Who we are

Wealth isn’t about luck.

It’s more likely the result of a solid plan that is designed to allow you to accumulate wealth—day after day, year after year.

This is the difference between being set for now…and being set for life.

Set in scenic and historical Williamsburg, The Optimal Service Group was founded in 1975 and is led by Joseph W. Montgomery, CFP®, AIF®, Managing Director-Investments. Joe has been recognized as a Top 100 Advisor and Top 100 Institutional Advisor by Barron’s and a Top 400 Advisor by the Financial Times from 2014-2019.1

With approximately $28 billion2 under advisement, The Optimal Service Group has a combined 350+ years of experience with 13 registered associates who hold professional designations of CFA, CFP, CAIA, CIS, AIF, FRM, CIMA CRPS, CPWA, QPFC and MBA.3

Our philosophy


1. The Earth is round.

Seems like a simple, irrefutable fact—yet there are people who swear up and down that this isn’t the case. The people we choose to work with don’t try to argue things that don’t make any sense. Our clients understand that the equation is simple: Diversification4 + time = potential success.

2. One year does not a portfolio make.

Imagine if the value of your whole life were judged by a single year—and someone else got to pick it. Not fair, right? Exactly. That’s why we take a big picture view of your finances. And we invite you to do the same.

3. Patience is more than a virtue; it’s a discipline.

Patience is a little like wealth—the more you have, the more resilient you are. Patience is an art and a discipline, like mastering the violin. You get good with practice. Achieving wealth demands patience. Those who bail may fail.

4. Wealth doesn’t make any sudden moves.

Panic isn’t a good look. It’s also wildly ineffective. We do neither. Instead, we strive to provide a consistent and diversified approach to your wealth.

5. Risk isn’t a what-if, but a when.

More often than not, people tend to overestimate their risk tolerance. Be honest with yourself about how much risk you can take and still sleep at night. Because it’s not a matter of “if” the market changes… but when.

6. Greed and fear undermine your future more than any market correction.

You think the market is unpredictable? Emotions are worse. Greed can cause you to lose trust in what works. Fear can cause you to lose faith in everything else. So we keep an even keel—and aim to outlast market corrections and emotional downswings.

7. Never underestimate a base hit.

Everyone loves a home run. But if you’re aiming to hit it out of the park day after day, year after year, you’re setting yourself up to fail—or at least be very underwhelmed. We strive for base hits to win the day.

8. Money is to wealth as weather is to climate.

Money comes and goes; it’s subject to storms. Wealth, on the other hand, is climate; it’s not defined by the day or the year, but by decades. It’s steady, gradual, and both shapes and reflects the environment.

9. Your future is a moving target.

We don’t take a set-it-and-forget-it approach. Playing the long game means course correcting in an effort to ensure that your money, your actions, and your life are aligned with your goals.

10. You shouldn’t be on the edge of your seat.

Romance and suspense have their place—but not in your portfolio. The story of your money should be less like a nail-biter… and more like a classic tale: One that’s thoughtful, artfully done, and designed to stand the test of time.
1) Click here to see IMPORTANT recognition disclosure information 
2) As of 12/31/22
3) Biographies and Designations here 
4) Diversification is an investment method used to help manage risk. It does not guarantee investment returns or eliminate risk of loss including in declining market.
Wealth takes its time, and so do we.

Wealth takes its time, and so do we.

If you want to have a real and unrushed conversation about your future, give us a call.