The Malcolm On Money Guide to Restricted Stock Units

When a raise at work materially boosts your discretionary income and ability to save—while in your twenties and thirties—cash probably matters most. But in your forties and beyond, especially at the highest marginal tax rates, receiving more of your compensation as equity gives you a shot at exponential growth and is far more likely to boost your net worth over time.

Generally, by the time you’ve reached the executive ranks of a company, a bigger paycheck rarely changes your day-to-day spending capacity in a meaningful way. By contrast, equity can move the needle tremendously. Whether via restricted stock units (RSUs) or performance share units (PSUs), if you’re negotiating a new executive compensation package, prioritize equity over cash.

When evaluating a job offer, it’s easy to get captivated by the headliners, particularly base salary, seniority level, and/or signing bonus. But if your current employer’s compensation package includes restricted stock units (RSUs), you could be leaving a substantial amount of money on the table by walking away too soon.  

One of the most overlooked—and potentially costly—mistakes senior managers and executives make when switching jobs is failing to consider the forfeiture value of unvested equity. Career mobility is vital, and sometimes a new opportunity simply can’t wait. But knowing the forfeiture value of your equity gives you critical negotiating power you may not realize you have. 

For most married couples, filing a joint tax return is generally simpler, cheaper, and better than filing separately. Joint filers are positioned in more favorable tax brackets and receive greater credits, so it’s advantageous to combine your returns.  

The exceptions to this general rule are narrow and highly specific—think unusually large medical bills relative to one spouse’s income, student-loan repayment plans that look only at the borrower’s return, or in the heat of a separation or divorce proceeding. In less common cases, a separate return can be a rational choice even if it means losing out on some breaks. 

For most people, the hardest part of the estate planning process is preparing and completing all the necessary paperwork. Yet for all the effort put into establishing the legal structure—identifying guardians, naming executors and powers of attorney, and making decisions about how assets should transfer—many stop short of doing the one thing that could make the entire plan work as intended: talking about it. 

You might assume that because your wishes are well thought out and carefully written, they will automatically be honored when the time comes. But legal documents don’t speak for themselves. And those who have been assigned critical roles—like your executor, guardian, or healthcare proxy—will require more than a title. They will need context, direction, and reassurance.

If you work in a high-earning occupation like technology or healthcare, you have probably found yourself sitting through your fair share of sales pitches for life insurance, wondering how you got there. And when those sales pitches are concealed behind buzz phrases such as “family banking” or “7702 plans,” you are right to be skeptical and keep your hand on your wallet.  

In most cases, you are better off buying inexpensive term coverage to protect against any income gaps for financial dependents and then investing the difference that would’ve gone toward a lifetime of monthly premiums into a low-cost index fund instead. However, for the right person with a long enough time horizon, a life insurance retirement plan (LIRP) can make sense. 

The capital markets have a way of making us feel like we should always be “doing something.” When stocks are plunging, doing nothing feels irresponsible. And when they rip higher, doing nothing conjures up a feeling that you’ll miss out on the next opportunity.  

That itch to act is human, and it’s gotten stronger in the age of push alerts, app badges, and celebratory screen flourishes after each trade. Regulators have warned that these “digital engagement” tricks can prompt people to trade more than they otherwise would, and research has tied push notifications to a measurable spike in trading within minutes. But all this constant activity amounts to nothing more than “tinkering.” 

Cash feels good. It’s certain. It’s liquid. It lets you sleep at night. But like keeping all your plants in the shade, too much “safety” can stunt growth. The question isn’t whether cash has a role in your broader financial strategy—it absolutely does. The question is where the line sits between prudent reserves and a drag on your long-term plan. 

As a general rule of thumb, it is a good idea to cap the amount you park in cash to just one full year of essential living expenses. This is because most white-collar professionals who are laid off don’t go a full 12 months without earning an income, and keeping significantly more than that on the sidelines exposes you to inflation risk without commensurate benefit. 

Building a portfolio of rental real estate has long been a favored strategy for families intent on creating generational wealth—often from scratch. Yet, parents who plan to pass their rental properties to their children sometimes overlook a fundamental question: Do your children actually want to inherit the properties you've spent decades managing? 

All too often, parents spend significant portions of their lives building and managing real estate portfolios and dealing with the inevitable headaches such as tenants, maintenance issues, and regulatory requirements—only to have their children inherit and quickly sell the properties in the end. It's a scenario that happens more frequently than many parents realize, rendering their lifetime of hard work and financial discipline effectively moot. 

Whether it’s due to uncertainty around tariffs or productivity gains brought on by advancements in artificial intelligence, a growing number of companies—including hyperscalers such as Microsoft and others—are making tough decisions to trim overhead. Whether the layoff notice comes with a generous severance or merely a handshake and well wishes, the fallout can be both emotionally and financially disorienting. 

While tech titans like Microsoft have long been known for offering competitive exit packages—including a few months’ salary, extended COBRA coverage, and stock vesting acceleration—those perks don’t erase the uncertainty that follows. These offers often emerge with little warning, and for employees who hadn’t planned on leaving the company anytime soon, the challenge is not just deciding what to do next but determining how to navigate a financial transition they didn’t ask for. 

Whether transforming the way we purchase and listen to music with Apple Music and the iPod, reshaping global communication with the iPhone, or redefining wearables with the Apple Watch, Apple Inc. has long been at the forefront of major tech trends. But with Microsoft, Alphabet, and Meta all sprinting ahead with the development of advanced large language models capable of handling complex reasoning, the spotlight is on artificial intelligence (AI) and Apple’s absence from the leaderboard.

Yet by focusing solely on AI, Apple risks overlooking a far more immediate and strategic opportunity in financial technology. Unlike its rivals, Apple already commands an extraordinary level of consumer trust, a fiercely loyal user base, and a well-established fintech infrastructure—making it uniquely positioned to expand deeper into financial services.