Growing for the Future: Caldwell Trust’s new downtown home represents the solid foundation, deep roots, and growth of the company

By Ryan G. Van Cleave | October 2022

Caldwell Trust Company has been a fixture of the community since it was founded in 1993 by Roland Caldwell. Though its headquarters remains in Venice, it’s had a presence in Sarasota since 1998, and just this year, the Sarasota office relocated to the historic Cain-Wilson Building at 27 South Orange Avenue. 

When it was being constructed in the 1930s, the Sarasota Herald claimed that the Thomas Reed Martin-designed building was “Second to none in terms of beauty and usefulness in all of Sarasota.” Caldwell Trust CEO and President R.G. “Kelly” Caldwell agreed. So much so, in fact, that in 2019 he approached its owner to see about acquiring the building which at that point housed the Wilson, Johnson, Jaffer, and Boyette law firm. “It looked exactly like a trust company building should look like,” Caldwell says about the high-ceilinged, one-story building with a dozen sturdy colonnades out front. 

“It was emotional for Mr. Wilson. He had great history with the building, buying it in the 1970s and growing it,” Caldwell explains. “I told him that if he’d sell it to us, we’d restore it and keep the same provenance. Too often we see beautiful buildings demolished, only to be replaced by something with less aesthetic appeal than the original structure.” Caldwell’s plan was to combine the legacy of stability that began with Martin’s design with his own company’s strong reputation, carrying both legacies far into the future. That plan resonated with Mr. Wilson.

The deal was closed in February 2020, just before COVID. Despite the problems of managing construction around the issues caused by a pandemic, things went relatively smoothly. Holly Logan of HV Logan Design LLC handled the interior design work, Nokomis-based S&E Renovations did the construction, and Hazeltine Nurseries created the outside design, which included updating the landscaping and the fountains. “It turned out better than I had imagined,” Caldwell says about the 10,000-square-foot building with a 2,000-square-foot portico that will be able to accommodate the steady growth the company has experienced for decades. “It’s a beautiful view during the day, but at night, it’s stunning.”

The newly named Caldwell Trust Company building indeed does look like a sturdy, successful financial institution, which makes sense since this independent trust company reached the mark of managing $1 billion in 2018. As of today, the company now manages $1.5 billion in assets of clients throughout the United States, while offering a full range of fiduciary services to individuals including services as trustee, custodian, investment advisor, financial manager, and personal representative. Caldwell Trust also manages 401(k) and 403(b) qualified retirement plans for employers. 

While Caldwell Trust has a full range of client services, over 80% of their business is investment management, and there’s more to that than most realize since their investment process is client focused. Caldwell says, “We do this by tailoring portfolios to meet each client’s investment goals, desired return objectives, risk tolerance, time horizon, liquidity needs, tax position, and any unique circumstances.” At Caldwell Trust, they believe no two investors are alike. 

Caldwell notes that local banks disappear all the time. They got bought up in mergers and are sold again every few years, so clients are always having to rebuild relationships. Since Caldwell Trust is a privately owned company, that’s not an issue. They’ve deliberately unhinged the trust department from banks to break up the bureaucracy challenges people face. 

One way Caldwell Trust helps clients is by sorting through the noise. For instance, the stock market has experienced incredible volatility thanks to COVID, the Ukraine War, and Iran’s actions, to name just a few worldwide headlines. “When China starts talking about invading Taiwan, clients ask us what they should do,” Caldwell says. “We sort through it all and help our clients make good decisions. It’s not easy since everyone has a different psychology. You might have two clients of the same demographics and situation, but they approach everything differently.” That’s where a local firm that takes the time to know its clients in a face-to-face, real-world manner thrives. No one is immune to the uncertainties of life, but a trustworthy financial partner you have a relationship with can put you on a personalized pathway to success regardless of what’s happening in the world. 

Another way Caldwell Trust succeeds is by staying true to the same tenets that management outlined in the original company charter. Caldwell says, “We will always be personal, traditional and independent, and we will remain faithful to ‘What We Believe,’ our founding principles. We have a plaque with these principles on the exterior of both offices in Sarasota and our headquarters in Venice, where we see them every day.”

Caldwell also has a deep appreciation for family and community. Though he earned a degree in electrical engineering from Georgia Tech, he started working for his father in the 1980s. “My dad was the driving force for getting our trust company off the ground, but I was there with him. I worked in the business since the beginning.” So, he’s seen how the company takes care of families for generations. He’s spent his entire career learning the industry and working to exceed client expectations and helping them achieve financial peace of mind. “We routinely work with three or four generations of a family, sometimes at the same time. It’s all about the continuity of relationships.”

Today, Caldwell Trust has around 40 employees, and it’s earned a reputation for having a family-oriented culture and strong ethic corporate citizenship. The Caldwell family also chooses to give back to the community, having donated more than $1 million to local nonprofit organizations, with a focus on youth and social causes. 

“Our new home is the building you’d want if you were going to be here forever,” Caldwell says about his company that’s been expertly navigating clients toward their financial goal since 1993, “and Caldwell Trust Company plans to be around for a long, long time.”

For more information on Caldwell Trust Company, please visit www.cwtrust.com or call 941.926.9336.