can help me and other advisors. I did that. Here's who you need to talk to. Here's what you need to do. I think it absolutely makes sense for a financial advisor to have their own advisor.

[C]

Yeah, I agree. I love this question. The old saying, the cobbler without shoes. Like, I bet a lot of advisors are guilty of not giving themselves the attention that they need, that they give their clients. And so having that third party can help you, help keep you accountable to that. And the same reason why we have some clients that are very smart in this industry and could probably do some of this themselves, but having that unbiased third party guiding you through these decisions, because even though you're an advisor, you're probably still. You're still human. Right. So there's still emotion involved in some of the decisions. And I'd go a step further. And if it's an advisor who's married. Right. And you're trying to make decisions together as a couple, might also be good to have an outside opinion giving that advice so that maybe the spouse doesn't think that you're just, you know.

[A]

Yes. Objective third party who can kind of come in. You're right. Mediate a little bit.

[C]

Yeah, mediate. That's the word.

[A]

Every financial advisor knows that many financial problems exist at a state of gray. There always isn't a black or white answer. And sometimes you need someone to say, well, did you think of this? Or how about this? And help you decide what's the best path forward. Even if there might be two or three paths that could make sense for you.

[C]

Yeah.

[A]

It's funny, I talked to Brian Portnoy this morning and he works with advisors and he said the hardest advisors to work with are the ones who don't have self awareness. They see that clients have behavioral issues or problems that they need to deal with, but they don't see that they obviously, being human, have those themselves. Every advice, every advisor has that. Right. And so, yeah, I think I lean on Bill Sweet as my advisor. Right. I invest in the funds and strategies that our clients invest in because our investment committee is.

[B]

I thought I was your advisor.

[A]

I do the opposite of what you tell me, Duncan. I think you do the opposite of what I tell you too. So I think neither of us are really.

[B]

I definitely take a lot of what

[A]

you say to heart anti advisors. But yeah, it's a great question and I think it's. It helped. Right. Like, Josh and his wife have sat down and did a full financial plan with our advisors. This is something that absolutely makes a lot of sense to do, to kind of pull yourself out of the equation and. Because the, the biggest blind spot is like the blind spot you don't see, obviously.

[C]

Right.

[A]

Everyone has their own type of emotional blind spot somewhere.

[C]

Right.

[A]

And you never see it in yourself, obviously.

[C]

Yep.

[A]

Someone else can see it immediately.

[B]

The best hitters still have hitting coaches, right?

[A]

Yep.

[C]

I mean.

[A]

Yeah, yeah. Good question though.

[C]

Good question.

[A]

All right.

[B]

Okay.

[A]

We got, we got one. Someone in the. Chris in the chat said Cliff is his therapist.

[B]

Nice, Nice.

[A]

All right.

[B]

Yeah. And I think AI is a lot of people's therapists right now. For better or for worse. Uh, okay, last but not least, we got one from June. My husband and I are looking to Set up investment accounts for our 16 and 19 year old children and we would greatly appreciate your guidance. We've been following your work for years and have always valued your thoughtful, practical approach to long term investing. As we begin planning for their long term financial future, we'd love to better understand the most appropriate investment options and how to structure everything from the start.

[A]

It's interesting, we get a lot of questions from people who have developed good financial habits that they want to instill those habits in their children and a ton of questions. Sometimes it is I want to start, you know, the right accounts from a young age, whether it's a 529 or HSA. This is older. This June actually emailed me and I said, well how old are your kids? And then she said, oh, they're 16 and 19, so this is a little older. So not sure about their like whole financial situation and the estate planning stuff, but it sounds to me like they want to get them off on the right foot in terms of the accounts. So like how do you think about the next year? Because I think about it in terms of my kids too. Like how do you. Do you just start it for them to get the ball rolling and hopefully they pick up on it and jump on the snowball. Like how do you think about this getting the kids involved in the equation?

[C]

Yeah, there's so many layers of this question and so many. It depends. But I think where I would start is like what is the parent's intent? Right. Are they the intent to grow the assets as much as they can off the bat? Right. Is the intent to teach the kids about stewardship and investing? Is the intent to kind of handle some of their own wealth transfer strategies? Right. If they have estate tax issues, are they thinking ahead to that?

[B]

Right.

[A]

So like the gifting angle essentially.

[C]

Yeah. Like there's just, there's so much here. What immediately comes to mind at that age is like if they're these kids are working part time jobs or have some earned income, throw some money in a Roth. Right? Like that's.

[A]

Yeah. The 19 year old, he's can already put it in a Roth, right?

[C]

Yeah. And if the 16 year old has earned income.

[A]

Has earned income. Right.

[C]

Yeah, yeah. So can you do that even if

[B]

you're just like mowing lawns in the neighborhood kind of thing and getting paid for it? Okay.

[A]

Yeah, it's not a bad. Yeah, you're right. I think that's probably the, that would be the layup one to me.

[C]

Yeah.

[A]

Is getting them give it a Roth ira open for them, assuming this isn't

[C]

some sort of like college savings question, if this is for them building their own personal wealth, like tax free growth kind of trumps obviously that's, you know, you're going to max out that contribution. But then from there if the, the idea is like how do we start teaching them and how do we, you know, then if you're comfortable, let them have access to those accounts and sit down and show them and try to get them interested. I've heard one strategy that I thought was interesting with young kids is like if the kid, the child wants to buy something, you know, if they want an iPad, then they need to buy stock in that company that they're buying. Right. That's not the best investment strategy. But as a way to get them interested at that age might be a good hook. And then from there if the parents are wanting to make bigger gifts, then you're getting into things like what kind of access do you want the kids to have? Right. That's more estate, trust work obviously. So there's a lot there. Roth IRA feels like the low hanging fruit.

[A]

Bill Sweet is in the chat and he says he tells both of his kids every morning, when you're 18, you're out of the house and you're on your own. Harsh. I do think one of the things that a lot of people who have saved and invested for years, one of the things most people will say is I wish I would have started earlier. Everyone has that feeling. And I think a lot of parents think like if I can start my kids out at 18 by putting a little bit of money away, the compounding is going to be so massive in 20, 30, 40, 50 years. Like they're not going to have to save as much and I'm going to get them started out on the right foot. And so I think that's where a lot of people come from. This, that's the thing, a lot of

[C]

people think yeah, yeah, or even at that age, helping them again, assuming they have part time jobs, let's say helping them quote unquote, budget and like have them put away some of their money even if it's 20 bucks. Right, just right to start kind of teaching that discipline. And yeah, I like, I've done it

[A]

a few times on my, a few times with my kids, I've done the mom and dad match. Right, you put a dollar in, we're going to put 50 cents in. Right? You put 20, we'll put 10. We're trying to get them to think that way. Still working on it.

[B]

I like the idea of buying them stocking things that they're using. So an iPad. So buy Apple Stocker. Because a lot of people just put money for their kids in like a savings account. And that, like 1% or whatever, 0.25% they were getting is really not too boring. It's not making anyone interested in personal finance.

[A]

Right. Or the savings by Starbucks, by Apple, by Disney. Those type of things. Yeah, yeah. Yep. Okay. All right. Good stuff. Thanks, everyone in the live chat, as always. It was hopping today. Even Bill Sweet came on there.

[B]

Yeah. Good turnout. Almost 1300 people watching right now across Twitter and YouTube.

[A]

Ask the compound. Showmail.com inbox is full every week. We appreciate your questions. Thanks to Taylor for coming back on the show.

[B]

Yeah, thanks.

[A]

First time.

[C]

Yeah.

[A]

Yep. We'll see you guys next time.

[B]

See everyone.

[A]

Thanks for listening to Ask the Compound.

[B]

All opinions expressed by Ben Carlson, Duncan Hill, and any of their guests are solely their own opinions and do not

[C]

reflect the opinion of Ritholtz Wealth Management.

[B]

This podcast is for informational purposes only and should not be relied upon for any investment decisions.

[C]

Clients of Ritholtz Wealth Management may maintain positions in the securities discussed in this podcast.