Insights
Typewriter with the word "Premium" typed on paper — illustrating Medicare premium costs for wealthy retirees

Do Wealthy People Pay More for Medicare?

Do wealthy people pay more for Medicare? Learn how IRMAA surcharges raise premiums for high earners — and why a Roth IRA can mean lower Medicare costs, even with millions saved. Oak Road Wealth Management, Lee's Summit, MO.

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Medicare Part A and Part B checklist on clipboard with stethoscope — Oak Road Wealth Management

How Much Does Medicare Cost Me Monthly?

Wondering how much Medicare costs per month in 2026? Oak Road Wealth Management walks through Part A, Part B, and Part D premiums, deductibles, and IRMAA surcharges — so you can plan with confidence.

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Welcome to Oak Road Wealth Management!

I’m Dan Shepard, Founder and President of Oak Road Wealth Management. Welcome to my new blog! I started Oak Road because I wanted to provide a better experience for investors. There’s a lot of bad information out there about what it takes to build wealth and create Financial Independence.

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What football can teach us about diversification

What a great weekend of football, turkey, family and friends! I hope you had a great one! Football has been on my mind and in honor of that time honored tradition, I wanted to relate our nation’s favorite pastime to investing.

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What REALLY matters when it comes to building wealth?

There’s a lot of noise out there! If you listen to the financial media or logon to your favorite financial news site, you will find contradictory information about what it takes to grow your money.

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The truth about Social Security

Last week, a new bill was introduced to congress which is being called the Social Security Reform Act of 2016. The proposed legislation includes a number of elements designed to ‘save’ Social Security.

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5 Ways to Use Your Tax Refund Wisely

We all know that eating our vegetables before dessert is a good idea. But just the same, few people would advocate only eating vegetables — you have to live a little, after all! The same principle applies to your tax refund, that one-year, interest-free loan the government appreciates so much.

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Accepting market cycles and focusing on the process

It would be an understatement to say that there’s a lot going on in the world right now, perhaps more than ever. We live in a drastically different political landscape than we did mere months ago. The world’s geopolitical landscape is changing quickly, and is as complex as ever.

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Choosing a Financial Advisor: Fee-Only vs Fee-Based

Like any industry, the financial industry is full of technical terms and jargon that can easily get confusing to anyone who doesn’t work in it — including the distinction between fee-only and fee-based financial advisors.

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