The Malcolm On Money Guide to Restricted Stock Units

For the first time in its 51-year history, Microsoft just announced that it will be offering voluntary retirement to thousands of its employees in the U.S. An estimated 7% of its U.S. workforce will be eligible for the buyouts, which includes personnel whose years of service plus their age totals 70 or more.  

While the move by Microsoft may feel uncharacteristic for a firm that has a history of celebrating its long-tenured workforce, it also reflects a practical response to the current market dynamics. Big tech companies like Microsoft have been looking for ways to trim their expenses as they pour hundreds of billions of dollars into building out their AI infrastructure for the future and reallocate resources toward the next phase of growth.

There is a particular kind of pressure that sets in during the final days before the tax filing deadline, and it’s equal parts urgency and avoidance. For many taxpayers, the realization that they’re up against a hard deadline, paired with the hope that it can still be wrapped up quickly is a source of anxiety.

For many taxpayers, especially those with increasingly complex financial lives, this is the moment when the temptation to “just get it done” using a do-it-yourself software solution sets in. But in reality, rushing through your tax filing might be the most expensive financial decision you can make.

In 2021—the early days of the current bull market—many software companies’ trading multiples seemed untethered from reality. At the time, however, very few shareholders complained that 15%, 20%, or even 25% of annual revenues were being paid out to company employees in stock-based compensation.

Equity grants were framed as a necessary cost of attracting top engineering talent, and buybacks designed to offset dilution were described as a sensible allocation of capital. But as the air has come out of many high-growth software names, and concerns mount that generative AI could commoditize swaths of traditional enterprise software, patience is wearing thin among the investor class.

There is a quiet shift happening among affluent retirees. After decades of saving, investing, and watching their portfolios compound, many are arriving at the realization that they are unlikely to live long enough to spend everything they have accumulated. 

For some, that realization brings peace of mind. For others, it introduces a new and more nuanced question about the purpose of continuing to hold assets that will almost certainly outlive them. 

Most taxpayers spend an extraordinary amount of energy trying to shrink their tax bill each year—often without considering how today’s decisions shape tomorrow’s outcomes. The trouble is that too many households reduce the entire tax conversation to “higher is bad, lower is good,” without recognizing that certain life events and income levels create rare opportunities to plan ahead.

But sophisticated tax planning isn’t about reflexively minimizing this year’s bill. It’s about managing your exposure across decades. And for married couples filing jointly in particular, the 24% bracket often represents an amazing opportunity.

For many senior managers and executives, the idea of stepping off the traditional career ladder to pursue one’s own idea of professional success can be fraught with emotion and uncertainty. The feeling typically presents as a persistent, low hum beneath the surface, after one too many board meetings, another late-night flight, or a growing realization that time has become more valuable than the next title or slight pay increase.  

And whether the goal is to launch a new business from scratch, transition into consulting, scale back to part-time, or retire early, a meaningful career pivot within the next five years demands far more than the decision to do it. It requires a series of conversations with yourself, your spouse or partner, and your team of financial advisors to ensure that your exit is strategic rather than hasty.

It would be an understatement to say that exchange traded funds (ETFs) have transformed the way that everyday investors access financial markets. What was once seen as a way for professional money managers to create thematic bets and add sector tilts to otherwise vanilla portfolios can now be executed with small dollar amounts in any brokerage account and a single ticker symbol.

For investors who do not have the time, training, or inclination to track and trade individual stocks, ETFs offer efficiency among other things. Rather than researching 25 semiconductor companies, you can, for instance, gain exposure to the industry through one fund. But while ETFs make investing easier, conducting due diligence is critical. In fact, their simplicity and convenience can sometimes lull investors into doing far less research than they otherwise would.

Since the passage of the Tax Cuts and Jobs Act in 2017, the mega “backdoor Roth IRA” conversion strategy has quietly gone from a niche financial-planning technique to mainstream conversation among high-income professionals. Online Search interest in the term has surged, particularly among executives in tech, medicine, and law, as this is the group most likely to be phased out of traditional and Roth IRA contributions based on income.

On paper, the strategy appears straightforward. Retirement savers may contribute tens of thousands of dollars beyond the standard 401(k) deferral limits and can ultimately convert those funds into the Roth account within the plan where funds can grow and compound tax-free. But as is often the case in tax planning, there are various traps lurking beneath the surface that high earners are discovering whenever they execute this strategy incorrectly. 

If you’ve spent any meaningful amount of time accumulating restricted stock units (RSUs), you already know they can be both a gift and a curse. On one hand, RSUs can be one of the most powerful wealth-building tools available to employees of publicly traded companies. On the other, those same shares can quietly compound over time, becoming the single largest source of risk in your overall financial picture.

It is generally advisable that investors regularly pare their holdings so that no single investment represents more than 20% of their overall portfolio’s value—substantially reducing their concentration risk. But for those who remain employed by the same company for decades, it can be easy to watch that one stock gradually grow to represent the lion’s share of your entire net worth. And once that happens, it becomes increasingly difficult to imagine parting with said stock as time goes on.

Within the past year, software stocks have gone from market darlings to all-out pariahs. After years of premium valuations supported by low interest rates, predictable recurring revenues, and the promise of endless digital transformation, much of the sector has experienced a sharp and indiscriminate selloff. 

But in some cases, valuations across enterprise software companies have compressed meaningfully, even as the underlying business lines continue to grow, generate positive free-cash-flow, and deepen customer relationships. Now, under the surface, are a few hidden gems that long-term investors might want to bear in mind.