Thoughts and musings from my desk to you.

Tax Efficiency: Vast Benefits Easily Overlooked

Traditional investment advice normally focuses on allocation into buckets. These buckets could be traditional mutual funds, or ETFs, or managed accounts holding individual stocks. In most cases, the allocation buckets are tactically rearranged, and the securities within mutual funds and managed accounts are also actively rearranged.

Considering that studies like the SPIVA Report from Standard & Poor’s routinely show that the vast majority of active managers underperform their benchmarks over any discernable timeframe, it makes you wonder what master “traditional advice” is serving.

Challenging the Status Quo

We get puzzled looks from new clients when we explain our position on taxable fixed income (bonds) in IRAs. Traditional planning advice recommends placing your highest growth assets in an IRA to maximize the tax deferral. We usually recommend the complete opposite approach, which becomes more and more preferable the higher the income of the current or future retiree.

The Importance of Tax Strategy

Just in time for Tax Day 2023, Gil talks tax strategy with the Houston Business Journal.

“With tax season upon us, it seems an appropriate time to discuss tax strategy with a local specialist. Investors might assume that the frontline professionals for advanced tax strategy are CPAs. However, some investors find that their CPAs work retroactively, focusing on preparing tax returns more than strategizing with their clients about optimal ways to reduce or eliminate taxes. Our highlighted executive today is not a CPA but has four decades of investing experience while navigating IRS rules and has developed a reputation as a specialist in reducing tax friction in his clients’ investment portfolios.”

Death and Taxes: Not So Certain After All

Gil published a piece in Forbes Council titled, “Death and Taxes: Not So Certain After All.”

After years of writing about the subject, long-time readers will surely realize how degrading taxes are to returns. With market liquidity at all-time highs and trading commissions now free, investors are seemingly incentivized to trade their accounts. The math is simple right? All one must do is spot a better opportunity and taxes are just a part of the game, right? Yes, but how big of a part?

Protecting Gains? It’s Complicated.

Clients generally understand how our low-turnover methodology equates to better returns over time. For example, with enough tax deferral, an 8% return can be augmented to a 10% return (in dollars). But that’s not all. Preserved gains that remain untaxed until death are tax-free in many circumstances. This can make low-turnover methodologies even more compelling. Despite the power of these factors, protecting gains and principal is still the first order of business at Segment.

Roth Conversions

Roth conversions remain one of the most underutilized tax planning strategies around.

Imagine the limited benefits of continued tax deferral for a 90-year-old retiree with a $500,000 IRA and an income of $100,000 a year. That income is comprised of pension distributions, IRA required minimum distributions (RMD), and some dividend income. Let’s say she has two grown children in their 60s, each earning $600,000 a year in a 41% tax bracket. Since Mom’s tax bracket peaks at 24% (up to around $170,000 worth of annual income), it would make perfect sense for her to do annual $70,000 Roth conversions, whittling down her $500,000 IRA and avoiding that next bracket of 32% above $170,000 in gross income.

Estate Taxes & IRAs – Collision Course

There are very few tax issues more complicated than the intersection of estate taxes, income taxes, and IRAs. Very few couples exceed the $24million exemption amount to begin with, and even fewer get this part of their planning correct. If not navigated well, this confluence of factors can conspire to cause 80% of an IRA or 401k to be lost to taxes. There are solutions, including going back three years to amend returns if this causes an aha moment.

Frankenstein Tax Policy

Mr. Biden’s new tax policy has proposed yet another angle to get more tax revenue from the “millionaires and billionaires.” This time he’s circling back to see if he can get a tax on unrealized (unsold) taxpayers’ gains after all. The new twist is that this tax policy is limited to those folks with more than $100 million in net worth. Under current law, only assets that are sold for a profit are taxable, and they are never taxed if held to death. Mr. Biden claims this is an “unfair” loophole incentivizing taxpayers to avoid sales.

Tax Loophole

There’s much wisdom in exercising caution when stirring up things long undisturbed. Politicians often run amok in efforts to garner “points” with their constituents. In this case, Mr. Biden ought to have let sleeping dogs lie. His recent attempt to discard the Step-up in Basis Rule, a popular tax loophole, was met with understandable resistance, and he has since relented.

Tax Rule Changes: Build Back Better Act

The language surrounding the Build Back Better Act suggests that it’s time for the rich to “pay their fair share.” But it is important to remember that 61% of all Americans pay no taxes. This vulnerability was addressed over 190 years ago, when Alexis de Tocqueville warned that the eventuality of non-taxpayers voting for the taxation of others would ultimately be America’s undoing. But don’t lose heart. We have been on such a brink before, and we voted in low-tax Ronald Reagan as a result.