DiMatteo Group Financial Services

09/02/2026

👉 Roughly 56 percent of IPOs bought at the offer price lost money after 3 years.

That's not the headline you see on day one.

You see the first-day pop. The company goes public, and its stock has averaged a 19 percent gain since 1980. Feels like a moment you should catch.

Here's what actually happens:

1️⃣ Institutional investors get the offering price before trading opens.

2️⃣ You buy at market open, after the move.

Then the real story starts.

🔎 This gap is based on research led by Professor Jay R. Ritter, who authored a 2026 report on IPO performance for the University of Florida. His analysis of 9,300 U.S. IPOs is one of the most comprehensive databases available.

Chasing IPOs can provide a thrill, but there are pros and cons.

A sound portfolio should reflect an investor's goals, risk, and time horizon. The risks of an IPO are not for everyone. 🎯

📋 Past performance does not guarantee future results. The return and principal value of IPOs and other stocks will fluctuate as market conditions change. And shares, when sold, may be worth more or less than their original cost.

08/27/2026

Two retirees can earn the same average return and have very different outcomes.

Why?

Because in retirement, timing matters.

An early market downturn in retirement can be more damaging than the same downturn later.

That is the sequence-of-returns risk.

The risk is not simply “the market went down.” It’s “the market went down while income still had to come out.”

A strong retirement strategy should look beyond average returns and address:

🔹 Where income will come from
🔹 How much cash or short-term reserves make sense
🔹 Which accounts to draw from first
🔹 When to rebalance
🔹 How RMDs and Social Security fit into the withdrawal strategy

Sequence-of-returns risk does not make many headlines.

But for anyone entering retirement, it can be one of the most important ideas to understand.

The goal is not to predict the next downturn. It’s about being prepared.

08/21/2026

As today is National Senior Citizens Day, we wanted to draw attention to something that can sometimes fall through the cracks: the Medicare Part B late enrollment penalty.

Most don’t know that if you miss your Initial Enrollment Period (the 7-month window around your 65th birthday), Medicare tacks on a 10 percent surcharge to your monthly premium for every 12 months you delay enrollment.

No cap. No expiration date.

Delay two years, pay 20 percent more. Delay by five years, you pay 50 percent. Every month. For life.

How to manage it?

You are only exempt from this penalty if you qualify for a Special Enrollment Period (SEP).

This usually means you delayed signing up because you (or your spouse) were still actively working and had "creditable" health insurance through that active employer.

If you’re concerned, ask your financial professional where to find the most up-to-date Medicare information.

08/20/2026

Happening Today

Today's the day!

Join us at 12:00 PM ET for our FREE HBRA Member Webinar:
Connecticut Employers: Is Your Business Ready for Retirement Plan Requirements?

We'll discuss:
✅ State retirement plan requirements
✅ Employer tax credits
✅ Retirement plan options
✅ Strategies Connecticut employers are using today

Plus, attendees will have the opportunity to schedule a complimentary personal wellness consultation.

Register here:
!event/2026/8/21/free-exclusive-webinar

We hope you'll join us!

Who We Are

08/19/2026

Donating appreciated stock to charity has pros and cons. So, most donors still write the check.

When you contribute appreciated securities directly to a donor-advised fund (DAF), you can manage capital gains tax on the gain and perhaps deduct the full fair market value.

The charity receives the full amount. Nothing is lost to taxes in between.

From there, you can focus grants to any eligible nonprofit on your own timeline. The funds can stay invested and may grow while you decide.

💡 If you're holding appreciated positions and giving is part of your strategy, how you give matters as much as how much you give.

📋 **Some donor-advised funds are considered mutual funds and are sold only by prospectus. The prospectus will provide information on charges, risks, expenses, and investment objectives and should be reviewed carefully before investing. Investment companies can provide a prospectus, or you may prefer to ask your financial professional.**

💡 Consider asking your financial professional to work with your tax, legal, or accounting professionals if a DAF sounds interesting.

08/18/2026

Just 2 Days Left

Are you confident your business is prepared for Connecticut retirement plan requirements?

Join Michael DiMatteo as he discusses:
✔ Connecticut retirement plan requirements
✔ Available employer tax credits
✔ SIMPLE IRA, SEP IRA and 401(k) options
✔ Common employer mistakes
✔ What Connecticut employers are doing now and why

Plus, attendees will have the opportunity to schedule a complimentary personal wellness consultation.

📅 Thursday, August 20
⏰ 12:00 PM ET

Register here:
https://hbra-ct.org/events/ #!event/2026/8/21/free-exclusive-webinar

08/14/2026

Some professionals assume their financial strategy is in better shape than it is. Not because they're careless. Because they're busy.

Today is National Financial Awareness Day. Four questions worth sitting with:

▸ If something happened to you tomorrow, would your family know what you have, where it is, and what to do?

▸ Are you on track to replace your income in retirement, or are you assuming you will be?

▸ Has your financial strategy changed as much as your life has in the last 12 months?

▸ If markets dropped tomorrow, do you have written goals or a general sense of what you'd do?

You don't have to answer all four today. But if one made you pause, that's the one worth paying attention to.

08/14/2026

Less than one week away!

We're just about one week away from our FREE HBRA Member Webinar:
Connecticut Employers: Is Your Business Ready for Retirement Plan Requirements?

Whether you're exploring retirement plan options for the first time or looking to improve your current plan, this session will provide practical information you can use immediately.

📅 Thursday, August 20
🕛 12:00 PM - 1:00 PM ET

Reserve your spot here:
!event/2026/8/21/free-exclusive-webinar

Who We Are

08/13/2026

Connecticut employers: the August 31 retirement plan deadline is approaching.

If your business has 5 or more employees and does not currently offer a qualified retirement plan, you may need to take action before August 31.

Many employers assume MyCTSavings is their only option. However, depending on the needs of the business and its employees, alternatives such as a SIMPLE IRA, SEP IRA, or 401(k) may also satisfy the requirement.

We've put together a brief overview of the options available, key considerations, potential tax credits, and factors business owners may want to evaluate before making a decision.

08/12/2026

✈️ Do you have a college student studying abroad this fall?

When Jessie DiMatteo LaChance studied abroad at the University of Granada in southern Spain during her time at UConn in 2018, she expected to gain academic credits, travel experience, and a chance to improve her Spanish.

What she didn't expect was gaining family.

She lived with a host family who welcomed her into their home and helped make her semester abroad one of the best experiences of her life. They stayed close over the years, and this past January, they traveled to the United States for the very first time to celebrate her wedding.

Eight years later, a study abroad experience is still shaping her life.

For families preparing to send a student abroad this semester, the memories and relationships can be priceless, but it's important to understand the financial side of the experience, too.

Families sometimes underestimate the true cost of studying abroad by 20-40%.

A few things to know:
📚 529 funds can cover tuition and housing at eligible foreign institutions, but not airfare, visa fees, or passport costs.

🏥 Most U.S. health plans provide little to no coverage abroad. Medical evacuation alone can cost $20,000 to $200,000, and most domestic plans don't cover it.

💳 Cards with foreign transaction fees can add roughly 3% to every purchase. Exploring no-fee options before departure may be worthwhile.

Most parents remember to ask, "Do you have your passport?"

The question that often gets overlooked is, "Are we prepared for what this semester may really cost?"

The right planning helps students focus less on financial surprises and more on the life-changing experiences that make studying abroad so special.

📝 A 529 plan is a tax-advantaged education savings plan. Before choosing a plan, it's important to consider not only the state tax treatment but also any associated fees and expenses. Availability of a state tax deduction will depend on your state of residence, as state tax laws and treatment may vary from federal tax laws. If you make nonqualified distributions, earnings will be subject to income tax and a 10% federal penalty tax.