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Pricing the Impossible

AN UNUSUAL STORY hit the news this week. GameStop, the struggling video game retailer, announced a bid to buy eBay. The offer was unexpected, but what surprised investors more was the economics of the proposed deal. eBay is many times larger than GameStop, making it difficult to understand how GameStop would be able to finance the acquisition. GameStop has offered $56 billion for eBay, comprised of cash and stock. For the cash portion, according to its May 3 press release, GameStop would use the $9 billion it has in the bank and borrow the remainder from TD Bank, which has committed up to $20 billion to the deal. But that, in a sense, is the easy part. The stock portion is what left investors with many more questions. That’s because GameStop’s total market value is in the neighborhood of just $11 billion, so it isn’t clear how it would be able to hand over $28 billion of shares. Its share price would somehow have to multiply for this to work. In an interview Monday on CNBC, GameStop’s chairman, Ryan Cohen, offered little clarity. When the reporter asked Cohen to explain his financing plan, the details were sparse. More than once, Cohen just repeated: “It’s half cash, half stock.” When the reporter challenged him to say more, Cohen stared back stone-faced. “I don’t understand your question…it’s half cash, half stock.” This went on for several minutes without much more clarity. Cohen’s parrying was amusing, and it’s an open question where this all ends up. In the meantime, this story is instructive for investors because it helps illustrate some of the stock market’s inner workings. For starters, it can help us understand the market’s seemingly split personality. At first glance, this story seems to highlight the more casino-like side of the stock market. After all, GameStop was the original “meme” stock, rising 30-fold in January 2021 when a YouTube personality promoted it to his followers. GameStop is now using its cult status as currency to support a deal that, according to conventional analysis, doesn’t add up. That said, it isn’t entirely irrational. Putting aside the financing, there is precedent for an online-only business merging with a traditional retailer. Amazon purchased Whole Foods, a grocer, in order to gain a retail footprint, and GameStop envisions something similar, where eBay customers could drop off goods at a physical location rather than hauling them to the post office. To be sure, eBay isn’t Amazon, and GameStop isn’t Whole Foods, but there is some logic to Cohen’s argument. How can we assess investors’ opinion of this deal? A pillar of Cohen’s pitch to investors is that he can make eBay much more profitable, such that it will essentially pay for itself. In an interview on Wednesday, he argued that under new management, eBay could operate much more efficiently. “There's 11,500 employees,” he said. “It doesn't make sense. I could run that business from my house. It doesn't need 11,500 employees.” The implication: Right now, it might not look like the math works for this deal, but if GameStop proceeds with the acquisition, its shares deserve to rise very considerably. Even if GameStop has to issue many new shares, in other words, each share would become much more valuable because of the addition of a newly more profitable eBay. Those additional profits, in Cohen’s view, would offset the dilution caused by the issuance of new shares. That’s the argument GameStop is making. What does Wall Street think? It turns out this question has a straightforward answer. GameStop has offered $125 per share of eBay. If investors were confident in this deal, then eBay’s shares would now be trading right around $125. That’s according to the principle of arbitrage, which says that there shouldn’t be a way to purchase a dollar for any less than a dollar. In other words, if eBay shareholders really stand to receive $125 a share, then it would be illogical for the shares to trade much below $125. But today, eBay shares are trading far below that, falling to as low as $105 on Wednesday. That tells us that investors have little confidence in the deal, most likely because of the difficult-to-explain financing. As Benjamin Graham famously wrote, in the short run, the stock market is a voting machine—a popularity contest—but in the long run, it’s a weighing machine. It’s rational. And though corners of the market often devolve into irrational and speculative excesses, that’s not always the case. More often than not, in my view, the market is better behaved than it’s commonly perceived to be, and I think that’s what we’re seeing here. eBay’s share price today tells us that investors are keeping their feet on the ground. In 1901, J.P. Morgan coordinated the acquisition of Carnegie Steel in a deal that, in its time, was the most audacious ever undertaken. Through massive leverage, it created the first company in the United States worth more than $1 billion. At the time, it was astounding. This tells us that unusual and unlikely things can happen. On the other hand, in 2001, the highly-leveraged merger of AOL and Time Warner was a disaster almost from the start.  Which way will the GameStop-eBay deal go? Right now, it’s anyone’s guess. And as with most things involving great amounts of financial engineering, my recommendation is to steer clear. But this case is instructive because it illustrates many of the principles that drive the market from day to day.   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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Long Term Care

"I haven’t signed up yet, but am seriously considering it. Will attend an information session soon and ask a lot of questions, and I really want to talk to someone who actually accesses benefits in-home. Assuming I get good answers, I’m fairly confident we will sign up. the peace of mind is the clincher."
- Joe D'Alessandro
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Slow on the Draw

RETIREMENT IS LIFE’S most expensive purchase. During our working years, we deprive our present selves of immediate pleasure by refusing to spend money for nicer cars, a bigger house or a vacation to boast about. Instead, we squirrel away those saved dollars with an eye toward keeping the future us fed, clothed and living indoors.  At age 64, after decades of choosing to save and invest a large chunk of each paycheck, rather than spend it, I’ve bought a choice: Fully retire to fully embrace life after work, or carry on in a career that still adds purpose to my life. I’ve chosen to stay, but I’ve whittled down my work hours too far to handle all of my family’s spending needs. Thus, I’m faced with reaching into savings for the first time. More about that later. But first, where is our money, and why? Taking advantage. The bulk of our retirement savings is invested in tax-advantaged accounts. Until we reached our mid-30s, neither my wife nor I had invested a dime in the stock market. Since that time, however, we’ve stuffed dollars from every paycheck into our workplace savings accounts. Initially, these contributions went into traditional accounts, but we switched to the Roth option when it became available. We also topped-off Roth IRAs every year, and stashed a smaller amount in a taxable brokerage account. A little less than half of our total investments reside in future-tax-free Roth accounts. Most of the balance is tax-deferred, traditional money, which is subject to ordinary income tax rates the year it’s withdrawn. The distinction between how these two types of accounts are taxed influences where we position assets between those accounts. Accordingly, we’ve looked at two scenarios that may raise our future tax rates: One begins in a little more than a decade, when required minimum distributions (RMDs) from my traditional retirement accounts begin at age 75, followed by my wife’s RMDs a few years later, plus my Social Security, begun at age 70. The other is triggered when the first of us dies and the surviving spouse moves into the single filer tax bracket.  Because we still owe ordinary income tax on the savings in our traditional accounts, we’re making Roth conversions and taking the tax hit now, at a known rate. We’re also seeking to curb the growth of our traditional accounts by keeping all our bonds there. By contrast, our Roth accounts, on which we should never owe future tax, are invested 100% in the stocks we expect to grow over time. Picking winners. In the beginning, my wife and I entertained thoughts of alternatives to stocks, such as real estate. Soon, however, we decided that maximizing market participation was our wisest wealth-building tactic. As our knowledge of finance grew, we further refined our focus by choosing broad-based, low-cost index funds over other options, for good reason: They out-perform actively-managed funds.. I don’t doubt the intelligence of active fund managers. On the contrary, I suspect they carry bigger brains than me, and know they command more resources to sniff-out future winning stocks. But they swim in a tank with fish just as big, and it's tough to get a fin up on the competition. The result: Each year, index funds finish strokes ahead of their active cousins. For the same reason, we’ve shied away from individual stocks. Have we lost out? I’d argue we profited. Simple diversity. Moving into retirement, my ideal portfolio is heavily influenced by decades of working closely with older patients in my physical therapy practice. I’ve followed a number of folks as they age from their vibrant, active 60s through the years of physical deterioration. Along the way, I’ve observed the cognitive decline that affects most of us as we age. I don’t count on escaping a similar fate.  Hence, rather than covering every corner of the stock market with a complicated collection of index funds, my wife and I have been shifting toward a two- or three-fund portfolio, to achieve the same result. We aim to hold shares in virtually every public company across the globe, housed in two funds, plus one bond fund. Our choice for U.S. stocks is Vanguard Total Stock Market Index Fund (symbol: VTSAX). For foreign stocks, we like Vanguard Total International Stock Index Fund (VTIAX).  Tending to just two stock funds cuts complexity, especially decisions like when to rebalance and how to go about it. Aside from the biases that affect most of us, there’s that issue of our aging brains, again. Why fret about realigning our investments when just keeping track of medical appointments has become a challenge? To further simplify our lives, at a bit more expense, we could let Vanguard Group, Inc. do all the work with their Vanguard Total World Stock Index Fund (VTWAX).. Picking our peril. Our nest egg is weighted a little heavily toward stocks, which means its sum will rise and fall with the market. That can be unnerving, but it’s the price we'll pay for the extra risk that gives us a shot at outpacing inflation.  Without the long-term growth provided by stocks, our buying power might not keep pace with our expected long lives. That strategy is fine when the market is riding high, but where do we go for spending money when stocks are in a slump? Selling depressed stocks in a pinch to raise cash is hazardous to our wealth. For that reason, the balance of our savings is in mostly short-term government bonds and cash, enough of a cushion to cover several years of expenses until the market regains its footing. To be sure, that money is mostly idle, but it's ready when needed. When I finally clock my last-day-forever in the clinic, we might buy an income annuity to replace earned income with insured money to add to my wife’s modest Social Security check, which she expects to start collecting in a little over a year.  This combination of regular monthly paychecks would provide a floor of income to keep the household going, and bolster our courage to boot, when the market hits the skids. Drawing it down. Meanwhile, we’ve yet to settle on a plan to siphon off savings to pay the bills not covered by my part-time income. At the moment, there’s little pressure to find the perfect formula. For starters, we’re not calculating the highest withdrawal rate our investments will bear to bankroll a spending spree. Also, part of our retirement preparation included holding steady to a frugal lifestyle and eliminating debt. Our low expenses give us breathing space to decide how to replenish our cash account. Why the dithering? It turns out nailing down a withdrawal plan is my toughest financial decision to date. But it’s not the math that has me stymied. Rather, it’s the emotion. Yes, I believe the research, and I’ve run analyses that assure me our money will probably outlive us.  Still, thinking of pushing start makes me queasy, so we’re sliding into the task. Instead of a rate, we’ve chosen the dollar amount that sustains our current lifestyle over the coming year. It falls short of the figure we expect to reach once we’ve limbered up our spending legs, but one allows us to work up to a rate that doesn’t outpace my level of comfort. Ed is a semi-retired physical therapist who lives and works in a small community near Atlanta. When he's not spending time with his church, family or friends, you may find him tending his garden and wondering if he will ever fully retire. Check out Ed’s earlier articles.  
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Dickie and his magic beans

"You can usually get 2lbs of Starbucks at Costco for about $18. And buy yourself a grinder and grind what you use daily; night and day difference in smell and taste."
- Mike A
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Sundry Memories of Mom

"“But I tend to them and pay bills as if she were looking over my shoulder, keeping things in order as she always did for the family.” What a sweet thought, Ed. I love how it depicts you reciprocating the gift of financial order your mom gave you."
- D.J.
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Retirement Toys

"Jeff, thanks for the link. That looks like an awesome way to spend some cash!"
- Mark Crothers
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Jonathan’s Advice for 2026 Graduates

"On the subject of 'expect to change jobs and careers', I would add, "Life is not a straight line. Expect lots zigs and zags in all areas of your life, not merely your career. It will not go as planned.""
- John Katz
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Saving for Grandchildren

OUR FIRST GRANDCHILD recently arrived, which naturally has us thinking about the smartest ways to build a strong financial foundation for her future. In 2019, I wrote Take a Break, which outlined saving strategies on behalf of children. Since then, the landscape has changed with the introduction of Trump accounts and Roth-conversion pathways for 529 accounts.  Families have four tax-advantaged savings approaches on behalf of young children plus the Roth IRA option once the child has earned income – 529 education savings account, a Uniform Gift to Minor (UGM) custodial account, a Coverdell account, and the new Trump account. Each option offers a different mix of tax benefits, contribution requirements and withdrawal rules. 529 Accounts Pros
  • Tax-free growth when used for qualified education expenses
  • High gift-tax contribution limits: $19K per contributor per year (indexed)
  • New ability to convert up to $35K into a Roth IRA for the beneficiary
Cons
  • Relatively complex with penalties and taxes on non-qualified withdrawals
  • Limited, state-approved investment options
  • Risk of underutilization if the child does not pursue qualifying education
Caveats
  • Technology and AI could significantly reduce education’s cost structure in the future
  • Roth conversions are capped at $35K lifetime
  • The 529 must be open 15 years, and contributions must age 5 years before conversion
  • Conversions require the beneficiary to have earned income (i.e. they could Roth anyway)
  • Annual Roth contribution limits still apply (e.g., $7.5K in 2026), so completing the full $35K conversion would take five years
UGM Custodial Accounts Pros
  • Brokerage account where up to $2.7K of unearned income can be tax-free each year
  • High gift-tax contribution limits: $19K per contributor per year (indexed)
  • Broad investment flexibility — stocks, bonds, funds, etc.
  • Few restrictions on how funds may be used for the child’s benefit
  • Potential for low taxes on capital gains, but subject to marginal “kiddie tax” at parent’s rates until tax-independency or age 24 
Cons
  • Higher income or capital gains could trigger the kiddie tax at the parents’ marginal rate
  • Assets count as the child’s for financial-aid purposes
Caveats
  • Custodians have some ability to spend down the account for legitimate child expenses if the child is a wild-child in the later teen years
Coverdell Accounts Pros
  • Tax-free growth for qualified education expenses
  • More flexible investment choices than most 529 plans
Cons
  • Low contribution limit: $2K per year plus income limits restrict who can contribute
  • Essentially irrelevant today given the expanded options within 529 plans
Trump Accounts Pros
  • $1K government seed deposit for children born 2025–2028
  • Contribution limit of $5K per year in 2026, indexed to inflation
  • Parent employers may contribute up to $2.5K per year (also indexed)
  • Tax-deferred growth with Roth-conversion opportunities beginning at age 18
  • No earned-income requirement for Roth conversions 
  • Roth conversions are ideal in low-income years starting after age 18 once the child has transitioned to tax-independency of parents or at age 24 when “kiddie taxation” ends. Early tax independence could even be a combined Roth plus student financial-aid strategy
  • Potential to convert large account values over several years at relatively low tax rates (potentially marginal 10-12% tax-rates, but averaging less due to the standard deduction).
Cons
  • Investment options limited to low-cost indexed stock funds (not necessarily a drawback)
  • Penalty-free withdrawals must wait until age 59½, but the accounts could be advantageous even including penalties
  • Limited custodian control and intervention possibilities if the teen is a wild-child
Caveats
  • If Roth conversions are not undertaken during the child’s low-income years, a UGMA invested to capture long-term capital gains tax-rates may outperform a Trump Account taxed at ordinary income tax-rates
  • Watch this space as future adjustments or eligibility changes are possible
  In effect, the 529 is a two-decade college savings program having some complexity and withdrawal limitations; the UGM is a reasonably flexible, 18-30-year college or house downpayment savings program; and the Trump account is a somewhat inflexible, sixty-year retirement accelerator   Resulting Playbook Here is our family’s intended playbook for tax-advantaged accounts in the grandchild's name:
  • Parents’ retirement account fundings remain their top priority - 401K’s at a minimum up to the match, HSAs with their triple tax advantages, and Roths as long as eligible within income limits.
  • A Trump account has already been initiated to secure the free $1K government seed contribution – grows to potentially $2.6K at age 18 after penalties and taxes.
  • Limited 529 funding has also been initiated to start the 15-year clock for potential later Roth conversions. 
  • The family’s next priority is to fund the Trump account which starts at $5K later this year. Maximizing the Roth conversion opportunity will require ~$116K of contributions (at 3% inflation) over 18 years which we grandparents intend to help fund. I estimate the Roth converted Trump account could grow to ~$2 million of tax-free money at age 60 (6% growth) assuming early-age Roth conversions, and the Wall Street Journal projects as much as $3 million (link likely paywalled).
  • The subsequent priorities are to start UGM taxable account and 529 account contributions in parallel to perhaps initial levels of about $35K each. This may take our family some years depending upon available resources for contributions.
For the UGM account, a balance of $35K should capture a sizeable chunk of the annual $2.7K tax-free income limit by investing in high-yield income alternatives. For the 529 account, $35K aligns with the Roth conversion limit. On a personal note, we had extremely positive UGM outcomes with our children. We saved taxes for two decades, and each child used the ~$60K balance as down payments on their first house shortly after college. Due to the 529’s withdrawal rigidities and potential technology impacts, we are unlikely to fund the 529 to the max. 
  • We will skip Coverdells as the alternatives offer ample savings opportunity in the child’s name ($200K+). 
  • Depending upon spare resources available for gifting, we can always reassess future contributions. 
That’s our plan, and we’re sticking to it…. until something changes.    John Yeigh is an author, coach and youth sports advocate. His book “Win the Youth Sports Game” was published in 2021. John retired in 2017 from the oil industry, where he negotiated financial details for multi-billion-dollar international projects. Check out his earlier articles.  
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The reality of Social Security and Medicare- My real life experience.

"Exactly. And yet many people don’t feel that way and likely would be opposed to tax increase to sustain it. I am convinced Americans simply do not make the connection between taxes and what they provide in a society of 340 million or that millions of us need more assistance than others."
- R Quinn
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First Place

"I’ve been blessed to see a lot of the world in my travels, but there is something about going back to the Smoky Mountains in the fall that always feels different. The air is cooler, the colors are deeper, and life seems to slow down just enough to remind me what peace feels like. It’s not just the scenery, although the mountains are hard to beat. It’s the feeling of returning to a place that settles my mind, quiets the noise, and reminds me of the simple things I love most. No matter where I’ve been, the Smokies in the fall always feel like coming home."
- Jeff Peck
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A Life You Build

"Grant thank you for sharing your story. 😊"
- Jeff Peck
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Pricing the Impossible

AN UNUSUAL STORY hit the news this week. GameStop, the struggling video game retailer, announced a bid to buy eBay. The offer was unexpected, but what surprised investors more was the economics of the proposed deal. eBay is many times larger than GameStop, making it difficult to understand how GameStop would be able to finance the acquisition. GameStop has offered $56 billion for eBay, comprised of cash and stock. For the cash portion, according to its May 3 press release, GameStop would use the $9 billion it has in the bank and borrow the remainder from TD Bank, which has committed up to $20 billion to the deal. But that, in a sense, is the easy part. The stock portion is what left investors with many more questions. That’s because GameStop’s total market value is in the neighborhood of just $11 billion, so it isn’t clear how it would be able to hand over $28 billion of shares. Its share price would somehow have to multiply for this to work. In an interview Monday on CNBC, GameStop’s chairman, Ryan Cohen, offered little clarity. When the reporter asked Cohen to explain his financing plan, the details were sparse. More than once, Cohen just repeated: “It’s half cash, half stock.” When the reporter challenged him to say more, Cohen stared back stone-faced. “I don’t understand your question…it’s half cash, half stock.” This went on for several minutes without much more clarity. Cohen’s parrying was amusing, and it’s an open question where this all ends up. In the meantime, this story is instructive for investors because it helps illustrate some of the stock market’s inner workings. For starters, it can help us understand the market’s seemingly split personality. At first glance, this story seems to highlight the more casino-like side of the stock market. After all, GameStop was the original “meme” stock, rising 30-fold in January 2021 when a YouTube personality promoted it to his followers. GameStop is now using its cult status as currency to support a deal that, according to conventional analysis, doesn’t add up. That said, it isn’t entirely irrational. Putting aside the financing, there is precedent for an online-only business merging with a traditional retailer. Amazon purchased Whole Foods, a grocer, in order to gain a retail footprint, and GameStop envisions something similar, where eBay customers could drop off goods at a physical location rather than hauling them to the post office. To be sure, eBay isn’t Amazon, and GameStop isn’t Whole Foods, but there is some logic to Cohen’s argument. How can we assess investors’ opinion of this deal? A pillar of Cohen’s pitch to investors is that he can make eBay much more profitable, such that it will essentially pay for itself. In an interview on Wednesday, he argued that under new management, eBay could operate much more efficiently. “There's 11,500 employees,” he said. “It doesn't make sense. I could run that business from my house. It doesn't need 11,500 employees.” The implication: Right now, it might not look like the math works for this deal, but if GameStop proceeds with the acquisition, its shares deserve to rise very considerably. Even if GameStop has to issue many new shares, in other words, each share would become much more valuable because of the addition of a newly more profitable eBay. Those additional profits, in Cohen’s view, would offset the dilution caused by the issuance of new shares. That’s the argument GameStop is making. What does Wall Street think? It turns out this question has a straightforward answer. GameStop has offered $125 per share of eBay. If investors were confident in this deal, then eBay’s shares would now be trading right around $125. That’s according to the principle of arbitrage, which says that there shouldn’t be a way to purchase a dollar for any less than a dollar. In other words, if eBay shareholders really stand to receive $125 a share, then it would be illogical for the shares to trade much below $125. But today, eBay shares are trading far below that, falling to as low as $105 on Wednesday. That tells us that investors have little confidence in the deal, most likely because of the difficult-to-explain financing. As Benjamin Graham famously wrote, in the short run, the stock market is a voting machine—a popularity contest—but in the long run, it’s a weighing machine. It’s rational. And though corners of the market often devolve into irrational and speculative excesses, that’s not always the case. More often than not, in my view, the market is better behaved than it’s commonly perceived to be, and I think that’s what we’re seeing here. eBay’s share price today tells us that investors are keeping their feet on the ground. In 1901, J.P. Morgan coordinated the acquisition of Carnegie Steel in a deal that, in its time, was the most audacious ever undertaken. Through massive leverage, it created the first company in the United States worth more than $1 billion. At the time, it was astounding. This tells us that unusual and unlikely things can happen. On the other hand, in 2001, the highly-leveraged merger of AOL and Time Warner was a disaster almost from the start.  Which way will the GameStop-eBay deal go? Right now, it’s anyone’s guess. And as with most things involving great amounts of financial engineering, my recommendation is to steer clear. But this case is instructive because it illustrates many of the principles that drive the market from day to day.   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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Long Term Care

"I haven’t signed up yet, but am seriously considering it. Will attend an information session soon and ask a lot of questions, and I really want to talk to someone who actually accesses benefits in-home. Assuming I get good answers, I’m fairly confident we will sign up. the peace of mind is the clincher."
- Joe D'Alessandro
Read more »

Slow on the Draw

RETIREMENT IS LIFE’S most expensive purchase. During our working years, we deprive our present selves of immediate pleasure by refusing to spend money for nicer cars, a bigger house or a vacation to boast about. Instead, we squirrel away those saved dollars with an eye toward keeping the future us fed, clothed and living indoors.  At age 64, after decades of choosing to save and invest a large chunk of each paycheck, rather than spend it, I’ve bought a choice: Fully retire to fully embrace life after work, or carry on in a career that still adds purpose to my life. I’ve chosen to stay, but I’ve whittled down my work hours too far to handle all of my family’s spending needs. Thus, I’m faced with reaching into savings for the first time. More about that later. But first, where is our money, and why? Taking advantage. The bulk of our retirement savings is invested in tax-advantaged accounts. Until we reached our mid-30s, neither my wife nor I had invested a dime in the stock market. Since that time, however, we’ve stuffed dollars from every paycheck into our workplace savings accounts. Initially, these contributions went into traditional accounts, but we switched to the Roth option when it became available. We also topped-off Roth IRAs every year, and stashed a smaller amount in a taxable brokerage account. A little less than half of our total investments reside in future-tax-free Roth accounts. Most of the balance is tax-deferred, traditional money, which is subject to ordinary income tax rates the year it’s withdrawn. The distinction between how these two types of accounts are taxed influences where we position assets between those accounts. Accordingly, we’ve looked at two scenarios that may raise our future tax rates: One begins in a little more than a decade, when required minimum distributions (RMDs) from my traditional retirement accounts begin at age 75, followed by my wife’s RMDs a few years later, plus my Social Security, begun at age 70. The other is triggered when the first of us dies and the surviving spouse moves into the single filer tax bracket.  Because we still owe ordinary income tax on the savings in our traditional accounts, we’re making Roth conversions and taking the tax hit now, at a known rate. We’re also seeking to curb the growth of our traditional accounts by keeping all our bonds there. By contrast, our Roth accounts, on which we should never owe future tax, are invested 100% in the stocks we expect to grow over time. Picking winners. In the beginning, my wife and I entertained thoughts of alternatives to stocks, such as real estate. Soon, however, we decided that maximizing market participation was our wisest wealth-building tactic. As our knowledge of finance grew, we further refined our focus by choosing broad-based, low-cost index funds over other options, for good reason: They out-perform actively-managed funds.. I don’t doubt the intelligence of active fund managers. On the contrary, I suspect they carry bigger brains than me, and know they command more resources to sniff-out future winning stocks. But they swim in a tank with fish just as big, and it's tough to get a fin up on the competition. The result: Each year, index funds finish strokes ahead of their active cousins. For the same reason, we’ve shied away from individual stocks. Have we lost out? I’d argue we profited. Simple diversity. Moving into retirement, my ideal portfolio is heavily influenced by decades of working closely with older patients in my physical therapy practice. I’ve followed a number of folks as they age from their vibrant, active 60s through the years of physical deterioration. Along the way, I’ve observed the cognitive decline that affects most of us as we age. I don’t count on escaping a similar fate.  Hence, rather than covering every corner of the stock market with a complicated collection of index funds, my wife and I have been shifting toward a two- or three-fund portfolio, to achieve the same result. We aim to hold shares in virtually every public company across the globe, housed in two funds, plus one bond fund. Our choice for U.S. stocks is Vanguard Total Stock Market Index Fund (symbol: VTSAX). For foreign stocks, we like Vanguard Total International Stock Index Fund (VTIAX).  Tending to just two stock funds cuts complexity, especially decisions like when to rebalance and how to go about it. Aside from the biases that affect most of us, there’s that issue of our aging brains, again. Why fret about realigning our investments when just keeping track of medical appointments has become a challenge? To further simplify our lives, at a bit more expense, we could let Vanguard Group, Inc. do all the work with their Vanguard Total World Stock Index Fund (VTWAX).. Picking our peril. Our nest egg is weighted a little heavily toward stocks, which means its sum will rise and fall with the market. That can be unnerving, but it’s the price we'll pay for the extra risk that gives us a shot at outpacing inflation.  Without the long-term growth provided by stocks, our buying power might not keep pace with our expected long lives. That strategy is fine when the market is riding high, but where do we go for spending money when stocks are in a slump? Selling depressed stocks in a pinch to raise cash is hazardous to our wealth. For that reason, the balance of our savings is in mostly short-term government bonds and cash, enough of a cushion to cover several years of expenses until the market regains its footing. To be sure, that money is mostly idle, but it's ready when needed. When I finally clock my last-day-forever in the clinic, we might buy an income annuity to replace earned income with insured money to add to my wife’s modest Social Security check, which she expects to start collecting in a little over a year.  This combination of regular monthly paychecks would provide a floor of income to keep the household going, and bolster our courage to boot, when the market hits the skids. Drawing it down. Meanwhile, we’ve yet to settle on a plan to siphon off savings to pay the bills not covered by my part-time income. At the moment, there’s little pressure to find the perfect formula. For starters, we’re not calculating the highest withdrawal rate our investments will bear to bankroll a spending spree. Also, part of our retirement preparation included holding steady to a frugal lifestyle and eliminating debt. Our low expenses give us breathing space to decide how to replenish our cash account. Why the dithering? It turns out nailing down a withdrawal plan is my toughest financial decision to date. But it’s not the math that has me stymied. Rather, it’s the emotion. Yes, I believe the research, and I’ve run analyses that assure me our money will probably outlive us.  Still, thinking of pushing start makes me queasy, so we’re sliding into the task. Instead of a rate, we’ve chosen the dollar amount that sustains our current lifestyle over the coming year. It falls short of the figure we expect to reach once we’ve limbered up our spending legs, but one allows us to work up to a rate that doesn’t outpace my level of comfort. Ed is a semi-retired physical therapist who lives and works in a small community near Atlanta. When he's not spending time with his church, family or friends, you may find him tending his garden and wondering if he will ever fully retire. Check out Ed’s earlier articles.  
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Dickie and his magic beans

"You can usually get 2lbs of Starbucks at Costco for about $18. And buy yourself a grinder and grind what you use daily; night and day difference in smell and taste."
- Mike A
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Sundry Memories of Mom

"“But I tend to them and pay bills as if she were looking over my shoulder, keeping things in order as she always did for the family.” What a sweet thought, Ed. I love how it depicts you reciprocating the gift of financial order your mom gave you."
- D.J.
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Retirement Toys

"Jeff, thanks for the link. That looks like an awesome way to spend some cash!"
- Mark Crothers
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Jonathan’s Advice for 2026 Graduates

"On the subject of 'expect to change jobs and careers', I would add, "Life is not a straight line. Expect lots zigs and zags in all areas of your life, not merely your career. It will not go as planned.""
- John Katz
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Saving for Grandchildren

OUR FIRST GRANDCHILD recently arrived, which naturally has us thinking about the smartest ways to build a strong financial foundation for her future. In 2019, I wrote Take a Break, which outlined saving strategies on behalf of children. Since then, the landscape has changed with the introduction of Trump accounts and Roth-conversion pathways for 529 accounts.  Families have four tax-advantaged savings approaches on behalf of young children plus the Roth IRA option once the child has earned income – 529 education savings account, a Uniform Gift to Minor (UGM) custodial account, a Coverdell account, and the new Trump account. Each option offers a different mix of tax benefits, contribution requirements and withdrawal rules. 529 Accounts Pros
  • Tax-free growth when used for qualified education expenses
  • High gift-tax contribution limits: $19K per contributor per year (indexed)
  • New ability to convert up to $35K into a Roth IRA for the beneficiary
Cons
  • Relatively complex with penalties and taxes on non-qualified withdrawals
  • Limited, state-approved investment options
  • Risk of underutilization if the child does not pursue qualifying education
Caveats
  • Technology and AI could significantly reduce education’s cost structure in the future
  • Roth conversions are capped at $35K lifetime
  • The 529 must be open 15 years, and contributions must age 5 years before conversion
  • Conversions require the beneficiary to have earned income (i.e. they could Roth anyway)
  • Annual Roth contribution limits still apply (e.g., $7.5K in 2026), so completing the full $35K conversion would take five years
UGM Custodial Accounts Pros
  • Brokerage account where up to $2.7K of unearned income can be tax-free each year
  • High gift-tax contribution limits: $19K per contributor per year (indexed)
  • Broad investment flexibility — stocks, bonds, funds, etc.
  • Few restrictions on how funds may be used for the child’s benefit
  • Potential for low taxes on capital gains, but subject to marginal “kiddie tax” at parent’s rates until tax-independency or age 24 
Cons
  • Higher income or capital gains could trigger the kiddie tax at the parents’ marginal rate
  • Assets count as the child’s for financial-aid purposes
Caveats
  • Custodians have some ability to spend down the account for legitimate child expenses if the child is a wild-child in the later teen years
Coverdell Accounts Pros
  • Tax-free growth for qualified education expenses
  • More flexible investment choices than most 529 plans
Cons
  • Low contribution limit: $2K per year plus income limits restrict who can contribute
  • Essentially irrelevant today given the expanded options within 529 plans
Trump Accounts Pros
  • $1K government seed deposit for children born 2025–2028
  • Contribution limit of $5K per year in 2026, indexed to inflation
  • Parent employers may contribute up to $2.5K per year (also indexed)
  • Tax-deferred growth with Roth-conversion opportunities beginning at age 18
  • No earned-income requirement for Roth conversions 
  • Roth conversions are ideal in low-income years starting after age 18 once the child has transitioned to tax-independency of parents or at age 24 when “kiddie taxation” ends. Early tax independence could even be a combined Roth plus student financial-aid strategy
  • Potential to convert large account values over several years at relatively low tax rates (potentially marginal 10-12% tax-rates, but averaging less due to the standard deduction).
Cons
  • Investment options limited to low-cost indexed stock funds (not necessarily a drawback)
  • Penalty-free withdrawals must wait until age 59½, but the accounts could be advantageous even including penalties
  • Limited custodian control and intervention possibilities if the teen is a wild-child
Caveats
  • If Roth conversions are not undertaken during the child’s low-income years, a UGMA invested to capture long-term capital gains tax-rates may outperform a Trump Account taxed at ordinary income tax-rates
  • Watch this space as future adjustments or eligibility changes are possible
  In effect, the 529 is a two-decade college savings program having some complexity and withdrawal limitations; the UGM is a reasonably flexible, 18-30-year college or house downpayment savings program; and the Trump account is a somewhat inflexible, sixty-year retirement accelerator   Resulting Playbook Here is our family’s intended playbook for tax-advantaged accounts in the grandchild's name:
  • Parents’ retirement account fundings remain their top priority - 401K’s at a minimum up to the match, HSAs with their triple tax advantages, and Roths as long as eligible within income limits.
  • A Trump account has already been initiated to secure the free $1K government seed contribution – grows to potentially $2.6K at age 18 after penalties and taxes.
  • Limited 529 funding has also been initiated to start the 15-year clock for potential later Roth conversions. 
  • The family’s next priority is to fund the Trump account which starts at $5K later this year. Maximizing the Roth conversion opportunity will require ~$116K of contributions (at 3% inflation) over 18 years which we grandparents intend to help fund. I estimate the Roth converted Trump account could grow to ~$2 million of tax-free money at age 60 (6% growth) assuming early-age Roth conversions, and the Wall Street Journal projects as much as $3 million (link likely paywalled).
  • The subsequent priorities are to start UGM taxable account and 529 account contributions in parallel to perhaps initial levels of about $35K each. This may take our family some years depending upon available resources for contributions.
For the UGM account, a balance of $35K should capture a sizeable chunk of the annual $2.7K tax-free income limit by investing in high-yield income alternatives. For the 529 account, $35K aligns with the Roth conversion limit. On a personal note, we had extremely positive UGM outcomes with our children. We saved taxes for two decades, and each child used the ~$60K balance as down payments on their first house shortly after college. Due to the 529’s withdrawal rigidities and potential technology impacts, we are unlikely to fund the 529 to the max. 
  • We will skip Coverdells as the alternatives offer ample savings opportunity in the child’s name ($200K+). 
  • Depending upon spare resources available for gifting, we can always reassess future contributions. 
That’s our plan, and we’re sticking to it…. until something changes.    John Yeigh is an author, coach and youth sports advocate. His book “Win the Youth Sports Game” was published in 2021. John retired in 2017 from the oil industry, where he negotiated financial details for multi-billion-dollar international projects. Check out his earlier articles.  
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Manifesto

NO. 54: WE NEED to be great savers to amass enough for retirement. But we shouldn’t get so good at saving money that, once we’re financially successful, we can’t bring ourselves to spend.

act

LOOK FOR INSURANCE gaps. Many folks agonize over whether their policies are too large or small. A bigger danger: not having coverage at all, because our life has changed but our insurance hasn’t kept up. Just had kids? It’s time for life insurance. Grown wealthy? Consider umbrella insurance. Working for yourself? You may need disability coverage.

humans

NO. 50: WE LIKE owning assets we can see and touch—but that doesn’t mean they’re good investments. Go back a few generations, and folks put great value on art, jewelry, fine furniture and land. But most tangible assets haven’t been good investments in recent decades. Homes are the exception, but they’re also a big, undiversified risk that come with high costs.

Truths

NO. 37: IF INFORMATION is publicly available, it’s hard to make money from it. As soon as news breaks—whether it’s economic or otherwise—investors trade on the information, so it’s almost instantly reflected in stock and bond prices. True, you could get an edge by better analyzing that public information than other investors. But how likely is that?

Portfolio builder

Manifesto

NO. 54: WE NEED to be great savers to amass enough for retirement. But we shouldn’t get so good at saving money that, once we’re financially successful, we can’t bring ourselves to spend.

Spotlight: In Retirement

Status of the Social Security and Medicare Programs

Released:
A SUMMARY OF THE 2025 ANNUAL REPORTS
Social Security and Medicare Boards of Trustees
“Based on our best estimates, this year’s reports show that……
The Old-Age and Survivors Insurance (OASI) Trust Fund will be able to pay 100 percent of total scheduled benefits until 2033, unchanged from last year’s report. At that time, the fund’s reserves will become depleted and continuing program income will be sufficient to pay 77 percent of total scheduled benefits……”
“As in prior years,

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Dealing with a reduction in Social Security benefits. Is there a backup plan?

A recent post on the Forum raised the issue of dealing with a cut in Social Security benefits – hopefully an unlikely or very temporary event. However, something still worth planning for. 
If the status of SS is not fixed, around 2033 benefits could be reduced by 23-24%. The Committee for a Responsible Federal Budget projects a 24% cut by late 2032 for retirees, equating to an $18,100 annual reduction for a typical dual-earning couple retiring in 2033.

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Are You Going to Get the Social Security Benefits You First Started Paying For?

My wife started her professional career in 1979, and I in 1980.
I previously wrote an article on Humble Dollar where I tried to research the points covered below by Mark Miller who is considered one of the nation’s leading experts on retirement and aging. In a recent article on Morningstar’s website he warns of the effects of the bill recently signed into law. He writes that if congress does nothing to shore up Social Security the trust fund is projected to be emptied by 2032,

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Not Qualified to Carry This Anymore

I’m turning into my mother more and more every day. Back when I was taking care of her, she’d hand me her credit card whenever we went shopping. She’d say, “I’m not qualified to carry this anymore.” She was afraid she’d lose it.
Now I catch myself doing the same thing. When Rachel and I go out, I sometimes give her my wallet to toss in her purse. I’m scared I’ll lose it. Since I’ve retired,

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Using AI to create a robust investment plan

I’ve been dabbling in AI.  Began using precursor “Expert Systems” about 20 years ago, but the new apps are more generalized and interesting. I’m aware of the limitations and anyone who wants to use something like Gemini or ChatGPT should also be aware. They can (and do) generate false information with apparent confidence. This can deceive users. Such disinformation has been given the name “hallucination” or “confabulation” by AI experts. Interesting names for inaccuracy.
However, using precise prompts seems to improve the response.

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My First Retirement Report Card

I’m three months retired today, my goodness the time has flown by!
When I managed my own business I always collated business figures into a quarterly report for better performance monitoring and to help give me a feel for how things were going. I guess the urge to do so is still ingrained within me, and I thought I’d do a similar but more holistic exercise with a first quarter retirement report for the quarter ending 07/31/25.

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Spotlight: Berard

Truth is Often Stranger Than Fiction

I just received my annual water bill, a tiny 158 dollars. It informed me that I will pay .00375 cents per gallon. When bottled water is even 5 a pint or 40 per gallon, that is roughly 10,000 times higher. It is often at 30,000 times higher.as many venues charge 15 a pint. Even at a buck a pint  , that is still thousands of times more , for exactly the same stuff that falls, every time it rains. I do have a water filter through the fridge, but, the water straight from the faucet is fine. I could see if bottled water was maybe ten cents a pint, for the packaging and the like, but….! For the 40 percent of the population that is good at math, please, check my figures  to ensure accuracy. I am a part of the 80 percent that are not good in math. Please, before we talk stocks and bonds, etc., cease getting ripped off buying water.  And I will not talk about wasting money on green hair, body piercings,  tattoos and the financially challenged buying expensive German brand SUVS , financing them for eight years, etc.
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Why, Oh , Why ?

Please, why would anybody buy any actively traded fund, especially in the large market cap category and especially in conventional accounts? As a whole, every investor , large and small, must collectively earn less than the market's return.  For every buyer there is a seller, of course, and once bid-ask spreads, fees, etc., are factored in, there has to be a slight loss. Also,  the active funds, due to the frequent trading , often have returns that are often  30, 40 or 50 percent lower, after taxes and sale of shares.   In  traditional, non tax sheltered venues, the difference between gross and net,  is tremendous.  Even in tax sheltered accounts, you are still paying much higher annual fees. I don't know if it still exists, but a few years ago, there was an S and P 500 fund that charged a 3 % load, and an annual fee of 1.2 percent. Why are there still funds that charge sales loads, period? If no one bought them, would they not go extinct? 2) Why do so many people buy or lease very expensive vehicles, take out, in many cases, 8 year loans, and then complain about the "high" price of the premium fuel it requires?    Why don't they care about the hundreds of bucks in monthly payments, the high insurance costs, the high repair and service costs. And the depreciation of the very fancy, fussy German brands , and Jaguar, Land Rover,etc., is much worse than the much more reliable Japanese car makers, just compare the resale value of a used MB, Audi to virtually any Toyota product. I know why the politicians mention gas prices constantly, they know that is an issue with so many Americans, and they are trying to relate. A lot of consumers  are angry that…
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Easier Is Often More Lucrative And Cheaper, And Not Only In Financial Topics

As autumn is upon us, and I observe my nice neighbors toil for hours on end, they are raking, blowing, vacuuming, etc., the millions of once beautiful leaves, alas, they are no longer attractive, just an enormous annoyance for the majority. I submit, as a former leaf raker, the following. When investing, simpler is generally the correct option for millions of people not named "Buffett", to wit, a 3 or even 2 fund portfolio would outperform a vast majority of more complicated accounts, a total world stock market fund, a short term treasury fund for liquidity, and so forth. I am convinced, and the data appears to confirm , that simpler when maintaining the grounds is also the rock solid  path to victory, the low cost "index funds" of the landscaping world, if you will. I offer the following, clearing the leaves should be no more labor intensive than simply mowing the lawn. All we need to do is run the leaves over with the mower, if a mulching blade is on the machine, one pass does it. A conventional blade may require a second pass, but, voila', the leaves are now shredded , and will soon compost into rich loam. Mowing the grass and bagging the clippings and dumping them is not the right way , either. Remove the bag, and let the clippings rot into loam. I think of the clippings as the dividends of the grass, let them compound , and over the years, they will add a lot of nutrients and growth. Having stock dividends and bond interest reinvested contributes a great deal to growth, of course, and is far better than spending the income on blue hair, tattoos and 20 dollar beer at a pro game. Not too long ago, it could be a bit…
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Credit Card Debt.

American credit card debt just broke the trillion dollar level.  Taking on  debt, “ bad” debt, credit cards , auto loans and similar, is a like attending a raucous party ,  taking in too much alcohol , etc. The aftermath , paying off high interest loans, is like the worst hangover, ever. It can take decades to recover from it. Often,  too much alcohol can kill you, quickly or long term, * alas , debt can kill you, quickly, ** or long term , *financially. Foreclosure, and often bankruptcy are far too common issues. * John Bonham , the drummer for Led Zeppelin, died after having 48 vodka drinks in 24 hours. ** A good friend ended up in the emergency room and nearly died after defaulting on a loan from a  , uh, * sub- prime” lender.
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Conflicting News

I am certainly nearer the end of my life than the beginning. and I thought it wise to ask around, talking with everyday people, trying to get a good, accurate analysis of the overall economic outlook. Some may find this silly, after all, why  not just heed the advice and wisdom of all of the experts, offering their views on market conditions, the direction of interest rates, both short and long term, etc.  But, nothing ventured, nothing gained. My plumber said he was " bursting at the seams with work", alas, the electrician stated, "I'm shocked how much business is down." My cousin, whom works for a railroad, told me, "We are on track for record profits!" The optometrist was convinced that " He sees a lot of great things, economically", and my audiologist was" hearing a lot of great news." My friend is in mining, sadly, his business is " a little rocky". A cousin works at a marina, thankfully," He saw "smooth sailing" ahead. A pilot buddy was thrilled his business was " really taking off", and the elevator people said business was " very volatile", soaring highs to plunging lows. My arborist was thrilled he was " branching out, more and more." The basement waterproofing company was doing well, even as its work was "drying up". My barber was concerned during Covid, it was a "close shave", but he survived. The restaurant people had "a lot on their plate", but the mortician said his business was "dead". The nutritionist weighed in with her opinion, and the fireworks seller's business was booming. The treadmill people were just "running in place", of course the meteorologist was concerned about turbulence, and the ornithologist was worried about his  nest egg. The lady whom makes honey is," busy as a bee". The…
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Things That Make Me Go, HUH?

Popcorn is a food item that in many cases, is marked up in price by an infinite amount. In many restaurants, pubs, etc., popcorn is available for free, yet, movie theaters sell a box for many dollars. Did you know that theaters make most of their money on food and drink, rather than the tickets? I feel that marking up prices to infinity, may be the reason. 2) I see many large pick up trucks, many with dual wheels, being driven with the tailgate open. That is because the owners think it gets them better mileage, alas, it is not true. Tests have been done showing that it matters not at all, whether the tailgate is up or down, the air tends to stay in the bed of the truck, it doesn't push against the closed tailgate. However, with it open, there is a high risk it could fall off, and it poses a danger of someone hitting it,not only another car, but maybe a bicycle rider, crossing behind you. If you have the dough to buy a very expensive truck, and pay high insurance, and those huge tires, and you probably financed the thing for many years, is it worth even trying to save a few pennies, by a failed strategy? The average price for a new vehicle is around 45 grand. Fancy trucks,with four wheel drive, can easily cost over 100 grand , and when it is financed over many years, that goes up quite a bit.  Another big expense with all wheel and four wheel drive is often , if a single tire is damaged and cannot be fixed, you must buy 4 or 6 new tires, otherwise, you will damage the complicated drive systems.  The cost of many things with a large truck , other than…
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