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Professional investors regularly lag behind the market, so we should respect their expertise when they ridicule ordinary investors.

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Should Retirees Get a Temporary Flat Tax Window on IRA and 401(k) Withdrawals?

"I will gladly help pay down that debt by doing Roth conversions at 12%."
- Randy Dobkin
Read more »

First Job, Lasting Impact

"William - I still have my Post Versalog slide rule. I earned my BS and MS degrees in mechanical engineering at NC State University."
- Jeff Bond
Read more »

Retirement Accounts

I WAS SCROLLING through social media recently and saw somebody dismiss retirement accounts as “paper wealth.” The argument was familiar: Your money is locked away and you’re waiting for permission to access it.

Post Example

There’s a grain of truth here. Retirement accounts do come with rules. But much of the discussion online ignores how flexible these accounts actually are. More important, it ignores the enormous tax advantages.

Most people today will likely live well beyond age 59½. Many will spend two or three decades in retirement. Even if somebody retires early, they’ll still need assets later in life.

That’s why ignoring retirement accounts at age 30 often isn’t wise. You could end up giving away 30 or 40 years of tax-advantaged compounding.

It also isn’t an all-or-nothing decision. We can use taxable brokerage accounts, Roth IRAs and 401(k)s together. Each account serves a different purpose.

Retirement accounts also provide rebalancing flexibility that taxable accounts don’t.

Inside a Traditional or Roth IRA, investors can rebalance portfolios without triggering capital gains taxes. Somebody who wants less stock market exposure can freely sell shares and buy bonds, Treasurys or other funds without generating an immediate tax bill. That matters over long periods of time.

The other misconception is that retirement accounts are completely inaccessible until age 59½. 

Let's talk about Rule 72(t), also called Substantially Equal Periodic Payments, or SEPP. This IRS rule allows penalty-free withdrawals before age 59½ if specific requirements are followed.

Using online 72(t) calculators, a $500,000 retirement account could potentially generate annual withdrawals of roughly $30,000 while avoiding the normal 10% early-withdrawal penalty:

72(t) calculator

The payments must continue for a required period and the IRS rules are strict. Still, the broader point remains: There are legal ways to access retirement funds earlier than many people realize.

The Rule of 55 is another example.

If you leave your employer during or after the year you turn 55, you can often withdraw money from that employer’s 401(k) without the normal 10% penalty. Again, the money is not completely locked away until 60.

Roth IRAs may also be flexible. Contributions can be withdrawn anytime tax- and penalty-free because taxes were already paid before the money went into the account.

That doesn’t mean people should tap retirement accounts early. But accessibility is very different from impossibility.

Roth IRAs also happen to be among the most powerful wealth building tools available.

Qualified withdrawals are tax-free. Dividends compound without yearly tax bills. Investors can buy and sell investments inside the account without triggering taxable events.

You may remember a famous example about Peter Thiel. According to reporting by ProPublica, Thiel reportedly grew a Roth IRA from $2,000 to more than $5 billion between 1999 and now. He turns 59½ in 2027, meaning those withdrawals could potentially be tax-free. Imagine if he had decided to skip retirement accounts because he wanted to “live now.”

Employer matches are another point often ignored online. Skipping a 401(k) match can be one of the costliest financial mistakes people make.

Suppose an employer offers a dollar-for-dollar match on the first 3% of salary contributed to a 401(k). Before the investments even grow, that’s effectively an immediate 100% return.

Very few opportunities offer that kind of risk-adjusted benefit.

In fact, somebody could theoretically contribute, collect the employer match, later withdraw the money, pay ordinary income taxes plus the 10% penalty, and still potentially come out ahead versus investing only through a taxable brokerage account with no match.

The tax advantages extend beyond employer matches.

Inside retirement accounts:

  • Dividends can compound without annual tax drag
  • Investors can rebalance without triggering taxable events
  • Capital gains taxes are deferred or eliminated, depending on the account type

Compare that with a taxable brokerage account, where dividends may create yearly tax bills and selling appreciated shares can trigger capital gains taxes.

Retirement accounts can also create opportunities for tax arbitrage.

Somebody contributing while in the 22% or 24% marginal federal tax bracket today might eventually withdraw money while in the 10% or 12% bracket during retirement.

State taxes can widen the advantage even more. Some states provide tax deductions on retirement contributions while later taxing retirement withdrawals lightly or not at all.

Early retirees often use Roth conversion ladders as well.

The process generally works like this:

  • Move money from a Traditional IRA or 401(k) into a Roth IRA
  • Pay taxes on the converted amount
  • Wait five years
  • Withdraw the converted funds penalty-free

Like Rule 72(t), there are strict rules involved. But these strategies exist because retirement accounts were never designed to be prison cells.

The larger point is that retirement planning should involve multiple tools working together. Taxable brokerage accounts provide flexibility. Roth IRAs provide tax-free growth. Traditional retirement accounts can reduce taxes during high-earning years.

None of these accounts are perfect by themselves. Together, however, they can create an extremely efficient system for building long-term wealth.

That’s why describing retirement accounts as “paper wealth” misses the bigger picture.

 

Bogdan Sheremeta is a licensed CPA based in Illinois with experience at Deloitte and a Fortune 200 multinational.  
Read more »

Don’t Push It

I'M ALL IN FAVOR of striving. But I’ve also belatedly come to see the appeal of acceptance. Should we strive for more, or should we accept what we currently have and what’s currently on offer? As I’ve noted in earlier articles, there’s great pleasure in striving. We love the feeling of making progress, even if our achievements don’t make us happy for long. It’s an instinct we no doubt inherited from our hunter-gatherer ancestors. Their striving is the reason they were able to survive and reproduce, and hence the reason we’re here today. Despite my terminal cancer diagnosis, I continue to set goals and strive toward them. Each day, I put in hours keeping HumbleDollar chugging along, trying to stay in shape and working on various writing projects. Still, striving in some areas of our life doesn’t preclude acceptance in others. We should accept the limits of our talents. We’re told that if we work hard, we can achieve anything we set our sights on. Really? We all know that’s not true of athletic and artistic endeavors. No matter how hard I worked, I simply never had the talent to be, say, a pro athlete or a concert pianist. Sometimes, gauging our talent is trickier. It took a while, but eventually I discovered during my career that I wasn’t an especially good manager and that my efforts to write about topics other than personal finance never turned out quite as well as I’d hoped. To be sure, some folks are more successful than their talents would suggest. Hard work may have played a role. But there was likely also an element of luck. That’s great—but it hardly seems like something we should bank on. We should accept that we’ll never be fully satisfied. We imagine that our next accomplishment will leave us happy forever, but then we end up moving the goal posts and targeting some new achievement. That’s just the way we humans are: We love to strive. But we should also accept that this striving will never leave us with that ultimate sense of accomplishment that we crave. That doesn’t mean we should stop striving. But we should accept that it’s the journey we enjoy, and the destination won’t leave us permanently happier. We should accept that we’re unlikely to outpace the market averages. Want to outperform most other investors? The surest way is not to try—by simply buying index funds and collecting the performance of the market averages. Because of fund expenses and trading costs, index funds typically trail behind their benchmark index. But that’s better than most active investors, who lag by even more. We should accept that there are things we can’t control. We might be able to control our own behavior, though even that can be a struggle. What if we try to control the behavior of others? Life can get awfully frustrating awfully fast. This is crystal clear in the world of investing. We can control how much risk we take, the investment costs we incur, and our own buying and selling. But we can’t control the behavior of other investors, as reflected in ever-fluctuating stock and bond prices. Instead, we need an investment strategy that doesn’t depend on others behaving the way we want, at least in the short-term. Got just a few years to invest? Don’t count on other investors acting on your wishes and bidding up the price of the stocks you own. We should accept our own mortality. We may continue to strive every day. But this can’t go on forever and, in my case, probably not for much longer. When do I stop striving and accept the inevitable? I don’t have the answer, but I suspect the question will be answered for me. With each passing month, I move more slowly and I have less energy. I haven’t chosen to strive less, but it seems I am. As I observe what’s happening to me, I imagine that I’m aging, like so many before me, but for me it’s happening over months, rather than decades. I’m not saying this slowing down is enjoyable. But it also isn’t so terrible—because I feel like it’s helping me to accept what’s to come. Jonathan Clements is the founder and editor of HumbleDollar. Follow him on X @ClementsMoney and on Facebook, and check out his earlier posts. [xyz-ihs snippet="Donate"]
Read more »

There is no such thing as a tax loophole, but here they are anyway

"This may be a bit academic but might be useful to some.
  1. Tax planning opportunities (whether you call them a loophole is semantic) when there is a difference in tax rates across time periods (IRA vs taxable account) / types of income (income, dividends, gains, etc.) / jurisdiction (MA vs. FL) / object of tax (married vs. single) / other factors. Within each cut, effective tax planning seeks to move money from a category with a higher tax rate to one with a lower tax rate.
  2. We create a mess (and opportunities for tax planning by creating the above wedges) when we comingle social / economic policy with tax policy. A progressive tax rate is a simple example ... it implicitly assumes that richer people ought to pay more. Likewise, why seek to favor investments via a lower rate on LT capital gains rate? Why promote marriage with a higher slab for married filing jointly versus two people living together and filing as individuals? In my view, every attempt to alter behavior via tax policy has unintended consequences which has created the "tax planning" industry.
Having said this, I think divorcing the social / economic and tax policy is not that easy or straightforward. So, I think we are stuck in this mess for the long haul. And, as a rational person, it makes sense to tax plan as much as possible."
- ram bala
Read more »

Country Club Venture Capital 

"My wife's friend runs a small home business making and altering Irish dancing costumes. They're not cheap — but given the hours she puts into crafting them and hand-applying all the sequins and embellishments, it's easy to see why. I'm just very grateful my girls never caught the Irish dancing bug when they were young!"
- Mark Crothers
Read more »

Resilient Investing

BACK IN 2010, at the Berkshire Hathaway annual meeting, a shareholder challenged Warren Buffett. Noting that shares of motorcycle maker Harley-Davidson had nearly tripled over the prior year, he asked Buffett why he had chosen to buy the company’s bonds rather than its stock. Buffett’s reply was a two-minute masterclass in how to think about investments. It’s worth walking through it point by point. To start, Buffett acknowledged that hindsight can be cruel. “I might have asked the same question,” he said. But then he reminded the investor that we should never judge an investment decision solely based on its result. Instead, he emphasized the importance of a sound decision-making process. He then detailed how he thought about the Harley decision at the time. Buffett started at a high level, with a discussion of asset allocation, and here he made a counterintuitive argument. Many of Berkshire Hathaway’s liabilities extended out more than 50 years, he said, and with such a long time horizon, it might seem like the company could afford to take an almost unlimited amount of risk in the stock market. Buffett acknowledged that was indeed the case. But, he said, “we would never have all our money in stocks,” even if, on paper, it seemed like the best choice. Buffett and his partner, Charlie Munger, still chose to hold substantial amounts in bonds, even if that meant giving up potential gains. Why? Buffett went on to explain why holding bonds made sense even in the absence of any clear need. For starters, bonds provide flexibility during stock market downturns. And since bear markets always arrive without notice, and can last multiple years, it makes sense to hold bonds, more or less, at all times. Perhaps not surprisingly, Buffett once mentioned that a trust he’d established for his family was similarly structured, with 10% in bonds, even though it had a long time horizon and could theoretically afford to be entirely in stocks. Coming back to the Harley-Davidson decision, Buffett referenced his mentor, Benjamin Graham. In his book Security Analysis, he had explained the relative benefits of “junior” and “senior” securities. “Junior securities,” Buffett said, “usually do better, but you’re going to sleep better with the senior securities.” What did he mean by junior and senior? In a typical corporate structure, where a company has issued both bonds and stocks, bondholders would have first claim on the company’s assets if it went into distress. Stockholders, on the other hand, would be further back in line. For that reason, bonds are said to be senior, while stocks are junior. It’s an important distinction. Because of this structure, bonds are inherently more secure than stocks. They are essentially IOUs. But also because of that structure, bonds will normally have lower returns than stocks. Companies know they don’t have to offer as much in the way of interest to bondholders because of their more senior position. This is the technical reason why, all things being equal, bonds offer both lower risk and lower returns than stocks. Buffett acknowledged that Harley-Davidson was a beloved company. “I kind of like a company where your customers tattoo your name on their chest.” Still, Buffett said, there were no guarantees. Even great companies can run into trouble. It was for this reason, Buffett said, that buying Harley-Davidson’s bonds was a relatively easy decision. “I knew enough to lend them money. I didn’t know enough to buy [the stock].” That’s because buying the stock would have required a much more detailed analysis of the motorcycle market, including an understanding of consumer trends and the effects of competition on Harley’s profit margins. Buying the company’s bonds, on the other hand, “was a very simple decision. It was just a question of, are they going to go broke or not?”  When we choose to buy bonds, in other words, we’re intentionally choosing the slow lane, but it’s for a reason: because bonds offer a level of certainty that stocks can never provide. And because of that certainty, we shouldn’t feel badly when bonds deliver meager returns. It’s by design. Buffett wrapped up the discussion acknowledging that if he’d opted for Harley’s stock, he would have made far more money for Berkshire shareholders. But that wasn’t the right yardstick, he argued. “We are running this place so that it can stand anything.” That, I think, is the most important thing we can take away from this story. The investment industry spends a lot of time talking about performance—and specifically, about outperformance. Of course, we all want to see our investments grow, but what’s most important, in my view, is that your portfolio be resilient enough to “stand anything.” One of the benefits of stock market downturns is that they give us an opportunity to stress test our emotional response to the market. After a roughly 10% downturn earlier this year, stocks are back at all-time highs, so this is a good time to take the temperature of your portfolio. If you lost some sleep during the downturn this spring, or the one we experienced last spring, this might be a good time to shift some of your portfolio to more senior, more secure, securities. If, on the other hand, you barely even noticed these downturns, that’s important information as well. Investing, in other words, isn’t just about numbers. Adam M. Grossman is the founder of Mayport, a fixed-fee wealth management firm. Sign up for Adam's Daily Ideas email, follow him on X @AdamMGrossman and check out his earlier articles.
Read more »

The Art of Spending Money

"Two purchases come to mind. The first was our Peloton bike at the beginning of 2021. I’ve completed over 1500 rides and over 4000 classes (including strength, stretching, and later rowing) in the five-plus years since, and it was a great investment in my health and to a lesser degree my husband’s. I’ve never been great about actually leaving the house to go to a gym, but I’m very good at working out at home. We actually offset the purchase of the bike and later rower with an annual wellness credit his company gives—didn’t cover the whole thing but took some of the sting off the price tag. The other was our 2018 Audi TT Roadster convertible. It’s the most indulgent thing we’ve ever bought for ourselves. Yes, it impresses people, but it’s also made us very happy. When my job got very stressful, a weekend drive in the convertible quite literally helped me breathe, and it was like a mini-vacation. We’d always wanted a convertible; that was even the title of one of my husband’s albums! It still only has a bit over 30K miles on it, so I think we’ll have it until we’re no longer able to climb in and out of it!"
- DrLefty
Read more »

Quinns visit to Mar-a-Lago

"Sorry, your comment confuses me. The visit and the deckhand incident were totally unrelated and years apart. Yeah, I was the quest of a company along with a dozen other people. I sure wouldn’t have been invited on my own. Your point?"
- R Quinn
Read more »

Take a Look In the Mirror

"I would say there is a slight difference, some potential misfortune can be planned for and avoided."
- R Quinn
Read more »

Help for divorcing daughter

"Are you sure this is still true after passage of the Social Security Fairness Act? "SBP is mainly to get through the working years as the benefit lessens the less time that you can collect (based on SS benefits).""
- ostrichtacossaturn7593
Read more »

Best method for buying home for permanently disabled daughter (SSI and ABLE account)

"Great question Nick. That was my first thought, too. I thought it would be a good and more affordable first step for her to get comfortable living on her own. However, she has a service dog, Maggie, so having a fenced-in yard for Maggie to play and do her "business" vs. Alyssa walking her on a leash at an apartment complex early in the morning before she heads to work was something we (especially my retired FDNY husband) felt was paramount for her safety. We also thought given market conditions investing in a property now would allow us to create longer term value for her as a homeowner vs renting."
- Dianne Baumert-Moyik
Read more »

Should Retirees Get a Temporary Flat Tax Window on IRA and 401(k) Withdrawals?

"I will gladly help pay down that debt by doing Roth conversions at 12%."
- Randy Dobkin
Read more »

First Job, Lasting Impact

"William - I still have my Post Versalog slide rule. I earned my BS and MS degrees in mechanical engineering at NC State University."
- Jeff Bond
Read more »

Retirement Accounts

I WAS SCROLLING through social media recently and saw somebody dismiss retirement accounts as “paper wealth.” The argument was familiar: Your money is locked away and you’re waiting for permission to access it.

Post Example

There’s a grain of truth here. Retirement accounts do come with rules. But much of the discussion online ignores how flexible these accounts actually are. More important, it ignores the enormous tax advantages.

Most people today will likely live well beyond age 59½. Many will spend two or three decades in retirement. Even if somebody retires early, they’ll still need assets later in life.

That’s why ignoring retirement accounts at age 30 often isn’t wise. You could end up giving away 30 or 40 years of tax-advantaged compounding.

It also isn’t an all-or-nothing decision. We can use taxable brokerage accounts, Roth IRAs and 401(k)s together. Each account serves a different purpose.

Retirement accounts also provide rebalancing flexibility that taxable accounts don’t.

Inside a Traditional or Roth IRA, investors can rebalance portfolios without triggering capital gains taxes. Somebody who wants less stock market exposure can freely sell shares and buy bonds, Treasurys or other funds without generating an immediate tax bill. That matters over long periods of time.

The other misconception is that retirement accounts are completely inaccessible until age 59½. 

Let's talk about Rule 72(t), also called Substantially Equal Periodic Payments, or SEPP. This IRS rule allows penalty-free withdrawals before age 59½ if specific requirements are followed.

Using online 72(t) calculators, a $500,000 retirement account could potentially generate annual withdrawals of roughly $30,000 while avoiding the normal 10% early-withdrawal penalty:

72(t) calculator

The payments must continue for a required period and the IRS rules are strict. Still, the broader point remains: There are legal ways to access retirement funds earlier than many people realize.

The Rule of 55 is another example.

If you leave your employer during or after the year you turn 55, you can often withdraw money from that employer’s 401(k) without the normal 10% penalty. Again, the money is not completely locked away until 60.

Roth IRAs may also be flexible. Contributions can be withdrawn anytime tax- and penalty-free because taxes were already paid before the money went into the account.

That doesn’t mean people should tap retirement accounts early. But accessibility is very different from impossibility.

Roth IRAs also happen to be among the most powerful wealth building tools available.

Qualified withdrawals are tax-free. Dividends compound without yearly tax bills. Investors can buy and sell investments inside the account without triggering taxable events.

You may remember a famous example about Peter Thiel. According to reporting by ProPublica, Thiel reportedly grew a Roth IRA from $2,000 to more than $5 billion between 1999 and now. He turns 59½ in 2027, meaning those withdrawals could potentially be tax-free. Imagine if he had decided to skip retirement accounts because he wanted to “live now.”

Employer matches are another point often ignored online. Skipping a 401(k) match can be one of the costliest financial mistakes people make.

Suppose an employer offers a dollar-for-dollar match on the first 3% of salary contributed to a 401(k). Before the investments even grow, that’s effectively an immediate 100% return.

Very few opportunities offer that kind of risk-adjusted benefit.

In fact, somebody could theoretically contribute, collect the employer match, later withdraw the money, pay ordinary income taxes plus the 10% penalty, and still potentially come out ahead versus investing only through a taxable brokerage account with no match.

The tax advantages extend beyond employer matches.

Inside retirement accounts:

  • Dividends can compound without annual tax drag
  • Investors can rebalance without triggering taxable events
  • Capital gains taxes are deferred or eliminated, depending on the account type

Compare that with a taxable brokerage account, where dividends may create yearly tax bills and selling appreciated shares can trigger capital gains taxes.

Retirement accounts can also create opportunities for tax arbitrage.

Somebody contributing while in the 22% or 24% marginal federal tax bracket today might eventually withdraw money while in the 10% or 12% bracket during retirement.

State taxes can widen the advantage even more. Some states provide tax deductions on retirement contributions while later taxing retirement withdrawals lightly or not at all.

Early retirees often use Roth conversion ladders as well.

The process generally works like this:

  • Move money from a Traditional IRA or 401(k) into a Roth IRA
  • Pay taxes on the converted amount
  • Wait five years
  • Withdraw the converted funds penalty-free

Like Rule 72(t), there are strict rules involved. But these strategies exist because retirement accounts were never designed to be prison cells.

The larger point is that retirement planning should involve multiple tools working together. Taxable brokerage accounts provide flexibility. Roth IRAs provide tax-free growth. Traditional retirement accounts can reduce taxes during high-earning years.

None of these accounts are perfect by themselves. Together, however, they can create an extremely efficient system for building long-term wealth.

That’s why describing retirement accounts as “paper wealth” misses the bigger picture.

 

Bogdan Sheremeta is a licensed CPA based in Illinois with experience at Deloitte and a Fortune 200 multinational.  
Read more »

Don’t Push It

I'M ALL IN FAVOR of striving. But I’ve also belatedly come to see the appeal of acceptance. Should we strive for more, or should we accept what we currently have and what’s currently on offer? As I’ve noted in earlier articles, there’s great pleasure in striving. We love the feeling of making progress, even if our achievements don’t make us happy for long. It’s an instinct we no doubt inherited from our hunter-gatherer ancestors. Their striving is the reason they were able to survive and reproduce, and hence the reason we’re here today. Despite my terminal cancer diagnosis, I continue to set goals and strive toward them. Each day, I put in hours keeping HumbleDollar chugging along, trying to stay in shape and working on various writing projects. Still, striving in some areas of our life doesn’t preclude acceptance in others. We should accept the limits of our talents. We’re told that if we work hard, we can achieve anything we set our sights on. Really? We all know that’s not true of athletic and artistic endeavors. No matter how hard I worked, I simply never had the talent to be, say, a pro athlete or a concert pianist. Sometimes, gauging our talent is trickier. It took a while, but eventually I discovered during my career that I wasn’t an especially good manager and that my efforts to write about topics other than personal finance never turned out quite as well as I’d hoped. To be sure, some folks are more successful than their talents would suggest. Hard work may have played a role. But there was likely also an element of luck. That’s great—but it hardly seems like something we should bank on. We should accept that we’ll never be fully satisfied. We imagine that our next accomplishment will leave us happy forever, but then we end up moving the goal posts and targeting some new achievement. That’s just the way we humans are: We love to strive. But we should also accept that this striving will never leave us with that ultimate sense of accomplishment that we crave. That doesn’t mean we should stop striving. But we should accept that it’s the journey we enjoy, and the destination won’t leave us permanently happier. We should accept that we’re unlikely to outpace the market averages. Want to outperform most other investors? The surest way is not to try—by simply buying index funds and collecting the performance of the market averages. Because of fund expenses and trading costs, index funds typically trail behind their benchmark index. But that’s better than most active investors, who lag by even more. We should accept that there are things we can’t control. We might be able to control our own behavior, though even that can be a struggle. What if we try to control the behavior of others? Life can get awfully frustrating awfully fast. This is crystal clear in the world of investing. We can control how much risk we take, the investment costs we incur, and our own buying and selling. But we can’t control the behavior of other investors, as reflected in ever-fluctuating stock and bond prices. Instead, we need an investment strategy that doesn’t depend on others behaving the way we want, at least in the short-term. Got just a few years to invest? Don’t count on other investors acting on your wishes and bidding up the price of the stocks you own. We should accept our own mortality. We may continue to strive every day. But this can’t go on forever and, in my case, probably not for much longer. When do I stop striving and accept the inevitable? I don’t have the answer, but I suspect the question will be answered for me. With each passing month, I move more slowly and I have less energy. I haven’t chosen to strive less, but it seems I am. As I observe what’s happening to me, I imagine that I’m aging, like so many before me, but for me it’s happening over months, rather than decades. I’m not saying this slowing down is enjoyable. But it also isn’t so terrible—because I feel like it’s helping me to accept what’s to come. Jonathan Clements is the founder and editor of HumbleDollar. Follow him on X @ClementsMoney and on Facebook, and check out his earlier posts. [xyz-ihs snippet="Donate"]
Read more »

There is no such thing as a tax loophole, but here they are anyway

"This may be a bit academic but might be useful to some.
  1. Tax planning opportunities (whether you call them a loophole is semantic) when there is a difference in tax rates across time periods (IRA vs taxable account) / types of income (income, dividends, gains, etc.) / jurisdiction (MA vs. FL) / object of tax (married vs. single) / other factors. Within each cut, effective tax planning seeks to move money from a category with a higher tax rate to one with a lower tax rate.
  2. We create a mess (and opportunities for tax planning by creating the above wedges) when we comingle social / economic policy with tax policy. A progressive tax rate is a simple example ... it implicitly assumes that richer people ought to pay more. Likewise, why seek to favor investments via a lower rate on LT capital gains rate? Why promote marriage with a higher slab for married filing jointly versus two people living together and filing as individuals? In my view, every attempt to alter behavior via tax policy has unintended consequences which has created the "tax planning" industry.
Having said this, I think divorcing the social / economic and tax policy is not that easy or straightforward. So, I think we are stuck in this mess for the long haul. And, as a rational person, it makes sense to tax plan as much as possible."
- ram bala
Read more »

Country Club Venture Capital 

"My wife's friend runs a small home business making and altering Irish dancing costumes. They're not cheap — but given the hours she puts into crafting them and hand-applying all the sequins and embellishments, it's easy to see why. I'm just very grateful my girls never caught the Irish dancing bug when they were young!"
- Mark Crothers
Read more »

Resilient Investing

BACK IN 2010, at the Berkshire Hathaway annual meeting, a shareholder challenged Warren Buffett. Noting that shares of motorcycle maker Harley-Davidson had nearly tripled over the prior year, he asked Buffett why he had chosen to buy the company’s bonds rather than its stock. Buffett’s reply was a two-minute masterclass in how to think about investments. It’s worth walking through it point by point. To start, Buffett acknowledged that hindsight can be cruel. “I might have asked the same question,” he said. But then he reminded the investor that we should never judge an investment decision solely based on its result. Instead, he emphasized the importance of a sound decision-making process. He then detailed how he thought about the Harley decision at the time. Buffett started at a high level, with a discussion of asset allocation, and here he made a counterintuitive argument. Many of Berkshire Hathaway’s liabilities extended out more than 50 years, he said, and with such a long time horizon, it might seem like the company could afford to take an almost unlimited amount of risk in the stock market. Buffett acknowledged that was indeed the case. But, he said, “we would never have all our money in stocks,” even if, on paper, it seemed like the best choice. Buffett and his partner, Charlie Munger, still chose to hold substantial amounts in bonds, even if that meant giving up potential gains. Why? Buffett went on to explain why holding bonds made sense even in the absence of any clear need. For starters, bonds provide flexibility during stock market downturns. And since bear markets always arrive without notice, and can last multiple years, it makes sense to hold bonds, more or less, at all times. Perhaps not surprisingly, Buffett once mentioned that a trust he’d established for his family was similarly structured, with 10% in bonds, even though it had a long time horizon and could theoretically afford to be entirely in stocks. Coming back to the Harley-Davidson decision, Buffett referenced his mentor, Benjamin Graham. In his book Security Analysis, he had explained the relative benefits of “junior” and “senior” securities. “Junior securities,” Buffett said, “usually do better, but you’re going to sleep better with the senior securities.” What did he mean by junior and senior? In a typical corporate structure, where a company has issued both bonds and stocks, bondholders would have first claim on the company’s assets if it went into distress. Stockholders, on the other hand, would be further back in line. For that reason, bonds are said to be senior, while stocks are junior. It’s an important distinction. Because of this structure, bonds are inherently more secure than stocks. They are essentially IOUs. But also because of that structure, bonds will normally have lower returns than stocks. Companies know they don’t have to offer as much in the way of interest to bondholders because of their more senior position. This is the technical reason why, all things being equal, bonds offer both lower risk and lower returns than stocks. Buffett acknowledged that Harley-Davidson was a beloved company. “I kind of like a company where your customers tattoo your name on their chest.” Still, Buffett said, there were no guarantees. Even great companies can run into trouble. It was for this reason, Buffett said, that buying Harley-Davidson’s bonds was a relatively easy decision. “I knew enough to lend them money. I didn’t know enough to buy [the stock].” That’s because buying the stock would have required a much more detailed analysis of the motorcycle market, including an understanding of consumer trends and the effects of competition on Harley’s profit margins. Buying the company’s bonds, on the other hand, “was a very simple decision. It was just a question of, are they going to go broke or not?”  When we choose to buy bonds, in other words, we’re intentionally choosing the slow lane, but it’s for a reason: because bonds offer a level of certainty that stocks can never provide. And because of that certainty, we shouldn’t feel badly when bonds deliver meager returns. It’s by design. Buffett wrapped up the discussion acknowledging that if he’d opted for Harley’s stock, he would have made far more money for Berkshire shareholders. But that wasn’t the right yardstick, he argued. “We are running this place so that it can stand anything.” That, I think, is the most important thing we can take away from this story. The investment industry spends a lot of time talking about performance—and specifically, about outperformance. Of course, we all want to see our investments grow, but what’s most important, in my view, is that your portfolio be resilient enough to “stand anything.” One of the benefits of stock market downturns is that they give us an opportunity to stress test our emotional response to the market. After a roughly 10% downturn earlier this year, stocks are back at all-time highs, so this is a good time to take the temperature of your portfolio. If you lost some sleep during the downturn this spring, or the one we experienced last spring, this might be a good time to shift some of your portfolio to more senior, more secure, securities. If, on the other hand, you barely even noticed these downturns, that’s important information as well. Investing, in other words, isn’t just about numbers. Adam M. Grossman is the founder of Mayport, a fixed-fee wealth management firm. Sign up for Adam's Daily Ideas email, follow him on X @AdamMGrossman and check out his earlier articles.
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The Art of Spending Money

"Two purchases come to mind. The first was our Peloton bike at the beginning of 2021. I’ve completed over 1500 rides and over 4000 classes (including strength, stretching, and later rowing) in the five-plus years since, and it was a great investment in my health and to a lesser degree my husband’s. I’ve never been great about actually leaving the house to go to a gym, but I’m very good at working out at home. We actually offset the purchase of the bike and later rower with an annual wellness credit his company gives—didn’t cover the whole thing but took some of the sting off the price tag. The other was our 2018 Audi TT Roadster convertible. It’s the most indulgent thing we’ve ever bought for ourselves. Yes, it impresses people, but it’s also made us very happy. When my job got very stressful, a weekend drive in the convertible quite literally helped me breathe, and it was like a mini-vacation. We’d always wanted a convertible; that was even the title of one of my husband’s albums! It still only has a bit over 30K miles on it, so I think we’ll have it until we’re no longer able to climb in and out of it!"
- DrLefty
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Quinns visit to Mar-a-Lago

"Sorry, your comment confuses me. The visit and the deckhand incident were totally unrelated and years apart. Yeah, I was the quest of a company along with a dozen other people. I sure wouldn’t have been invited on my own. Your point?"
- R Quinn
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Manifesto

NO. 57: WE FAVOR possessions for their lasting value, but often we get greater happiness when we spend money on experiences. Forget the new car. Instead, take the family to Paris.

Truths

NO. 69: RECEIVING a pension or Social Security benefits is akin to owning bonds. Most pensions are like a fixed-interest bond, while Social Security is like an inflation-indexed bond. One implication: If you’ll receive a hefty portion of your retirement income from these two sources, you may have the leeway to invest more heavily in the stock market.

think

MARKET EFFICIENCY. As news breaks that effect the economy and individual companies, investors immediately buy and sell stocks in response, so share prices reflect all publicly available information. Because the market is so efficient, it’s all but impossible for investors to beat the market averages over the long haul, especially after figuring in their own investment costs.

act

SHARE YOUR PAYSTUB and financial statements with your kids. This show and tell will give you a chance to discuss the importance of saving, the power of compounding, and how much of your income goes toward taxes, housing and other items. Any one conversation might be brief and appear to have little impact. But over time, your children will learn a lot.

Best of Jonathan Clements

Manifesto

NO. 57: WE FAVOR possessions for their lasting value, but often we get greater happiness when we spend money on experiences. Forget the new car. Instead, take the family to Paris.

Spotlight: Markets

Decision Frameworks

IN THE SUMMER of 1966, author John McPhee spent two weeks lying on a picnic table in his backyard. Why?
McPhee was suffering from writer’s block. As he described it, “I had assembled enough material to fill a silo, and now I had no idea what to do with it.”
Investors find themselves in a similar situation today. There’s no shortage of financial information around us. But that doesn’t make it easier to know what to do with it. 

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AI Rally Market Risks

LAST WEEK, OPENAI founder Sam Altman sat down for an interview with venture capitalist Brad Gerstner and Microsoft CEO Satya Nadella. Both are investors in OpenAI, so it seemed like a friendly audience. But Gerstner posed a question that seemed to make Altman uncomfortable.
Since introducing ChatGPT three years ago, OpenAI has posted impressive growth, but Gerstner wondered whether the company was, nonetheless, getting ahead of itself.
“How can a company with $13 billion in revenues make $1.4 trillion of spend commitments?” Gerstner asked.

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Going to Extremes

STOCK MARKET Investing requires a near superhuman ability to withstand pain. That’s the conclusion of a recent report by investment researcher Michael Mauboussin.
Mauboussin surveyed all stocks trading on U.S. exchanges over a 40-year period, between 1985 and 2024. He found that the median stock experienced a decline of 85% at one point or another. Worse yet, more than half of these stocks never fully recouped their losses. The median stock recovered to just 90% of its prior high-water mark.

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Private Equity Traps

IN APRIL 2005, art dealers Robert Simon and Alex Parish traveled to New Orleans to attend an auction. They were particularly interested in a work titled Salvator Mundi. The painting was in bad shape, having been neglected for years. But Simon and Parish ended up bidding on it and taking it home for $10,000.
After some restoration work, the pair succeeded in having it authenticated as a work of Leonardo da Vinci.

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Stock Tokens

RECENTLY, The Wall Street Journal ran a story about a new type of investment known as a digital stock token. For now, they aren’t available in the U.S., but they’re coming soon, so it’s worth taking a closer look.
What are stock tokens? At the most basic level, they’re a technology designed to make stock market investing quicker and easier than it is today. With tokens, trading won’t be limited to traditional business hours.

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The Boy Who Couldn’t Risk

I prepared this article  as “homework” for a personal finance elective at a college-preparatory high school I might be contributing to in the Fall. Perhaps it would be helpful to parents whose kids are smitten with the Magnificent 7 or crypto.
After a stock market decline, people may perceive more risk than before, when the decline may have taken some of the risk out of the market.
—Robert Shiller
The investor’s chief problem—and even his worst enemy—is himself.

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Spotlight: Rao

How to minimize the caregiving burden on our adult children when we need help? 

I was reading an article focusing on the caregiving burden on adult children.   Shocking statistics: 63 million Americans — nearly 1 in 4 adults — now provide care to an adult with health or functional needs, or to a child with a serious medical condition or disability — a record high.   Nearly half of caregivers are struggling with finances.  More than 20% have taken on more debt, about a third have used up short-term savings, 30% have stopped saving, and roughly 20% are leaving bills unpaid or paying them late, according to the data. Return-to-office requirements are not helping.  More than 60% of caregivers are balancing their caregiving responsibilities while still employed. And half report they reduced hours, have taken unpaid leave, or even quit their job entirely. See link below:  https://finance.yahoo.com/news/63-million-adults-are-moonlighting-as-caregivers-with-little-support-130037767.html  We can minimize the caregiving burden for our children by moving to CCRC or assisted living, providing for long term care, downsizing and relocating closer to them, preparing a robust estate plan, and saving enough to provide for all future expenses. Even if we do these, the stress and emotional toll on children or relatives will still be significant. Many of you have experienced this already.  What should we do to make sure our children do not have to sacrifice so much when we need help due to our deteriorating health?  How are your family and friends managing to provide such help to their loved ones? 
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What Financial/ Life advice would you give a 2024 college graduate?

Times have changed a lot since we graduated from high school or college. We have experienced many ups and downs in life and observed what works and what doesn't. Some financial and life lessons we learned are still valuable to the next generation. Let us share it here! Sundar Mohan Rao    
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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. Riley Moynes on the four phases of retirement. The four phases he identifies are honeymoon, loss of identity, trial and error, and reinvention. Based on my observations of recent and long-term retirees in two 55-plus communities, these four phases do indeed reflect what happens in retirement. But I also think two further phases need to be added. Phase 1: Honeymoon. New retirees start traveling to exotic places, visit long-lost friends and relatives, and splurge on expensive things. Freedom from a nine-to-five job is liberating. Decades of saving and investing provide sufficient cash flow and a big enough nest egg to make retirement feel like one long vacation. This phase can get derailed by unforeseen events. I know many who retired during the pandemic and stayed home for a while. The retirement honeymoon can also get derailed by a sudden change in your health or your partner's, or by the need to care for elderly parents. Moynes says that, “Phase 1 lasts for a year or so, then it begins to lose its luster. We begin to feel a bit bored, and we ask ourselves, ‘Is that all there is to retirement?’” When I retired, I didn’t spend much time in the honeymoon phase. I was clear about what I wanted to do and got busy right away. Phase 2: Loss of identity. This is the…
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What life lessons would you like to pass on to the next generation?

After making progress on estate planning, documenting financial records, and updating family history, it suddenly occurred to me that I should make a list of life lessons I have learned along my life journey.   Obviously, these life lessons are a lot more than strictly financial, but certainly they will contribute to overall success and a fulfilling life for the next generation.   I came up with these and put them in a document along with my financial records. Hopefully, someday it will help the next generations in my family.  Here is my list of 10.   1. Live your own dreams, not someone else's 2. Believe and invest in yourself 3. Focus on health, family, financial security and a purpose larger than yourself 4. Be a lifelong learner 5. Be self aware and know who you are and what makes you tick 6. Learn from failures and keep moving 7. Be positive to overcome life's many challenges 8. Give to receive 9. Start small, think big 10. Leave everyone better than you found them   Everyone has different life experiences and value systems. What life lessons would you like to pass on to the next generation?      
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Money Matters

DURING THE PANDEMIC, I started devoting more time to retirement planning. But I had more questions than answers. I called a friend who was a financial planner. “Retirement planning is confusing,” I told him. “I have a lot of questions.” He laughed and said, “The answer is money. What’s the question?” While his answer was humorous, it reflected what most retirees already know: Money is crucial for a good retirement. While it isn’t the only thing you need for a happy retirement, it certainly helps. How much money do you need? There are many variables, including an individual’s cost of living, retirement aspirations and health, so general guidelines can be risky. Still, we know retirement can be expensive even if you don’t travel extensively. Health care expenses continue to rise. Even general inflation often puts a squeeze on retirees’ budgets. One rule of thumb says you need 80% of your pre-retirement income to maintain your standard of living once you stop working.   What does that mean in terms of savings? Americans spend roughly 20 years in retirement, on average, but some people will live far longer. Experts say, at retirement age, folks should have savings equal to 10 to 12 times their annual income. For instance, if your annual income is $80,000, you might target $800,000 to $960,000 in retirement savings. If you have other sources of retirement income, such as a pension, you can likely make do with less savings. Most folks don’t come close to hitting such savings targets. According to the Federal Reserve, households headed by someone age 65 to 74 had average retirement account balances of $609,000 and median, or typical, savings of $200,000. Ideally, you should start saving for retirement early in your career, socking away perhaps 10% to 15% of your income. To get…
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Still Learning

WHEN I LOOK BACK at my career, I see that the key to my long tenure with one employer was my desire to learn new skills and help expand the business. That mindset, I believe, helped me survive multiple rounds of layoffs. I’m hoping that same mindset will help with retirement. Many retirees say, “I just want to relax. Get rid of the alarm clock. No more classes or schedules for me.” While that feels good for a while, I’m not sure such an attitude will sustain their happiness for long. The fact is, retirement brings with it a sense of lost identity. Many retirees miss the workplace’s routine, their colleagues and even the office politics. Meanwhile, research suggests lifelong learning offers psychological benefits for seniors. During my stay at a 55-plus community in Atlanta, I saw a 90-something-year-old gentleman carrying a bag full of books every few weeks to his room. One day, I asked him what he was up to. He said, “I go to the public library and take books from there. Every two weeks, I try to read at least two books. That keeps my mind sharp.” I could see he was on a mission. I also learned something important from our 18-month-old grandson. Several weeks after getting a book about cars, trucks and various animals, he wanted me to show him new books and new toys, not the old ones. It’s fascinating to see how curiosity and desire to learn drives a child’s development. Humans are wired to learn, adapt and grow. That is essential for our survival and progress. The same could be said for retirement. Focusing on curiosity and learning can make for a happier retirement. There are many retirees who seem to thrive on learning new things and taking up new hobbies.…
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