ESPPs Become Even More Attractive During a Market Downturn
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.
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Every Investment Portfolio Needs Its Anchor Investments
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.
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What Happens to Your RSUs When You Retire
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.
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The Five Essential Documents that Every Estate Plan Must Have
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.
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The Importance of Having an Estate Plan as a Single Person
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.
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Here's What You Should Know Before Drafting and Funding a Trust
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.
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An IRS Letter Is Not the End of the World -- Unless You Ignore It
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.
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The Double Tax Benefit of Gifting Appreciated Stocks to Charity Instead of Cash
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.
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Here’s How a “TOD” Designation Can Simplify the Transfer of Your Home to Heirs Without Sacrificing Control
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.
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Give Yourself Permission to Spend Your Inheritance
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.
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Have a Concentrated Stock Position to Unwind? Here's an Approach to Consider.
Workers who climb the ranks within a company for senior- or executive-level positions likely have accumulated a meaningful amount of that company’s stock along the way. With this, deciding whether or not to sell company stock upon retirement can put you at an emotional and financial crossroads.
It is a decision that requires separating professional identity from financial reality—a challenge that can be surprisingly complex. After years of aligning personal successes with the company’s growth, stepping away can feel like losing a part of yourself. Add to that the difficulty of accepting that the "someday" you have envisioned for decades has finally arrived, it's easy to see why many soon-to-be retirees find themselves hesitating when it’s time to turn those paper gains into actual dollars.
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The Value of Making Non-Deductible IRA Contributions
For high-income earners who often find themselves phased out of many tax deductions, the rules around saving for retirement are no better. However, there is one complex yet beneficial maneuver available: non-deductible contributions to a traditional IRA.
While contributions to traditional IRAs are typically appealing because they can be deducted from your taxable income, those with higher earnings may hit income thresholds that disallow this deduction. The opportunity to make non-deductible contributions, though, remains a viable strategy.
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Does Your Portfolio Actually Need Alternative Investments
In the past few years, alternative investments have surged in popularity among retail investors looking to diversify beyond the perceived limitations of traditional stocks and bonds. Once reserved exclusively for the ultra-wealthy and institutional investors, alternative investments—including private equity, real estate, private credit, hedge funds, farmland, and even collectibles like art and wine —are now more accessible than ever.
Today, the appeal of this alternative asset class lies in its potential for outsized returns. However, it was initially intended to provide investors with a hedge against inflation, as well as the promise to reduce a portfolio’s correlation with the stock market, which offers a buffer in times of volatility. Therefore, it is possible that there is a misunderstanding between the banks, brokerages, and other financial institutions offering alternatives to retail investors and the investors who are eagerly embracing them.
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Drafting a Trust Is a Waste of Money if You Don’t Retitle Your Assets Too
A revocable living trust is often seen as the cornerstone of a well-constructed estate plan. It allows individuals to bypass probate, maintain privacy, and when the time comes, it ensures a smoother transfer of assets to beneficiaries. However, many individuals stop short of completing the most critical step: retitling their assets into the name of the trust.
When you establish a revocable living trust, you essentially create a legal entity to hold your assets during your lifetime and to distribute them after your death. For the trust to function as intended, ownership of your assets—such as real estate, bank accounts, and any investment interests—must be transferred into the trust's name. Failing to do so renders the trust an empty shell, leaving those assets outside its purview.
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Here’s Why Fintech is Poised to Rebound in 2025
After a turbulent few years marked by valuation compressions, rising interest rates, and fading investor enthusiasm, 2025 is shaping up to be a comeback year for the fintech sector. Several factors, including an anticipated slate of high-profile initial public offerings (IPOs), a more favorable regulatory and tax environment, and a resurgence in key fintech stocks, suggest that the industry is entering a new phase of growth and innovation.
Fintech, long viewed as a disruptive force in the financial world, is again capturing the attention of investors who are now more optimistic about its potential for profitability and long-term value creation. Investors would be wise to consider how the sector's improving fundamentals, coupled with macroeconomic tailwinds like the anticipated decline in short-term interest rates, have likely created an attractive entry point for long-term growth opportunities.
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The Case for Paying off Your Home Mortgage While Markets Are at All-Time Highs
Out of 252 available trading days in 2024, the S&P 500 Index notched 57 new all-time highs, with the most recent record close at 6,090.27. This record-breaking market performance has left many investors sitting on massive unrealized gains, prompting the question of whether or not now is the time to sell and lock in some of those profits.
While the question itself is obviously straightforward, the answer is not. As markets continue to power higher, it can be challenging to find attractive opportunities to redeploy the cash from a sale. But for investors who have a more moderate to conservative risk tolerance, a possible solution is to pay off their home mortgage using the proceeds from some of those highly appreciated stocks or other investments.
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Investors Are Increasingly Losing Their Life Savings to Scammers Impersonating Financial Advisors Online
The world of personal finance can be an intimidating place to navigate, especially when it comes to entrusting someone with your hard-earned money. While many financial professionals are legitimate, ethical, and focused on helping their clients achieve their financial goals, there is an unfortunate reality: scammers are constantly evolving their tactics to exploit well-meaning, unsuspecting investors.
Recently, fraudsters have gone so far as impersonating legitimate companies and professionals, creating fake websites, social media profiles, and other online presences to lure victims into their traps. Thus, it is up to would-be investors to remain vigilant, verify the authenticity of the professionals they engage with, and pay attention to signs of potential fraud before making financial commitments.
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Your Investment Strategy Must Evolve Once You Reach Financial Independence
For many investors, financial independence is the ultimate goal. It’s the point where your assets generate enough income to cover your living expenses, giving you the freedom to work on your own terms or choose to retire completely.
However, reaching this milestone should also prompt a critical shift in your investment strategy. While the path to financial independence often involves seeking higher returns to accelerate wealth accumulation, continuing to take on too much risk once you've achieved that goal can be detrimental to your long-term financial security.
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The Benefits of Creating a Living Inheritance for Your Heirs
As Baby Boomers continue to enter retirement, following decades of diligent saving and investing, many are finding themselves sitting on a nest egg that is significantly larger than they will realistically need to live on. In fact, according to Fidelity's most recent 401(k) Millionaire study, the number of people with $1 million or more in their 401(k) accounts reached another all-time high.
For many, this creates an opportunity to rethink the traditional approach to inheritance. When most people think about leaving an inheritance to their next generation(s), they imagine passing on assets after they’ve passed away, ensuring their children and grandchildren are financially secure for years to come. While this traditional approach to inheritance has its merits, there is an increasingly popular alternative that offers profound emotional, financial, and practical benefits: a living inheritance.
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The Case for Consolidation Among Cybersecurity Stocks
A recent survey by PwC of nearly 4,000 business and tech executives representing some of the largest global companies suggests that in 2024, 79% of organizations intended to increase their cybersecurity budgets from 2023. The survey also notes that the cost of security breaches, as well as the number of high-dollar breaches, continues to increase. And although cyber attacks are the top concerns cited, only half the organizations surveyed indicate they are ‘very satisfied’ with their technology capabilities in key cybersecurity areas.
If you couple those findings with the U.S. Securities and Exchange Commission’s (SEC) recent rollout of new rules requiring public companies to disclose material cybersecurity incidents to shareholders, you get the business case for why the cybersecurity sector is ripe for both growth and consolidation over the next few years and why investors might want to pay attention.
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