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Employee Benefits Explained: A Complete Guide for Employees

Based on the conversations we have with prospects and newer clients at Stillwater, the average American worker spends less time on their employee benefits elections than they should. Why? Most people do not understand their options. It’s overwhelming and time consuming to learn.

What if I told you that for high performing professionals, those benefits could be equal to 30-40+ percent of your total compensation. Would you spend more time or consider hiring a professional to support you in making those decisions? Most should.

When Stillwater thinks of employee benefits, we break it down into different categories to help our clients mentally account for everything. Here in this post, we will focus on numbers one and two.

  1. Medical & Healthcare Benefits
  2. Dental & Vision Benefits
  3. Income Protection Benefits
  4. Retirement & Financial Wellness Benefits
  5. PTO & Leave Benefits
  6. Voluntary & Supplemental Benefits
  7. Executive & Specialized Benefits
  8. Wellness & Fringe Benefits

Medical & Healthcare Benefits

  • Health Insurance (HMO, PPO, EPO, POS & HDHP)
  • Health Savings Account (HSA)
  • Flexible Spending Account (FSA)
  • Dependent Care FSA
  • Health Reimbursement Account (HRA)

Health insurance tends to be the one area of employee benefits where people spend the most time. However, they tend to focus purely on the cost of the monthly premium. For those starting their careers, cost is a major factor. For high performers with strong cash flow, we help them shift their mindset from cost alone, to benefits and cost as a pair. First, it’s helpful to understand the different types of health insurance plans offered.

Health Maintenance Organization (HMO)—where doctors, hospitals, and other healthcare professionals have agreed to accept payment at a specified level for any service they perform in a dedicated network

  • Typically, the least expensive option due to the smaller provider network
  • In network coverage only—pay full cost for out-of-network care
  • Primary care physician (PCP) acts as gatekeeper for specialist referrals

Preferred Provider Organization (PPO)—the plan with the most freedom

  • Most expensive option because it offers in-network and out-of-network coverage
  • Larger networks come with higher cost
  • No PCP referral required

Exclusive Provider Organization (EPO)—a hybrid health insurance plan that operates like an HMO by strictly covering in-network care, but mirrors a PPO with a larger network and by eliminating the gatekeeping of a PCP in some cases

  • Lower monthly premiums than PPO plans while maintaining a large network
  • In network coverage only—pay full cost for out-of-network care
  • Potentially a good choice if your preferred doctors are all in-network

Point-of-Service (POS)—another hybrid health insurance plan but more expensive than EPOs due to the ability to seek out out-of-network care with a referral

  • PPO, POS, EPO, HMO & HDHP → order from most expensive to least expensive as a general rule—can vary by carrier, region, and group size
  • Flexibility to see out of network doctors for care
  • May still require PCP for coordination of care

High-Deductible Health Plan (HDHP)—most commonly structured as PPOs but IRS determines eligibility based upon deductible and out-of-pocket max

  • Lowest premiums, but highest deductibles and out-of-pocket maxes (OOPM)
  • Large networks and specialist referrals not required for PPOs
  • No primary care physician (PCP) required for PPOs

Health Savings Accounts (HSA)—paired with high-deductible health plans (HDHP) acting as a savings or investment account for qualified medical expenses

  • Triple tax advantaged: tax deduction for contributions, grows tax free, and can be distributed tax free if used for qualified medical expenses
  • Limits: $4,400/single | $8,750/family for 2026
  • Some employers will make contributions—does not expand the annual limits
  • Portable if you leave your job—unlike FSAs or HRAs
  • Eligible for those with ACA Bronze or Catastrophic plans for those on marketplace

Flexible Spending Account (FSA)—employer-sponsored, tax-advantaged spending accounts used to pay for out of pocket qualified medical expenses commonly paired with HMO or PPO plans

  • Employer owned, unliked HSAs which are employee owned and managed
  • Contributions are pre-tax and effectively become a tax deduction, like HSAs
  • Limits: $3,400 per person | $680 annual rollover of unused funds for 2026
  • Use it or lose it—have to use rollover within 2.5 months otherwise funds go back to your employer—all employers do not offer the rollover or grace period

Dependent Care FSA—just like a healthcare FSA, except for qualified dependent care expenses

  • Employer owned, tax-advantaged spending account
  • Contributions are pre-tax and treated as a tax deduction
  • Limits: $3,750/year Married Filing Separately | $7,500/year Single or Married Filing Jointly for 2026
  • Use it or lose it with no rollover eligibility but grace period to file claims for prior year qualified expenses—company specific rules

Health Reimbursement Account (HRA)—paired with HMO or PPO plans, an account funded by employers to help employees reimburse themselves for qualified out-of-pocket medical expenses

  • Account owned, managed, and contributed to by employer
  • Annual contributions outlined by employer and subject to change
  • Helps employees cover their deductible and potentially other qualified out of pocket medical expenses beyond that
  • Employer determines rollover eligibility, if any, otherwise use it or lose with no portability between jobs

This shows the level of depth we offer clients here at Stillwater Private Wealth. Education plays a large role so clients can make informed decisions.

Key terms to know include deductible, out-of-pocket max (OOPM), co-pays, co-insurance percentage, drug formulary, and more. The deductible tells you what you are responsible for before most insurance coverage kicks in. You meet your deductible first with the help of certain co-pays, more insurance coverage then begins with co-insurance, your out-of-pocket max is eventually reached at which point insurance covers the rest of qualified medical expenses. Whether those expenses are incurred in or out-of-network is important to consider as the financial implications can be wildly different.

That is an oversimplified explanation and summary of key terms, but those are just the most common you will run into. There are countless other terms, deadlines, maximums, and considerations to keep in mind. It becomes its own job. The most important things to understand from a financial planning perspective are your deductible, out-of-pocket max, drug formulary, and in-network providers.

Dental & Vision Insurance

Dental and vision insurance work similarly in the sense you pay a monthly premium, they include deductibles, co-pays, and co-insurance percentages, but tend not to have out-of-pocket maxes (OOPM) like their health insurance counterparts.

Understanding your network, coverage in and out of network, and plan type is equally important. Common dental coverage typically includes preventative care costs like cleanings, exams, and X-rays, a percentage of basic procedures like cavities or extractions, and a lower percentage of major procedures like crowns, bridges or dentures.

Common vision coverage typically includes annual exams, an annual eyewear allowance for contact or eyeglass frames, and lenses covered in full or with a co-pay. Eye related surgeries are covered by health insurance if they are deemed medically necessary, otherwise they tend to not be covered by vision insurance alone.

Large dental or vision bills tend to surprise employees who do not take the time to fully understand their coverage. Relying on your doctor’s office to understand the financial impact can be costly mistake because they get paid one way or another.

Income Protection Benefits

  • Group Term Life Insurance
  • Group Permanent Life Insurance
  • Group Short-Term Disability (STD)
  • Group Long-Term Disability (LTD)
  • Accidental Death & Dismemberment (AD&D)
  • Critical Illness, Accident & Hospital Indemnity Insurance

Retirement & Financial Wellness Benefits

  • 401(k) Plans
  • 403(b) Plans
  • Stock Options (ISOs/NSOs)
  • Restricted Stock Units or Awards (RSUs/RSAs)
  • Pension Plans or Defined Benefit Plans
  • Retirement Benefit Accounts
  • Trump Account Contributions
  • Student Loan Assistance

Paid Time Off & Leave Benefits

  • PTO
  • Paid Holidays
  • Jury Duty
  • Bereavement Leave
  • Personal Leave
  • Sick Leave

Voluntary & Supplement Benefits

  • Pet Insurance
  • Legal Plans
  • ID Theft Protection
  • Supplemental Life Insurance

Executive & Specialized Benefits

  • Deferred Compensation Plans
  • Directors & Officers (D&O) Liability Insurance
  • Executive Disability Coverage

Wellness & Fring Benefits

  • Wellness Stipends
  • Health Insurance Stipends
  • Gym Memberships
  • Commuter Benefits
  • Remote Work Stipends
  • Tuition Assistance
  • Professional Development

If this feels like a lot, it’s because it is. That is why it can equal 30-40+ percent of total compensation packages for high performing professionals. There’s a lot to consider and doing so alone could mean leaving money on the table or being unaware of gaps that could impact your financial plan.

This is why we help clients at Stillwater navigate their open enrollment periods. For those who work for themselves, we help connect you with employee benefit specialists, insurance brokers, and help you identify the right retirement plan for you and your business.

Open enrollment is either here now, or right around the corner. Take the time to review your benefits this year or hire someone who can help.

DISCLAIMER 

The information provided does not constitute medical, insurance, legal, tax, or financial advice. Before making any medical, insurance, investment or financial decisions, you should consult with a medical professional, qualified insurance professional, attorney, tax advisor, or financial professional who can consider your individual circumstances.

SOURCES

+ Aetna. Accessed July 2026. HMO, PPO, POS, EPO, & HDHP: What’s the Difference? Information describing common types of health insurance plans and their features. Accessed July 2026. (aetna.com)

+ Aetna. Accessed July 2026. HSA vs. FSA vs. HRA: What Is the Difference Between Them? Information comparing health savings accounts, flexible spending accounts, and health reimbursement arrangements. (aetna.com)

+ HealthEquity. Updated April 2025. Health Reimbursement Arrangements (HRA) Guide. Information explaining how health reimbursement arrangements work and their key benefits. (healthequity.com)

+ Principal. Accessed July 2026. Dental Insurance. Information describing dental insurance coverage, benefits, and plan options. (principal.com)

+ Guardian. Last updated January 30, 2026. Life Insurance vs. Disability Insurance: Why You Should Consider Having Both. Last updated January 30, 2026. Information comparing life insurance and disability insurance and their respective purposes. (guardianlife.com)

Back To School: Education Planning & 529 Roadmap

Historically, education planning has been viewed solely as college tuition and room & board planning along with some other ancillary expenses you incur along the way. As a former college student, that is just the beginning of the costs.

With the passing of the One Big Beautiful Bill Act (OBBBA) last year, education planning should be viewed in an even more comprehensive manner. At Stillwater, our job is to educate our clients about the tools they have at their disposal, which expenses qualify, and help them make informed decisions.

However, the question on many parents’ minds is how will education evolve? It is already so expensive. Will the cost of education continue to rise at this rate? Will college even be necessary in the future with AI? How does this change planning?

Higher Education Still Pays

The future education landscape may evolve, but the value of education, especially higher education today still persists. According to JP Morgan’s College Planning Essentials: 2026 Edition, the average annual earnings by highest educational degree are as follows:

  • High School Graduate—$50,410/year
  • Bachelor’s Degree—$91,430/year or 81% higher
  • Professional Degree—$177,000/year or 251% higher

In short, higher education continues to pay and it is not yet showing signs of reverting despite AI momentum mounting. However, the selected major plays an important role in determining the return on your investment. The average salary between a computer science major and education major is stark. If you plan on taking on student loans, this is a vital part of the decision-making process.

So, how is Stillwater addressing the uncertainty in education’s future evolution in our planning? For those with education related goals, we often find that a combination of 529 plans and taxable accounts tend to be the optimal solution.

529 plans are used for dollars earmarked for K-12 tuition, certifications, or college tuition, room & board, and other qualified education expenses. Taxable accounts then provide flexibility to help those concerned with overfunding 529 plans earmark dollars for similar goals without subjecting them to potential penalty if things change. They also allow you to pay for non- qualified expenses that you incur along the way related to education.

The key is making sure those dollars are working for you in the market, regardless of the account type. A savings account at your local bank likely won’t cut it, despite where rates sit today.

529 Plan Overview: Savings Plans vs. Pre-Paid Tuition Plans

A 529 plan can either be a tax-advantaged education savings plan or pre-paid tuition plan. Both are designed to pay for qualified education expenses. The savings plan offers the opportunity to invest contributions, which comes with market risk, but also the opportunity for higher returns. Most state plans over managed investment allocations as well as the option to make your own investment decisions.

Pre-paid tuition plans lock in current tuition rates, meaning your returns are effectively equal to the rate of tuition inflation. However, the plan is often tied to public in-state college tuition, so it doesn’t account for children picking different universities. This introduces the risk that the eventually chosen school’s tuition rises faster than the public in-state benchmark.

This century, the annual average college tuition inflation has been nearly 4% compared to an inflation rate of 2.56%. What this should tell you is that investing towards these goals to keep pace or outpace that historical inflation rate associated with higher education is a required for most, not an option.

Contributions & Taxes: 529 Plans vs. Taxable Accounts

Focusing on 529 Savings Plan vehicle, who can contribute? Parents, grandparents, beneficiaries, extended family, and friends. At the same time, it’s important to understand the FAFSA impact certain kinds of 529 Plan ownerships might have for those trying to qualify. For example, grandparent-owned accounts do not count toward FAFSA calculations, but parent-owned accounts do.

How much can you contribute? It depends on a few factors. The average investor will want to keep the annual gift tax exclusion in mind, which is $19,000 for 2026 per person. That means a married couple can give a single beneficiary as much as $38,000 combined this year. However, for married couples who want to front load contributions, that option exists as well. Those who exceed these annual gift tax limits or superfund will have to file gift tax returns as a result. See a summary below:

  • Annual Gift Tax Exclusion—$19,000/per person for 2026
  • Superfunding Limits—$95,000/per person per beneficiary
    • Or, $190,000/per person per beneficiary
    • Requires a gift return to be followed
  • Aggregate Contribution Limit—Determined by your state
    • How much you can contribute to a plan for a single beneficiary over the lifetime of the account
    • Different than a balance limit

From a tax planning perspective, 529 Plans offer:

1. Income tax deductions or credits tied to contributions
→ Depending on your state & the state plan you use
2. Tax-deferred or tax-free growth
→ No potential taxation until withdrawn
3. Tax-free withdrawals
→ If used for qualified education expenses

Taxable accounts, on the other hand, have no contribution limits, but the tradeoff is the lack of tax advantages. When an investment appreciates and you sell it, you either pay short-term or long-term capital gains or losses. Investment income along the way, dividends or interest, are also taxable in the year they are received.

Therein lies the tradeoff. 529 Plans offer potential up-front tax benefits, tax deferral, and the potential for tax free distributions. Taxable accounts are taxable along the way, but give you the flexibility to avoid the 10% penalty if not used for qualified education expenses in the future. They can also be a source for future contributions, if needed.

Qualified Education Expenses

What is considered a qualified education expense? The most common expenses that come to mind are college tuition & fees, room & board, and certain supplies, but what else?

  • College tuition & fees
  • K-12 tuition & materials—$20,000/year cap for 2026
  • Books & supplies—if required for courses
  • Room & board—college only, half time enrollment minimum
  • Computers & internet—college only
  • Student loan payments—$10,000 lifetime limit per borrower

Your college or university will post their cost of attendance (COA) each year to serve as your guiding light for how much can be reimbursed for certain qualified expenses categories.

There are many more like K-12 tutoring and standardized tests fees, but we wanted to list the most common expenses. Some are not as straightforward as they look either. For example, room & board when you live off campus is calculated differently. You have to use the college or university’s COA figure as the cap. That means if the rent, utilities, etc. exceed the COA, you can only use up to the cap from the 529 Plan. The rest, in theory, would come from a taxable account or another source.

That is oftentimes the biggest misconception. There are regular college related expenses that are not considered qualified in the eyes of the IRS for 529 Plans. Carefully planning around the target university’s COA helps reduce the chances of overfunding.

Rollover Options & Beneficiary Changes

So, what happens if you send your child through college and there’s a leftover balance? That’s a good problem to have, and one worth discussing.

First, you retain the right to change the beneficiary. To avoid the penalty or taxes, the new beneficiary must be an eligible member of the original beneficiary’s family. These eligible members include: siblings, parents, children, spouses, cousins, and potentially the account owner.

529 Plans can also be rolled over into Roth IRAs for beneficiaries with earned income. See the rules below:

  • Account Age—The 529 Plan must be at least 15 years old
  • Contribution Age—Contributions must be at least 5 years old before they are rollover eligible
  • Rollover Caps—Subject to annual IRA contributions limits, $7,500 for 2026
  • Lifetime Limit—$35,000 aggregate lifetime cap per beneficiary

Role of Taxable Accounts in Education Planning

529 Plan tax benefits can be great, so why would someone want to pair a 529 Plan with a taxable account? Reason one, they are unsure if their child will have an interest in going to college. Maybe, they decide to go the trade school route instead at a much lower cost or start a business and forgo schooling all together.

That dovetails into reason number two, the fear of “overfunding” the account. For those who take distributions from 529 Plans for non-qualified education expenses, you are subject to a 10% penalty plus regular capital gains taxation. This is a risk for those who are super focused on optimizing. However, the flaw with that mindset is that the child’s decision is an unknown variable that can be difficult to predict. If done proactively, the planning starts at birth. Instead, the focus should be making informed decisions, and not fretting variables you cannot control.

The benefit of the taxable account is twofold. One, the optionality to make further 529 plan contributions down the line when they are needed, or two, to cover non-qualified expenses. Beyond that, the assets can easily pivot to working towards other financial goals instead. They provide flexibility, because if your child does go to trade school, or starts his/her own business, you can avoid the 10% penalty and the associated taxes to access the capital.

Myth or Fact: 529 Plan Edition

1. 529 Plans are scam—MYTH. Believe it or not, we have heard this before just like we sometimes hear it with 401(k) plans. In short, if you have an education related financial goal like paying for K-12 tuition, college, or trade school, then 529 Plans are not a scam. They can offer immediate and long-term tax benefits when used for qualified educational expenses.

2. Overfunding is a real risk—FACT. While 529 Plan overfunding is a real risk, the important takeaway is to not obsess over a variable you may not be able to control. If education is important to you, funding a 529 Plan may be a priority. Focus on the target university’s cost of attendance and the projected growth rate of those costs. However, if your child decides to go another route, you still have options.

3. I can only invest in my own state’s 529 Plan—MYTH. However, if you want the tax deduction or tax credit for specific states, you may need to use your state’s plan. Understanding the tax parity rules and rules that apply to your state is important.

4. If there is a leftover balance in a 529 Plan, you have to take the 10% penalty—MYTH. Optionality exists to either change the beneficiary to an eligible member, or rollover the balance over time to a Roth IRA for the beneficiary.

Education planning has become more than just basic K-12 and college tuition planning. Given recent changes, and the nuances, there is chance you are leaving money on the table when it comes to this area of financial planning.

With school starting back up, right now represents a great opportunity to review your education plan from a financial perspective. It also offers an opportunity to remind parents that qualified expenses must be reimbursed in the calendar year they are incurred. Do not forget!

DISCLAIMER
The information provided does not constitute legal, tax, or financial advice. Before making any investment or financial decisions, you should consult with a qualified attorney, tax advisor, or financial professional who can consider your individual circumstances.

SOURCES
+ Fidelity Investments, 529 Plan Basics (Jan. 2, 2026), fidelity.com.
+ MassMutual, Understanding 529 Prepaid Plans Versus 529 Savings Plans (Sept. 18, 2023), massmutual.com.
+ Education Data Initiative, Average Cost of College Over Time: Yearly Tuition Since 1970 (Sept. 23, 2025), educationdata.org.
+ Saving for College, 529 Qualified Expenses: What Can You Use 529 Money For? (June 12, 2026), savingforcollege.com.
+ TIAA, The New Rules That Have Money Rolling Into 529 Accounts, tiaa.org
+ JP Morgan, College Planning Essentials: 2026 Edition. https://am.jpmorgan.com/us/en/asset-management/adv/investment-strategies/college-planning-essentials/

Federal Student Loan Action Required?

Federal Student Loan Changes Under OBBBA: Existing Borrower Deadlines & Decisions

At Stillwater Private Wealth, we help clients problem solve for anything that impacts their financial lives. Few changes are as consequential to personal finances right now as the sweeping changes to federal student loans.

If you are a federal student loan borrower on an income driven repayment (IDR) plan, like SAVE, the email you will receive from the US Department of Education on July 1st SHOULD NOT be overlooked. You have 90 days to act, or the government will act for you.

Significant changes go into effect that impact your student loans in response to the One Big Beautiful Bill Act (OBBBA). The overhaul restructures repayment options, borrowing limits, and loan types.

The focus of this post will be on existing federal student loan borrowers, not new borrowers. Because your loans were taken out before July 1, 2026, you are in a uniquely grandfathered position. You have more flexibility than new borrowers, but there are still sunsets on the horizon that you need to be aware of.

Protection of Existing Options

Unlike new borrowers, you can still choose from the following:

1) Standard Repayment Plan—Fixed 10-year term & payments
2) Graduated or Extended Plans—Lower initial payments or terms up to 25 years
3) Income-Based Repayment (IBR)—Payments tied to income & the only legacy IDR plan that survives permanently under the OBBBA

You can still join the income-based repayment (IBR) plan until July 1, 2028, as long as you have no new loans post-July 1, 2026. Same goes for PAYE and ICR, but they are subject to the sunset in 2028. Switching to PAYE or ICR now would mean switching again within the next two years.

As you will notice, the SAVE plan is the one income-driven repayment (IDR) plan not on the list. The US Department of Education stopped accepting applications for new enrollments due to ongoing legal challenges and placed existing borrowers in forbearance.

For those in the SAVE plan you will have 90 days from July 1, 2026, to choose a new plan, or the federal government will either choose the Standard Repayment Plan or the Tiered Standard Plan for you. The kicker? Neither qualifies for Public Service Loan Forgiveness (PSLF) for various reasons. DO NOT let the government make that choice for you.

July 1, 2028 Sunset—PAYE, ICR & IBR

If you are currently enrolled in Pay As You Earn (PAYE) or Income-Contingent Repayment (ICR) plans, your plans will sunset on July 1, 2028. Borrowers must transition to different repayment plans, like Standard, RAP or IBR, before that date.

While PAYE and ICR borrowers are not required to make changes now, it is worth evaluating your options today. The sunset will be here before you know it.

New Options Available

For existing SAVE, PAYE, or ICR borrowers, your new options are:

1) Tiered Standard Plan
2) Repayment Assistance Plan (RAP)
3) *Income-Based Repayment (IBR) – assuming no new loans post-July 1, 2026 & elected before July 1, 2028

Tiered Standard Plan

The Tiered Standard Plan is an amortized, fixed-payment plan that ranges from 10, 15, 20 or 25 years determined by the balance of your outstanding debt. For IDR borrowers, it could lead to a significant increase in your monthly payment. IT IS NOT income driven.

Repayment Assistance Plan

If you are looking for an income driven option, the new Repayment Assistance Plan (RAP) is the option that will eventually replace all previous IDR loans— except IBR plans. Repayments range from 1-10% of your adjusted gross income (AGI). For those with dependents, your monthly payment drops $50/per dependent.

It is worth mentioning that once you choose RAP, you cannot switch back to a standard plan. Consider it an irrevocable decision.

The good news is, if your RAP payment does not cover your monthly interest, the government will waive the remaining interest so your loan balance will not grow further. It is also eligible for PSLF, unlike the Tiered Standard Plan. For those who do not qualify for PSLF, any remaining balance is forgiven after 360 monthly payments (or 30 years).

IBR maintains its 20- or 25-year forgiveness depending on when you borrowed the loans. Again, this is for individuals who do not qualify for PSLF.

Critical Tax Warning & Considerations

Be mindful, that any forgiven RAP or IBR balance, not for PSLF purposes, at that point is taxable at the federal level as ordinary income, and could also be taxable at the state level as well. This is a potential tax bomb if not planned for properly.

This is different than Public Service Loan Forgiveness (PSLF). PSLF is tax-free at forgiveness at the federal level. It is worth confirming your state’s stance on PSLF taxation if it applies to you.

Why Action May Be Needed

You’re busy. This is a big decision with a meaningful impact on your financial life and goals. Are you confident you are making the best decision possible for your unique situation? That’s why financial planners exist.

If you’re married and considering IDR plans, you should also be considering whether to file married filing jointly (MFJ) or married filing separately (MFS). If you qualify for PSLF, you cannot afford to let the federal government pick a plan for you.

The burden can seem insurmountable. If that feeling is familiar, please speak to a financial professional who can help you navigate this decision. We are here to help.

DISCLAIMER

The information provided does not constitute legal, tax, or financial advice. Before making any investment or financial decisions, you should consult with a qualified attorney, tax advisor, or financial professional who can consider your individual circumstances.

SOURCES

+ U.S. Department of Education. (2026, March 27). Next steps for borrowers enrolled in the unlawful SAVE plan. ed.gov
+ Student Loan Borrower Assistance (National Consumer Law Center). (2026, April 28). The SAVE plan is ending: What borrowers in SAVE need to know. studentloanborrowerassistance.org
+ Best Colleges. (2026). SAVE plan ending: What borrowers need to do next. bestcolleges.com
+ CNBC. (2026, May 31). Student loan ‘big beautiful bill’ changes take effect July 1. cnbc.com
+ Tate Esq. (2026). Big Beautiful Bill student loan changes: What the law does. tateesq.com

Trump Accounts for IBM Employees: What You Need to Know

For new parents, or soon-to-be parents, family planning and education planning can be a whole new world. There are UTMA/UGMA accounts, 529 Plan accounts, Minor Roth IRAs, and now Section 530A Child Savings or Trump Accounts.

If you are looking for full breakdown on Trump Accounts and the other investment vehicles, please see our last blog post in June Trump Accounts: A Guide for New Parents – Stillwater Private Wealth.

This post is more targeted. Most employees are contributing up to their employer’s retirement plan match. Why? It can offer anywhere from 25-100% immediate return on that contribution. After you invest, it is a different story, but you get the point.

For IBM employees, while your company no longer offers matching 401(k) contributions (hello retirement benefit accounts), IBM does now offer, “IBM-funded contributions to Section 530A Child Savings Accounts, or Trump Accounts,” per IBM earlier this year.

What does it mean for you? IBM will contribute:

  • An additional $1,000 for eligible children born between 2025 and 2028
  • A second $1,000 IBM contribution when parents contribute $4,000 within 24 months of their child’s birth or the federal government’s effective date of July 2026, whichever occurs later

While Trump accounts are not our preferred investment vehicle for children, receiving the $1,000 seed funding from the federal government plus matching contributions from your employer makes it worth funding to those necessary levels, in our opinion.

If you want to take advantage of IBM employer matching contributions, here are your next steps.

  1. Open a Trump account for your eligible child at https://trumpaccounts.gov/
    • a. Receive the $1,000 seed funding from the federal government
    • b. Inform IBM of your eligible account to receive their matching $1,000 contribution
  2. Wait until the next calendar year to make your $4,000 contribution
    • a. Inform IBM of your contribution to receive their matching $1,000 contribution
    • b. ***You wait until next year because the annual maximum contribution is $5,000 and that includes employer contributions—IBM will not be eligible to make that second matching contribution until the next calendar year

This is what we view as the cleanest approach. Maybe IBM has already considered the annual contribution limits, and you can make the $4,000 contribution in year one. It is worth confirming with them first to avoid any potential headache.

If you have any questions or want to discuss family, education, or any other financial planning needs further, the Stillwater team is here to help IBM employees. 

DISCLAIMER 

The information provided does not constitute legal, tax, or financial advice. Before making any investment or financial decisions, you should consult with a qualified attorney, tax advisor, or financial professional who can consider your individual circumstances.

SOURCES

+ IBM HR. (2026, January). Announcing IBM Contributions Contd.

 

Trump Accounts: A Guide for New Parents

What is a Trump Account?

Per the trumpaccounts.gov website, these accounts are intended to help children in the US jumpstart the American Dream. The goal is to help, “build long-term financial security for millions of children by creating tax-advantaged investment accounts for US citizens under the age of 18.”

Created by the One Big Beautiful Bill Act (OBBBA) of 2025, Trump accounts act as a custodial IRA owned legally by the child, but administered by an adult. Here’s what you need to know:

  • Eligibility—any child with a valid SSN who is a U.S. citizen and has not yet reached age 18 can open a trump account
  • Contribution Limits:
    • Contributions—made with after-tax dollars, meaning your tax professional needs to keep track of the basis (post-tax vs. pre-tax)
    • Annual Limit—up to $5,000/year total from family, friends, or employer
    • Employer Contributions—employers can contribute up to $2,500/year, but it counts towards the $5,000/year annual limit
    • Governments & Charities—can contribute without counting against the $5,000/year annual limit, the government seed funding for example
  • $1,000 Government Seed Funding—only available to US Citizens born between January 1, 2025, and December 31, 2028
  • Accessibility—accounts generally cannot be withdrawn from before January 1st of the calendar year in which the child turns 18
  • Tax Benefits—there is no tax credit or deduction received for making contributions
  • Taxation—this account type is tax-deferred until the child reaches age 18, at which point they become a Traditional IRA, where growth remains tax-deferred
    • Meaning any taxation on interest, dividends, or capital gains is deferred into the future (until distributions or conversions are made)
    • It also means you cannot access the money until age 59 ½ without incurring a 10% penalty (in most cases)
  • Gift Tax Status—as it stands right now, Trump Accounts lack the specific language qualifying them for the annual gift tax exclusion, like with 529 Plans
    • That means contributions to these plans would require the filing of a Gift Tax Return or Form 709 because they are treated as taxable gifts of future interest
  • Investments & Structure—must be invested in certain mutual funds or ETFs that track the S&P 500 or another index of primarily American equities, per the IRS
    • Invested in a Treasury-approved default investment option (not self-directed)

Our Thoughts on Trump Accounts

In short, Trump Accounts can help teach great financial habits and build investment discipline.
However, outside of capturing the $1,000 seed funding if you have children born between 2025-2028, or matching contributions from your employer, we believe other investment vehicles are better suited to help you and your children achieve your financial goals.

Other Investment Vehicles for Children

  • UTMA/UGMA—Uniform Gift/Transfer to Minors Act
    • Taxable accounts for minors with no investment minimums and wider range investment options & custodian choices
    • Interest, dividends, and capital gains could be taxed in the current tax year based on the kiddie tax rule
  • Minor Roth IRAs
    • Roth IRAs, for minors with earned income, that allow them to start investing for their retirement early
    • Subject to the same contribution limits and distribution rules as all Roth IRAs
  • 529 Plans
    • Investment accounts designed to help pay for qualified educational expenses in K-12 and college in a tax-free fashion
    • Contributions in many states also provide tax credits or deductions as well

Disclaimer: Understand each account’s impact on FAFSA for those trying to qualify***

Whether your goal is to help your child pay for their education, be prepared for life after high school or college, or get a jumpstart on retirement savings, these account types are likely better options.
The gift tax return filing requirement of Trump Accounts adds unnecessary cost and complexity to your tax situation for no immediate tax or other benefit. Now, if your work is offering to match contributions, then it may be worth considering.

Final Verdict on Trump Accounts & Investment Vehicles For Children

  1. Open a Trump account to receive the $1,000 seed funding if you have children born between the years 2025-2028 & inquire about employer contributions at work
  2. Consider a 529 Plan if you want a tax-advantaged way to help pay for your kids’ K-12 or college expenses with the potential for a tax benefit tied to contributions
  3. Consider a UTMA/UGMA if you want to help your child begin saving and investing for a car, home, or other financial goals in an account that they can access at any age
  4. Consider a Minor Roth IRA if your child has earned income and you want them to begin investing for retirement or simply build strong financial habits
  5. Consider converting the Trump Account to a Roth IRA when your child turns age 18 before their earned income or other income begins to rise

DISCLAIMER 

The information provided does not constitute legal, tax, or financial advice. Before making any investment or financial decisions, you should consult with a qualified attorney, tax advisor, or financial professional who can consider your individual circumstances.

SOURCES 

+ U.S. Department of the Treasury & IRS. (2025, Dec.). Treasury, IRS issue guidance on Trump Accounts established under the Working Families Tax Cuts; notice announces upcoming regulations. https://www.irs.gov/newsroom/treasury-irs-issue-guidance-on-trump-accounts-established-under-the-working-families-tax-cuts-notice-announces-upcoming-regulations

+ Trump Accounts Official Website. (n.d.). https://trumpaccounts.gov/

+ AICPA & CIMA. (2026, March).Trump Accounts: What CPAs need to know. https://www.aicpa-cima.com/resources/article/trump-accounts-what-cpas-need-to-know

 

Tax Loss Harvesting: After Tax Returns Matter

In a world hyper‑focused on investment fees, tax efficiency and after‑tax returns oftentimes take a backseat. In our opinion, that is a mistake. It is not about what you make. It is about what you keep.

No one likes to lose money, myself included. However, when life gives you lemons you need to make lemonade. A recent example of life handing investors “lemons” has been the market volatility introduced by the Iran war and its impact on the Strait of Hormuz.

The reason for market stress always changes, but one potential investment strategy remains available for taxable investors—tax loss harvesting. As Vanguard outlines in their Advisor Alpha research, tax loss harvesting can add up to 150bps or more to annualized net portfolio returns.

How Tax‑Loss Harvesting Works

Tax‑loss harvesting allows investors to generate a tax asset by selling an investment at a loss and reinvesting the proceeds into a similar, but not substantially identical investment to maintain market exposure.

Why does an investment being substantially identical matter in the context of loss harvesting? Wash sale rules. These IRS rules outline that you cannot purchase a substantially identical investment 30 days before or 30 days after the sale date. If you accidentally do, a wash sale can remove any benefit you planned to receive from tax loss harvesting.

 Key Benefits:

  • Maintains desired asset class or market exposure
  • Realizes capital losses to use now and or later
  • Potentially improves after‑tax returns without timing the market

 Example of Tax‑Loss Harvesting in Practice

  • SELL: Vanguard S&P 500 ETF (VOO)
  • BUY: Vanguard Large‑Cap ETF (VV) – same day

✔ Maintains U.S. large‑cap exposure
✔ Realizes a capital loss for tax purposes

Why Is Tax‑Loss Harvesting Important?

 Tax‑loss harvesting helps investors keep more of what they earn in two primary ways:

  1. Offsets current‑year capital gains, or reduces other income by up to $3,000/year
  2. Creates capital losses that carry forward to future tax years to offset gains from: business sales, real estate transactions or other liquidity events

For investors with equity compensation from work, think about planning ahead for your company’s anticipated tender offer or IPO.

Reddit (RDDT) investors likely needed tax loss harvesting leading up to the IPO to offset sales post lock-up, whereas Figma (FIG) investors may be loss harvesting after the IPO now that the lock-up period has expired and the price continues to fall. For RDDT investors selling pre-IPO it would have meant loss harvesting non-RDDT investments to proactively generate losses ahead of the IPO. For FIG investors selling post-IPO, it could mean investing in a sector ETF with strong enough correlation, like iShares ETF (IGV), until the wash sale rules are met.

This is called proactive planning. Tax preparation, or filing, looks in the rear-view mirror. Tax planning looks into the future. You need both.

How Does This Apply in Practice? A Client Example

Let’s consider a new‑client onboarding for a husband and wife seeking tax planning, investment management, and proactivity. Their previous firm deployed a tactical investment strategy that routinely sold ETFs as markets changed. While tactically flexible, this type of investment strategy creates a hidden tax cost in taxable accounts.

For this client, taxable assets make up the majority of their liquid net worth. To them, the strategy was costly and ate into their after-tax returns. In our opinion, any investor should understand the tax drag of the portfolios they are invested in.

Morningstar measures this tax drag through their proprietary Tax Cost Ratio, which reflects how much of a fund’s returns are lost to taxes (assuming the highest tax rates). Buying and selling funds regularly only adds to that drag.

 Example:

  • Gross Return: 10%
  • Tax Cost Ratio: 2%
  • Net After‑Tax Return: 8%

An S&P 500 Index ETF has a tax cost of about 0.50%, while a private credit mutual fund has a tax drag of about 3.75%. Even if they both have the same returns, the after-tax returns are wildly different.

Where Tax‑Loss Harvesting Comes In

 After onboarding, we worked with the clients to establish a capital gains budget for 2026. This allowed us to begin to implement our investment strategy in a tax‑aware manner. The budget also helps our client avoid tax surprises.

Shortly after rebalancing, geopolitical headlines escalated with the Iran war, markets pulled back, and opportunity presented itself. We harvested losses across select holdings, replaced them with compliant alternatives, and used those losses to offset both short‑ and long‑term capital gains without changing the portfolio’s overall market exposure.

The Financial Impact of Loss Harvesting

 Without Tax‑Loss Harvesting

  • Account Value: $100,000
  • Short‑Term Capital Gains: $3,000
  • Long‑Term Capital Gains: $7,000

Assumptions

  • 32% Federal Tax Rate – per IRS
  • 3% State Tax Rate – assuming flat 3% tax rate, not state-specific
  • 8% NIIT Rate – per IRS
  • 20% Long‑Term Capital Gains rate – per IRS

Taxes Owed

  • Short‑Term: $3,000 × 38.8% = $1,164
  • Long‑Term: $7,000 × 26.8% = $1,876

Total Tax Drag:

  • $3,040 (304 basis points)

With Tax‑Loss Harvesting

  • Account Value: $100,000
  • Short‑Term Capital Loss Harvested: $5,000
  • Net Short‑Term Gains: $0
  • Net Long‑Term Gains: $5,000

Taxes Owed

  • Long‑Term: $5,000 × 26.8% = $1,340

Total Tax Drag:

  • $1,340 (134 basis points)

The Difference

  • 304 bps – 134 bps = 170 bps, or $1,700 retained by the client.

These clients maintained their exposure across equities, bonds, and alternatives, while simultaneously generating a tax asset that helps them keep more of their own hard-earned money.

Execution Matters

 For busy professionals, entrepreneurs, and retirees, the question you need to ask yourself is, “Do I have the time, and the discipline, to execute this strategy properly?”. Tax and investment planning can sometimes be opportunistic, and you need to be ready to act. Tax‑loss harvesting often requires:

  • Real‑time decision‑making
  • Market‑hour execution
  • Awareness of wash‑sale rules
  • Access to appropriate replacement securities

This is where proactive planning and professional oversight make a difference.

Conclusion—Tax Loss Harvesting Needs To Be A Part of Your Investment & Tax Strategy

 If you have been investing since 2020 and regularly adding capital to your portfolio, you have likely had three-four major opportunities to harvest losses. This does not include other market or sector pullbacks we experience each year. If you have not taken advantage of any them, it may be quietly eroding your after‑tax returns. Tax‑loss harvesting is not just about this year—it is about:

  • Future tax planning around liquidity events
  • Retirement income efficiency
  • Long‑term wealth preservation

Federal capital losses can carry forward through all stages of life, until death, while state tax laws vary. This is a financial planning strategy that is underutilized, but as you can see, it can be incredibly powerful.

 Key Takeaways 

  1. After‑tax returns are king—it is not about what you make, it is about what you keep
  2. Tax‑loss harvesting can offset capital gains & reduce other income
  3. Tax losses can carry forward to future years & become a “tax asset”
  4. Proactive planning & execution during market hours is not optional
  5. Keep wash sale rules in mind when executing the strategy

DISCLAIMER 

The information provided does not constitute legal, tax, or financial advice. Before making any investment or financial decisions, you should consult with a qualified attorney, tax advisor, or financial professional who can consider your individual circumstances.

SOURCES

+ Charles Schwab. (n.d.). Wash-sale rule: How it works & what to know. https://www.schwab.com/learn/story/wash-sale-rule-how-it-works-what-to-know

+ Internal Revenue Service. (n.d.). Topic no. 409, capital gains and losses. U.S. Department of the Treasury. https://www.irs.gov/taxtopics/tc409

+  Internal Revenue Service. (n.d.). Topic no. 559, net investment income tax. U.S. Department of the Treasury. https://www.irs.gov/taxtopics/tc559

+ Internal Revenue Service. (2026). IRS releases tax inflation adjustments for tax year 2026, including amendments from the One Big Beautiful Bill. https://www.irs.gov/newsroom/irs-releases-tax-inflation-adjustments-for-tax-year-2026-including-amendments-from-the-one-big-beautiful-bill

+ Vanguard. (2025). Advisor’s alpha: Clients and their advisors thriving together for 25 years.

+ Morningstar (n.d.). Tax cost ratio.