Investments

Tax Traps: The Hidden Costs of High-Yield Savings vs. Stock Market Gains

Tax Traps: The Hidden Costs of High-Yield Savings vs. Stock Market Gains

The current interest rate environment has driven many to explore high-yield money market accounts and certificates of deposit (CDs) as viable investment vehicles. With interest rates on these instruments at levels unseen in over a decade, it's easy to understand the appeal. However, there is an irony in using these vehicles as long-term investment strategies, especially when compared to the potential tax advantages the stock market offers.

My Biggest Investment Mistake

My Biggest Investment Mistake

During my first year in college, I read my first investment book, "The Intelligent Investor" by Benjamin Graham, widely regarded as one of the greatest stock traders ever. Filled with excitement, I took copious notes, convinced I had stumbled upon the secret to success in the stock market. With this new knowledge, I eagerly deposited $600 into a trading account and made my first trade, purchasing ten shares of Columbia Sportswear Company stock ($COLM) at $56.80 per share.

Why Long-Term Investment Strategies Shouldn't Be Driven by Federal Reserve Interest Rate Decisions

Why Long-Term Investment Strategies Shouldn't Be Driven by Federal Reserve Interest Rate Decisions

As a financial advisor, I often hear clients express concern over the Federal Reserve's interest rate decisions and how these might impact their long-term investments. While it's natural to be attentive to such economic indicators, focusing solely on interest rate changes when planning your long-term investment strategy can be a misstep. Here’s why it’s important to maintain a broader perspective.

Is Your Stock Certificate the Next Big Thing?

Is Your Stock Certificate the Next Big Thing?

Rummaging around your stuffed filing cabinet, you come across a stock certificate. A glint of excitement enters as you think about the potential value of this forgotten relic. It is not uncommon to stumble upon an old stock certificate in its physical form. There are steps to take to research if the old stock certificate is worthless or if it is a lottery ticket. 

Tax Lot Identification: It’s Not What You Make, It’s What You Keep

Tax Lot Identification: It’s Not What You Make, It’s What You Keep

At HIGHLAND Financial Advisors, tax efficiency is a cornerstone of our investment management strategy. After all, it is not what you make but what you keep. One of the key strategies we use to achieve this is tax lot identification in our trading procedures.

Teeing Up Your Financial Future: Unveiling the Hidden Links Between Golf and Financial Planning

Teeing Up Your Financial Future: Unveiling the Hidden Links Between Golf and Financial Planning

Picture this: you stand at the tee box, surveying the undulating terrain ahead with excitement and apprehension. With each club selection and calculated swing, you inch closer to the elusive hole, navigating obstacles and seizing opportunities. Little do you know, every decision you make on the course mirrors the principles of prudent financial management, offering valuable insights into crafting a secure and prosperous future.

The Return of Brood XIII: What Cicadas Can Teach Us About Financial Planning

The Return of Brood XIII: What Cicadas Can Teach Us About Financial Planning

After spending 17 years lying dormant underground, a new generation of Brood XIII cicadas will soon emerge across large swaths of the eastern United States. This phenomenon is one of the most remarkable examples of cyclical events in the natural world.

It's fascinating to think that the last time Brood XIII was about to turn in for its 17-year slumber, Steve Jobs introduced the iPhone to the world for the first time. A year later, a mysterious person named Satoshi Nakamoto wrote a paper describing something he called Bitcoin, which began trading for less than a penny.

Dinner with a Time Traveler

Dinner with a Time Traveler

It's January 1, 2018, and you just won the lottery for $5,000,000. 

You are sitting in our office, discussing your plans for the money, and you decide it's a good idea to invest the proceeds for the long term. 

You decide on a portfolio of 25% US Bonds, 60% US Stocks, and 15% International Stocks. 

 After feeling pretty good about your lottery winnings and the investment decisions you made, you leave our office and treat yourself to a meal. 

Monkey Business: Unveiling the Psychology of Financial Decision-Making

Monkey Business: Unveiling the Psychology of Financial Decision-Making

The fascinating interplay between human decision-making and financial outcomes has long intrigued behavioral economics and psychology scholars. However, research has expanded this inquiry beyond human subjects, delving into the behavior of our primate cousins, specifically Capuchin monkeys. Situated on an island off the coast of Puerto Rico, researchers conducted an experiment seeking insights into economic behaviors, risk psychology, and the recurrence of financial crises in our societies, shedding light on the parallels between monkey behavior and human decision-making processes.

The Myth of CASH

The Myth of CASH

In personal finance, the attraction of cash equivalents for long-term goals has persisted as a seemingly safe and stable investment strategy. Cash equivalents, including savings accounts, money market funds, certificates of deposit (CDs), and Treasury bills, are often viewed as low-risk options that offer liquidity and "preservation of capital." However, the belief that investing primarily in cash equivalents can secure one's financial future in the long term is a myth that should be challenged.

Demystifying Backdoor Roth IRA Contributions: Answering the Top FAQs

Demystifying Backdoor Roth IRA Contributions: Answering the Top FAQs

As the April 15th tax filing deadline rapidly approaches, so does the 2023 Roth IRA contribution deadline. Roth IRAs are among the most efficient yet under-utilized retirement saving strategies. By saving after-tax money in a retirement account, individuals can enjoy tax-free investment growth and distributions in retirement.

When Can Investing Resemble Gambling?

When Can Investing Resemble Gambling?

I'm reading Daniel Kahneman's book Thinking, Fast and Slow. Kahneman is the 2002 Nobel Prize-winning psychologist and economist known for his work in behavioral economics. One section of the book discusses how investing can resemble gambling when individuals overestimate their ability to predict market movements, a phenomenon deeply connected to Daniel Kahneman's concepts of the "Illusion of Skill" and "Illusion of Validity." These cognitive biases describe the human tendency to overvalue our ability to make accurate predictions or decisions in situations where chance plays a significant role or the information is unreliable.

A Tax Tale: The Story of Reporting Income Taxes From Stock Compensation

A Tax Tale: The Story of Reporting Income Taxes From Stock Compensation

Sarah, a savvy pharmaceutical executive, has accumulated Non-Qualified Stock Options (NQSOs) and Restricted Stock Units (RSUs) as part of her compensation package. Sarah had always been meticulous with her finances and records of her stock option grants, exercise dates, and the fair market values at the time of exercise. As her stock compensation vested over the years, she knew proper tax reporting was crucial to avoid any IRS headaches.  

Why Investing is so Difficult

Why Investing is so Difficult

Buy low, sell high. This four-word phrase is the only thing you need to know to invest successfully. Why, then, is something so simple as buying low and selling high such a difficult skill to be successful at? The answer is that we all have emotions that drive our investment decisions.

Understanding the Pros and Cons of Rental Property Ownership

Understanding the Pros and Cons of Rental Property Ownership

A common question I often hear from clients considering purchasing a rental property or who may have just inherited one through the passing of a family member or divorce is whether they should manage the property themselves or hire a professional management company.

High Rates Don't Put the Brakes on Stocks

High Rates Don't Put the Brakes on Stocks

Some investors have asked if stocks make sense in a world where short-term US Treasuries yield north of 5.5%. 1 While a notable relationship exists between high short-term interest rates and stock market returns, it's important to understand that correlation does not imply causation. Here's a breakdown of the dynamics:

Why Stock Valuations Are Not Predictive of Future Portfolio Returns

Why Stock Valuations Are Not Predictive of Future Portfolio Returns

Financial markets are complex and unpredictable. Valuation metrics, such as price-to-earnings (P/E) ratios, enterprise value-to-EBITDA, and the price-to-book (P/B) ratio, have traditionally been seen as indicators of a stock's intrinsic worth and, by some, predictors of future returns. However, the belief that valuations can reliably forecast future markets deserves a deeper investigation into why they may not serve as a crystal ball for investors. 

Three Questions Answered Regarding your Company's Restricted Stock Units (RSUs)

Three Questions Answered Regarding your Company's Restricted Stock Units (RSUs)

A Restricted Stock Unit (RSU) is a form of compensation that some companies use to reward their employees. RSUs represent a promise to give an employee a certain number of shares of company stock at a future date, typically once certain conditions are met, such as a specified vesting period or performance goals. RSUs are a common form of equity-based compensation used in publicly traded and private companies.

3 Reasons Every High Net-Worth Family Should Fund a Health Savings Account

3 Reasons Every High Net-Worth Family Should Fund a Health Savings Account

Health Savings Accounts (HSAs) are not only a savvy investment option but also offer numerous benefits, especially for high-net-worth families. An HSA is a tax-advantaged savings account designed for individuals with high-deductible health plans (HDHPs) to help cover out-of-pocket medical expenses. While the utility of HSAs is universal, they hold advantages for high-net-worth families and have steadily grown in popularity since their inception.