Recent Videos

Understanding the New Charitable Contribution Rules from the One Big Beautiful Bill Act
Ryan Morrissey Ryan Morrissey

Understanding the New Charitable Contribution Rules from the One Big Beautiful Bill Act

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, are planning a large gift, or just want to maximize your tax benefits, I’m sharing practical tips about when and how to make your contributions in light of these updates.

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Should You Open a Trump Account for Your Child’s Future?
Ryan Morrissey Ryan Morrissey

Should You Open a Trump Account for Your Child’s Future?

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 thinking about the best way to jumpstart your child’s financial future, you’ll want to tune in for my honest comparison of the Trump account's pros, cons, and quirks, plus tips on making the most of these new opportunities.

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How the One Big Beautiful Bill Act Impacts Retirees
Ryan Morrissey Ryan Morrissey

How the One Big Beautiful Bill Act Impacts Retirees

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 older, I cover everything you need to know to optimize your retirement strategy. Whether you're curious about Social Security taxation, itemized deductions in high-tax states, or planning smart Roth conversions, this episode is packed with insights to help you make informed financial decisions for your golden years.

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Required Minimum Distributions Explained
Ryan Morrissey Ryan Morrissey

Required Minimum Distributions Explained

This week on the show, we’re discussing the specifics of Required Minimum Distributions (RMDs) as we head into the second half of 2025. Whether you’re approaching your first year of RMDs or have been taking them for a while, I break down everything you need to know, from when you need to start taking distributions based on your birth year, to how RMDs are calculated, which accounts are affected, and the potential tax consequences for missing a withdrawal.

I’m also sharing eight practical strategies you can use to lower your future RMDs, including asset diversification, Roth conversions, tax-efficient income planning, optimizing Social Security timing, and even using charitable contributions to your advantage. With real-world examples and actionable tips, this episode is packed with valuable insights for anyone looking to navigate their retirement withdrawals as tax-efficiently as possible.

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How the Big Beautiful Bill Impacts Solar & Electric Vehicle Tax Credits
Ryan Morrissey Ryan Morrissey

How the Big Beautiful Bill Impacts Solar & Electric Vehicle Tax Credits

With the recent passage of the Inflation Reduction Act, also known as the Big Beautiful Bill, significant changes are coming to both solar panel and electric vehicle tax credits.

I break down what these changes mean, how they can affect your savings, and what steps you might want to take before these credits disappear.

From figuring out if solar panels make sense for your home to understanding how electric vehicle credits work (and when they’re expiring), this episode is packed with actionable insights and tips, especially for those planning for retirement or looking to cut down on monthly expenses.

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Risk and Reward of Withdrawing Social Security Benefits to Invest Them
Ryan Morrissey Ryan Morrissey

Risk and Reward of Withdrawing Social Security Benefits to Invest Them

This week, I’m addressing a listener's question: Should you collect Social Security at age 62 and invest the money, or wait until your full retirement age, or even age 70, for a bigger benefit?

I break down the math and the risks, weighing the advantages of guaranteed annual increases and cost-of-living adjustments against the potential (and pitfalls) of stock market returns. 

I also explain key rules, such as the earnings limit for early filers, tax implications, and who might benefit from collecting early.

Whether you’re eager to take Social Security as soon as you can or are considering holding out for a larger payment, listen in for the practical insights you need to make a smart decision for your financial future.

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Five Reasons a Brokerage Account Might Be Better Than an Annuity for Your Investments
Ryan Morrissey Ryan Morrissey

Five Reasons a Brokerage Account Might Be Better Than an Annuity for Your Investments

I’m exploring a common dilemma faced by anyone receiving a lump sum of money, whether from an inheritance, the sale of a business, or another windfall: Should you invest in a traditional brokerage account or opt for an annuity?

On this week's episode, I discuss the key differences between annuities and brokerage accounts, highlighting the five major pitfalls of annuities that are often overlooked.

You'll learn why transparency, flexibility, and tax efficiency make brokerage accounts a better fit for many investors, especially those seeking to beat inflation and maintain control of their funds.

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Facts vs. Fiction in Retirement Planning
Ryan Morrissey Ryan Morrissey

Facts vs. Fiction in Retirement Planning

From the truths about making large purchases in retirement to whether you really need to pay off your mortgage before you stop working, I’m sharing years of financial expertise to challenge a few retirement myths so you can make balanced, informed decisions. We’re talking strategies for charitable giving, clearing up misconceptions about reverse mortgages, and explaining why inflation may be your biggest risk in retirement. 

If you’re looking for practical advice on enjoying your savings while still planning for the long run, or if you want to protect yourself from financial scams and fraud, this episode is full of actionable tips to build your financial confidence for the years ahead.

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Seven Smart Reasons to Leave Your Old 401(k) with a Previous Employer
Ryan Morrissey Ryan Morrissey

Seven Smart Reasons to Leave Your Old 401(k) with a Previous Employer

Building on last week’s discussion about why rolling over your old 401(k) into an IRA could be a smart move, this episode flips the script. It explores seven compelling reasons you might want to leave your 401(k) with your previous employer instead.

I break down factors like fees, company stock advantages, penalty-free withdrawals, legal protections, and unique investment options that could all influence your decision.

If you're approaching retirement or just planning your next career move, this episode is packed with insights to help you make the best choices for your financial future.

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Five Reasons to Roll Over Your Old 401k into an IRA
Ryan Morrissey Ryan Morrissey

Five Reasons to Roll Over Your Old 401k into an IRA

In today's episode, I’m diving into a topic that’s top-of-mind for anyone who’s switched jobs: what should you do with your old 401(k) plan? I discuss five key reasons why moving them into an IRA could simplify your financial life, from consolidating accounts for better control to gaining access to a broader range of investment options, reducing fees, optimizing Roth and after-tax funds, and making it easier to work with a financial advisor.

Whether you’re planning your next career step or just want to make your retirement savings work harder for you, this episode is packed with practical advice to guide your decision. Stick around until the end, and don’t forget to tune in next week when I cover situations where rolling over your 401(k) might not be the best choice!

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Retirement Reality Check with Michael Sheldon
Ryan Morrissey Ryan Morrissey

Retirement Reality Check with Michael Sheldon

This week on the show, I’m joined in person by investment veteran Michael Sheldon, who brings over 26 years of experience in the financial services industry. We dig into essential strategies for investing as you approach and enter retirement, covering asset allocation, diversification, income planning, and how to handle inevitable market volatility. 

Whether you’re a pre-retiree, a recent retiree, or just looking to strengthen your investment approach, Michael offers some great actionable insights designed to help you build a resilient portfolio and stay on track toward your long-term financial goals.

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Breaking Down the FERS Retirement System for Federal Employees
Ryan Morrissey Ryan Morrissey

Breaking Down the FERS Retirement System for Federal Employees

On this week’s episode, I’m discussing the Federal Employees Retirement System, or FERS, a program that covers nearly all civilian federal workers. If you’re a federal employee curious about when you’re eligible to retire, how your pension is calculated, what the Thrift Savings Plan offers, or how special early retirement and survivor benefits work, this episode is your go-to resource.

We’re breaking down the three key components of FERS: your Basic Benefit Plan (a pension), Social Security, and the Thrift Savings Plan, as well as important details like cost-of-living adjustments and tax considerations. Whether you’re just starting your federal career or planning your retirement right now, you’ll get practical insights to help you make the most of your retirement benefits.

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Four Costly Mistakes to Avoid When Claiming Social Security While Working After 65
Ryan Morrissey Ryan Morrissey

Four Costly Mistakes to Avoid When Claiming Social Security While Working After 65

Thinking about collecting Social Security while you’re still working? It’s a tempting option, but there are several crucial mistakes you’ll want to avoid. Using real-life stories, I’m laying out the four big pitfalls, like earning over the social security limit, jeopardizing your health savings account, mishandling Medicare enrollment, and forgetting about tax withholding.

These missteps can lead to unnecessary penalties, and so I want to give some actionable strategies to help you make the most of your benefits without unpleasant surprises. 

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Applying Warren Buffett's Investment Wisdom to your life
Ryan Morrissey Ryan Morrissey

Applying Warren Buffett's Investment Wisdom to your life

It’s been announced that Warren Buffett is stepping down as CEO of Berkshire Hathaway. In this episode, I’ll discuss Buffett’s humble beginnings, his approach to investing, and the philosophy that built one of the most successful companies in history.

I’ll also break down Warren Buffett’s wisdom into seven powerful, practical tips that align with my own approach to advising clients. Listen for tips on starting your investment journey early, staying the course during tough markets, and prioritizing temperament over intellect.

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Top Five HSA Mistakes That Are Costing You Money and How to Avoid Them
Ryan Morrissey Ryan Morrissey

Top Five HSA Mistakes That Are Costing You Money and How to Avoid Them

On the show today, I’m discussing something that could be a game-changer for your retirement savings: Health Savings Accounts, or HSAs. If you’re on a high-deductible health plan, you might be eligible for this unique, triple tax-free account, but are you making the most of it?

I’m sharing the top five mistakes’ people make with their HSA accounts. If not avoided, those mistakes can cost you serious money and limit your financial options later in life. I’m covering everything from choosing the right HSA provider to maximizing your investments within the account, tracking expenses, and even strategizing for retirement healthcare needs.

Plus, I’ll give you actionable tips to avoid these common pitfalls and explain how an HSA can function as a powerful retirement savings tool.

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Six Dave Ramsey Tips That Could Hurt Your Retirement Plan
Ryan Morrissey Ryan Morrissey

Six Dave Ramsey Tips That Could Hurt Your Retirement Plan

Radio personality Dave Ramsey is a huge name in the personal finance niche. While he’s celebrated for helping countless listeners take control of their finances, many of his recommendations have sparked debate within the financial planning community.

I’m going to break down six of the most controversial opinions promoted by Ramsey, including advice on retirement withdrawals, debt payoff strategies, Roth accounts, investing approaches, mortgages, and the use of credit cards. I will also weigh up the pros and cons of Ramsey’s methods, highlighting where they might help and where they might hinder your journey towards a successful retirement.

Whether you’re a Dave Ramsey fan or just curious about best practices for financial wellness, this episode offers a thoughtful, practical take on some hotly contested money moves.

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Social Security Survivor and Spousal Benefits Demystified
Ryan Morrissey Ryan Morrissey

Social Security Survivor and Spousal Benefits Demystified

Welcome to a special milestone episode of Retire with Ryan! In this 250th episode, we’re digging into one of the most frequently asked topics by listeners: Social Security. I answer four real-life listener questions about Social Security benefits - covering issues such as survivor benefits after divorce, spousal and ex-spousal benefit eligibility, changes to the Windfall Elimination Provision and Government Pension Offset, and rules for collecting benefits based on a former spouse’s record.

I’m breaking down complex Social Security rules in an easy-to-understand way and sharing practical advice for retirees and those planning their dream retirement.

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Six Tactical Moves for Navigating Down Markets
Ryan Morrissey Ryan Morrissey

Six Tactical Moves for Navigating Down Markets

This time, we're featuring financial insights from co-host Ryan Morrissey, who's here to help you navigate this turbulent financial landscape. We'll explore the recent volatility sparked by President Trump's tariff announcements and discuss the remarkable market rebound that followed. Ryan also lays out six strategic moves you can make to optimize your investment strategy during these downturns, whether it's buying the dip, rebalancing your portfolio, or taking advantage of tax efficiencies. Stay tuned for valuable tactics and practical advice to bolster your financial well-being and prepare for a successful retirement. Let's get started with Retire with Ryan!

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4 Strategies to Avoid Tax Tsunami When Working Beyond 73 Years Old
Ryan Morrissey Ryan Morrissey

4 Strategies to Avoid Tax Tsunami When Working Beyond 73 Years Old

As you get closer to the age of 73, it's more and more important to understand the financial strategies you can use to avoid a "tax tsunami" or "tax bomb."

In this episode, I break down the basics of RMDs, explaining how they are calculated and the importance of planning ahead. You’ll want to make a note of these four key strategies to reduce your RMDs and ensure a smoother financial journey as you transition into retirement. 

From starting withdrawals before the age threshold to considering Roth conversions and qualified charitable distributions, we share practical insights to help you navigate these financial waters.

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