Client Question: How Do I Give My Kids a Head Start on Investing?

Published May 12, 2026

At a Glance

  • Time is the greatest investing advantage a child has — even modest early contributions can compound meaningfully over decades.
  • 529 plans, custodial accounts, and custodial Roth IRAs each offer different trade-offs around taxes, control, flexibility, and financial aid.
  • The account matters, but the family conversations around money, investing, and stewardship often matter even more.

Spring is graduation season, and that means it is also the season when we hear a version of this question almost weekly: parents and grandparents asking how to give the young people in their lives a real head start with their money — not just a check tucked into a card, but something with staying power.

It's a thoughtful instinct. Children and grandchildren have one asset working in their favor that no investor can buy back later: time. A modest contribution made when a child is five or ten years old has decades to compound before it's ever drawn down. That is the entire engine behind multi-generational wealth, and it's available to any family willing to start.

The challenge is choosing the right vehicle. Each account type below carries trade-offs — tax treatment, control, financial aid impact, flexibility — and the right answer depends on what the money is for and how much control you want to keep. Here is how we typically frame the choices for clients.

529 Plans: The Workhorse for Education

For most families, a 529 plan is the first account we'd consider. It's built for one purpose — education — and the tax benefits are hard to beat: tax-deferred growth, tax-free withdrawals for qualified education expenses, and no federal contribution limits. Annual contributions above the gift tax exclusion ($19,000 per donor per beneficiary for 2026) start to use lifetime gift exemption, but a five-year "superfunding" election lets grandparents accelerate up to five years of gifts into a single year — a useful tool when timing matters.

Qualified expenses have broadened meaningfully. In addition to college, families can use up to $10,000 per year for K–12 tuition, fund graduate school, or apply $10,000 (lifetime) toward student loan repayment. Unused balances can be rolled to another family member or, in some cases, into a Roth IRA for the beneficiary. We covered the broader question of how to sequence different education dollars in How to Pay for College.

One caveat worth flagging: 529 ownership matters for financial aid. A 529 owned by a parent generally has a smaller impact on need-based aid than one owned by the student or, historically, by a grandparent. Recent FAFSA changes have softened the grandparent-owned 529 penalty, but the rules continue to evolve — coordinate before opening accounts in a grandparent's name if aid eligibility is on the table.

Custodial Accounts (UGMA/UTMA): Flexibility With Real Trade-offs

Not every gift to a child is meant for tuition. For families thinking about a future car, a wedding, a down payment on a first home, or simply a longer-horizon investment account, a UGMA or UTMA custodial account is often the right tool. These accounts are simpler than a trust to set up and can hold a wide range of investments — stocks, bonds, mutual funds, ETFs — and, in the case of UTMAs, even more complex assets like real estate, art, or intellectual property.

There are no contribution limits, and the money can be used for anything that benefits the child while they're still a minor. But here is the trade-off we make sure parents understand before they fund one: at the age of majority — typically 18 to 21, depending on the state — the child takes full ownership and can use the money however they choose. We've seen this work beautifully when families pair the account with conversations about money. We've also seen it become a teachable, expensive lesson when those conversations don't happen. (We've written before about why those conversations matter and how to start them in Family Conversations About Money.)

Custodial accounts also trigger the "kiddie tax," which applies to a minor's unearned income. For 2026, the first $1,350 is tax-free, the next $1,350 is taxed at the child's rate, and amounts above that are taxed at the parent's marginal rate. And because these accounts are considered the child's asset, they typically reduce financial aid eligibility more than a parent-owned 529 would. None of this disqualifies them — but it does mean they should be funded with intention, not as an afterthought.

Custodial Roth IRAs: The Long Game

For the family that wants to give a young person a true generational gift, it's hard to compete with a custodial Roth IRA. Decades of tax-free compounding, followed by tax-free withdrawals in retirement, is precisely the kind of asymmetric outcome time can produce. A child who funds a Roth at age sixteen and never contributes again can still reach retirement with a meaningful balance — without ever paying tax on the growth.

The catch: a Roth IRA requires earned income. Babysitting, lifeguarding, tutoring, a summer job at the family business — all qualify, but the contribution is capped at the lower of the child's actual earnings or the annual limit ($7,500 for 2026). Documentation matters. We typically recommend keeping a simple log of hours and pay, particularly when the earnings come from informal work, so the contributions are defensible if questioned.

Don't Skip the Other Half of This: the Conversation

Setting up accounts is the easy part. The harder, more valuable work is the financial literacy that goes around them. The young people in our clients' families who arrive at adulthood prepared to handle money tend to share a common experience: they grew up in households where money was discussed openly, where investment statements were reviewed at the kitchen table, and where they were brought into decisions early — not handed a portfolio at twenty-two.

Reviewing a 529 statement together is a free lesson in compounding. Letting a teenager help allocate a custodial Roth across a few low-cost funds is a free lesson in diversification. The accounts are the vehicle; the conversations are the road.

One Note on What's Coming

There is one more account type worth flagging that the original framing here didn't anticipate: Trump Accounts, a new vehicle created under recent legislation that adds another option to this toolkit. They have their own contribution rules, tax treatment, and trade-offs, and they fit alongside — not in place of — the accounts above. We'll cover them specifically next week.

How We'd Approach This With Your Family

There is no single right answer to "how should I invest for my kids." The right answer is the combination of accounts that fits your goals, your tax picture, and the role you want money to play in the next generation's life. For families with meaningful gift capacity, the question is often less "which one" and more "in what order, and how do they coordinate with the estate plan." That coordination is where we add the most value — and it's the same lens we apply to estate planning more broadly (see Protecting What's Yours (After You Pass)).

If you're thinking about funding accounts for children or grandchildren this year — particularly before a graduation, a wedding, or a year-end gifting deadline — we're happy to sit down and walk through which combination makes sense. Reach out and we'll set up a time.


Past performance does not guarantee future results. All investments include risk and have the potential for loss as well as gain.

Data sources for returns and standard statistical data are provided by the sources referenced and are based on data obtained from recognized statistical services or other sources we believe to be reliable. However, some or all information has not been verified prior to the analysis, and we do not make any representations as to its accuracy or completeness. Any analysis nonfactual in nature constitutes only current opinions, which are subject to change. Benchmarks or indices are included for information purposes  only  to  reflect  the  current  market  environment;  no  index  is  a directly  tradable investment.  There  may  be  instances  when  consultant  opinions  regarding any fundamental or quantitative analysis do not agree.

The  commentary  contained  herein  has  been  compiled  by  W.  Reid Culp,  III  from  sources  provided  by  TAGStone  Capital,  as well  as  commentary  provided  by  Mr.  Culp,  personally,  and  information independently  obtained  by  Mr.  Culp.  The  pronoun  “we,”  as  used  herein,  references collectively the sources noted above.

TAGStone Capital, Inc. provides this update to convey general information about market conditions and not for the purpose of providing investment advice. Investment in any of the companies or sectors mentioned herein may not be appropriate for you. You should consult your advisor from TAGStone or others for investment advice regarding your own situation.


At a Glance

  • How to pay for college depends not just on how much you save, but on which dollars you use—and in what order—which can affect taxes, financial aid, and long-term goals.
  • 529 plans are often the most tax-efficient option, but brokerage accounts, cash, and income may still play an important role.
  • Retirement savings should generally be preserved, with college funding decisions made as part of a coordinated plan rather than semester by semester.

College Payment Strategies: Where Should the Money Come From?

Everyone knows college is expensive. But how you choose to pay for it—especially which dollars you use and in what order—can have long-term consequences that extend well beyond the college years.

This year, the average tuition and fees for a private college are nearly $45,000 per year, and for some schools the total cost of attendance can be significantly higher. The good news is that many families don’t end up paying the full sticker price. Grants, scholarships, and financial aid packages can help reduce costs. But once those are factored in, an important question remains:

Where should the rest of the money come from?

This post focuses on practical college‑funding decisions for mass‑affluent families. In a follow‑up post, we’ll address how higher‑net‑worth families approach education funding from an estate and gift‑planning perspective.

Consider All Your Options

First, take stock of the possible funding sources available to you. Each comes with distinct trade-offs that matter differently depending on wealth level, tax exposure, and time horizon. These may include 529 college savings plans, taxable brokerage accounts, traditional savings accounts, cash from current income, gifts from family members and loans. Each come with their own rules and tax treatment. And which sources you tap—and in what order—matters.

  • 529 plan: Contributions to a 529 college savings plan grow tax-deferred. Withdrawals are tax-free when they’re used to cover qualified education expenses—anything else will likely come with an income tax hit and a 10% penalty on the earnings portion of the withdrawal. The good news is that qualified education expenses cover more than just tuition. You can use tax-free withdrawals to pay for room and board, textbooks, computers and more. One important note: 529 plans owned by parents are treated as parental assets and may reduce financial aid awards.
  • Brokerage account: When you sell assets to make a withdrawal from a brokerage account, any profit is subject to capital gains tax. Long-term capital gains are taxed at preferential rates, but even so, brokerage account funds are generally less tax-efficient than 529 plans in covering education expenses. Your brokerage account balance is also factored into financial aid eligibility.
  • Savings account: Interest earned on a savings account is taxed as ordinary income. Withdrawals don’t create taxable events. Like brokerage accounts, savings accounts can reduce financial aid eligibility, more so if held by the student.
  • Current income: Making payments from your income doesn’t offer a direct tax advantage, but it can help you avoid tapping into accounts you’d rather not touch. Income is a major factor in financial aid determinations.
  • Gift from a family member: Family members can gift up to $19,000 ($38,000 for married couples) per recipient in 2025 and 2026 with no tax consequences. Gifts received can affect financial aid if they’re deposited into an account owned by the student or a parent. Family members can also pay tuition directly, avoiding the annual gift tax exclusion limit and any impact on financial aid decisions for students and parents.
  • Student loans: Parents have access to student loans in the form of Federal Direct Parent Plus Loans and private student loans, both of which can help bridge the gap when savings, income and other resources aren’t enough. Federal loans may offer lower interest rates than private loans. As a parent, you can deduct up to $2,500 in student loan interest from your taxes every year.

Conventional Wisdom—and Where It Breaks Down

As a rule of thumb, families should first take advantage of any “free” money such as scholarships and grants before deciding which source of funding to draw from. Next, consider drawing from taxable accounts before tapping into tax-deferred accounts. The goal here is to let your tax-deferred assets grow as much as possible so they can take advantage of the miracle of compound growth. When these sources of income are exhausted, you may turn to federal or private student loans, which charge interest and can therefore be the most expensive way to pay for college.

Of course, rules of thumb are broad—and they often break down for families with significant assets, concentrated wealth, or long planning horizons. The strategy that works for one family may not work for yours. That’s where we can help. Together, we can examine your complete financial picture to come up with a withdrawal plan that aligns with your situation and helps keep you on track toward your long-term goals. For instance, it may make more sense to take 529 withdrawals first if your taxable accounts are likely to trigger short-term capital gains, which are taxed at a much higher rate than long-term gains.

The American Opportunity Tax Credit is another factor to consider. Your tuition payments may qualify you for a maximum tax credit of $2,500, but any expenses covered from a 529 plan don’t count toward the tax credit. Making sure you pay tuition bills from more than your 529 can help ensure you maximize the “free” money from the tax credit. At the same time, the size of the credit phases out for higher earners, which can change the calculus depending on your income.

Avoid Touching Your Retirement Savings

Securing your retirement is fundamentally more important than funding college. That’s because college is something that can be financed with loans if needed. Retirement is not.

Your best bet is to steer clear of using funds from your 401(k) or IRA accounts. While there is a provision allowing penalty-free withdrawals from IRAs for education expenses, it’s generally not worth it to make them. Withdrawing early from a retirement account can mean sacrificing years of tax-advantaged growth. And because these accounts are subject to annual contribution limits, the amount you withdraw can’t always be replaced quickly.

There are many different factors to consider and weigh when designing a college payment strategy. Fortunately, you don’t have to wade through them alone. If you’re wondering about ways to pay for college, reach out and we’ll help you find the approach that’s best for you.


Past performance does not guarantee future results. All investments include risk and have the potential for loss as well as gain.

Data sources for returns and standard statistical data are provided by the sources referenced and are based on data obtained from recognized statistical services or other sources we believe to be reliable. However, some or all information has not been verified prior to the analysis, and we do not make any representations as to its accuracy or completeness. Any analysis nonfactual in nature constitutes only current opinions, which are subject to change. Benchmarks or indices are included for information purposes  only  to  reflect  the  current  market  environment;  no  index  is  a directly  tradable investment.  There  may  be  instances  when  consultant  opinions  regarding any fundamental or quantitative analysis do not agree.

The  commentary  contained  herein  has  been  compiled  by  W.  Reid Culp,  III  from  sources  provided  by  TAGStone  Capital,  as well  as  commentary  provided  by  Mr.  Culp,  personally,  and  information independently  obtained  by  Mr.  Culp.  The  pronoun  “we,”  as  used  herein,  references collectively the sources noted above.

TAGStone Capital, Inc. provides this update to convey general information about market conditions and not for the purpose of providing investment advice. Investment in any of the companies or sectors mentioned herein may not be appropriate for you. You should consult your advisor from TAGStone or others for investment advice regarding your own situation.