ESPPs: Employee Stock Purchase Plans (Easy Street Pretty Please?)

Are you lucky enough to be an employee who receives benefits in the form of equity? There is a mélange of ways companies can incentivize and reward their employees via equity, and employee stock purchase plans (“ESPPs”) are a well-known perk. This discussion will focus on qualified ESPPs, or Section 423 ESPPs, as they must meet regulatory requirements to offer tax advantages. In contrast, non-qualified ESPPs are more flexible regarding regulatory requirements but do not offer tax advantages. It is always prudent to check which type of plan you have before making any investment decisions.

ESPPs are relatively simple as far as contributions go. They are funded by after-tax payroll deductions and there is no withholding, not even for Social Security or Medicare. The deductions are held in the plan until a specified purchase date, at which point they are invested in company stock. Participants state the amount they want to contribute to the plan, which the IRS limits to $25,000 of the stock’s market value per year, and plans generally allow participants to elect deductions between 1% and 15% of a participant’s compensation.

ESPPs offer discounts and lookbacks. Most ESPPs build in a 10-15% stock price discount below market value. Then the lookback provision bases the purchase price not on the stock price at the time of purchase but on the price either at the beginning of the offering period or at the end of the purchase period, whichever is lower.

The tax treatment is a bit more complicated, but stay with me. When you sell the stock, you either pay ordinary income tax (called a disqualifying disposition) or long-term capital gains tax (called a qualifying disposition) on the gain, and you pay ordinary income tax on the discount. To receive the favorable long-term capital gains treatment, you have to hold the shares for more than one year from the purchase date and more than two years from the offering date. If you hold the shares according to these guidelines, you receive a lower percentage of ordinary income taxes and a higher percentage of capital gains taxes, which means you pay less in taxes overall.

Here’s an illustration of the tax treatment for both disqualifying and qualifying dispositions for those who are inclined.

Assumptions:
Offering date price $10 
Market price on purchase date $12
Purchase price @ 10% discount with lookback = $9
Sell price = $14

Disqualifying disposition:
< 2 years from offering date and < 1 year from purchase date
Market price on purchase date – purchase price = ordinary income
$12 – $9 = $3 ordinary income
Sell price – tax basis* = short-term capital gain
$14 – $12 = $2 short-term capital gain

Qualifying disposition:
> 2 years from offering date and > 1 year from purchase date
Offering date price – purchase price = ordinary income
$10 – $9 = $1 ordinary income
Sell price – tax basis* = long-term capital gain
$14 – $10 = $4 long-term capital gain

*Tax basis = ordinary income + purchase price

In both examples, the tax burden is the same, a total of $5. However, the disqualifying disposition is broken down into $3 taxed at ordinary income rates and $2 taxed at short-term capital gains rates. The qualifying disposition is broken down into $1 taxed at ordinary income rates and $4 taxed at long-term capital gains rates. Therein lies the savings from observing the hold periods.

Let’s not forget about the discount either. While the 10% discount in the above examples may not seem like a significant amount, it can add up with share volume and is basically free money. What would you do if I offered to give you $10 in return for you giving me $9?

Accumulating shares over time through an ESPP can help build wealth. Still, you need to be careful not to end up with a concentrated position that exposes you to unnecessary risk should your company encounter adverse circumstances. You also need to account for your access to other stock-related benefits, including stock awards, restricted stock units, and stock options, and how this might add additional exposure. The key with all investing is diversification, so any ESPP holdings should be appropriately allocated within your global portfolio, which in and of itself should be rebalanced as your company holdings increase over time.

Your Next Healthy Habit: The HSA

One of the top 10 questions I get from clients is should I open an HSA (Health Savings Account)? It is open enrollment season and HSAs have risen in popularity over the last few years, so let me take the opportunity to address the question here.

First, what are HSAs?

HSAs are personal savings accounts that can only be used for qualified health care expenses and out-of-pocket costs not covered by health plans. They offer tax benefits, spending flexibility, and portability.

Second, who is eligible?

To contribute to an HSA, you must be enrolled in a qualifying high-deductible health plan (HDHP). For 2022 the HDHP for individuals must have a deductible of at least $1,400 and an out-of-pocket medical expense limit of $7,050, and the HDHP for families must have a deductible of at least $2,800 and an out-of-pocket medical expense limit of $14,100.

Third, how do I get one?

You can enroll in an HDHP and an HSA through your employer if available, or find an HDHP on the health insurance marketplace and an HSA through a financial institution.

Here is a summary of the advantages and disadvantages of HSAs:

Advantages:

  • If you make contributions with pre-tax dollars, they are excluded from your gross income.
  • If you make contributions with after-tax dollars, you can deduct them from your gross income on your tax return.
  • Contributions can earn interest and be invested.
  • Your investments can grow and compound on a tax-deferred basis, which means there are no capital gains taxes on earnings.
  • Withdrawals are tax-free for qualified health care expenses.
  • You don’t have to make withdrawals in the year that the expenses are incurred (just save the receipts for the year in which you do make the withdrawals).
  • Any unused money at the end of the year rolls over to the next year (unlike Flexible Spending Accounts (FSAs)).
  • The account is always owned by you even if you change employers or terminate employment.
  • When HSA money is used to pay for health care costs in retirement, it has more buying power than money from retirement plans like 401ks where you will owe income taxes on withdrawals.

Disadvantages:

  • It can be challenging to budget how much to save as medical expenses are often unpredictable.
  • HSAs have low contribution limits – the 2022 contribution limit is $3,650/year for individuals with additional catch-up contributions of $1,000 between ages 55 and 65. (This amount is reduced by any employer contributions excluded from gross income.)
  • Once you enroll in Medicare at age 65 you can no longer contribute.
  • If you withdraw funds for nonmedical expenses before age 65, you will have to pay income taxes on the money and an additional 20% penalty. If you withdraw funds for nonmedical expenses after age 65, you don’t have to pay a penalty but you will have to pay income taxes on the money.

For an HSA to be worth it, you should be relatively healthy and good with recordkeeping. If this describes you, consider adding HSAs to your financial to-do list. “I don’t like tax savings” said no one ever.

Quarantine Dispatch

It is a time of tremendous contradiction in the economic world. Stocks and bonds are moving more in tandem than ever. Unemployment is at a high not seen since the Great Depression yet the market is only in correction territory, which means a drop of 10% that happens on average every 12-24 months. The level of personal savings has surged and personal income has increased, but personal spending has fallen drastically. What can account for these disconnects?

Another way to put it is, why on earth is the market doing so well when the economic forecast is so dismal? It could be that health data has leveled off and the vaccine narrative has accelerated so psychological panic has subsided. It could be the short-term effect of trillions of stimulus dollars the Federal Reserve is pumping into the economy to shore up liquidity. It could be that today’s stock market prices accurately reflect the post-Covid economic landscape. It could be the unflagging optimism that is the warp and woof of human nature.

The federal government acted swiftly and massively in their monetary and fiscal stimulus efforts and it made a difference. For now deflation is winning over inflation. The supply chain has not seized up. The Federal Reserve has indicated their willingness to provide more stimulus and Congress is currently negotiating the HEROES Act, which may include more help for state, local, and tribal governments, an extension of unemployment benefits, and more household payments. There seems to be no end in sight for relief as long as the need persists.

We know that the stock market discounts future earnings to yield today’s prices, which means that the recovery is already priced in. The Efficient Markets Hypothesis (EMH), a cornerstone of modern financial theory, states that at any given time stock market prices reflect all available information. The EMH rules out the possibility that investors can time the market or use fundamental or technical analysis to identify securities that are over- or undervalued. However, we know that EMH is inadequate if we consider Warren Buffet’s outperformance of the market over long periods of time.

Investor optimism makes things even rosier. Behavioral finance theory, which addresses the psychology of investors and how their cognitive biases affect stock market outcomes, could help to explain the gap between perception (the stock market) and reality (the economy). Behavioral finance states that investors are not rational or self-controlled and as such make emotional decisions that defy economic theory. We could be seeing hints of Alan Greenspan’s “irrational exuberance” here, although we are far from a speculative bubble.

What happens next? No one has a crystal ball and the best we can do is make educated guesses. Many financial experts predict that the stock market bottom we saw on March 23 will be retested due to increased mobility and a consequent second wave of infections. But that second wave has not yet come. With restrictions lifted across the county, people have been slow to return to past habits. We have not seen appreciable increases in TSA checkpoint travelers, hotel occupancy rates, or dine-in restaurant attendance in locations that have reopened. It is possible – and I am hopeful – that the increased mobility will be mitigated by a beneficial combination of warmer weather, differences in individual susceptibility to infection, social distancing, hygiene practices, and widespread testing and follow up.

Socially Responsible Investing Comes of Age

For many contemporary investors, portfolio construction goes beyond diversification and asset allocation. At the beginning of 2018, more than a quarter of professionally managed portfolios in the U.S. used socially responsible, sustainable, or impact investing strategies, accounting for $12 trillion in assets overall, according to the Forum for Sustainable and Responsible Investment (also known as US SIF). To the surprise of many, this growing trend is not limited to the millennial demographic, extending across all age groups as more investors seek to align their portfolios with their values.

What is all the excitement about? Here are the three models that generally define the social investment movement:

Socially Responsible Investing
Introduced in the early 1970s, this model of investment was based on screening out or excluding problematic companies from portfolios. Companies were excluded based on their involvement in negatively viewed topics such as weapons, alcohol, tobacco, gambling, fossil fuel production, and so on.

Sustainable Investing
Introduced in the early 2000s, the focus shifted from the exclusion of offending companies from portfolios to the inclusion of companies based on positive screens. These screens are known as ESG screens, which stands for environment, social justice and corporate governance. Positive ESG company profiles can emphasize environmental sustainability, human rights, consumer protections, and diversity, among other issues.

Impact Investing
In 2007, the term impact investing emerged. Impact investing refers to investing in companies that are developing solutions to global sustainability challenges. These challenges include climate change, sustainable agriculture, renewable energy, access to education, affordable housing, and improved health care, among other topics. The impact investing platform also recognizes companies that promote women’s leadership and gender equality, and companies that support community investing, including microfinance services. Notably, these companies also engage in shareholder advocacy and solicit public engagement.

Investors today have more investment choices than ever before, and the dynamic social investment realm is compelling. Investors truly can make a difference by tilting their portfolios toward companies prioritizing the triple-bottom line of people, planet and profit. And the profit component should not be underestimated – since US SIF began tracking the data in 1995, social investments have had a compound annual growth rate of 13.6%. This should prove once and for all that there doesn’t have to be a compromise on returns compared to conventional investments, and depending on the benchmarks, the social investments may even outperform.

For sources, see Bloomberg News.

College Savings Plans: The Magic Number is 529

For a standout option for college savings, look no further than 529 plans. 529 plans are investment accounts with tax-deferred earnings and tax-free withdrawals, as long as they are used for qualified education expenses. 529 plans, also known as “qualified tuition plans,” are sponsored by states, available directly from plans or through advisors, and take their name from Section 529 of the Internal Revenue Code.

There is a second, little-known category of 529 plans called “prepaid tuition plans,” somewhat antiquated plans where you can lock in a tuition rate through the purchase of credits. However, these plans have many limitations and states are beginning to drop them. The first category of 529 plans discussed here have far greater visibility and popularity.

Along with tuition, 529 plans can be used to pay for qualified education expenses including room and board, fees, books, computers and related equipment, and supplies. However, earnings on withdrawals used for non-qualified expenses are subject to federal and state income taxes and a 10% federal penalty tax. 529 plans offer flexibility with choice of schools and can be used at a variety of institutions, including colleges, universities, trade or technical schools, and some foreign schools.

In addition to the benefit of tax-deferred earnings and tax-free withdrawals, some states offer tax deductions or credits for 529 plan contributions. In many cases, if the maximum deduction is met in one year, the deduction can roll over into subsequent years. Almost all states mirror federal law and offer state tax exemptions on withdrawals.

You don’t have to save in your state’s plan. The key is to first look at your state for tax deductions or credits, and if there is one, it usually makes the most sense to claim it. But if you live in a state with no income tax or you don’t have any tax deductions or credits available, by all means shop around with other states’ plans and compare and contrast their performance.

529 plans are very accessible, with investment minimums as low as $10 and high contribution limits. Individuals can apply the $14,000 annual gift tax exclusion to their contribution for one year ($28,000 for couples), or make up to 5 years worth of contributions at once by contributing $70,000, without triggering the gift tax ($140,000 for couples). For high-net-worth folks, this gifting strategy can be used to reduce the size of their taxable estate. Lifetime maximum account values are between $300,000-$400,000 per beneficiary, depending on the state, and a beneficiary can have multiple accounts as long as the total money in all accounts does not exceed the state limit on contributions. Anyone can contribute to 529 plans – grandparents, parents, aunts, uncles, friends, and so on.

The 529 account owner retains full control of the assets throughout the lifetime of the account, including the right to take the money back (although this would be a non-qualified withdrawal and subject to federal and state income taxes and the 10% federal penalty tax). If the original beneficiary gets a full scholarship, ends up with an unused balance, or doesn’t go to college, the account owner can change beneficiaries or transfer assets to another family member, as many times as needed. The IRS’s definition of family member is generous, including step-siblings and first cousins, for example. Account owners can also use the plan for their own educational needs.

To minimize impact on financial aid, it’s generally best for 529 account owners to be the custodial parent(s). Assets in a 529 plan held by a custodial parent count against need-based aid up to a maximum of 5.6%, whereas withdrawals from a 529 plan held by grandparents or non-custodial parents are considered untaxed income to the beneficiary the following year, and could reduce need-based aid by as much as 50%.

529 plans exclusively use mutual funds and offer two investment options. The first is an age-based portfolio option, similar to a target date retirement fund, where the investments shift from aggressive (high percentage of stocks) to conservative (high percentage of bonds and cash) as the beneficiary gets close to college age. The idea is that the portfolio increases the chance of gain early on and reduces the risk of loss later on. The second option is a static portfolio, where the funds stay the same over time, and the account owner rebalances as they see fit, up to once a year. Within both of these options you can still choose your risk tolerance and have a diversified portfolio. 529 plans are undeniably worth it – as JP Morgan Asset Management tracks it, even in its worst 18-year period, a 50/50 mix of stocks and bonds outperformed tuition inflation.

Lastly, a quick note about direct-sold versus advisor-sold plans. Advisor-sold plans have on average a 4.75% commission attached to them, increasing plan cost and cutting into plan returns. According to Morningstar, most 529 plan assets are invested in age-based portfolios, which are automatically rebalanced over time, and account owners tend to stick with this allocation. It makes you wonder, what is the need for an advisor then? In fact, Morningstar’s 2016 ranking of the best 529 plans overwhelmingly puts direct-sold plans at the top of the list.