Retire With Ryan
Medicare open enrollment is here, running from October 15th to December 7th, and it's especially important for those who rely on Medicare. Plans change each year—and so may your needs. Not reviewing your Medicare coverage could leave you exposed to unexpected costs or disrupt your access to preferred doctors and medications. On this week's show, I explore five key steps to help ensure you get the right coverage for 2027. You will want to hear this episode if you are interested in... [01:40] Reviewing Medicare coverage for 2027 [02:49] How to check provider status: annual notice of...
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For those actively planning for a secure retirement, smart tax planning is essential—especially as 2026 comes to a close. Tax laws and contribution limits keep evolving, and timely adjustments can help you keep more of your hard-earned money. On the show this week, I share seven critical tax strategies that can boost your retirement savings while minimizing your tax liability. Here’s a deeper look at each move and how to integrate it into your financial plan. You will want to hear this episode if you are interested in... [01:41] Maxing out pre-tax retirement plans [04:32] Making...
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I break down the upcoming Social Security cost-of-living adjustment (COLA) for 2027, share my predictions on the new numbers, and explain what you should do to prepare. With inflation still affecting retirees, I explain how the COLA is calculated, what it means for your benefits, and the factors that could affect your retirement income next year. This episode has essential tips to help you make the most of the upcoming increases and manage your retirement finances confidently. You will want to hear this episode if you are interested in... [01:10] projected 2027 COLA estimates ...
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What should you do if the stock market crashes right after you retire? In this episode, I discuss what happens if you experience a major market decline in your early retirement years, explain the concept of sequence of return risk, and share a few strategies to safeguard your hard-earned nest egg and maintain peace of mind. You will want to hear this episode if you are interested in... [01:20] What to do if the stock market crashes right after retiring [04:09] Sequence of return risk explained [07:14] Preparing for market declines in retirement [13:43] Tax strategies during market...
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How much have you thought about Health Savings Accounts (HSAs) and what happens to them once you enroll in Medicare? Whether you’re nearing age 65, wondering if you can keep contributing to your HSA, or curious about how you can use your HSA funds in retirement, this episode covers it all. I explain the rules around HSA contributions after enrolling in Medicare, the types of medical expenses you can pay for tax-free, and what happens to your HSA if there’s still money in it after you pass away. You will want to hear this episode if you are interested in... [01:51]...
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As you transition into retirement, tax planning might not be at the top of your to-do list—but overlooking it can lead to costly mistakes. This week, I break down the five biggest tax pitfalls new retirees face, from unexpected taxes on Social Security benefits to costly Medicare premium surcharges and missed Roth conversion opportunities. I’m also sharing a few of my favorite strategies to avoid unnecessary state taxes and manage your retirement distributions with confidence. You will want to hear this episode if you are interested in... [01:45] Without planning, your risk...
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Roth IRAs are a powerful retirement tool, much loved for their promise of tax-free growth and withdrawals. But embedded in the rules for Roth IRAs are two little-understood 5-year rules. Misunderstanding these can trip up even savvy savers, potentially exposing your hard-earned gains to taxes and early withdrawal penalties. This week I’m giving you an expert breakdown to clarify how the rule works and bust some common misconceptions. You will want to hear this episode if you are interested in... [01:13] Tax-deferred growth and conditions for tax-free distributions [05:39] Taxes...
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Long-term care coverage is an essential, yet often misunderstood, aspect of retirement planning in the United States. Although many people will require some form of long-term care as they age, most are unprepared for the high costs and limited coverage options available. On the show this week, I’m debunking common myths like the notion that Medicare will fully cover all long-term care costs and taking a deep dive into the four main ways retirees can pay for these expenses. You will want to hear this episode if you are interested in... 00:00 Understanding the options for...
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On the show this week, I’m helping you understand why bond prices have been dropping, what actions investors should take, and whether bonds still have a place in a retirement portfolio. I discuss the different types of bonds and how interest rates impact bond prices. I also dig into the importance of maintaining a diversified portfolio and the role bonds can play in reducing overall volatility during retirement. You will want to hear this episode if you are interested in... [02:03] Types of Bonds and issuers [03:21] Risks of investing in junk bonds [04:39] Why have bond prices...
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Retirement is often imagined as the reward after decades of hard work—a time for travel, relaxation, and quality time with loved ones. But for many Americans, the anxiety of running out of money casts a long shadow over these golden years. Studies reveal that concerns about outliving savings are more prevalent than fears of dying prematurely. This week we’re discussing the five key reasons retirees run out of money and sharing practical steps you can take to secure your financial future. You will want to hear this episode if you are interested in... [02:16] Even high-income...
info_outlineIf you watched President Trump’s recent State of the Union address, you probably heard about the new Trump accounts, also known as 530A accounts. In this episode, I break down how these tax-advantaged investment accounts are designed to work, who qualifies, and—just as importantly, what we still don’t know. There’s been a lot of excitement, especially around the $1,000 seed money for eligible children. But before you rush to open one, there are several unanswered questions that deserve your attention.
What Are Trump Accounts—and Who Qualifies?
Trump accounts were introduced under the 2025 “Big Beautiful Bill Act” and are designed to help U.S. children build long-term wealth. Parents, grandparents, and others can contribute up to $5,000 per year per child until age 18. To jumpstart participation, children born between January 1, 2025, and December 31, 2028, are eligible for a $1,000 federal seed contribution.
Unlike a Roth IRA, these accounts do not require earned income to contribute. That’s a major difference. Most children can’t fund retirement accounts because they don’t have income. These accounts are meant to give them a head start from birth.
To qualify, a child must be a U.S. citizen, have a valid Social Security number, and be under age 18. Parents can apply either by filing IRS Form 4547 with their 2025 tax return or by visiting trumpaccounts.gov.
You’ll Want to Hear This Episode If You’re Interested In…
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[01:00] How the $5,000 annual contribution limit works
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[01:45] Why these accounts don’t require earned income
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[02:35] How to open an account through your tax return or online
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[03:00] The upcoming authentication process in May 2026
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[03:40] Whether you can invest in individual stocks like Nvidia or Tesla
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[04:30] Why Treasury guidance suggests broad index funds instead
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[05:10] Whether billions in seed money could move the stock market
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[06:00] Which financial institutions may (or may not) offer these accounts
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[07:45] Potential gift tax filing requirements for contributions
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[08:45] How withdrawals at age 18 might be taxed
The Investment Confusion and Market Impact
One of the biggest points of confusion right now is how the funds will actually be invested. The Trump accounts website shows mockups featuring individual stocks like Nvidia, Caterpillar, Home Depot, and Tesla. That certainly grabs attention. But Treasury guidance suggests investments may be limited to broad U.S. equity index funds or mutual funds, not individual stocks.
If that holds true, I actually think that may benefit most investors. Broad-based index funds have historically outperformed many individual stock pickers over time. But it’s important to understand what you’re signing up for before you contribute.
Another question I address is whether these accounts could meaningfully impact the stock market. With over 3 million sign-ups already, the initial $1,000 seed funding could total more than $3 billion. Add in private contributions and potential employer matches, and that number could grow to $7–8 billion invested when markets reopen after July 4.
That sounds significant, but compared to total daily trading volume, it’s less than 2%. It may provide a small positive impact, but it’s unlikely to cause a dramatic market surge.
Taxes, Custodians, and the Big Unknown at Age 18
There are still major tax questions. Because contributions are considered gifts and the child doesn’t have immediate access to the funds, this could create gift tax reporting complications. Even if contributions fall under the $19,000 annual exclusion (for 2026), a gift tax return may still be required due to the lack of “present interest.”
Then there’s the big question: how will withdrawals be taxed at age 18? There’s no upfront deduction for contributions, which means this isn’t structured like a traditional IRA. But it’s also not clearly a Roth. My expectation is that only the gains will be taxed, but we don’t yet know whether that will be ordinary income or capital gains.
Until we get final guidance, I strongly believe record-keeping will be critical. Track contributions carefully. If custodians change or records are lost, your child could face unnecessary tax complications later.
For now, here’s what we do know: if your child, or a grandchild, niece, or nephew, qualifies for the $1,000 seed money, make sure the account gets opened. Even with unanswered questions, that initial funding is meaningful.
Resources Mentioned
- TrumpAccounts.gov
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Retirement Readiness on Demand Discount Code: RETIRE99
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