Podcast Summary: Jill on Money with Jill Schlesinger
Episode: 529 Plans vs Trump Accounts
Release Date: July 22, 2025

Introduction

In this enlightening episode titled "529 Plans vs Trump Accounts", Jill Schlesinger, CFP®, alongside her co-host Mark, delves into critical financial topics affecting everyday individuals. The focus centers around education savings plans, retirement strategies, and listener-submitted financial dilemmas. The episode is designed to demystify complex financial instruments and provide actionable advice without the overwhelming jargon.

Navigating Timeshare Contracts

The episode kicks off with a listener query from Regina, a retired senior citizen grappling with a burdensome timeshare contract. Regina explains:

Regina [03:06]: "I only paid $800 when I first purchased it. The maintenance fees were about $700 a year, and now they're up to around $1,500."

Jill empathizes with Regina's predicament, quoting her late mother-in-law:

Jill Schlesinger [03:45]: "Timeshares are for suckers."

Mark adds practical insights by sharing a common strategy:

Mark [03:19]: "A friend told me she just stopped paying her maintenance and never heard from the timeshare again."

However, Jill cautions against this approach due to potential legal repercussions, particularly concerning taxes tied to the maintenance fees:

Jill Schlesinger [03:50]: "I'm afraid of repercussions. Could a lien be placed on my current home if I were to do that?"

The discussion emphasizes the complexity of exiting timeshare agreements and suggests consulting directly with the timeshare company for possible solutions.

Retirement Planning and Financial Security

The conversation transitions to Jenna's scenario, a 54-year-old approaching retirement with a substantial but risky investment portfolio:

Jenna's Profile [04:43]: "They have combined IRAs about $1.3 million... Roth IRAs of $590,000, all in high-tech stocks."

Jill and Mark dissect Jenna's financial landscape, highlighting the importance of diversification and risk management. Jill advises:

Jill Schlesinger [06:35]: "Looking at that $900,000 inheritance, that's pretty solid. They are in great shape."

Mark reinforces the need for strategic planning, especially concerning Social Security:

Mark [07:07]: "I don't get why you would plan on drawing at 62."

The hosts advocate for delaying Social Security benefits to maximize financial security, especially when substantial savings are already in place.

Education Savings: 529 Plans vs Trump Accounts

A significant portion of the episode addresses Mei Mae's question regarding the suitability of 529 plans compared to the newly introduced Trump savings plans:

Mary [11:30]: "What is your opinion about a 529 versus the Trump savings plan?"

Jill provides a clear preference:

Jill Schlesinger [11:45]: "I think the 529 plan is far preferable because the other one, the Trump plan, you don't get tax-free withdrawals. It's basically like an IRA. You're going to pay the money."

She emphasizes the tax advantages inherent in 529 plans, making them a superior choice for educational savings.

Mark adds practical advice on choosing between financial products based on liquidity needs:

Mark [11:55]: "CD has a slightly higher rate but not liquid. Depending on when you need the money would be the determining factor."

This segment underscores the importance of aligning financial products with individual needs and timelines.

Listener Feedback and Encouragement

The episode also features feedback from Curtis, a 72-year-old widower, reflecting on retirement's rewarding aspects:

Curtis [12:07]: "Being financially independent, entering your golden years, it's just tremendously empowering. The freedom I currently experience reminds me of grade school letting out for the summer."

Jill and Mark respond with encouragement, reinforcing the value of financial independence and thoughtful retirement planning.

Conclusion

As the episode wraps up, Jill and Mark reiterate their commitment to providing valuable financial insights and invite listeners to engage via their website, jillonmoney.com. They encourage audience participation and promote their subscription service, Jill on Money Live, which offers additional resources like webinars and exclusive content.

Notable Quotes

• Jill Schlesinger [03:45]: "Timeshares are for suckers."
• Mark [07:07]: "I don't get why you would plan on drawing at 62."
• Jill Schlesinger [11:45]: "I think the 529 plan is far preferable because the other one, the Trump plan, you don't get tax-free withdrawals."

Key Takeaways

• Timeshare Management: Exiting timeshare contracts requires careful consideration and professional consultation to avoid legal and financial pitfalls.

• Retirement Strategy: Diversification and strategic planning, including the timing of Social Security benefits, are crucial for a secure retirement.

• Education Savings: 529 plans offer significant tax advantages over alternative savings plans, making them a better choice for funding education.

• Financial Independence: Achieving financial independence provides empowerment and opens up opportunities to enjoy life's possibilities fully.

Final Thoughts

This episode of Jill on Money serves as a valuable resource for listeners navigating the complexities of personal finance. Through real-life scenarios and expert advice, Jill and Mark provide clarity on managing finances effectively to secure a prosperous future.