Upticks: How 529 Plans, Trump Accounts, and Asset Ownership Can Create a Financial Head Start
By Luke Sullivan on September 16, 2026
Families often want to give children and grandchildren a stronger financial starting point, but deciding how to help can be difficult. Education accounts, custodial accounts, trusts, retirement accounts for minors, and ordinary investment accounts each serve different purposes and come with different rules.
This week’s episode of Upticks explores several sides of that challenge. Jake shares what he learned from opening a 529 plan and a Trump Account for his newborn son. Jake and Cory also examine an extraordinary cryptocurrency theory before responding to a listener who believes the financial system is structured to help people who already have money.
Together, the discussions reinforce an important principle: the earlier someone begins developing financial knowledge and owning productive assets, the more options that person may have later.
Editor’s Note: The YouTube video above features a shortened segment from this week’s discussion about whether the financial system is rigged against younger people. To hear the complete conversation—including Jake and Cory’s thoughts on 529 plans, Trump Accounts, cryptocurrency, and the national debt—listen to the full episode using the podcast player above. Enjoy!
Starting early with a 529 plan
A 529 plan is a tax-advantaged account designed to help families save for qualified education expenses. Contributions are made with after-tax dollars, but earnings can grow without current federal taxation, and qualifying withdrawals are generally received federal income-tax-free.
The eligible expenses have expanded beyond traditional college tuition. Depending on the circumstances, 529 funds may be used for qualified postsecondary education, apprenticeships, certain student-loan repayments, credentialing expenses, and qualifying K–12 education costs.
State tax benefits vary. Missouri taxpayers, for example, may currently deduct qualifying contributions of up to $8,000 per taxpayer, or $16,000 for a married couple filing jointly, from Missouri taxable income.
Families also have options when the original beneficiary does not use the entire balance. The beneficiary may generally be changed to another qualifying family member. Under current federal rules, qualifying unused funds may also be transferred directly to the beneficiary’s Roth IRA, subject to the annual Roth contribution limit, a $35,000 lifetime limit, a 15-year account-age requirement, and restrictions involving recent contributions.
Those provisions can make a 529 more flexible than some families initially assume. Still, the account should be coordinated with the family’s education expectations, cash flow, estate plan, and other savings priorities.
Understanding Trump Accounts
Jake also opened a Trump Account for his son. Trump Accounts are a new form of traditional IRA for eligible minors. A qualifying child born during calendar years 2025 through 2028 may receive a one-time $1,000 federal pilot contribution if the required election is made and the other eligibility requirements are satisfied.
Other children may still be eligible to have an account opened without receiving the pilot contribution. Additional contributions are subject to annual limits and other rules, and the money must generally remain invested until the calendar year in which the child turns 18. Eligible investments are limited to qualifying index-tracking mutual funds or exchange-traded funds.
A Trump Account is not necessarily a substitute for a 529 plan. The two accounts have different objectives, tax treatment, investment rules, access provisions, and eligible uses. A family might use one, both, or neither depending on what the broader financial plan is intended to accomplish.
The account itself is not the complete strategy. It is one tool for beginning earlier.
Be cautious with extraordinary financial predictions
The episode also examines a social-media theory suggesting that the United States could use cryptocurrency and stablecoins to reduce the real burden of the national debt while strengthening its financial position relative to other countries.
Jake and Cory treat that scenario as speculation rather than an established government plan. Their broader concern is useful beyond this particular claim: extraordinary financial predictions should be evaluated carefully, especially when the person promoting the idea may benefit from more people purchasing the asset.
New technologies may eventually change parts of the financial system. That possibility does not mean every confident prediction is probable or that a family should build its financial plan around it.
The more durable approach is to separate what is known, what is possible, and what is merely being promoted as inevitable.
Is the financial system rigged—or tilted?
A listener then raised a more personal concern: people who already have money appear to receive better advice, better tax planning, less expensive credit, and greater access to investment opportunities.
Cory suggested that “tilted” may be a more accurate word than “rigged.”
The financial system strongly rewards ownership. Someone who owns stocks, bonds, real estate, or a business can participate in economic growth and compounding. Someone whose income is consumed by housing, food, insurance, transportation, and debt payments has less money available to purchase those assets.
That difference can compound. Greater assets can create access to better credit terms, professional guidance, tax-planning opportunities, and a larger margin for financial mistakes.
This does not mean an advisor inherently causes an account to grow or that every asset owner succeeds. It means that people who can consistently acquire productive assets are generally positioned differently from people who remain dependent entirely on their next paycheck.
Financial information is not the same as financial understanding
Jake and Cory disagree slightly on whether the country primarily has a financial-literacy problem or a behavior problem.
Financial information has never been more abundant. Books, podcasts, articles, courses, and online tools can explain investing, budgeting, taxes, and credit. Yet abundant information can also become overwhelming, contradictory, or difficult to evaluate.
People are also introduced to spending and borrowing at a young age. They learn how to use credit, take out student loans, purchase consumer products, and respond to advertising before many of them learn how ownership and compounding work.
Improving financial literacy therefore requires more than distributing information. It also requires credible starting points, practical habits, and opportunities to apply what is learned.
The fundamentals remain relatively simple even when implementation is not: spend less than income, avoid high-cost revolving debt, establish appropriate reserves, begin investing consistently, and seek qualified guidance as the financial situation becomes more complex.
Creating a better starting point
A 529 plan, Trump Account, custodial account, trust, or investment account cannot guarantee a particular outcome. What these tools can provide is an earlier opportunity to save, invest, learn, and participate in ownership.
Parents and grandparents can help by creating appropriate accounts, discussing how money works, modeling thoughtful financial behavior, and gradually involving younger family members in financial decisions.
Young adults may not begin with the same resources or access. They do, however, benefit from something that cannot be recreated later: time.
The earlier someone learns to use that time intentionally, the more room there may be for ownership and compounding to influence the future.
Watch the shortened YouTube discussion above or listen to the full episode using the podcast player to hear Jake and Cory explore all three decisions.
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