DiMatteo Group Financial Services

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.

10/05/2026

Cyber criminals pay extra attention to accounts tied to money.

A 2026 FBI study found that over 12,400 of those victims lost more than $100,000 each, and the average reported loss across elder fraud victims that year was $38,500. Here are a few habits to fine-tune your digital security this month:

🔐 Turn on multi-factor authentication everywhere it's offered. Yes, it’s annoying, but according to a 2026 CISA report, using it makes an account roughly 99 percent less likely to be broken into. It only takes a minute to set up.

🔐 Give every account its own password. Reusing one password means one leaked login unlocks everything else. A password manager handles this without requiring you to remember dozens of them.

🔐 When you go to the dentist, put a reminder on your calendar to also change your passwords. Changing passwords often makes your accounts just that much harder to reach.

🔐 Pause before clicking. Phishing remains the most commonly reported cybercrime in the country, more than any other category the FBI tracks.

🔐 Check statements regularly, and turn on account alerts. Catching something small and wrong early is a lot easier to unwind than catching something large and wrong months later.

🔐 Consider freezing your credit if you're not actively applying for new credit or loans. This takes 15 minutes, one time.

None of this requires becoming a security expert. Pick the one or two that you've been putting off, and do it this week.

10/02/2026

Some financial decisions get a second chance. A handful don't.

▪️ When you actually retire. In EBRI's 2026 Retirement Confidence Survey, 46 percent of retirees left the workforce earlier than they expected.

▪️ Stepping into a parent's finances. A 2026 Care.com report found sandwich-generation caregiving duties typically begin around age 34.

▪️ Receiving an inheritance. Ohio State research found nearly one in five people who inherited $100,000 or more had spent or lost the entire amount within two years.

▪️ Selling a business. For a typical owner, roughly 80 percent of their net worth is tied up in the business itself, per the Exit Planning Institute.

▪️ Writing (or updating) a will. Only 24 percent of Americans currently have a will, down from 33 percent in 2022, according to Caring.com.

None of these moments announce themselves on schedule. The families who handle them well are usually the ones who started talking years before circumstances forced their hand.

10/01/2026

📚 October is National Book Month!

At DiMatteo Group Financial Services, education has always been an important part of who we are. Whether it's sharing a meaningful book, an educational resource, or practical insights relevant to someone's stage of life, we believe knowledge has the power to create opportunity, confidence, and positive change.

In that spirit, we're excited to host our October Book Drive benefiting the Shelton Plumb Library.

If you have gently used books looking for a new home, we'd love your help.

📍 Drop-Off Location DiMatteo Group Financial Services 1000 Bridgeport Avenue, Suite 506 Shelton, CT

🕘 Monday-Friday 8:30 AM - 5:00 PM

Simply stop by during normal business hours and let us know you're here for the book drive.

Our team will collect donations throughout October and deliver them to the Shelton Plumb Library during the first week of November.

Thank you for helping us support literacy and lifelong learning in our community. 📚

09/30/2026

Last Thursday, we had the pleasure of hosting our Executive Connections Reception at Centre Club Tampa.

The evening brought together business owners, executives, and professionals from across the Tampa Bay area for meaningful conversations, new connections, and valuable insights.

In today's fast-paced business environment, there is still tremendous value in building relationships face-to-face, sharing ideas, and learning from one another's experiences.

It was rewarding to see so many professionals come together to exchange ideas, expand their networks, and create meaningful connections throughout the evening.

Thank you to everyone who attended and helped make the event such a success. We look forward to creating more opportunities for Tampa Bay professionals to connect, collaborate, and grow.

09/29/2026

What would you tell your 25-year-old self about money?

Getting insight from people who’ve been in your shoes can be powerful when you are young.

Here’s ours:

💡 Time is more powerful than timing.

At 25, it can feel like you have forever to start investing. But the biggest advantage you have isn't picking the perfect investment—it's giving your money more years to grow.

If we could go back, we'd say:

🔹 Start investing before you think you're "ready."
🔹 Build sound habits over chasing returns.
🔹 Lifestyle inflation is sneaky; don't let every pay rise become a spending rise.
🔹 An emergency fund isn't boring. It can help when you least expect it.
🔹 You don't need to know everything to get started.

What would you add?

Drop your best insight in the comments. Someone who's 25 today may need to hear it.

09/28/2026

Just 2 days away.

This Wednesday, Michael DiMatteo, Director of Business Development, will be partnering with PIA National to discuss the retirement plan options and strategies insurance agency owners should be considering in today's evolving landscape.

As the firm that manages the PIA 401(k) Plan, we're privileged to work alongside agencies across the country and help business owners evaluate their retirement plan options.

Topics will include SECURE 2.0 tax credits, SIMPLE IRA vs. 401(k) considerations, retirement plan options for solo entrepreneurs, employee attraction and retention strategies, and how the PIA 401(k) Plan compares to other available solutions.

Looking forward to connecting with agency owners and discussing the retirement plan opportunities available in today's evolving landscape.

There's still time to register. Send us a message for registration details.