Boyle began his career in Real Estate Development in 1983 specializing in historic rehabilitation in Boston. One notable development was Independence Hall in Chelsea, where Abraham Lincoln gave a speech while a congressman. Boyle formed a construction company, Titan Building Company, so he could personally oversee this work, including rebuilding the original curved stairs used by President Lincoln. Boyle has since been involved with the development of over one hundred real estate projects during the last forty years.

In 1996, Boyle founded Landmark Senior Living Communities to act as Simsbury’s assisted living operational arm and to ensure delivery of quality housing and personal services to seniors residing in facilities developed by the Company. 

In 1997, Boyle founded his first software company, BangZoom Software, which provided inventory tracking software. Following the success of BangZoom, Boyle started Landmark Technology Partners in 1998, which served the banking and investment community, including Alpha Card/American Express.

In 2008, Boyle founded Shazzle LLC. Passionate about privacy, Boyle foresaw the erosion of an individual’s fundamental right to privacy, and so developed ShazzleChat, the world’s first chat application that uses a smartphone or tablet as the server. Boyle received US Patent 14/467,359 for Shazzle’s decentralized architecture, which allows Shazzle to deliver user messages without ever receiving user data. Shazzle has nothing to copy or database. Privacy restored. Boyle received U.S. Patent 14/486,420 for decentralized electronic payments, to bring privacy to internet payments. Boyle has received one additional patent, and has two further patent applications pending for authentication, and a decentralized internet.

Boyle co-founded Landmark Recovery of Louisville, LLC, with his son Matthew to combat the nation’s growing addiction problem. Landmark placed state-of-the-art Smart Recovery therapy in repurposed buildings at significant capital cost savings, helping to transform this growing industry.

Boyle has stepped back from day-to-day management of his business interests, although he still remains active as an investor and consultant.