The Malcolm On Money Guide to Restricted Stock Units

For opportunistic investors, employer stock purchase plans (ESPPs) become more attractive in a bear market. This is because stocks are bought at an additional “discount” on top of the price cut that is inherently built into the plan. 

ESPPs are employer-sponsored investment plans that allow employees to purchase company stock at a discounted price—typically 15%. However, when a stock is in bear market territory, it means that the company’s stock price is down 20% or more from its 52-week high. This indicates that at a minimum, you could feasibly buy the stock at a 35% discount with respect to its recent trading range. 

Investors often chase the next big thing, focusing on the latest headlines and quarterly earnings beats. But the most resilient portfolios—the ones that weather market shocks and grow meaningfully over decades—aren’t built on speculation. They’re built on conviction.

At the core of these portfolios lies what may be best described as “anchor investments,” which are a small handful of high-conviction stocks that act as the ballast of a long-term investment strategy. An anchor investment isn’t just a company you happen to like. It’s a stock you understand deeply, believe in fundamentally, and would be comfortable holding through several periods of volatility and uncertainty.

While in the middle of your career and possibly raising a family—likely in your 30s, 40s or 50s—it can be challenging to plan for the days when full-time employment is an option for you rather than a requirement. Nevertheless, it is important to keep in mind that the decisions you make during your pre-retirement years directly affect when you can retire and the lifestyle you will enjoy in those years.

The closer you get to your desired retirement date, the less of your overall net worth you should have concentrated in the stock of your employer. Your company stock is likely a significant portion of your overall investment portfolio, and thus your retirement plan. And the more volatile that stock is, the tougher it becomes to incorporate those shares into a retirement income plan.

Having a comprehensive estate plan is essential for everyone, regardless of age or asset level, because it ensures that your wishes are clearly documented and legally enforceable in the event of incapacity or death. An estate plan protects your loved ones from unnecessary legal complications, minimizes potential disputes, and provides clear instructions for managing your healthcare, finances, and assets.  

Without a plan in place, critical decisions about your well-being and the distribution of your estate may be left to the courts, often at a higher emotional and financial cost to your family. Establishing an estate plan is a proactive step that gives you control, preserves your legacy, and provides peace of mind for you and those you care about.

When people think about estate planning, it is often pictured as something only married couples with 2.5 children, 2 dogs, and a sprawling estate with a white picket fence consider. In reality, it is something single and unmarried individuals can also explore, but this planning becomes even more critical because of the lack of a "default" decision-maker like a spouse. 

Whether you are early in your career, approaching retirement, or anywhere in between, creating a thoughtful estate plan is an essential step towards protecting yourself and the assets you've worked hard to build. It allows you to appoint someone to handle your affairs quickly and privately rather than dragging personal matters through public probate proceedings. It also helps to protect your estate from avoidable taxes and legal fees. 

Establishing a revocable living trust is the bedrock of any well-crafted estate plan. However, its effectiveness depends entirely on how – and whether – you choose to fund it. This entails taking a thoughtful, strategic approach to determining which assets should be placed in the trust and how their ownership is structured.  

Funding your trust should not be viewed as a simple paperwork exercise. Rather, it’s a critical process that shapes how your estate will be managed and distributed. Each asset presents its own set of legal, tax, and practical considerations, making it essential to evaluate not just whether it should be included, but how it should be titled to best serve your broader planning goals. 

For tax payers, few things can cause a spike in in your blood pressure faster than receiving a letter from the Internal Revenue Service (IRS). But before you go into a doom spiral imagining all of the worst-case scenarios, it is important to take a step back and understand what an IRS notice actually means.  

Yes, the IRS has the authority to assess taxes, impose penalties, and even in extreme cases, seize assets. More often than not, it is a routine matter that can be resolved without much trouble as long as it is handled properly. 

Every December, Americans scramble to find last-minute ways to lower their tax bills. And one of the most common strategies—particularly among high-income earners—is to make charitable donations often by writing a check to support their favorite cause. 

While cash contributions are simple and straightforward, they are not always the most tax-efficient way to give. For those who own stocks that may have appreciated significantly from when they were purchased, donating shares instead of cash can provide a double tax benefit. In this instance, the donor not only avoids capital gains taxes on the appreciation but also receives a deduction for the stock’s full fair market value. 

For most Americans, your home is likely your most valuable asset. In fact, for centuries, it has been the greatest source of inter-generational wealth transfer by a wide margin. This explains why many parents weigh the idea of designating their adult children as co-owners on the property's title as an estate planning mechanism.  

Unfortunately, most stop short out of fear, and for good reason. Giving up financial control of such an important asset is a scary thought for many seniors. Thus, ensuring a smooth transfer of ownership to heirs while retaining full control during one’s lifetime is a common concern for older homeowners.

Inheriting money or investment assets from a loved one often brings a complex mix of emotions. On one hand, there’s gratitude and an acknowledgment that someone cared enough about you to leave behind a financial legacy. On the other, there is an unspoken pressure to preserve what was left behind. It’s almost as if spending even a penny or making any changes would somehow dishonor the person’s memory.  

This hesitation is especially common with investments such as stocks, mutual funds, and rental real estate. And even when a person inherits an asset that does not make financial sense to hold onto long-term, they feel it would be wrong to sell or adjust what their parent or loved one thoughtfully built over decades.