DorchesterAdvisors

09/30/2026

Your investments and Medicare - Medicare choices at age 65 can be one-time decisions between:
• Medicare Advantage (lower premiums, more restrictions) or
• Original Medicare + Medigap + Part D (higher premiums, less restrictive coverage)

At 65, “Advantage” often looks appealing because most people are healthy. Later in life, the flexibility and broader coverage of Original Medicare may matter more. The correct choice also depends on your health, longevity assumptions, and comfort with risk.

Deciding whether you value lower cost now or more predictable coverage later is the key.

Either way, the impact on your retirement income and your portfolio can be significant. If you are currently grappling with your Medicare decision and need additional information, ask me for a quick reference guide.

More: https://bit.ly/Peak_55_Social_Security

www.DorchesterAdvisors.com

09/23/2026

Two investment giants make the case for informed but patient investing. Charlie Ellis says successful investing is “Winning the losers Game” – By this he means that at the top performance levels professionals win by making the fewest mistakes. DFA (Dimensional Funds Advisors) makes a similar point using Federer’s tennis success. And, Howard Marks, another investment giant has advised that you can either try to find consistent winners - which is hard, or avoid losers, which may be easier to do.

Winning at Tennis and Markets: https://www.dimensional.com/us-en/insights/winning-at-tennis-and-markets

www.Dorchesteradvisors.com

Stocks are like tennis: Even having just a marginal winning percentage can lead to long-term success.

09/16/2026

Risk is more than volatility : Investors often simply equate risk with market fluctuations. But true financial risk can take many additional forms—permanent loss of capital, liquidity, withdrawal timing, falling short of financial goals, and even our own behavior.

At Dorchester Advisors, we take the broader approach. We start with your goals and time horizon, determine the return your portfolio needs, and then build a strategy designed to manage the risks that could derail your investment plan.

Read more about the many faces of risk for High Net Worth ("accredited investors")?
https://bit.ly/Investing_Risks_that_Matter



www.DorchesterAdvisors.com

09/09/2026

Corporate Executives: Did you receive payments from your executive compensation plan (for example: options, RSU, Deferred compensation)? If so, do check with your CPA if you owe any estimated taxes. It may save you interest payments and penalties. The next deadline is 15 Sep for 2026.

As an investment advisor, we are well versed with executive compensation and its nuances.

www.DorchesterAdvisors.com

09/02/2026

Social Security claiming decisions often boil down to two options:
• Maximize lifetime benefits OR
• Delay claiming to age 70 for the highest monthly income for the rest of your life

Delaying can offer stronger financial security—a larger, guaranteed check later in life, when earning power is lowest.

So the key question is: Do you want the biggest total payout or the most reliable income in later years?
Let your health, longevity, risk-taking temperament, and financial goals guide your decision.

If you are currently grappling with your Social Security Claiming decision and need additional information, ask me for a reference guide.

https://bit.ly/Peak_55_Social_Security

www.DorchesterAdvisors.com

08/26/2026

Corporate Executives: Did you receive payments from your executive compensation plan (for example: options, RSU, Deferred compensation)? If so, do check with your CPA if you owe any estimated taxes. It may save you interest payments and penalties. The next deadline is 15 Sep.

As an investment advisor, we are well versed with executive compensation and its nuances.

www.DorchesterAdvisors.com

08/21/2026

A well-designed portfolio should do more than diversify. It should help you grow wealth, generate sustainable retirement income, manage taxes, and control risk.

At Dorchester Advisors, we focus on three key elements:

• Asset allocation — balancing growth and risk
• Asset location — improving tax efficiency
• Portfolio simplification — reducing unnecessary complexity and overlap

More investments and more accounts don’t necessarily mean a better portfolio. Often, informed simplicity creates greater clarity and control.

Read more about our approach to designing portfolios for High Net Worth ("accredited investors").
https://bit.ly/Smarter_Simpler_Portfolios



www.DorchesterAdvisors.com

08/15/2026

Successful Investors know that investment ideas are plentiful. Their challenge is to analyze them effectively without wasting their time. Enter M.E.C.E.

A Mckinsey & Co. analytical approach where MECE stands for “Mutually Exclusive Collectively Exhaustive”.

I have found that a robust asset allocation model is a very good proxy for the MECE concept in investing. It allows an investor to assign a new investment idea to the correct bucket (asset class) and determine if the new idea is additive to their portfolio. And, they can do it faster than by simply starting at square one and analyzing an idea in isolation each time. Food for thought!

www.DorchesterAdvisors.com

08/06/2026

Retirement changes one important financial reality: you no longer receive raises in your income unless your portfolio is designed to create them.

Too many investors enter retirement relying on fixed income streams that gradually lose purchasing power to inflation and taxes. A well-designed retirement strategy should seek to create sustainable and adaptable income over time — not just income for today.

Helping clients navigate that challenge is a core focus of my practice. If you’d like a second opinion on your retirement income plan, I’d be happy to talk.

www.DorchesterAdvisors.com

07/31/2026

Retirement income planning isn't just about how much you've saved—it's about how long your money needs to last. Research shows that wealthy retirees should:
• Plan for longevity. Living longer may require a different withdrawal strategy and spending plan.
• Avoid short planning horizons that can increase the risk of income shortfalls later in retirement.
• Build reliable lifetime income with Social Security, pensions, and annuities.
Not sure if your retirement income plan is robust? Let's talk.

Retirement income planning isn't just about how much you've saved—it's about how long your money needs to last. Research shows that wealthy retirees should: • Plan for longevity. Living longer may require a different withdrawal strategy and spending plan. • Avoid short planning horizons that c...