Missing the Boat
Sanjib Saha | Feb 5, 2022
I’VE BEEN WAITING since late last year for a stock market correction. No, I’m not sitting on a pile of cash and looking to time the market. Instead, I’m simply hoping to trim my tax bill. Last October, I sold the recently vested shares of my company stock and used the proceeds to buy Vanguard Total Stock Market ETF (symbol: VTI). This sell-high-buy-high exchange was meant for diversification, but I also hoped that the market would drop later. I could then harvest tax losses by temporarily replacing the Vanguard fund with a combination of Russell 1000 and Russell 2000 ETFs. Given the prospect of an interest rate hike to counter rising inflation, a market correction was a distinct possibility. The market seemed to move in my favor by November’s end. My Vanguard ETF dropped below my purchase price, but the extent of the unrealized loss wasn’t worth the effort of tax-loss harvesting. I waited for a bigger drop, but a market rally wiped out my unrealized loss. My hopes were renewed during the fourth weekend of January, as I glanced through Barron’s. My Vanguard ETF shares had dropped more than 6% the week before. Another 3% drop would be enough for some meaningful tax-loss harvesting. I planned to keep an eye on the market on Monday. I logged onto my brokerage account on the morning of the 24th and was pleased to see a further decline, but I didn’t pull the trigger. The rapid price swings made me nervous. What if the market rose substantially between selling my Vanguard Total Market shares and buying the replacement funds? Anything’s possible in a volatile market. I decided to wait another week, hoping the market would settle down. Instead, the market pulled off a weekly gain and I missed the boat. For now,…
Read more » Grateful Debt
Sanjib Saha | Jul 18, 2022
THE AGE-OLD DEBATE about not borrowing to buy depreciating assets came up again in a recent HumbleDollar article. Despite being a big proponent of debt-free living, I could relate to the story of borrowing to buy a car. In fact, I’m guilty of having gone deeply into debt in my younger days to feed my passion for music—and I don’t regret it. I grew up listening to Indian music of various genres, but it wasn’t until my college days that I came to really appreciate the sound quality and texture of music. Our dorm had a high-fidelity stereo, plus a decent collection of vinyl records and audio cassettes. I’d spend hours in the common room, listening to classic rock or favorite Bollywood film scores. My newfound love of music, alas, came to an end after I left college and moved back home to Kolkata. We had a portable radio and cassette player in our house, but it didn’t satisfy my craving for quality sound. My life felt so incomplete without a good audio system that I decided to buy one once my paychecks started coming in. I grabbed a coworker named Natesh, who shared my love for music, and we visited an upscale audio showroom near our office. Luckily, the store stocked a nearly identical sound system to the one in my dorm. It was a top-of-the-line modular audio system named Uranus 2 by Sonodyne, one of the most innovative stereo makers in India. I instantly fell in love with the set and wanted to take it home. There was just one small problem. I couldn’t afford it. In the late 1980s, premium audio products weren’t cheap in India. The model I wanted would cost almost a year of my take-home pay. That helped explain why the salesperson didn’t take us…
Read more » Bonding With Bonds
Sanjib Saha | Dec 5, 2019
FOR MANY YEARS, I didn’t own bonds or anything similar, except some bank certificates of deposit. Frankly, I was clueless. My first dilemma: Should I invest in bonds if I have a mortgage? It didn’t make sense to me to borrow from the bank and, at the same time, lend out my money at a lower interest rate to a bond issuer. I felt I should pay off my mortgage first. A few friends and even a financial advisor recommended otherwise. Their objections notwithstanding, I followed my intuition. I was relieved to find out later that my view wasn’t so naïve after all. Fast forward a few years and I had the mortgage paid off. A magical side effect: My entire paycheck no longer disappeared. For the first time in my career, I realized I could take a long break from work if I had to. This feeling of freedom planted the idea of early retirement in my head. I probed my financial readiness and realized that bonds would now play a vital role. For the next few months, I researched bonds, including different kinds, the risks, credit ratings, taxation, liquidity and so on. Alas, I was left with more questions than answers. What percentage should I allocate to bonds? Individual bonds or bond funds? Is credit risk real? Should I worry about duration or convexity? What about inflation? Tax-exempt or taxable? Government or corporate? Overwhelmed and confused, I needed a simpler approach, so I started over, but this time with a basic question in mind: What are the big problems with my retirement finances and can bonds solve them? This gave me much needed clarity. My financial situation posed two challenges. First, my modest nest egg needed a high stock allocation to survive a longer-than-average retirement, and yet I also needed…
Read more » Options in Disguise
Sanjib Saha | Jun 28, 2022
DO YOU INVEST IN options? Think twice before saying that you’d rather go to Vegas. My bold claim: Options investing has a lot in common with investing in stocks and corporate bonds. Intrigued? Let’s recap a European style call option. It’s a discretionary contract that allows someone to buy an underlying asset at a set strike price at a future date. Let’s say the buyer of the call, Bob, has an option on a stock with a strike price of $100. Bob will only exercise the contract if it’s profitable. If the stock price rises to $150 by the time the option expires, Bob can acquire the shares for $100 and immediately sell them for a $50 profit. On the other hand, if the stock price drops to $80, Bob has no obligation to exercise the option. His call option will simply expire worthless. Bob’s only chance at profit comes if the underlying asset clears the strike price. That brings us to the option seller, Shelly. She owns the underlying stock and is participating in a covered call, meaning she’s selling a call option on an asset she already owns. In return, Shelly receives a call premium from Bob. Selling covered calls is a popular strategy for generating extra income. In exchange for the income she receives from selling the covered call, Shelly risks having to sell the stock at the strike price. If the shares rise to $150, Shelly must still sell for $100. The covered call limits her payoff. If the asset doesn’t exceed the strike price, Shelly keeps her shares and pockets the income. What if the stock falls? Shelly still has her option premium, but that may be more than offset by the share price decline. Now, let’s consider the positions of stock and bond investors…
Read more » A Narrow Escape
Sanjib Saha | Aug 12, 2022
I ENVY THOSE WHO can remain patient and calm in almost any situation. Thanks to my neurotic personality, I find it hard to wait for an outcome over which I have little control. This year, I narrowly escaped that sort of agonizing experience. What happened? We found ourselves selling our home during 2022’s suddenly cooling real estate market. I was surprised last year when the red-hot property market pushed our modest home past the $1 million mark. With prices so high, we decided to sell our paid-off house and move to one that offered more space and privacy. The place we settled on as our next home was a 50-year-old house in dire need of repairs and a facelift. We wanted to remodel it before moving in—and before selling the house we currently lived in. The remodeling started last summer at a sluggish pace. It was great not to live in a house that’s being remodeled, but it also made it harder for us to monitor progress and deal with contractors. The work dragged on, thanks to supply issues, contractor delays and COVID. I pretended to stay patient. My anxiety started rising as whispers about a possible cooling of the housing market grew louder. After all, we had to sell the old house after we moved into the new one. If it didn’t sell within a reasonable time and at a reasonable price, it would mess up our financial plans. I neither fancied being a landlord nor wanted to leave a large chunk of our assets locked up in real estate. As mortgage rates ticked higher, we revised our plan. Instead of waiting for the remodeling to be wrapped up, we decided to move in by early spring. We called up a moving company and set a date in March. We…
Read more » Spring Cleaning
Sanjib Saha | Mar 19, 2020
AS THE STOCK MARKET repeatedly hit new highs in recent years, my net worth reached levels I hadn’t expected. But instead of feeling good about it, I was getting annoyed. Most of my retirement dollars had been invested over the past decade at high stock market valuations. I could use a good bear market so that, in my few remaining years in the workforce, I bought stocks cheap. I also worried that a prolonged downturn at the worst possible time might derail my early retirement plans. Indeed, the bull seemed unstoppable even a month ago. But the coronavirus has ended my wait. The bull market’s demise hasn’t just been a psychological relief. It’s also allowed me to get my financial house in better order. I’ve been busy executing trades I’d planned for whenever a market plunge might occur. What trades have I made? My investments needed a spring cleaning, so that’s where I started. Although I mostly invest in low-cost, broadly diversified index funds, a small portion of my taxable account was in a few narrower funds focused on technology, small-cap and value stocks. My original intent was to overweight some promising stock market asset classes, but I’ve come to realize they didn’t add much to my portfolio. Problem is, these holdings had climbed in value and I was reluctant to sell, because of the taxes it would trigger. The market plunge changed that, allowing me to sell without generating big tax bills. I also took tax losses in a few other funds focused on dividend-oriented stocks and international markets, where I wanted to keep my exposure. I used the proceeds to purchase similar—but not substantially identical—funds. This allowed me to maintain my market exposure, while sidestepping the wash-sale rule. With these trades out of the way, I turned my focus to…
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- 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.The reality of Social Security and Medicare- My real life experience.
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