Investments

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.

When Should I Exercise & Sell My Non-Qualified Stock Options? – Using Merck's (MRK) Stock History

When Should I Exercise & Sell My Non-Qualified Stock Options? – Using Merck's (MRK) Stock History

In contrast to the first half of 2023, the second half has had volatile, lackluster returns for some of the stock market and pharmaceutical stocks. Market fluctuations can significantly impact wealth creation, especially when navigating stock compensation.

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.

How Money Can Buy Happiness (Part 2)

How Money Can Buy Happiness (Part 2)

Earlier this year, I explained two principles you can follow to obtain the most happiness from your spending https://www.highlandplanning.com/learning-center-1/how-money-can-buy-happiness-part-1. In today’s article, I will cover three more concepts that can help bring more joy in your life with your spending. Below are the five principles outlined in the book Happy Money.

A Look Back at The First Half of 2023

A Look Back at The First Half of 2023

The S&P 500 index rose 16.9% on a total return basis over the first half of of 2023. If you factor in July, the index is up over 20%. After a challenging year for investors in 2022, when the index lost almost 20%, it’s hard to complain about this year’s progress. With the S&P nearly doubling the long-term average annual return in 2023, it’s easy to say the market is healthy and all companies are doing well, right?

The Pass-Through Entity Tax

The Pass-Through Entity Tax

The "Tax Cuts and Jobs Act" (TCJA) of 2017 brought a significant shift in the taxation landscape for individuals and businesses. One of the changes was the $10,000 cap on deductions for state and local taxes (SALT). This limit impacted the tax strategy of many high-tax states, pushing them to find ways to mitigate the impact of this cap on their taxpayers.

Investment Diversification Strategy: Just How Diversified Are You?

Investment Diversification Strategy: Just How Diversified Are You?

One of the most fundamental principles of investing is diversification. Diversification does not overload your portfolio into any investment but instead spreads the risk across different areas. Ideally, your portfolio is invested in several diverse types of investments, but as you'll see below, there is more to diversification than buying stocks, bonds, or funds.

The World Wide Web 30 Years Later

The World Wide Web 30 Years Later

April 30th marked the 30th anniversary of the World Wide Web being introduced to the public for the first time. Tim Berners-Lee was a 37-year-old researcher at CERN, a physics lab in Switzerland when he created the first website and launched it on the Web as we know it today. 1.8 billion websites later, Lee's invention has revolutionized the way human beings interact and learn on a global scale.