Retire With Ryan

This episode is your introduction to the world of conservative investing, so it's perfect for you if you're looking to preserve your principal and grow your money at a steady pace. I'm walking you through seven standout investment choices for 2026, ranging from high-yield online money market accounts to short-term bond funds, CDs, and Treasury bonds. We'll discuss how to shop around for the best r...

In this episode, I'm helping you kick off 2026 by reflecting on financial habits that pave the way for a successful retirement. As we set our goals for the year ahead, I share the four key traits I've observed in successful retirees, drawn from years of experience working with people from all walks of life. You'll hear practical advice on how to work hard and invest consistently, the importance of...

As we turn the calendar to 2026, I reveal my forecasts for the stock market, interest rates, and top asset classes, and take a look back at how my 2025 predictions stacked up against reality. From the S&P 500's rollercoaster performance to the ongoing rivalry between growth and value stocks, and even a showdown between bitcoin and gold, I break down what the numbers were, where I hit the mark, and...

2025 has been a year of significant highs and lows, a bittersweet time marked by personal loss but also tremendous growth in our community of listeners and clients. As we wrap up the year, I wanted to take a moment to reflect and, more importantly, to give back by answering the most pressing questions on your minds. In this episode, I'm tackling the top 10 most asked financial questions I received...

529 college savings plans are a favorite tool for families looking to fund education, but recent updates have made them even more compelling. With the passing of the One Big Beautiful Tax Act in 2025, there have been some exciting changes to what you can use 529 funds for, including expanded coverage for K-12 tuition, test fees, vocational programs, and support for learning differences. I also dis...

In the season of giving, we're discussing making charitable contributions in 2025 and 2026. Americans are known for their generous donations to worthy causes, but understanding the best ways to give and maximize your tax benefits is key. This episode covers four effective strategies for making charitable contributions, from utilizing Qualified Charitable Distributions (QCDs) from your retirement a...

Healthcare planning is a huge part of getting ready for your retirement. In this episode, I tackle one of the most pressing updates for retirees: the latest changes to Medicare premiums for 2026, including important surcharges, deductibles, and strategies to help you manage your healthcare expenses.  I'm helping you understand the significant increases in Medicare Part B premiums and deductibles,...

As 2025 comes to a close, we're here to help you make the most of year-end tax planning. I'm explaining seven actionable strategies to help you minimize your tax liability and optimize your retirement savings before the New Year.  From maximizing retirement plan contributions and exploring Roth conversion opportunities to using donor-advised funds for charitable giving and getting the most from yo...

There are important changes coming to 401 (k), 403 (b), and 457 retirement plans in 2026, so I'm focusing on how these updates may impact catch-up contributions for individuals over age 50. With the Secure Act 2.0 on the horizon, higher earners will soon have to make their catch-up contributions as Roth (post-tax) rather than pre-tax contributions, potentially affecting their take-home pay and tax...

If you've spent any time on social media or read personal finance blogs, you've likely encountered a buzz around Roth IRAs and, specifically, Roth conversions. This week I'm discussing the details of Roth conversions, what they are, how they work, and why they're crucial for those looking to optimize their retirement finances. Roth IRAs hold a special appeal: the promise of tax-free income in reti...

Retirement planning is an ever-evolving process, and staying informed about changes to Social Security, Medicare, and tax limits is crucial to making the most of your golden years. On this episode of Retire with Ryan, I'm sharing important updates on the 2026 Social Security cost of living adjustment (COLA), projected changes to Medicare Part B premiums, and strategies for managing income in retir...

With the term "financial advisor" being used so broadly these days, it's harder than ever for retirees and investors to make sense of who's actually guaranteed to act in their best interest. So let's talk about the key responsibilities of fiduciaries, explore the differences between fee-only advisors and those who earn commissions, and go through why full disclosure and ongoing advice matter so mu...

Every year, Medicare Open Enrollment presents an important opportunity for retirees and individuals enrolled in Medicare to review, update, and make changes to their health and prescription drug coverage. If you're on Medicare or approaching retirement, understanding the enrollment period and your options is crucial to ensuring comprehensive and cost-effective health care. I'm sharing the seven es...

This episode is essential listening for anyone who's inherited an IRA, especially in light of the game-changing SECURE Act. If you've inherited a retirement account from a non-spouse since 2020, this episode is packed with details you need to know to avoid unexpected tax bills and penalties. I explain the new rules for inherited IRAs, explaining the requirements and options for non-designated, non...

You might have seen those viral articles promising a mysterious multi-thousand-dollar Social Security "bonus," but are they actually legit? On the show this week, I separate fact from fiction, debunking the myths and sharing seven actionable strategies to help you get the most out of your Social Security over your lifetime.  Whether you're curious about how working longer, delaying your benefits,...

The Social Security Fairness Act, which was signed into law at the start of 2025, has been in effect for about nine months since this game-changing legislation repealed both the Windfall Elimination Provision and the Government Pension Offset, restoring and increasing Social Security benefits for millions of retirees, especially teachers and public employees who worked in jobs exempt from Social S...

It's one of the most frequently asked questions by my clients as they prepare for retirement. And while a million dollars may sound like a lot, the reality is a bit more complex. There are several key factors to consider when planning your retirement, including factoring in taxes, evaluating withdrawal strategies, and understanding the cost of living where you plan to retire. Let's break down how...

Are you turning 65 soon or starting to think seriously about healthcare in retirement? This week, I discuss the complicated world of Medicare—with a focus on the seven most costly mistakes people make when enrolling.  From missing crucial deadlines and underestimating penalties, to overlooking the true costs Medicare doesn't cover and getting tripped up by income-related surcharges, I give practic...

Paying for education is a major expense for many families, so I'm breaking down why 529 plans remain the preferred way to save for college, thanks to their tax advantages and flexible growth. I unpack updates, such as increased limits for K-12 tuition withdrawals, expanded uses for trade and vocational schools, and the new ability to roll funds into ABLE accounts for individuals with disabilities....

For married couples planning their retirement, understanding spousal Social Security benefits can seem like a labyrinth. This week, I'm answering a listener's question about how spouses can maximize their Social Security benefits. Join me as I break down the key rules, eligibility requirements, and strategies that can help you and your spouse make the most of your benefits over your lifetimes.  Wh...

The power of Health Savings Accounts (HSAs) as a tool for both managing health expenses and building your retirement savings is often overlooked. On this episode, I'm sharing the basics of HSAs, highlighting their triple tax-free advantage, and explaining why they might be one of the best ways to maximize your retirement savings, even compared to more familiar accounts like IRAs and 401(k)s. I als...

The future of Affordable Care Act (Obamacare) subsidies is a pressing issue for retirees and anyone shopping for health insurance on the ACA marketplace.  With the generous subsidies brought by the American Rescue Plan Act set to expire at the end of 2025, I break down exactly how these subsidies work, what changes are coming in 2026, and what that means for your wallet. We're talking eligibility...

The One Big Beautiful Bill Act affects charitable contributions for retirees and individuals considering their tax strategies. I'm walking you through three major changes: the restoration of the charitable cash deduction for non-itemizers, new limitations on how much can be deducted for larger contributions, and a cap on itemized deductions for high earners. Whether you give to charity every year,...

The brand-new "Trump account" is a tax-deferred savings option for American children created by the One Big Beautiful Bill Act. I break down who's eligible for up to $1,000 in free government contributions, how these accounts work, and how they stack up against other popular savings vehicles like 529 plans, IRAs, custodial accounts, and regular brokerage accounts. If you're a parent or grandparent...

The One Big Beautiful Bill Act, signed into law on July 4th, brings about several important tax changes. I'm discussing what these updates mean, especially for retirees, and sharing practical advice on how to take advantage of new deductions and avoid unexpected tax hits.  From permanent adjustments to tax brackets and an increased standard deduction, to special benefits for those aged 65 and olde...