In 1983, Chuck left Amfac to establish the Landmark Suites of America and became the largest franchisee of what would later be named Embassy Suites. In 1991, he cofounded an all suite brand, Crown Sterling Suites to manage over 24 hotels across 20 major US markets. He accurately anticipated, during its infancy, the then untapped market demand for the all-suite concept. He developed and presided over Crown Sterling Suites until it was sold in early 1996 for approximately US$500 million.
At the same time he was building value for this brand, he was developing resorts in Maui. He still has a special gleam in his eyes when The Kea Lani is mentioned. This resort, with 416 suites and 37 villas, was located in the then relatively unknown destination of Wailea on Maui. It singlehandedly elevated the all-suite product into the luxury category when it opened in December 1992. It was also in Maui that he turned his attention to the education of young hotel talent for mid management positions. Together with professional trainers and senior academics, he founded VITEC, the predecessor of what is now the University of Hawaii Maui Campus Hospitality School.
By the time the Kea Lani opened, Mr. Sweeney was widely regarded as a visionary in the hotel industry, and one of its most successful developers and entrepreneurs. He is known for his ability to build strong management teams, for strategic operations planning and for his branding and marketing skills. During his career, Mr. Sweeney has conceptualized, developed, and operated 54 hotels and resorts throughout the continental U.S. and Hawaii with approximately 16,000 guest rooms/suites, at an estimated aggregate development cost of more than US$1 billion.
In 1997, Chuck Sweeney co-founded Trinity Investment Trust, LLC. He brought together a team whose multi-disciplined background equipped Trinity with the skills and resources necessary to execute its investment plan. Staunch proponents of a lean organization, Trinity's principals had both intensive and extensive experience in all aspects of the global real estate and hotel industries. Their collective expertise covered the entire spectrum of property development, investment, value enhancing asset management and finance, both in commercial property as well as hotels and resorts. They made their mark in Japan with the establishment of the first foreign owned REIT to be listed on the Tokyo Stock Exchange.
Together, Trinity's principals and associates were involved in transactions totaling in excess of US$9 billion. They were recognized for their ability and experience, and respected globally by individual and institutional investors, international hotel and resort owners and developers, major hotel corporations, and the international investment banking and funds communities.
As a full service firm, Chuck Sweeney and his partners created a company which had the in-house capability to perform each of the following functions: sourcing and identifying investment opportunities, market and asset analysis, risk/reward analysis, commitment and contract negotiation, debt sourcing, executing a successful closing, development and construction management, regimented asset management, and implementation of a successful exit strategy.
In 2018, Chuck retired as Chairman of Trinity Investments and now concentrates on Landmark Hotels, Inc. new developments in the upper and upscale segment in California and Hawaii. He also is carving out time for his other passions - producing premium wine and spending quality time with his grandchildren.