Oak Road

Insights

Number 5 on a yellow plate representing the Roth IRA 5-year rule

Do You Have to Keep Money in a Roth IRA for 5 Years?

Think your Roth IRA locks your money up for 5 years? It doesn't — at least not all of it. Here's what the 5-year rule actually controls.

Chalkboard drawing of a stock market chart rising then sharply crashing downward, illustrating a market downturn and its effect on retirement accounts like an IRA.

Can I Lose My IRA If the Market Crashes?

Market drops feel personal when it's your retirement on the line. See how diversification and asset allocation shape what actually happens to your IRA.

Couple reviewing their financial plan together on a laptop at home

Is It Worth It to Pay for a Financial Advisor?

Wondering if a financial advisor is worth the cost? Oak Road Wealth Management explains the real value — from investment strategy to behavioral coaching and retirement confidence.

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.

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.

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.

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.

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.

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.