Caldwell Trust Company

06/08/2026

Celebrating Excellence in Fiduciary Leadership!

We are proud to celebrate Caldwell Trust Company’s own Ali Orme, AFIM®, CTFA®, on advancing her professional credentials and deepening her commitment to the Sarasota community.

Achieving the Certified Trust and Fiduciary Advisor (CTFA®) designation is a major milestone in our industry. Requiring a rigorous mastery of trust administration, estate planning, and tax law, this certification further strengthens the specialized expertise Ali brings to our clients every day.

At Caldwell Trust, exceptional wealth management is built on a foundation of continuous professional growth and local stewardship. Ali's latest achievement perfectly exemplifies the high standard of fiduciary excellence our team strives to deliver.

Please join us in congratulating Ali on this outstanding milestone!

06/03/2026

A few of our team members from our Sarasota office recently had the privilege of touring the incredible Easterseals Southwest Florida campus!

Seeing firsthand how they champion abilities, foster inclusion, and transform lives in our community was truly inspiring as we believe in lifting up the organizations that make our region a better, more supportive place for everyone. Supporting our neighbors and investing in local impact - that’s just , "The Way It's Meant to Be." 💙

Thank you, Easterseals, for the warm welcome and for the vital work you do every day to create a community where everyone can thrive!

Sonya Kristie Ali Orme

06/03/2026

Retirement isn’t just about saving—it’s about planning. At Caldwell Trust, we help you create a thoughtful, strategic roadmap for your financial future so you can retire with confidence, clarity, and peace of mind.

05/25/2026

PROTECTING FUTURES THEY FOUGHT FOR

This Memorial Day, Caldwell Trust Company honors the brave men and women who gave their lives in service to our nation.

Their sacrifice secured the freedoms, families, and futures we hold dear today.

We remember their courage with gratitude and reverence. 🇺🇸 🇺🇸 🇺🇸

05/21/2026

Choosing a trustee is one of the most important decisions in your estate plan. The right trustee safeguards your wealth, honors your wishes, and protects your beneficiaries from avoidable mistakes and fees. This article walks through key criteria and pitfalls to avoid. What qualities matter most to you when selecting a trustee?

Learn how to choose the right trustee in Florida while avoiding common mistakes to protect your legacy and ensure your beneficiaries are supported.

05/18/2026

Thoughtful investment management is one of the most effective ways to preserve wealth, support your lifestyle, and create a meaningful legacy for future generations. From aligning portfolios with your family’s values to planning for taxes and estate transitions, a disciplined strategy can help ensure your wealth endures. Learn more about thoughtful investment management in our latest blog:

Discover how investment management can help you build and preserve long-term wealth for future generations through strategic planning and risk management.

05/15/2026

Thoughtful financial planning does more than grow your assets—it aligns your wealth with your values, protects your family, and creates clarity around retirement, legacy, and philanthropic goals. This blog explores practical ways to turn intentions into a tailored plan. Which area of your financial life feels most important to refine this year?

Discover how financial planning can help you set clear goals, build strategies, and navigate life's milestones for a secure financial future.

05/12/2026

Recently, beneath the lights and timeless atmosphere of The Ringling, Sarasota’s story felt more alive than ever. Nearly 100 years ago, John Ringling helped place Sarasota on the map by bringing the circus winter quarters to our community. His vision helped shape a city known for culture, creativity, and connection, and that spirit could still be felt throughout the evening’s National Travel & Tourism Week Celebration.

As a Milestone Sponsor, Caldwell Trust Company was honored to be part of a night that celebrated not only Sarasota’s history, but the people whose leadership and dedication continue shaping its future, such as Roland Caldwell, founder of Caldwell Trust Company.

Roland was widely respected as a trusted leader in Sarasota’s financial community, with many area banks, businesses, and clients relying on his expertise and steady guidance. His commitment to sound judgment, integrity, and service to others helped shape the values that continue to guide Caldwell Trust Company today.

Tourism has always been more than visitors and destinations. In Sarasota, it is the arts, the relationships, the local businesses, and the shared experiences that bring people together and strengthen our community. That momentum continues to carry forward through ongoing community engagement and gatherings like the upcoming The Argus Foundation event in November, where leaders will once again come together to discuss Sarasota’s growth, leadership, and future.

Events like these are a reminder that Sarasota’s story is still being written by the people and organizations who choose to invest in it.

Thank you to Visit Sarasota County for bringing our community together to celebrate the legacies, partnerships, and visionaries that continue to shape Sarasota today.


Sonya Kristie Ali Orme Alisa Ivey Craton Sher Vieira Hunter Carpenter Kelly Caldwell

05/12/2026

Changing jobs or approaching retirement?
A 401(k) rollover is not always the automatic “right move.”

In some situations, rolling over your 401(k) into an IRA can give you more flexibility and investment options. In others, keeping funds in your employer plan may offer advantages around fees, creditor protection, or early withdrawal rules.

Before making a decision, it’s important to understand:
• When a rollover may make sense
• When it may not
• Tax implications to consider
• Common mistakes people make during the process

Read the full breakdown here:
https://hubs.la/Q04g90N50

Discover when to roll over your 401(k) and when to keep it in place. Evaluate your options to align with your financial goals effectively.

05/06/2026

Last year, as we expanded into Vero Beach and launched our first East Coast presence, it marked an exciting new chapter for our firm and the families we serve.

We’re proud to see our Market Director, David L. Osgood, featured on The Lulich Corner podcast, hosted by Jordan Lulich of Lulich & Attorneys. In the conversation, David shares the thinking behind our award-winning “Legacy Has a New Address” campaign and what it takes to build wealth that truly lasts.

He also reflects on how thoughtful planning, disciplined strategy, and a long-term perspective can help families preserve and transition wealth with clarity and confidence.

This moment is not just about growth. It is about deepening our commitment to helping clients create meaningful, lasting legacies.

🎧 Watch: [https://loom.ly/jGv1n7g](https://loom.ly/jGv1n7g)
🎧 Listen: [https://loom.ly/B48231Y](https://loom.ly/B48231Y)



Kelly Caldwell Sher Vieira