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.

• [1:33] Larry’s process for writing a book
• [7:33] How the industry has embraced passive investing
• [17:19] Using tennis to explain the difficulties of active management
• [21:20] Why do we think we can outperform the market? 
• [26:57] What approach is prudent for most people?
• [30:08] Should retirees focus on dividend-producing investments? 
• [35:02] How to determine the amount of risk to take in your portfolio
• [39:23] Diving into the concept of indexed annuities 

• Retirement Readiness Review
• Subscribe to the Retire with Ryan YouTube Channel
• Connect with Larry Swedroe on LinkedIn
• The Only Guide to a Winning Investment Strategy You'll Ever Need
• Think, Act, and Invest Like Warren Buffett
• Your Complete Guide to a Successful and Secure Retirement

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Happy Holidays and welcome to a special Christmas Eve episode of Retire with Ryan!

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.

• [1:25] Sign up for my weekly newsletter and get a free chapter of my book!
• [3:19] How much is the McCallister house worth? 
• [5:19] Calculating how much the McCallisters made 
• [7:48] What did the McCallisters pay in taxes?
• [10:47] What was their cashflow? 
• [13:13] College costs for a family of five
• [15:03] How much are they saving for retirement?
• [18:43] Did the family have life insurance? 
• [19:36] The type of estate planning they had

• Retirement Readiness Review
• Subscribe to the Retire with Ryan YouTube Channel
• How Rich Were the McCallisters?
• Historical 401K Limits
• Details about Home Alone
• The McCallister House on Realtor.com
• Home Alone Fan Speculations
• A Brief History of the 401K

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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.

• [1:40] Two ways to generate income in retirement
• [3:07] Real-life scenario: When you might want an annuity
• [12:36] How an indexed annuity works 
• [16:39] Do annuities have inflation adjustments? 
• [20:13] Calculating the rate of return
• [23:42] Why a good financial advisor is important

• Retirement Readiness Review
• Subscribe to the Retire with Ryan YouTube Channel
• Tenon Financial
• Andy Panko on LinkedIn
• The 7 Myths About Indexed Universal Life Insurance 
• ImmediateAnnuities.com 
• Financial Planning Association
• Charles Schwab Income Annuity Calculator 

www.MorrisseyWealthManagement.com/contact

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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. 

• [1:39] Sign up for my newsletter at RetireWithRyan.com
• [3:05] What is a donor-advised fund?
• [4:51] How is this different from other contributions?
• [5:51] Who should consider a donor-advised fund? 
• [10:15] Who offers donor-advised funds?
• [11:05] Pros/cons of donor-advised funds
• [12:40] Additional benefits of using a donor-advised fund
• [13:27] How to choose the right charity
• [14:34] What are your next steps?

• Sign up for my newsletter at RetireWithRyan.com
• Retirement Readiness Review
• Subscribe to the Retire with Ryan YouTube Channel
• Charity Navigator
• Pros and Cons of Donor-Advised Funds

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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.

• [1:19] Sign up for my weekly newsletter 
• [2:28] Area of low potential for changes 
• [4:25] Area of moderate potential for changes 
• [10:05] Area of high potential for changes 
• [14:18] What to do if you’re in a high-tax state

• Retirement Readiness Review
• Subscribe to the Retire with Ryan YouTube Channel

www.MorrisseyWealthManagement.com/contact

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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.

• [1:42] How Medicare open enrollment works
• [3:45] Do you need a supplemental plan? 
• [5:13] How CMS changes impact plans
• [9:37] Comparing Medigap vs Medicare Advantage
• [12:41] The typical annual rate increase
• [15:21] How Medigap plans work when you move
• [16:12] When to choose a Medicare Advantage plan
• [19:34] How Medicare Part D works
• [21:38] How to choose between Medigap vs Advantage plans
• [24:06] How to choose a broker to work with
• [27:05] Start researching your Medicare options early
• [28:06] How to get a free copy of Danielle’s book

• Retirement Readiness Review
• Subscribe to the Retire with Ryan YouTube Channel
• 10 Costly Medicare Mistakes You Can't Afford to Make
• Boomer Benefits
• 2025 Medicare IRMAA Surcharge Updates, #228

www.MorrisseyWealthManagement.com/contact

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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.

• [1:25] How to get a FREE copy of “10 Costly Medicare Mistakes” 
• [2:20] The cost of Medicare Parts A, B, and D in 2025
• [4:26] When you would pay a higher Medicare premium 
• [8:32] What you can do to appeal the IRMAA Surcharge 
• [10:02] What you can do to avoid the IRMAA Surcharge 

• Retirement Readiness Review
• Subscribe to the Retire with Ryan YouTube Channel
• 2025 Medicare Parts A & B Premiums and Deductibles
• Form SSA-44: Medicare Income-Related Monthly Adjustment Amount

www.MorrisseyWealthManagement.com/contact

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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. 

• [1:39] What are 529 plans? 
• [3:04] Repaying student loans
• [4:14] Covering K-12 expenses
• [5:20] Tax deferral 
• [8:10] Roth conversion
• [12:40] Potential state tax deductions

• Retirement Readiness Review
• Subscribe to the Retire with Ryan YouTube Channel
• How To Complete a Fidelity 529 To Roth IRA Rollover
• 6 Ways To Use An Old CHET 529 Plan

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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.

• [0:51] Should you consider investing in small-caps? 
• [1:59] What are small-cap stocks? 
• [3:28] Pros and cons of small-cap stocks
• [5:00] The growth potential of small can stocks
• [7:03] Why is there a projected turnaround? 
• [8:23] How do you invest in small-cap stocks?
• [11:17] How to invest in value stocks

• Retirement Readiness Review
• Subscribe to the Retire with Ryan YouTube Channel
• Is the small-cap Premium Dead?
• The Russell 2,000
• The S&P 600
• VB Vanguard small-cap S&P Index
• IJR ETF
• SPSM
• SLYV

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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.

• [2:37] The state of the Presidential election
• [6:00] How the stock market is impacted
• [6:50] How will a Harris presidency impact the market? 
• [8:01] How will a Trump presidency impact the market? 
• [12:57] Nothing will fundamentally change how you invest

• Retirement Readiness Review
• Subscribe to the Retire with Ryan YouTube Channel
• State Street Global Advisors

www.MorrisseyWealthManagement.com/contact

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