Oak Road

Insights

Torn paper reading 'Roth' and 'IRA' representing the decision of when not to do a Roth conversion

When Should You Not Do a Roth Conversion?

When should you not do a Roth conversion? A fee-only fiduciary breaks down the 3 red flags to watch for before you convert.

Highway signs pointing to 'Stock Market' and 'Bond Market,' representing the asset allocation choices behind the question, is rebalancing a good idea

Is Rebalancing a Good Idea?

Is rebalancing a good idea, or just extra trading? A fee-only fiduciary breaks down the real risk-control and tax tradeoffs — before you decide.

Pie chart made of colored paper wedges and fanned cash, representing portfolio rebalancing and asset allocation

What Is the Meaning of Rebalancing?

Is your portfolio quietly getting riskier without you noticing? Learn what rebalancing means and how it fixes that automatically.

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.