DiMatteo Group Financial Services

10/16/2026

Your holiday checklist is growing—but is your financial plan on it? 📝

Before the year wraps up, take some time to review:

✅ Holiday spending and cash reserves
✅ Retirement contributions
✅ Tax planning opportunities
✅ Charitable giving
✅ Insurance coverage and estate planning documents
✅ Business finances and succession plans

At DiMatteo Group Financial Services, we help individuals, families, and business owners see how these pieces fit together and decide what deserves attention.

If a financial review has been on your “I’ll get to it” list, let’s schedule a conversation and set clear priorities for the year ahead.

Call our team at 203-924-5420 to get started.

10/15/2026

📚 Mid-Month Book Drive Reminder! 📚

October is National Book Month, and there's still time to make a difference in our community!

We're collecting new and gently used books at our office through the end of the month to support the Shelton Plum Memorial Library. Donations can be dropped off during regular business hours, Monday through Friday from 8:30 AM to 5:00 PM.

📍 1000 Bridgeport Avenue, Suite 506
Shelton, CT 06484

A simple book donation can help inspire learning, imagination, and a love of reading for readers of all ages. Thank you for helping us support our local library and strengthen our community one book at a time! 📖❤️

10/14/2026

A mother in California picked up the phone and heard her daughter's voice, panicked, saying she'd been kidnapped and needed money immediately.

What she'd heard wasn't her daughter. It was an AI-generated clone of her voice.

In a 2025 study, scientists found that when people heard a cloned voice, they correctly identified the voice as AI-generated only about 60 percent of the time.

The FBI attributed more than $890 million in 2025 losses to AI-enabled fraud, and voice cloning is one of the main drivers behind that number.

It is not only older adults being targeted. Younger family members get these calls too, often framed as a sibling or friend in trouble. Older adults just tend to lose the most per incident.

Two ways to protect your family.

🔐 Agree on a private code word or question with the people a scammer is most likely to impersonate (kids, parents, spouse)

📞 If a call like this comes in and you have not set up a code word yet, hang up, then call the real person back

When in doubt, slow down and verify.

10/10/2026

Mental health touches every aspect of our lives, including our relationships, careers, caregiving responsibilities, and financial well-being.

For many individuals and families, stress often stems from uncertainty. Whether it's a health challenge, caring for a loved one, navigating a life transition, or making important financial decisions, carrying those concerns alone can feel overwhelming.

One thing we've learned over the years is that support matters. Sometimes that support comes from family and friends. Sometimes it comes from mental health professionals. Sometimes it comes from trusted advisors who can help bring clarity to complex decisions.

No one is meant to navigate life's challenges entirely on their own.

Earlier this year, through the DiMatteo Family Charitable Foundation, we were proud to support Griffin Hospital's new EmPATH Unit, helping expand access to compassionate care and support for individuals experiencing a mental health crisis.

Today, we're reminded of the importance of awareness, empathy, and ensuring people have access to the resources they need.

10/09/2026

Breast Cancer Awareness Month is an opportunity to prioritize health.

Early detection through regular screenings is one of the most effective tools we have in the fight against breast cancer.

Here are a few small things we can do this October:

✅ Schedule your annual screening if you haven't yet

✅ Educate yourself and others on risk factors and preventative lifestyle habits

✅ Support research and organizations dedicated to advancing breast cancer prevention and care

Taking charge of your health today makes all the difference for tomorrow. 🎗️

10/09/2026

Stocks finished the third quarter mixed. The S&P 500 gained 2.03%, and the Nasdaq Composite rose 2.47%, while the Dow Jones Industrial Average slipped 2.70%. Halloween is next on the calendar, with U.S. consumers expected to spend \$13.5 billion USD this year and 6.26 million Canadian children in their trick-or-treating years.

Stocks were mixed in the third quarter as economic, geopolitical, and corporate earnings news pushed the broad market higher while weighing on the Dow Industrials.

10/08/2026

October is National Book Month, and our book drive is officially underway!

Books have the power to inspire, educate, and create opportunities. By donating a book, you're helping foster a love of reading while supporting stronger connections within our community. Together, we can put more stories, knowledge, and resources into the hands of those who need them most.

Join us in making a difference, one book at a time. ❤️📖

10/07/2026

Thank you to everyone who joined us for our recent Roth vs. Traditional: Keep More of What You've Earned Lunch & Learn with our friends at Ledgerly LLP.

Whether you attended in person or virtually, we appreciated the thoughtful questions and engaging discussion.

One of the biggest takeaways from the event was that the Roth vs. Traditional decision isn't about which account is universally "better." Rather, it's about understanding when it may make the most sense to pay taxes based on your unique situation.

Your current tax bracket, retirement timeline, existing retirement accounts, Medicare considerations, and legacy goals can all play a role in the answer.

For many individuals, having multiple tax buckets can create valuable flexibility throughout retirement.

A special thank you to Mike Abrahamian and Andrew D'Amico from Ledgerly LLP for partnering with us and sharing their tax-planning expertise. Discussions like these reinforce the importance of bringing financial planning and tax planning together when making significant retirement decisions.

And of course, thank you to our in-person attendees who joined us for Colony Grill pizza and Jessie's homemade cookies while we learned together!

🎥 Missed the event or want to revisit the discussion? Watch the recording below:

Enjoy the videos and music you love, upload original content, and share it all with friends, family, and the world on YouTube.

10/06/2026

When most business owners think of a retirement plan advisor, they think investments and retirement savings.

But as Michael DiMatteo, CPFA®, CRPS™ shares in our latest Making Cents video, the role of a retirement plan advisor has expanded significantly. Today, retirement plan conversations often lead to discussions about employee retention, executive compensation, fiduciary responsibilities, and long-term business strategy.

A well-designed retirement plan can be much more than a benefit. It can be a powerful tool for supporting both your employees and your business goals.

Watch the video and learn more.

10/06/2026

Will your future income keep pace with the life you are preparing for?

On October 14th, the Social Security Cost-of-Living Adjustment (COLA) for 2027 will be announced.

The annual adjustment is designed to help benefits keep up with inflation, but the same principle can be applied more broadly.

Your retirement income may need to be adjusted as your life, expenses, and priorities change.

Healthcare, insurance, travel, home maintenance, and support for family members can all affect the income you may need to generate.

Ask yourself:

▪️ Has your expected retirement spending changed?
▪️ Are certain future expenses rising faster than you thought?
▪️ Does your income strategy account for inflation?
▪️ Are you strategizing for the lifestyle that you budgeted for years ago?

A thoughtful retirement income strategy should evolve as your life and expenses change.