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The step-up in cost basis is the most wonderful of tax breaks. It’s just a shame somebody has to die first.

How do I invest for Dividend Income? Should I?

"I prefer total stock market index funds. Long term capital gains from selling these are taxed the same as qualified dividends."
- Randy Dobkin
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The budget-less, automated financial life of two old retirees living paycheck to paycheck- sort of, okay, not really. By Quinn

"One should not interpret as advice postings of how the Quinns manage money. He's admitted to irrationally continuing to reinvest dividends in his outsized position in company stock."
- Randy Dobkin
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Wellcare for Part D by Andrew Forsythe

"“You pay your Part D IRMAA directly to Medicare, not to your plan or employer. You’re required to pay the Part D IRMAA, even if your employer or a third party (like a teacher’s union or a retirement system) pays for your Part D plan premiums. If you don’t pay the Part D IRMAA and get disenrolled, you may also lose your retirement coverage and you may not be able to get it back.” https://www.medicare.gov/drug-coverage-part-d/costs-for-medicare-drug-coverage/monthly-premium-for-drug-plans"
- parkslope
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The Choice to do Nothing

"I don't disagree with you BB. The risk has all been shifted to the employee. That was my concern when my employer switched to a defined contribution plan. Like I said, 38 years later it didn't work out well for some of the guys."
- Dan Smith
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In defense of billionaires

"The estimate is about 35% of all wealth inherited, so what? I wish some would come my way. Are they bad people, have they taken from anyone else? That CEO is the problem of the shareholders not you and me. And there are very, very few billionaires who are CEOS who can be fired."
- R Quinn
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California Free by Ken Cutler

"William, thanks for reading and commenting. A 24 year semi-retirement...that's a lengthy, gradual off-ramp. Best wishes for your next chapter."
- Nuke Ken
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New ArticlesAll Articles »

Mob Rule

BENJAMIN GRAHAM was Warren Buffett’s teacher and mentor. He also ran an investment fund that specialized in uncovering demonstrably undervalued stocks.
One day in 1926, Graham was at his desk, reading through a government report on railroads, when he noticed a potentially important footnote. It referenced assets held by a number of oil pipeline companies. But there wasn’t a lot of detail, so Graham boarded a train to Washington and found his way to the Interstate Commerce Commission (ICC),

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Sticking With Stocks

AT A FAMILY DINNER in the early 1980s, I remember one of my brothers—probably then age 20 or so—saying, “But isn’t the economy built on sand?”
My economist stepfather offered one of his trademark droll responses: “The economy’s always built on sand.”
The same could be said for the stock market. In the minds of many investors, it’s always teetering on the verge of collapse. After two years of rising share prices, and amid concerns about high stock valuations,

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Begin by Quitting

MANY FOLKS CLAIM TO be ready for retirement, both financially and psychologically. But they’re often surprised to discover that the reality is different from what they expected.
I started planning well in advance of my 2023 retirement. I read dozens of books on the subject, and talked to many classmates and friends who’d already retired. Of all the books and videos that I reviewed, one talk on YouTube stood out: a TEDx Talk by Dr.

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Having the Last Word

IT WAS 1982 OR thereabouts. After attempting to be a landlord for several years, I decided it wasn’t for me. I sold the house and the four-family apartment building I’d been managing.
The final task in closing out this adventure would come at tax time. Keeping the books was the one aspect of being a landlord that I didn’t mind. I understood how accumulated appreciation would be recaptured and how capital gains tax would affect that year’s taxes.

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In Love With Bonds

WHEN I WAS GROWING up, I’d receive Series E savings bonds as birthday gifts from my parents. It was the start of many to come. My parents had great respect for savings bonds and, as I got older, I came to hold them in high regard as well.
Savings bonds never offered the highest interest rate. At a defense plant where I worked, a guy in the accounting department questioned my bond buying. He noted that savings bonds paid less interest than the certificates of deposit then available.

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Underwater Overseas

IS IT WORTH OWNING international stocks? There’s far from universal agreement. The traditional argument for investing outside the U.S. is straightforward: diversification—since domestic and international stocks don’t move in lockstep, and sometimes diverge significantly.
At the same time, however, international stocks have lagged behind their U.S. counterparts for so many years that it’s been trying the patience of even the most tenacious investors. Domestic stocks have outpaced international stocks in eight of the past 10 years.

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Get Educated

act

WHEN MAKING a purchase, ponder not just its virtues, but also the maintenance, repairs and other hassles involved—because those’ll eventually loom large. Take the country home. It may initially seem like a great escape. But soon enough, you’ll be just as focused on the drive back and forth, and on the chores you’ll have to do once you’re there.

Truths

NO. 70: WE INVEST now so we—or our heirs—can spend later. The goal of investing isn’t to get rich or beat the market. Instead, it’s about paying for the house down payment, kids’ college, retirement and other goals. Like a pension fund, we should identify our future financial obligations—and then figure out the surest way to meet those obligations.

humans

NO. 46: DIVERSIFICATION has been described as Wall Street’s only free lunch—but some folks take the notion too far. They’ll spread their money across multiple financial advisors, multiple funds that invest in the same market sector and far too many financial firms. The result can be high investment costs and an overly complicated financial life.

Money Guide

Add Alternatives?

ALTERNATIVE investments—including hedge funds, real estate partnerships, natural resources and venture capital funds—have long fascinated investors. Folks love the idea of owning sophisticated and often exclusive investments that not only have the potential to post gains when stocks are suffering, but also could deliver outsized long-run returns. Indeed, in recent decades, there’s been much chatter about the so-called endowment model, which is closely associated with the late David Swensen, who oversaw Yale University’s endowment. Swensen pioneered a strategy of investing relatively little in U.S. stocks and bonds, and instead allocating substantial sums to alternative investments—and he did so with great success. But while alternative investments have been a big winner for Yale, everyday investors should probably be leery. Why? There are three reasons. First, many alternative investments involve high costs. That’s mostly because alternative investments are usually actively managed. In addition, it seems managers believe they can charge a premium price for such exotic fare. Second, while past performance is always a shaky guide to future returns, this seems to be especially true for alternative investments. Hedge funds, commodities and other alternatives have attracted heaps of investor dollars in recent decades, only to post disappointing returns. That disappointment has extended to stock market downturns, when alternatives haven’t always delivered the portfolio protection that investors expected. Finally, amid all the hoopla over alternative investments, experts often fail to mention that investors already have easy access to a low-cost investment that’s had a long history of faring well during rough stock markets. Want to lose less money when share prices next plunge? A low-cost short-term government bond fund may be all you need. Next: Stocks Overpriced? Previous: How Much Abroad?
Read more »

Manifesto

NO. 47: IF WE NEED a financial advisor, we should hire one who’s legally required to act as a fiduciary—meaning he or she should only make recommendations that are in our best interest.

Second LookAll Articles »

Retirement

Telling Your Story

WANT THE LAST WORD? Write your own obituary.
It’s the final opportunity to tell the world you were a great person and that others should regret never having known you. You can write what you want because, in most newspapers, the obituaries are essentially paid ads—and pricey, to boot. No one is going to challenge your obituary’s veracity, at least not publicly, unless it’s outrageous.
Was she really well liked by everyone she met?

Read more »

Family Finance

Cut It Out

IT ISN’T EASY STICKING to a budget. I get it. Surprise expenses pop up all the time. How can you possibly be expected to live on a strict dollar amount each and every month?
The answer is, you don’t. But the key is to make sure you have enough financial breathing room, so you aren’t living paycheck to paycheck. That brings me to three common budget busters. These areas of your financial life, if ignored,

Read more »

Investing

When Fantasy Fails

I’M A LIFELONG football fan who’s played fantasy football for 20 years. What do I have to show for it? Zero league titles, a staunch ambivalence about fantasy football—and three investing maxims.
Every fantasy football season starts with the draft. Three intoxicating forces combine to make the draft a great time: predictions, customization and pride. I’ve come to realize that the draft accounts for about 90% of the appeal of the whole fantasy football concept.

Read more »

Lists

He Asked, I Answered

I’VE BEEN CHALLENGED—by Mr. Clements, no less. Jonathan didn’t actually say it, but his challenge was to defend my unorthodox views on investing and retirement, and the actions I’ve taken as a result.

Some of my decisions will seem illogical to others. Some don’t maximize investment returns. Some are very conservative, others not so much.

I don’t like math. I don’t like details. I haven’t used a spreadsheet in 30 years. I focus on the big picture and long-term goals.

Read more »
Home Call to Action

Mindset

Predictably Wrong

I DON’T USUALLY FOLLOW the NFL. But this year, I’ve made an exception—because the current season offers a valuable lesson not just for football fans, but also for investors.
Teams devote huge amounts of time, energy and money to determining who’s the best quarterback for their team. Yet, this year, three quarterbacks are leading their teams when most experts, who get paid to evaluate talent, didn’t give them much of a chance.
Brock Purdy leads the San Francisco 49ers.

Read more »

Free Newsletter

Get Educated

Manifesto

NO. 47: IF WE NEED a financial advisor, we should hire one who’s legally required to act as a fiduciary—meaning he or she should only make recommendations that are in our best interest.

act

WHEN MAKING a purchase, ponder not just its virtues, but also the maintenance, repairs and other hassles involved—because those’ll eventually loom large. Take the country home. It may initially seem like a great escape. But soon enough, you’ll be just as focused on the drive back and forth, and on the chores you’ll have to do once you’re there.

Truths

NO. 70: WE INVEST now so we—or our heirs—can spend later. The goal of investing isn’t to get rich or beat the market. Instead, it’s about paying for the house down payment, kids’ college, retirement and other goals. Like a pension fund, we should identify our future financial obligations—and then figure out the surest way to meet those obligations.

humans

NO. 46: DIVERSIFICATION has been described as Wall Street’s only free lunch—but some folks take the notion too far. They’ll spread their money across multiple financial advisors, multiple funds that invest in the same market sector and far too many financial firms. The result can be high investment costs and an overly complicated financial life.

Money Guide

Start Here

Add Alternatives?

ALTERNATIVE investments—including hedge funds, real estate partnerships, natural resources and venture capital funds—have long fascinated investors. Folks love the idea of owning sophisticated and often exclusive investments that not only have the potential to post gains when stocks are suffering, but also could deliver outsized long-run returns. Indeed, in recent decades, there’s been much chatter about the so-called endowment model, which is closely associated with the late David Swensen, who oversaw Yale University’s endowment. Swensen pioneered a strategy of investing relatively little in U.S. stocks and bonds, and instead allocating substantial sums to alternative investments—and he did so with great success. But while alternative investments have been a big winner for Yale, everyday investors should probably be leery. Why? There are three reasons. First, many alternative investments involve high costs. That’s mostly because alternative investments are usually actively managed. In addition, it seems managers believe they can charge a premium price for such exotic fare. Second, while past performance is always a shaky guide to future returns, this seems to be especially true for alternative investments. Hedge funds, commodities and other alternatives have attracted heaps of investor dollars in recent decades, only to post disappointing returns. That disappointment has extended to stock market downturns, when alternatives haven’t always delivered the portfolio protection that investors expected. Finally, amid all the hoopla over alternative investments, experts often fail to mention that investors already have easy access to a low-cost investment that’s had a long history of faring well during rough stock markets. Want to lose less money when share prices next plunge? A low-cost short-term government bond fund may be all you need. Next: Stocks Overpriced? Previous: How Much Abroad?
Read more »
Second LookAll Articles »

Retirement

Telling Your Story

WANT THE LAST WORD? Write your own obituary.
It’s the final opportunity to tell the world you were a great person and that others should regret never having known you. You can write what you want because, in most newspapers, the obituaries are essentially paid ads—and pricey, to boot. No one is going to challenge your obituary’s veracity, at least not publicly, unless it’s outrageous.
Was she really well liked by everyone she met?

Read more »

Family Finance

Cut It Out

IT ISN’T EASY STICKING to a budget. I get it. Surprise expenses pop up all the time. How can you possibly be expected to live on a strict dollar amount each and every month?
The answer is, you don’t. But the key is to make sure you have enough financial breathing room, so you aren’t living paycheck to paycheck. That brings me to three common budget busters. These areas of your financial life, if ignored,

Read more »

Investing

When Fantasy Fails

I’M A LIFELONG football fan who’s played fantasy football for 20 years. What do I have to show for it? Zero league titles, a staunch ambivalence about fantasy football—and three investing maxims.
Every fantasy football season starts with the draft. Three intoxicating forces combine to make the draft a great time: predictions, customization and pride. I’ve come to realize that the draft accounts for about 90% of the appeal of the whole fantasy football concept.

Read more »
Home Call to Action

Lists

He Asked, I Answered

I’VE BEEN CHALLENGED—by Mr. Clements, no less. Jonathan didn’t actually say it, but his challenge was to defend my unorthodox views on investing and retirement, and the actions I’ve taken as a result.

Some of my decisions will seem illogical to others. Some don’t maximize investment returns. Some are very conservative, others not so much.

I don’t like math. I don’t like details. I haven’t used a spreadsheet in 30 years. I focus on the big picture and long-term goals.

Read more »

Mindset

Predictably Wrong

I DON’T USUALLY FOLLOW the NFL. But this year, I’ve made an exception—because the current season offers a valuable lesson not just for football fans, but also for investors.
Teams devote huge amounts of time, energy and money to determining who’s the best quarterback for their team. Yet, this year, three quarterbacks are leading their teams when most experts, who get paid to evaluate talent, didn’t give them much of a chance.
Brock Purdy leads the San Francisco 49ers.

Read more »