The start of a new year is often when people set goals for the next 12 months and begin making plans to achieve them. Naturally, this means it’s the perfect time to assess your financial situation and determine how much you might invest in the coming year. 

By researching your current budget, you’ll be able to determine how much of your money you can comfortably contribute toward your investment goals. This process also provides useful information for your financial advisor to help guide your decisions.

Whether you’re creating your first investment budget or updating a current one, there are four basic steps you should follow. These ensure that you’ll be able to maximize your investments while still being able to comfortably meet your other financial obligations.

1. Assess your current financial situation

Take a look at your current budget to get a sense of how much money you’re taking in each month, how much you’re spending, and how much you’ll be able to set aside. This process will also update you on the progress you’re making toward any short-term or long-term goals.

Check the past two or three months of your financial activity and plot out the following:

Creating this budget will show how much of your income you could potentially contribute to an investment portfolio. It will also let you determine if there are any areas where you might be able to adjust your spending. For example, you may opt to reduce the amount you spend each month on dining out or cancel some subscriptions in order to have more discretionary income available to invest.

2. Determine how much you can invest

One common recommendation for dividing up your after-tax income is a 50/30/20 distribution, which aims to strike a balance between meeting your basic needs, spending on discretionary items, and addressing long-term goals. This distribution commits:

Investments complicate this model to some degree, as you can consider them as a form of both savings and discretionary spending. Depending on your personal financial situation, you may opt to invest a larger share of your income (such as 25 percent) or a smaller share (10-15 percent).

Even if a larger share of your income goes toward covering basic needs and you only have a small share of your budget available for investing, you can still take this step. One common misconception is that you need to have a substantial amount of money available in order to invest. In reality, you can start an investment portfolio with a modest sum that fits your budget. You can even opt to commit a set dollar amount for investing each month rather than a specific share of your income.

Time is the most important consideration when investing. The earlier you start an investment portfolio, the longer it will have to grow. Committing to regular contributions toward your portfolio, even if it’s just a small amount of money, will allow you to grow your assets more quickly over time.

Look into setting up automations to help support your investment goals. These could include an automatic transfer to shift some of your income to your investment portfolio each time you receive a paycheck. 

3. Set your goals for investing

Once you know how much you can comfortably set aside, you should set goals you’d like to accomplish through your investments. Some common goals include having enough money to:

Your goals will dictate your investment strategies, since they will help you decide how much risk you’re willing to take on and how long you’ll need to save. For example, saving for retirement takes place over a long period of time and usually includes an adjustment of risk strategy (from higher-risk investments at a young age to more conservative investments as you near retirement). Saving for a children’s college fund is also a long-term process, typically accomplished with a tax-advantaged 529 plan. By contrast, investments intended for wealth accumulation often have a shorter timeframe and may pursue more of a high risk, high reward strategy. 

You may decide that short-term financial obligations should take precedence over investing. These could include paying off high-interest debts or building up an emergency fund sufficient to cover at least three months of living expenses. Once you have achieved these goals, you’ll be in a better financial situation and can invest more comfortably.

4. Make adjustments as necessary

An investment plan is not something you set and forget. You’ll need to revisit it periodically and make adjustments to reflect changes to your budget as well as your investment goals. 

You may be able to invest more of your income if you receive a raise, pay off a debt, or no longer need to pay for an expense such as child care. However, you may also want to reduce the amount you invest if you have taken a pay cut or are coping with higher expenses.

You should ideally review your investment plan at least once a month with your financial advisor. This will allow you to make adjustments quickly based on any changes to your circumstances.

To set up a meeting with Grey Ledge Advisors, contact us online or call 203-453-9075.

Generosity warms the heart, and our neighbors.

As is our annual holiday tradition, in honor of our clients, and in place of greeting cards and other branding items, Grey Ledge Advisors is donating to the highly respected and impactful Operation Fuel of Connecticut. 

As you know, it is our job to be aware of good investments, and there are fewer, more meaningful ways to celebrate the spirit of this season than to ensure that our neighbors are warm…and cozy. 


If you are not familiar with Operation Fuel, they serve more than 10,000 families every year, and they do so despite diminishing emergency grants and increased demand. We are honored to support this organization and the basic needs they meet. We invite you to learn more about why we selected Operation Fuel for our 2023 client honorarium.


Warm — and cozy — regards,

Ken Russell and the

Grey Ledge Advisors Team

Thanksgiving is a wonderful opportunity to get together with your family for a holiday that’s all about good food and gratitude. It can also be easily spoiled if conversations turn confrontational, which is why some subjects — namely politics and religion — are usually considered off-limits. 

Many people include financial matters on the list of off-limits topics during the holiday, but having the family together presents a perfect opportunity to discuss important financial matters — especially estate planning. While this may seem like an uncomfortable topic to bring up, effective communication with your loved ones is a critical part of the process. 

You don’t want this topic to come up by surprise, so give advance notice to your family that you’d like to make it part of the day. It doesn’t have to be the central discussion during the big meal; setting aside some time after the feast, or at some point during the long weekend, will suffice. 

Here are a few ways a family discussion about estate planning can be useful:

It helps set expectations

There has been considerable discussion about the massive wealth transfer that is expected to take place between Baby Boomers and younger generations. Fortune recently determined that the average Baby Boomer has a net worth of $970,000 to $1.2 million. An analysis by Cerulli and Associates estimates that the Baby Boomers and their parents (the Silent Generation) will pass on about $72.6 trillion to their Gen X and Millennial heirs.

This transfer of assets could have major ramifications for younger generations, especially for Millennials whose economic advancement has been hampered by challenges such as the Great Recession. Receiving a substantial sum could allow them to purchase a home, strengthen their retirement account, start an investment portfolio, or achieve other long-delayed financial goals.

However, there may also be a significant disconnect between what younger generations think they’ll inherit from their parents and what their parents are actually planning to leave them. While the figure in the Cerulli analysis is impressive, it’s worth noting that 42 percent of the wealth to be transferred is from ultra-high net worth households. A recent survey by Alliant Credit Union found that while 52 percent of Millennials believe they’ll receive an inheritance of at least $350,000, 55 percent of Baby Boomers said they were planning to leave less than $250,000 to their heirs.

Other factors also affect how much the older generations intend to leave for younger ones, or how much they’ll actually be able to pass on. Retirees must balance factors such as long-term care costs, higher costs due to inflation, and longer life expectancies to ensure that they don’t outlive their savings, and this can also limit how much money they’ll be able to pass on to their heirs.

A discussion about your finances can help set realistic expectations, and is also a good starting point for a conversation on estate planning. 

It gets the ball rolling

Failing to discuss what happens to a loved one’s assets after their death is a key source of wealth transfer problems. If you make your heirs aware of your plans and involve them in the process, it makes the process much smoother. 

An initial discussion on estate planning can simply inform your children of any plans and preparations you’ve made. Estate planning allows you to inventory all of your assets, including debts and liabilities, so you might share this information to help set expectations and discuss what you’d like to leave as an inheritance or as charitable donations. Your initial discussion can also be a useful way to inform your children about where your assets are being held, such as the names of any bank accounts, investment portfolios, and retirement accounts.

Clearly establish what steps you’ll be taking as part of your estate planning. This might include determining how your assets will be divided, setting up a will or a living trust, making preparations for long-term care, establishing health care directives, and setting up your power of attorney for financial and health care decisions in case you are incapacitated.

A Thanksgiving meeting is also a good way to get input from your offspring on your estate planning. You’ll be able to determine who is best suited to share the responsibility of this process, and make sure they’re ready for it. Your children may challenge some of your own assumptions as well; for example, you may believe that your family will want to keep a vacation home and discover in the course of the conversation that they’d prefer to sell it.

It can be the first in a series of important conversations

Estate planning is far too weighty a topic to cover in one conversation. While a discussion on Thanksgiving is a good starting point, you should regularly revisit the subject in the ensuing months and years.

Your initial talk might simply make a checklist of what you’re looking to accomplish as part of your estate planning, then make a plan for an ongoing dialogue. Perhaps you’ll want to set up weekly or monthly check-ins to keep your children up to date on your plans.

Financial advisors can help you prepare a family meeting to discuss your estate planning. These professionals will also take a considerable amount of stress off your children while also providing helpful expertise in organizing your assets, making sound investment decisions, and minimizing tax liabilities. They’ll also coordinate with attorneys overseeing the legal aspects of estate planning.

Every major life event comes with a transition period. It happens with children starting school, people getting hired for a new job, and couples getting married. In each of these cases, there’s the initial excitement over a new chapter in your life, the nervousness about what lies ahead, and eventually a comfortable routine.

Retirement is no different. Once you’ve reached that point in your life where you can comfortably leave the workforce and enjoy your newfound freedom, you’re likely to be excited early on, then grow more restless before becoming accustomed to your new situation. 

All retirees typically go through a few stages of retirement, whether it’s over a period of a decade or just a few years. Here’s a look at what you’re likely to experience in each stage, and how you might adjust your investment decisions along the way.

Pre-retirement

The pre-retirement stage occurs when you become more concerned about your post-career life than any advancement or change to the career itself. At this point, you’ll likely be satisfied to continue in your current role until it’s time to retire.

Retirement planning is essential during the pre-retirement stage, which typically extends about five to 10 years before your actual retirement. This is the time to see how your retirement portfolio is performing against your expected retirement needs; if you’re running a little short, you may need to use this time to catch up with additional contributions or possibly pursue a more aggressive growth strategy. If your savings are on track, you may want to shift to a more conservative strategy aimed at preserving the assets you’ve built up.

Assess your current debts and expenses as well as the income sources you’ll have in retirement, such as savings, pensions, retirement funds, investments, and home equity. You’ll also need to consider some major changes that come with retirement, such as changes to your health insurance that come when you move off an employer’s plan and the possibility of downsizing to a smaller home.

By meeting with a financial advisor, you can use this information to set your retirement goals and realistically plan for a lifestyle you’ll be able to afford. This planning should be an ongoing, flexible process that extends into your retirement, helping to ensure that you don’t outlive your assets and that you have enough to leave something behind for your loved ones or a meaningful charitable cause.

Honeymoon

As the name suggests, the honeymoon stage is marked by excitement and optimism over your long-awaited retirement. You’re now free to spend your time however you’d like! 

This is also a time when retirees tend to splurge a bit, dipping into their savings to take a long-awaited dream vacation. Although it’s a major expenditure, it will also take up a smaller share of your overall savings and won’t have as substantial an impact on its growth potential as it would if you tapped into it later in life.

This stage is a good time to track your income and expenses, monitor your investments, and see how well your assets are supporting you. Your financial advisor can discuss any concerns you may have, and recommend strategies to meet upcoming expenses such as the potential for higher health care costs.

Disenchantment

The honeymoon period is usually rather brief. After awhile, retirees start to feel bored or frustrated with the succession of wide open days, and may feel like they’ve lost their sense of purpose. 

This stage may also be accompanied by growing concerns about your finances and whether you’ll be able to meet your needs as your retirement extends for several more years. This can also be a confusing time to set a budget due to factors such as required minimum distributions from retirement accounts, Social Security eligibility, and unpredictable health care costs.

This is an especially important time to take long-term care expenses into account and meet with your financial advisor on how you can continue to prepare for them. You should also review and update any documents related to the transfer of your assets in the event of your death or incapacitation, including your power of attorney, will, and estate plan.

Reorientation

During the reorientation stage, you’ve had time to experience retirement and can now consider what adjustments you’d like to make. Reorientation is all about finding a new purpose and pursuing new passions now that you’ve decoupled from work. You may find yourself volunteering more, taking on new hobbies, or creating a bucket list of travel destinations.

Some retirees decide during this phase that they’d like to return to the workforce, although this is usually in a seasonal or part-time capacity. Doing so can help give more structure to your days while also bringing in some extra income.

If you’re earning extra money through a job, your financial advisor can discuss options for investing this money. They can also update your retirement plan to adjust for any financial changes that your reorientation may create.

Routine

In this final stage, you’ve established an identity and daily routine you’re satisfied with. This is similar to the routines that come with earlier adjustments in life, but you’ll have more self-direction in your decisions.

Your finances should also be routine, in that your income should be enough to meet your expenses. Your financial advisor can help you monitor your assets to make sure this is the case, and can also help you make any adjustments necessary.

By Ted Reagle

With the Federal Reserve recently raising the target Fed Funds rate to the 5.25% to 5.5% range, now remains a great opportunity—the best in a long time—for retirees to lock in attractive low-risk returns for the portion of their retirement portfolio that they do not want exposed to stock market volatility. 

As we saw last year, even short- and medium-term bond funds were quite volatile and did not provide the countermeasure to stock market declines that investors anticipated. So, locking in guaranteed returns at attractive rates in the fixed income allocation of an IRA or other investment account can be very reassuring for investors, especially after enduring nearly a decade in which returns on CDs and U.S. Treasuries were anemic.

Today, interest rates on CDs, U.S. Treasuries, and money market funds are at their highest level in 22 years. Investors can currently earn in the 5% range on any of these low-risk investments. 

Interestingly, many retirees may not be aware that these rates are available to them because the bank or institution where their IRA accounts are held may not be publicizing or offering competitive rates. These low-risk investment choices can be readily bought in an IRA or taxable brokerage account at firms like Fidelity, Schwab, Vanguard, and many others.

The window to take advantage of these attractive interest rates could likely last for several more months before interest rates start to decline. Investment pundits anticipate that the Fed could increase rates by a quarter percentage point once more before the end of 2023, and that the Fed will begin to reduce rates either by the end of the year or in 2024 as inflation is brought down to the desired 2% range. 

The Fed has raised interest rates for the past 16 months to combat inflation. Higher interest rates tend to reduce demand for goods and services because borrowing costs are higher, which in turn cools inflation. Inflation peaked at 9% in 2022, but fell to 3% in August 2023. 

With the availability of 5% returns on low-risk investments, some retirees may be inclined to significantly reduce—if not completely eliminate—their allocation or exposure to the stock market. This could prove to be sub-optimal, however. Most retirement account investors will want to continue to invest a portion of their portfolio in the stock market to enable their accounts to continue to grow sufficiently and keep pace with inflation during their retirement years. 

Historically, fixed income investments such as the ones we’ve been discussing and longer term bonds  have earned in the 5% range. By contrast, the US stock market has earned in the 10% range, though stocks experience greater market volatility. 

A portfolio comprised of 60% stock and 40% fixed income investments has evolved into a “typically appropriate” allocation for retirement accounts that strike a good balance between the desire to minimize risk with the need for the portfolio to continue growing to sustain income throughout one’s retirement years. For many retirees, investing 100% in fixed income will not provide sufficient long-term returns to support a lengthy life expectancy.

Fitch ratings

I also wanted to touch on the recent news that Fitch Ratings, one of the major bond rating services, has downgraded U.S. government debt, generally perceived to be the safest and most risk-free investment available, from their highest rating of AAA to AA+.  This is the second time in history that U.S. debt investments have been downgraded, the other time being in 2011. 

Fitch cited the federal government’s growing deficit, now at $34 trillion, as one of the main reasons for the downgrade. The rating agency also cited factors including deteriorating confidence in the government’s fiscal management due to partisan divisions and repeated standoffs over the debt limit, higher interest rates, and the failure to address medium-term challenges related to government entitlement programs.

The government deficit continues to increase in 2023, and interest expenses are increasing $180 billion this year as the cost to service government debt has risen with the increase in interest rates.  And Social Security, Medicare, and Medicaid entitlement programs are expected to continue to grow as the US population continues to age. These programs account for two-thirds of all government spending. Finally, tax revenues are down 10% so far in 2023, further exacerbating the deficit.

While the federal deficit is worrisome, the Fitch downgrade should not discourage investors from investing in CDs or Treasuries. The U.S. dollar remains the reserve currency for the world. There is global demand to own Treasuries. The U.S. economy is growing, 2.4% in the most recent quarter. Inflation is coming down. So overall the U.S. economic picture looks pretty good.

Many older adults have high levels of regret about their finances, according to responses to a 2020 survey of Americans over age 50 conducted by the University of Michigan Health and Retirement Study.

The survey found that nearly 60% of participants regretted not saving more for retirement. Forty percent regretted not buying long-term care insurance, 37% regretted not working longer, and 23% regretted taking Social Security too early.

Financial regrets may be common, but they don’t have to be inevitable. And even if you have regrets about how you prepared for retirement, these errors don’t have to be permanent. There are options for course correction, even after you’ve stopped working.

Here are four tips to help you avoid or mitigate financial mistakes in retirement.

1. Plan for long-term care expenses

One mistake that clients may make after retirement is not considering long-term care planning,

including the potential need for nursing home or assisted living expenses. These costs can deplete your assets and put a strain on your loved ones.

Someone turning 65 today has almost a 70% chance of needing some type of long-term care services and supports in their remaining years, according to the U.S. Administration on Aging. The average person requires care for three years. 

You may want to explore options for long-term care insurance and create a comprehensive estate plan that addresses the potential costs of long-term care.

2. Account for inflation

Nearly two-thirds of retirees said inflation and the rising cost of living was the “biggest financial shock” in retirement, according to surveys conducted from January to March 2023 by Edward Jones and The Harris Poll.

Respondents cited inflation as a shock more often than the combined total of the next three top

responses — unexpected medical or dental expenses (22%), major home expenses or repairs (20%), and significant declines in the value of investments (19%).

If your earlier retirement planning didn’t account for high inflation, it might be time to re-examine your retirement finances.

3. Keep managing your investments

Whether it’s to deal with inflation or for any other reason, you might want to revise your investment and/or withdrawal strategies to help your money last in retirement. You should have a retirement income plan in place that matches your current lifestyle.

4. Prepare for surprises

Even with a good retirement income plan, your finances need to be ready to deal with surprises. Unplanned expenses such as a roof replacement or a large unexpected medical bill could cause problems.

Some of these problems might be harder to deal with now than in the past. Higher inflation means those unexpected expenses might cost more than before, while you’re also spending more on the day-to-day cost of living.

Plan to put some of your retirement income aside for unforeseen costs. An emergency fund of three to six months is generally sufficient to cover or defray these expenses.

By Brant Walker, Chief Investment Strategist

“Now is always the hardest time to invest, especially when the market is exhibiting schizophrenic behavior.” 

This statement could apply to virtually any period in the last three-and-a-half years, starting with the impact of the COVID-19 pandemic and its associated disruptions. Before we take a look at the first half of 2023, it will be useful to review the market trends that have characterized this uncertain period and what they mean for current and forward-looking investing climates.

How we got here

The year 2020 started on a high note, with the S&P 500 index closing 2019 with a stellar total return of 28.9%. Then the potential gravity of the coronavirus became clear in February 2020. In five short weeks, the S&P lost 33 percent of its value, bottoming out on March 16th.

Around that time, the federal government began rapidly printing money to buttress businesses that had to shut down and employees that were ordered to stay home, many of whom lost their jobs. This infusion of cash buoyed the market, and stocks finished the year up 16.3%. 

The year 2021 was also an excellent time for stocks due to continued money creation and the wide distribution of COVID-19 vaccines, which helped restore a sense of normalcy and optimism. The S&P 500 index again finished strong, with a 27% gain for the year.

The following year, reality set in. The elevated money creation of the previous two years led to excess demand, driving inflation to a 40 year high of over 9%. The Federal Reserve reacted, perhaps belatedly, by raising interest rates from zero to where they stand today, at just over 5%. The stock market acted as it often does in a period of sharply rising rates and dropped, tumbling 19.5%. 

2023 so far

After a brief but steep stock market loss in early 2020, followed by two years of strong returns, and another significant downturn in 2022, where are we today after the first two quarters of 2023? To date, the market has done another about face by returning close to 15 percent. Schizophrenic indeed.

We are dealing with an unusual combination of data points that will need to be carefully monitored and addressed as 2023 unfolds. First, the yield curve has been inverted for well over a year, meaning short-term interest rates (think money market funds and bank CDs) are higher than longer term interest rates. In normal times it would be the other way around. 

Money funds now pay close to 5% and some short-term CD’s can be had for 5.5%. Long maturity U.S. Treasury bonds are yielding under 4%. This is due to the Federal Reserve trying to slow the economy and raise unemployment to get inflation back down to the 2% range. 

Despite this effort, the economy remains resilient. The national unemployment rate is near a 40-year low, and inflation remains stubbornly above 2%. Fiscal policy in Washington is also hampering the Federal Reserve’s intention of lowering inflation, as government spending and new social programs continue to pour money into the system. 

It may take more time than anticipated to get inflation down to target, and this is a risk to the markets — both stock and fixed income. Hence, we are approaching the second half of 2023 in a cautious stance.

The impact of AI

We also feel it is worthwhile to spend a few moments on artificial intelligence (AI). Some say the growing capabilities of AI have the potential to change the world, similar to the invention of electricity and the automobile. Time will tell, but we do know that a handful of technology stocks that are on the forefront of AI have appreciated rapidly due to current hype and their possible future potential. 

The situation is similar to market behavior in 1999, when the internet was still in its infancy. Anything labeled internet, and any company that had .com attached to its name, soared in value. There’s a reason this trend was referred to as the “dot com bubble,” though. In March of 2000, the highly touted tech stocks came back to earth. Some took years or decades to recover to their 1999 highs. Some have never recovered.

The bubble also allowed a handful of companies to dominate the tech sector and drive the majority of market returns. A similar trend is happening today, with six stocks accounting for most of the year-to-date market return in the S&P 500. We don’t know exactly how the AI cycle will play itself out. History doesn’t always repeat,but it often rhymes.

Year-over-year market changes

The benchmark S&P 500 stock index has returned 19.6% for the year ending June 30, 2023. The benchmark iShares Core US Aggregate bond index ended the same period in negative territory, logging a -3.5% return. These returns are in stark contrast to calendar year 2022, when the S&P 500 logged a negative total return of 18.1% and the iShares Aggregate bond index lost 14.6%. 

Usually, one would expect bonds to act as a buffer when stocks fell as much as they did in 2022. In calendar year 2022, both stock and bond markets began, in retrospect, at levels that would prove to be highs for the year. Both markets plummeted in sawtooth fashion before reaching their lows on or around November 1. 

This was caused by the Federal Reserve lifting short-term interest rates from essentially zero to the 5% level that is prevailing today.  Early in 2022 most market participants expected interest rates to stay near zero or increase on a much slower trajectory than what has actually happened, causing stocks and bonds to plummet. 

Stocks have staged a strong recovery since last November as the market has become more comfortable with interest rates at 5% and the economy remains resilient. In addition, the labor market remains strong, and the unemployment rate sits near historic lows.

Economists have been predicting an economic recession for the better part of a year based on the “inverted” yield curve, where short-term interest rates are higher than long-term rates. Inverted yield curves often presage economic recessions as the Fed attempts to slow economic activity and cool inflation. Some market pundits have quipped that this is the most widely predicted recession that never happened, at least up until now.

Year-end forecast and expectations

Market performance in the back half of 2023 depends on several variables which are yet to unfold. The first and most prominent factor will be how far the Fed increases its interest rates before the economy and inflation cool to acceptable levels. Recent reports show the economy remains resilient, inflation is still too high, and job creation has been surprisingly strong. 

Elevated government spending based on recent bills passed in Washington is complicating the Fed’s action to slow the economy. Common stocks are highly valued based on historical standards, particularly with short-term interest rates above 5% and potentially headed for 6%. 

We may have to “thread the needle” in the back half of 2023 for the markets to remain resilient. Meaning inflation, the economy, and the labor market will need to cool without triggering a deep recession. We suspect the second half of 2023 may be more challenging than the first half.

By Ken Russell Jr.

Successful entrepreneurs are unique individuals with an affinity for risk-taking behavior that assists them in building their wealth. However, some of these very same traits can become a detriment to maintaining the assets they’ve created. There are three key characteristics that can often turn successful entrepreneurs into unsuccessful investors:

Control: Entrepreneurs, especially those who found their own companies, are known to be extremely controlling people. After all, they’re trying to bring their own vision to life and take the reins of numerous aspects of their business. Even if they employ others who assist them in running their company, the entrepreneur is the final arbiter of virtually every material business decision. 

When an entrepreneur is accustomed to being the decision maker on so many financial considerations involved in running a business, they’re often less willing to cede control of their investment decisions. They might also be overconfident in their own abilities, leading to the problems attendant in emotional investing.

Concentration: Doing one thing, and doing it extremely well, is frequently the key to entrepreneurial success in the United States. A concentrated focus on “owning” your business space is a proven path to growth.

While this focus is highly beneficial in running a business, it can lead to problems when entrepreneurs try to manage their own investment decisions. An entrepreneur may be an undisputed expert in the operations involved in providing a service or bringing a product to market, but that won’t often translate to an ability to navigate the complex issues involved in investing.

Use of Leverage: Entrepreneurs usually invest some of their own capital to start or expand a business, but they also tend to rely heavily on financial leverage. “Using someone else’s money” is an excellent way to increase the return on one’s own equity ownership in a business, as it preserves a founder’s personal capital, serves to spread some of the financial risk to either lenders or note holders, and supports the growth of the business.

Leverage can also strongly influence an entrepreneur’s approach toward investing, and it may be difficult to break this behavior later. They may be willing to favor a more conservative approach to avoid losing their own capital or the capital of their investors, but they may also favor a riskier approach when using borrowed money — a behavior which can carry over when investing personal assets.

From Entrepreneur to Investor

Now let’s say that a successful entrepreneur has reached the point where he or she is able to monetize their ownership in the business, perhaps through an outright sale or a significant distribution that transforms their illiquid investment into a fully liquid one. While this transaction can leave them with a sizable amount of capital, the characteristics noted above can significantly impede their ability to maintain or grow their assets.

For example, many years ago, my team and I visited with a nationally known businessman that had just sold his company for a significant amount of money. My team pitched him and his family on our investment process and a host of other wealth preservation services. His response was something along the lines of, “What you do sounds fabulous, but if you did that my sons would have nothing to do!”

He proceeded to trust his sons with the management of his wealth. Over the next decade, their poor decision making had cut the value of his portfolio in half. 

While it may take some time to accomplish, entrepreneurs can abandon the characteristics that made them successful in business when weighing their investment options. This will significantly increase the chances that they can sustain and grow their assets. Here are some tips on how to do so: 

Cede control and heed a financial advisor: Here’s the hard reality: while you may have been a professional business owner when you were running your company, you will be using an amateur advisor if you try to manage your liquid wealth by yourself. It’s akin to leaving the management of your company to an intern when you go on vacation. 

When you use a financial advisor, you’re still directing the strategic goals of the investment process. However, you’re ceding control of the day-to-day portfolio management process to professionals, who will be taking steps to ensure the sustainability of your money for decades.

Less concentration, more diversification: The business concentration that created your wealth in the first place will jeopardize it if you remain concentrated after you’ve acquired more liquidity. Sticking with what you know can be a form of risk mitigation when operating a business. Following this same strategy in public equity investing can be a fatal flaw.

Take steps to diversify your investments as soon as possible. For example, if you receive stock as part of the sale of your company, sell it as soon as your holding period requirements are met. If you’ve made your money in the private healthcare or services sector, don’t over-invest in the public side of those sectors when your wealth becomes liquid. 

Leverage your time, not your money: The use of borrowed money is an excellent return on investment optimizing strategy when running a business. But the continued use of margin debt in an equity portfolio is an unnecessary risk-taking behavior. 

To be sure, there may be occasional – and temporary – reasons to apply leverage to a portfolio if it involves optimizing the timing around tax deferrals or cost basis changes. But the continued use of leverage in an attempt to enhance portfolio returns – or fund one’s lifestyle – can have disastrous outcomes for your liquidity at the worst possible time. 

I’ve been in this industry long enough to witness unforeseen market events in 1987, 1998, 2000, 2007, and 2020. These events generated countless margin calls which decimated investor portfolios. 

An unleveraged portfolio has the ability to wait out equity market downturns. A nervous lender does not afford a leveraged portfolio the luxury of time.

To learn more about how a financial advisor can help you invest the wealth you’ve created through your business, contact Grey Ledge Advisors at 203-453-9075.

Investing in the stock market offers numerous opportunities for profit, but it also carries inherent risks. Market participants have used two popular investment approaches — the contrarian and trend following strategies — to try to enhance profits and minimize risk, to varying degrees of success.

In this blog post, we’ll explore the merits, drawbacks, and intricacies of each approach, providing insights for investors seeking to make more informed decisions in their pursuit of long-term success. We’ll also look at real-life examples of these strategies in action, including the pitfalls and challenges associated with each approach.

The Contrarian Approach: Seeking Value in Unloved Stocks

Contrarian investing involves seeking out-of-favor stocks with low valuations, as they often have most of the negative factors already priced in. While this approach may sound simple in theory, it requires a keen eye for detail, patience, and the discipline to execute an investment effectively.

Strengths: Contrarian investing can uncover hidden gems in the market, as undervalued stocks may offer significant growth potential once their true value is recognized by the broader market. This approach can also lead to lower portfolio volatility due to its focus on fundamentally strong companies trading at discounted prices.

Pitfalls: Identifying true value in out-of-favor stocks can be challenging, and investors must be prepared to weather disappointments and potentially prolonged holding periods. For instance, AT&T and Verizon are businesses that, on paper, appeared to be great contrarian investment opportunities due to their low valuations. However, the negative price action ultimately proved justified due to managerial overspending and a continuing decline in revenues. These cases illustrate the importance of being meticulous about which businesses you select for contrarian investing.

Example: Unilever, which underperformed due to the management’s search for a “purpose” for their brands, resulting in a price multiple difference between the European conglomerate and its US competitor Proctor and Gamble. Contrarian investors saw potential in Unilever’s valuable brands and the involvement of activist investors. Today, the company has caught up to P&G — and significantly outperformed this competitor — as it has focused on profit, changed its business divisions, and announced an external CEO with a great track record of growing brand-oriented businesses, who will be taking over in July 2023.

The Trend Following Approach: Riding the Momentum of High-Performing Stocks

Trend following investors seek to capitalize on the momentum of stocks with strong price performance, trusting that better-performing companies will continue to outperform their competitors. This approach requires investors to buy and hold more expensive stocks, often in the face of market noise and short-term fluctuations.

Strengths: Trend following can generate significant returns when executed well, as market leaders often continue to deliver strong performance over time. This approach can also benefit from the compounding effect of reinvesting gains into high-performing stocks.

Pitfalls: The trend following approach carries the risk of entering positions too late or failing to exit before a trend reversal. Additionally, trend followers may be prone to herding behavior, driving stock prices to unsustainable levels and creating market bubbles. In such cases, investors who do not exit in time may experience significant losses.

Example: In the beginning of the last decade, Apple began to outperform and grow bigger than Nokia, the leader in smartphone manufacturing at the time. Apple’s stock price became very expensive as it factored in a higher market share for phones, and many investors fled for less expensive Nokia shares. True trend following investors stayed invested in Apple, which dominated the smartphone industry over the next decade.

Strategies for Success in Contrarian and Trend Following Investing

To maximize the potential benefits of these investment approaches, investors should:

1. Develop a clear understanding of their risk tolerance, investment goals, and level of expertise.

2. Conduct thorough research on the companies they invest in, analyzing fundamentals, competitive position, and management quality.

3. Stay informed about market trends, economic indicators, and geopolitical events that may impact their investments.

4. Regularly review their investment portfolio, rebalancing and adjusting positions as needed based on changing market conditions and individual circumstances.

By considering these factors and understanding the potential pitfalls of each approach, investors can make more informed decisions and increase their chances of achieving long-term investment success.

At Grey Ledge Advisors, we believe that a successful investment strategy cannot be bound by a single approach but should rather be adaptive to various market environments. Our investment philosophy is rooted in a holistic blend of contrarian and trend following methodologies, allowing us to take advantage of opportunities across the full spectrum of market conditions. We strive to take a nuanced, opportunistic view of the market landscape, considering both the potential undervalued gems and the high-performing trendsetters in our decision-making process.

By integrating these complementary approaches, we aim to balance risk and reward, seek consistent returns, and ultimately, strive towards fulfilling our clients’ financial goals.

By Brant Walker

Like most processes, investment decisions moved more slowly in the pre-Internet days. When I started my investment management career nearly 40 years ago, a bank or analyst would send you a report through the mail — a multi-day process in itself — and you’d spend a day processing it before making your choices.

Today, anyone trying to invest on their own is being bombarded by information from all sides. Between 24-hour news networks, business news websites, social media chatter, and the ability to track a stock’s performance literally minute-by-minute, it can be difficult to choose how to proceed.

This noisy environment has only heightened the emotional aspects of investing. There has been extensive research into “behavioral finance,” or how human psychology affects investment decisions — often negatively. By better understanding this concept, you can put more trust into unbiased indicators, building your portfolio based on impartial information rather than gut feeling.

How emotions affect investment decisions

Many emotions come into play when you invest your money. You may be anxious about meeting your financial goals, excited to see your portfolio grow in value, eager to find investments that will produce a huge return on investment, nervous about market downturns, or depressed when an investment decision turns out to be a poor one.

Emotion-driven decisions can occur at any time. Some examples include:

However, emotion has the biggest impact on the market during periods of prominent gains or losses. During a strong market, people are more likely to underestimate risk, be overconfident in their own abilities, and chase after popular investments. During market downturns, people are more likely to panic and sell off investments in an effort to limit losses.

There are also several cognitive biases that affect investment decisions. One of the most common is confirmation bias, where people only consider evidence that supports their investment decisions and ignore other data, such as warning signs that a stock might be overvalued. 

Anchoring bias is also a common factor that influences investment decisions. This occurs when you measure the performance of an investment on some irrelevant point of reference, like the price of a stock when you purchased it or a stock’s previous peak value. 

Greed and fear

Greed and fear are the most powerful emotions affecting investment decisions. Greed spurs people to pursue higher gains by making riskier decisions, taking chances on speculative stocks, and pursuing short-term gains. Fear is the dominant option during bear markets or more volatile conditions, causing people to favor lower risk investments with smaller yields.

Concerns about losing your hard-earned money are a particularly potent factor in behavioral finance, leading to something called loss aversion bias. This occurs when a person gives priority to minimizing losses on their investments instead of actively pursuing gains. 

Loss aversion bias can lead to considerably different investment decisions. Since people tend to be more risk-averse when faced with a positive income, they might sell a well-performing stock too early out of fear that its value might go down. Conversely, they may also engage in riskier behavior in an effort to avoid losing money, such as doubling down on a declining investment in hopes that it will recover.

Optimism and pessimism

Market trends drive the broader emotions of optimism and pessimism, which also tend to cause people to make buying or selling decisions at the exact opposite of the optimal time. When the market is on the upswing and stock values are rising, people are optimistic and more willing to buy. When values are declining, people are more pessimistic, less willing to buy, and more willing to sell the stocks they have in an effort to avoid losses.

You might notice that these decisions directly contradict the classic “buy low, sell high” investment strategy.

Two recent market downturns show how a pessimistic outlook can impact your investments. Tumbling stocks during the Great Recession drove investors to pull their money from the market, only for stock values to grow steadily over the next several years during the economic recovery. There was a similar response when the stock market cratered at the start of the COVID-19 pandemic, with stock values recovering even faster.

Once more, without feeling

When investing your money, you should always take the time to research your options and avoid quick decisions. While monitoring the performance of your investments is important, tune out the noise and do periodic check-ups instead of frequent adjustments; this can help you retain focus on a long-term strategy instead of responding to short-term trends.

Other strategies to take the emotion out of investing include:

Working with an investment advisor will also help you avoid emotions when investing. This professional will provide you with unbiased recommendations and help you determine your goals and strategies.