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.

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.

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. 

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.

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.

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.

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.

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!

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.

In this episode, I address listener concerns about the future of Social Security, especially given recent changes under President Trump's administration and the involvement of the Department of Government Efficiency (Doge). I’ll dive into the current state of Social Security, the potential impact on your benefits, and how you can maximize those benefits moving forward. With solvency concerns looming, I’ll help you better understand what’s at stake and how to make smart decisions for your retirement.

In this episode of Retire with Ryan, I’m talking about the growing threat of smishing, a type of phishing scam where fraudulent text messages try to trick you into revealing personal information like your social security number, bank account details, or credit card information. I’ll explain how these scams are targeting individuals like you and share some important tips on how to protect your phone and investment accounts from being compromised. It's crucial to stay informed and secure, and I’m here to help you navigate these risks.

Maximizing your retirement plan contributions is one of the most powerful ways I can help you secure your financial future. As we near the end of the first quarter of 2025, it’s the perfect time to review your contributions.

In this episode, I break down how you can ensure you're contributing the maximum allowable amount and why it’s essential to do so. I explain how to calculate your contribution limits based on your salary and pay frequency, so you can easily determine how much you should be setting aside per pay period. 

If you haven’t adjusted your contributions for the year, don’t worry—I’ll walk you through how to quickly get back on track to ensure you’re maximizing your retirement plan. By taking action now, you can set yourself up for greater savings down the road.

What’s the best way to protect your retirement savings when the market feels unpredictable? In today’s episode of Retire with Ryan, I cover the growing uncertainty caused by political decisions and how they affect your investments. From tariffs to immigration changes and government cutbacks, I’ll share insights on how to navigate this volatility and keep your portfolio secure. Whether you’re nearing retirement or already there, this episode will provide actionable steps to ensure your investments remain on track despite external economic pressures.

In this episode, I dive into the latest developments with the Social Security Fairness Act and what these changes mean for retirees who were previously ineligible for Social Security benefits. With potential increases in payments and retroactive benefits, this episode is packed with critical insights for anyone impacted by the new law. I break down real-world examples to show exactly how these changes will affect individuals—particularly teachers, former public employees, and those with pensions exempt from Social Security. Whether you’re waiting for retroactive benefits or trying to understand the tax implications, I’ve got you covered with the essential information you need.

What is the best way to access equity in your home for retirement income? In this episode of Retire with Ryan, host Ryan Morrissey is joined by Mitch Cooper, a Certified Reverse Mortgage Professional with Mutual of Omaha, to explore this very question. Mitch returns to the show to share his expertise on reverse mortgages, a powerful tool that allows retirees to tap into the equity of their homes without having to sell. Whether you’re considering this option for supplemental income or simply want to understand how it works compared to other alternatives like home equity loans, this episode provides valuable insights into how reverse mortgages can help secure your financial future in retirement.

In this episode of Retire with Ryan, we’re diving into the ins and outs of 1031 Exchanges with expert Eric Brecher. As Executive Vice President at the Chicago Deferred Exchange Company, Eric brings years of experience in navigating this complex IRS provision, which allows real estate investors to defer capital gains taxes when selling property. If you're interested in real estate investments and the potential tax advantages that come with them, this episode is a must-listen. Eric explains everything from the basics of a 1031 Exchange to key strategies, common pitfalls, and the crucial role of a Qualified Intermediary.

When it comes to retirement plans, the general rule is that you can’t access funds in your retirement account(s), without penalty, until age 59 ½. If you withdraw funds prior to 59 ½, you’ll get hit with a 10% penalty and income tax (if coming from a non-Roth account). But there are some instances in which you can make withdrawals penalty-free. We’ll dive into this in this episode of Retire with Ryan.

Will AI stocks like NVIDIA continue their meteoric rise, or are we heading toward a market correction? What do recent Federal Reserve decisions mean for your investments and mortgage rates? And is it time to reconsider small-cap stocks?

In this episode, I sit down with Michael Collins, CEO of WinCap Financial, to explore the biggest financial trends of 2025. We discuss the future of AI-driven investing, the Federal Reserve's impact on interest rates, and whether large-cap stocks will remain dominant. This episode is a must-listen!