Thimble Island Private Wealth

10/26/2026

Growth happens when you step away from the day-to-day and learn from others.

Earlier this month, Matt and Logan traveled to San Antonio for LPL Financial's Growth Forum, where advisors from across the country came together to share ideas, challenge assumptions, and learn from one another.

We're proud that Logan was invited to participate in a fireside chat and share his perspective as part of the event.

10/22/2026

⚓ It's time for another Thimble Thursday! This month, we're spotlighting Matt.

Whether you've connected with Matt through a client meeting, one of our Financial Fridays webinars, or a community event, you know he's passionate about helping people navigate important financial decisions.

But there's more to Matt than financial planning.

⛳ Most Unique Golf Course Played: Cabot Cliffs
🍕 First Job: Pizza Delivery Driver
💡 Financial Lesson He Wishes He'd Learned at 25: "Your biggest advantage isn't how much you earn. It's how early you start."
🎤 While Matt insists he doesn't do karaoke, he's been known to sing Taylor Swift with his daughters in the car.

Want to get to know Matt a little better? Learn more here: https://www.thimblepw.com/team/matthew-fleming

10/21/2026

The latest Weekly Market Commentary examines how personal AI agents could disrupt inertia-based businesses while leaving strong moats intact.
Read it here: https://www.thimblepw.com/market-commentary

10/20/2026

💡 Looking for ways to save more for retirement while managing taxable income?

For some business owners and high-income professionals, a cash balance plan may offer opportunities beyond traditional retirement plans.

Learn how cash balance plans work and the key considerations involved: https://www.thimblepw.com/blog/cash-balance-plans-a-tax-advantaged-retirement-strategy-for-business-owner

10/19/2026

X marks the spot… but can YOU find Capt. $tacks? 🏴‍☠️💰

Word on the high seas is that Capt. $tacks has officially dropped anchor on the Branford Town Green! ☠️🍂

Our favorite financial pirate is back, representing Thimble Island Private Wealth, where we help you Chart Your Course to Financial Freedom! 🧭💰

While Capt. $tacks may be guarding his treasure, our crew is here to help you navigate your financial future!

📍 Can you spot him? Take a stroll through the Branford Town Green, snap a photo with the Captain, and tag Thimble Island Private Wealth so we can see your pirate sightings! 📸

⚓️ Fair winds and following seas!

10/15/2026

🏴‍☠️ Well, well, well… look who’s making a comeback. 👀
A familiar face. A legendary comeback. 💰⚓

Can you guess who’s returning?

10/15/2026

🚨 Social Security's largest increase in four years is coming.

Benefits are set to rise 3.6% in 2027, adding about $900 annually for the average retiree.

Check out this Wall Street Journal article for a closer look at what the increase means and why it's happening.

Amount of earnings subject to Social Security tax will rise to $192,300

10/15/2026

📣 Medicare Open Enrollment starts today.

From October 15 through December 7, Medicare beneficiaries can review and make changes to their coverage for the coming year.

If Medicare is part of your retirement planning picture, now is a good time to review your current coverage and evaluate whether it still aligns with your needs.

10/14/2026

The latest Weekly Market Commentary examines strong business lending, tighter credit spreads, and housing constrained by mortgage rate lock-in. Read it here: https://www.thimblepw.com/market-commentary

10/13/2026

Retiring within the next 5-10 years? Now is the time to start thinking through the decisions that can have the biggest impact on your future.

Join us this Friday as we discuss: ✔ Retirement income ✔ Social Security ✔ Healthcare costs ✔ Retirement readiness

📅 October 16
🕛 12:00 PM ET
📍 Virtual & Free

Reserve your spot today: https://lpl.zoom.us/webinar/register/WN_aQYOiI0VSvKGj1g7MKWfEw #/registration