Investment Management

That’s a smart question because true diversification isn’t just about owning a bunch of different funds. It’s about owning the right mix for your goals, risk tolerance, and timeline.

At Chesapeake, we look at more than just how your assets are spread out. We ask:

• Are your investments diversified across asset classes, sectors, and geographies or just different versions of the same thing?
• Are you holding too much in cash alternatives or too much risk?
• Do your investments align with your income needs, tax picture, and withdrawal strategy?
• Have we stress-tested your portfolio against different market scenarios?

Diversification alone won’t prevent losses, but the right strategy can help you weather volatility with more confidence and fewer regrets.

If you’re not sure how your portfolio would hold up in a downturn, let’s take a look.

All investing involves risk including loss of principal. No strategy assures success or protects against loss. There is no guarantee that a diversified portfolio will enhance overall returns or outperform a non-diversified portfolio. Diversification does not protect against market risk.

It depends on three things: your time, your interest, and what’s at stake.

If you enjoy managing investments, have the time to stay on top of changing markets, and understand how taxes, asset allocation, and long-term planning work together, you might be fine on your own.

But here’s when hiring a professional can make a big difference:

• You’re too busy to manage the details consistently
• You’re unsure how to coordinate investments with taxes, cash flow, or retirement goals
• You’ve made emotional decisions in past market cycles
• Your finances are getting more complex (equity comp, business ownership, inheritance, etc.)
• You want accountability, not just access to information

At Chesapeake, we're not here to take control, we're here to bring clarity and strategy. Because the goal isn’t just beating the market, it’s building the life you actually want.

In most cases, yes. Rebalancing keeps your investments aligned with your goals and risk tolerance, especially as markets move.

Over time, certain parts of your portfolio may grow faster than others. That can leave you overexposed to risk or too conservative for your goals without realizing it.

Here’s why annual (or more frequent) rebalancing matters:

• It resets your risk level to match your original strategy
• It forces discipline—you sell high, buy low, and avoid emotional drift
• It keeps your portfolio aligned with your life stage and timeline
• It helps with tax efficiency when done strategically

At Chesapeake, we monitor client portfolios continuously and rebalance not just on a calendar, but when thresholds are meaningfully out of alignment. It's not about being reactive, it’s about being intentional.

Rebalancing a portfolio may cause investors to incur tax liabilities and/or transaction costs and does not assure a profit or protect against a loss.​

There's no one-size-fits-all portfolio, but there is an appropriate mix that fits your life.

Age can be a helpful starting point, but your investment strategy should also reflect:

• Your goals (retirement, early exit, major purchases, legacy giving)
• Your timeline for needing the money
• Your risk tolerance—and your real emotional comfort with volatility
• Your income and tax picture
• What other assets or income sources you have

At Chesapeake, we don't use cookie-cutter formulas like "100 minus your age." We build portfolios based on where you're headed, not just how old you are.

An appropriate investment mix is one that helps you pursue your goals without losing sleep along the way.

Yes and in fact, that’s when having a good advisor matters most.

Anyone can look smart in a rising market. But during a downturn, emotions run high, headlines get loud, and the risk of costly mistakes skyrockets.

Here’s how we help clients at Chesapeake when markets get rough:

• We bring perspective, helping you focus on your long-term plan, not short-term panic
• We review and rebalance your portfolio, if needed, to keep it aligned and opportunistic
• We look for tax-loss harvesting opportunities to reduce your tax bill
• We evaluate your cash alternatives and reserves so you're not forced to sell low
• We hold space for your questions and concerns—without judgment

Most importantly, we help you avoid emotional decisions that can set you back years. Because it’s not timing the market—it’s time in the market that drives long-term success.

Smart question—because fees can quietly eat away at your long-term growth if you're not careful.

Here’s how we help clients reduce unnecessary costs and keep more of what they earn:

• Choose cost-efficient investments

We use institutional-quality, low-cost funds and ETFs when appropriate—no overpriced products with layers of hidden fees.

• Minimize trading and turnover

Too much buying and selling can trigger taxes and transaction costs. A disciplined, long-term approach is often more cost-effective.

• Avoid high-commission products unless absolutely necessary

If we ever recommend a commission-based solution (like insurance), we’ll explain why, how we’re paid, and what alternatives exist.

• Consolidate accounts

Scattered investments can lead to redundant fees and missed opportunities. We help simplify and streamline.

• Focus on tax efficiency

Keeping more of your return isn’t just about investment fees, it’s also about limiting what you owe Uncle Sam.

At Chesapeake, we believe in full fee transparency, cost-conscious strategy, and long-term value, and not quick wins or hidden charges.

It depends on how much you’re investing and how your advisor is compensated.

At Chesapeake, our investment management fees are tiered, which means the more you invest, the lower your percentage fee becomes. Here’s a general breakdown:

• Smaller portfolios: Around 30% per year
• Mid-sized portfolios: Often closer to 80%–1.00%
• Larger portfolios: As low as 35%, depending on complexity and total assets managed

These fees cover more than just managing your investments. You also get:

• Ongoing rebalancing and performance monitoring
• Integrated tax planning and withdrawal strategies
• Proactive planning and check-ins
• Direct access to your advisor, not a call center or junior staff

And we’re always upfront about costs, before you commit to anything.

In retirement, your portfolio should shift from just growing wealth to sustaining it without running out. That means balancing growth, income, and preservation in a way that supports your lifestyle and preserves flexibility.

Here’s what we focus on with clients:

• Diversified income sources

A smart mix of dividends, interest, and planned withdrawals, so you’re not forced to sell during market dips.

• Reduced risk, but not zero growth

You still need some exposure to growth assets (like stocks) to keep pace with inflation and extend portfolio life.

• Asset location and tax planning strategy

What you own is important, but where you own it (Roth, IRA, taxable) matters just as much for tax-efficient withdrawals.

• Cash alternatives and short-term reserves

We often set aside 1–2 years of spending in cash alternatives or conservative assets to avoid panic-selling during downturns.

• Flexible withdrawal plan

Not a fixed “4% rule,” but a dynamic strategy that adjusts to markets, spending, and evolving goals.

At Chesapeake, we design retirement portfolios that are built to weather volatility and support real-life needs, not just theoretical models.

A good advisor doesn’t start with products; they start with your goals.

At Chesapeake, we use a personalized, data-backed approach that aligns your investments with your life, not just your risk score.

Here’s how we build your portfolio:

1. Understand your goals and timeline

Retirement, a home purchase, legacy planning, each goal has its own time horizon and risk profile.

2. Assess your true risk comfort

Not just a questionnaire. We talk through how you actually feel about market ups and downs and how much volatility your plan can afford.

3. Build a diversified allocation

We select investments across asset classes (stocks, bonds, real assets, etc.) based on your needs, not trends.

4. Focus on cost and tax efficiency

We use high-quality, low-cost funds where possible and build with taxes in mind from day one.

5. Review and adjust as life evolves

Your portfolio is dynamic. As your life changes, your investment strategy should too.

You won’t get cookie-cutter models or “hot picks.” You’ll get a clear, personalized portfolio designed to support your goals with confidence and clarity.

There is no guarantee that a diversified portfolio will enhance overall returns or outperform a non-diversified portfolio. Diversification and asset allocation do not protect against market risk.

A plan participant leaving an employer typically has four options (and may engage in a combination of these options), each choice offering advantages and disadvantages.

• Leave the money in his/her former employer’s plan, if permitted
• Roll over the assets to his/her new employer’s plan, if one is available and rollovers are permitted
• Roll over to an IRA
• Cash out the account value.

So maybe you should roll it over, but only if it makes sense for your long-term goals.

Rolling over your 401(k) to an IRA managed by an advisor can give you:

• More investment flexibility (not limited to your old plan’s lineup)
• Personalized asset allocation aligned with your full financial picture
• Proactive tax planning strategies (like Roth conversions or withdrawal planning)
• Ongoing advice and rebalancing as your needs evolve
• Consolidation if you have multiple old 401(k)s scattered around

That said, staying in your 401(k) might make sense if:

• You have extremely low fees or institutional investment options
• You’re still working and want to delay RMDs
• You’re between 55–59½ and plan to retire early (some withdrawal rules are more favorable in a 401(k))

At Chesapeake, we don’t roll over accounts just to “gather assets.” We’ll do a side-by-side comparison and help you decide what’s truly in your best interest.

It depends: on your strategy, your timeline, and your risk tolerance.

Here’s what actually matters:

• What mix of investments you hold

(Higher risk = potentially higher return—but also more volatility)

• How long you plan to stay invested

(Time helps smooth out short-term ups and downs)

• How disciplined your strategy is

(Emotional investing often leads to underperformance)

• How much you lose to taxes, fees, and poor timing

(A 7% return on paper doesn’t help if you only capture 4%)

At Chesapeake, we build portfolios around your goals, not market predictions. And we focus on helping you capture more of your return by managing risk, minimizing taxes, and keeping you on track.

Active management means a fund manager or advisor is actively picking investments, trying to outperform the market.

Passive management means you're tracking a market index (like the S&P 500) with low-cost funds and minimal trading.

Here’s how they compare:

At Chesapeake, we use a thoughtful blend of both, depending on your goals, timeline, and tax situation. Sometimes passive funds are best. Other times, strategic active management may add value—especially in complex markets or niche areas.

The key is not choosing a side, but choosing what works best for you.