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!

In an ideal world, everyone should aim to keep 3–6 months of living expenses in an emergency fund. But let’s face it, building that kind of safety net isn’t always easy. For many pre-retirees, most savings are tied up in retirement accounts, leaving limited options for unexpected expenses. So, what can you do if an emergency arises? In today’s episode, I’ll walk you through how to access emergency funds from your 401(k) and explore strategies to help you stay prepared for life’s unexpected challenges.

If you retire early (before 65), you’re too young to qualify for Medicare. So, what are your health insurance options? In this episode of Retire with Ryan, I’ll address five different options you have to get health insurance. I’ll also share some ways you can lower the cost of your premiums to keep coverage affordable until you qualify for Medicare.

President Biden recently signed the Social Security Fairness Act into law, bringing significant changes to Social Security benefits for millions of public school teachers and former public employees. This new legislation eliminates provisions that previously reduced or limited their benefits. In this episode, I’ll break down how the bill works, who it impacts, what it means for you, and what steps you need to take to claim any additional benefits you may be eligible for.

Happy New Year! As we step into 2025, it’s time to reflect on the lessons of the past year and anticipate what’s ahead. In this episode, I take a deep dive into my 2024 market predictions—where I was right, where I went wrong, and the key takeaways to help guide your investment decisions moving forward. The S&P 500 delivered a remarkable 23.8% return, Bitcoin soared by 121%, and interest rates shifted more than expected. How did these compare to my forecasts? I’ll share the details and insights that shaped last year’s performance. Then, we’ll turn our focus to 2025, where I outline predictions for major asset classes, the S&P 500, interest rates, and the ongoing battle between Gold and Bitcoin.

In this episode, I’m joined by Larry Swedroe, a thought leader in evidence-based investing and former Chief Research Officer at Buckingham Strategic Wealth. Larry has authored over 18 books that have shaped the way people think about personal finance, and now, after 28 years in the industry, he’s sharing the most valuable lessons he’s learned in retirement planning and investing. In this episode, we dive into his latest book, Enrich Your Future: Keys to Successful Investing. Through 40 captivating stories, Larry exposes the myths and misconceptions that many investors hold, often perpetuated by Wall Street, and replaces them with clear, actionable strategies. From understanding how overconfidence derails financial success to learning how to balance risk as you approach retirement, this conversation offers invaluable guidance for anyone looking to achieve financial independence.

To celebrate the season, I’m embracing the holiday spirit with a financial twist on the iconic Christmas movie, Home Alone. This 1990 classic has become a Christmas staple, featuring young Kevin McCallister, who’s accidentally left behind while his family flies to Paris for Christmas vacation. Armed with creativity and courage, Kevin outsmarts two bumbling burglars with a series of clever traps before his family returns home. But today, I’m looking at Home Alone through a different lens. As your financial advisor, I’ll break down the McCallister family’s finances. How rich were they? What would their stunning Chicago home be worth today? And what kind of jobs could support such a luxurious lifestyle? With a budget of just $18 million, Home Alone has grossed nearly $500 million worldwide—and I’ve probably contributed to that total with how many times I’ve rewatched it! So, grab some eggnog, settle in by the fire, and let’s explore the McCallister family’s financial plan.

How can an annuity help you secure income in retirement? Annuities often come with a reputation for being complicated, expensive, and overhyped—but they aren’t one-size-fits-all. The truth is, while they’re not the best solution for everyone, there are situations where they can provide the guaranteed monthly income some retirees need. In this episode, I’m joined by Andy Panko, CFP®, RICP®, EA, and President of Tenon Financial. Together, we’ll cut through the confusion and explore when an annuity might actually be the right fit for your retirement strategy.

Last year, Americans donated $558 million to charities. 69% of those donations come from individuals. They also donated 4.1 billion hours to charities. If you are someone making a donation to a charity, you need to know how they can help you reduce your taxes. One way to do that is through a donor-advised fund. What is a donor-advised fund? How does it work? Should you consider using one for charitable giving? I’ll cover the details in this episode.

What could a Trump White House and Republican-controlled Congress mean for your finances? In this episode, we break down the potential tax changes—from individual tax brackets to business deductions and state taxes—that could impact your bottom line. Tune in to understand the areas with low, moderate, and high potential for change and what steps you should consider if you live in a high-tax state.

How does Medicare Open Enrollment work? Do you need a supplement plan? How do you choose between a Medigap or Medicare Advantage plan? Navigating these questions can be overwhelming. That’s why Danielle Roberts—co-founder of Boomer Benefits and the author of “10 Costly Medicare Mistakes You Can't Afford to Make”—joins me in this episode to help you avoid common pitfalls during Medicare Open Enrollment.

On November 8th, 2024, Medicare announced that in 2025, Medicare Part B will cost $185 per month per person—an increase of about $10.30 from 2024. Keep in mind, if your income is above a certain point, you’ll have to pay an “Income-Related Monthly Adjusted Amount,” or “IRMAA” tax. Is there a way to avoid paying the IRMAA surcharge? I share some strategies in this episode of Retire with Ryan.

In this episode, we’re diving into the often-overlooked tax benefits of 529 plans. Most people know that 529 plans can help cover college expenses, but there are other valuable perks beyond just tuition savings. From paying down student loans to making the most of tax deferral advantages, this episode breaks down five key tax benefits you may not be aware of. Let me help you maximize the potential of your 529 plan.

The S&P 500 is having another stellar year, yet small-cap stocks—representing the smallest publicly traded companies in the United States—haven't performed as well. While this might seem like a downside, it can also present unique opportunities for investors. In this episode, we’ll dive into the pros and cons of investing in small-cap stocks, the potential growth they offer, and how you can get started.

The 2024 election is just days away, and soon you'll have your final chance to cast your vote. With so much at stake, many are anxious about how the markets might respond based on who takes the White House. In this episode of Retire with Ryan, I’ll dive into what we could expect from a Trump or Harris presidency—and explain why, no matter the outcome, it shouldn't drastically change your investment strategy.

In some states, probate is avoidable. However, in many states, you can avoid having your estate go through the probate process. I recently went through the probate process when my grandfather passed away and I helped my father settle his estate. It is far easier for your family to settle your estate once you’re gone if it doesn’t go through probate. So, in this episode, I’ll cover 7 things you can do to keep your estate from landing in probate.

Protecting your finances from hackers is more critical than ever. Cybercriminals are getting more sophisticated, accessing sensitive information like social security numbers and attempting to steal directly from financial accounts. I recently experienced this firsthand when someone impersonated one of my clients. The fraudster knew my client’s social security number and tried to withdraw funds under the guise of an emergency. Fortunately, we were suspicious and confirmed the scam before any money was lost. This encounter highlights the importance of being proactive about securing your accounts. That’s why, in this episode, I’ll share seven essential Steps to protect your Schwab accounts from hackers.

Age 59 ½ is the magic age at which you can start taking distributions from retirement accounts without a penalty. This listener is wondering if he can convert part of his IRA to a Roth IRA even though he’s not 59 ½. And if he goes ahead with the conversion, will it be subject to the 10% penalty? Listen to this episode to find out.

It can be overwhelming to think about what you can do to minimize your tax burden. That’s why, in last week’s episode, we covered 7 year-end tax moves for retirees. This week, we’ll tackle what those nearing retirement need to dive into at the end of every calendar year. We all need to be mindful of how our decisions impact our tax burden and this is a great place to start!

Tax planning—and anything related to taxes, in general—isn’t most people’s favorite topic. But because we’re getting toward the end of the year, it’s actually a great time to think about tax planning and all of its benefits. In this episode of Retire with Ryan, I’ll share 7 things you should think about that can (and will) help save you money in retirement.