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Video · 2026-07-15 · 32m · 6 moments

Can Your Portfolio Survive Market Timing?

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01
Data

If you strip out both the best and worst days in the market, you end up with returns only marginally better than simple buy-and-hold, because the two effects offset each other.

Ben Carlson explains that missing the 25 worst days makes $1 grow to $236, missing the 25 best days makes it grow to only $8, but missing both best and worst days nets out close to plain buy-and-hold returns.

transcript

Ben Carlson: This shows $1 invested in the S&P 500 in 1990. If you missed the 25 worst days $236 does turned into. If you missed the best 25 days, it turns into $8... what if you miss 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.

explains mechanism · 1provides context · 1

02
Mechanism

The market's best and worst days cluster together in time because panic selling and panic buying both occur during the same volatile downtrends, which is why you can't selectively avoid only the bad days.

Ben shows that historically the best and worst trading days happen right next to each other (e.g., 2008, 2020) because volatile downtrends produce both panic selling and panic buying.

transcript

Ben Carlson: 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.

supports · 1

03
Claim

New investors mistakenly believe the market must revert to some past mean level after hitting a new top, when in fact a new high doesn't preclude much higher prices years later.

Duncan observes that many young or new investors assume the market 'has to' fall back to an old level after reaching a peak, which Ben confirms is a common but mistaken belief.

transcript

Duncan: 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.

extends · 1

04
Claim

For someone with $90,000 in credit card debt, no assets, and a negative net worth, Chapter 7 bankruptcy to fully discharge the debt is probably the cleanest option, especially before a new business accumulates assets.

Ben advises that a friend with $90k in credit card debt, no assets, and a new business should strongly consider Chapter 7 bankruptcy to discharge the debt cleanly before the business gains assets worth protecting.

transcript

Ben Carlson: I would also talk to a bankruptcy attorney. Chapter 7 fully discharge the debt. Like, it doesn't take all that long from what I understand. It's probably the cleanest option... bankruptcy attorneys can tell you, they'll probably tell you it's better to resolve this now before the business has any assets.

05
Claim

People avoid discussing death and estate planning, but failing to have those conversations while alive leaves outcomes up to chance or the courts, so proactive planning and even bringing in a financial advisor as a neutral party is important.

Taylor argues that because mortality is uncomfortable to discuss, families often avoid estate planning conversations, but doing so leaves things to chance; a financial advisor can serve as an objective third party to facilitate those talks.

transcript

Taylor: 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... 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.

06
Claim

Even financial advisors are human and have emotional blind spots they can't see in themselves, so it makes sense for financial advisors to have their own personal financial advisor.

Ben argues advisors benefit from having their own advisor because everyone has blind spots invisible to themselves, comparing it to how even the best hitters still need hitting coaches.

transcript

Ben Carlson: The biggest blind spot is like the blind spot you don't see, obviously. Everyone has their own type of emotional blind spot somewhere. And you never see it in yourself, obviously... Someone else can see it immediately. The best hitters still have hitting coaches, right?

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