After searching for hats to fit his head, style and personality he sought to understand how hats were made. He sought a millinery in Washington, DC who showed him in one session how hats are made. Determined to learn the art of hat making, he began to research online and studied more about the craftsmanship and its culture.

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In his research, he discovered the rich history of creatives and artisans known as milliners, a person who makes and designs hats. His love for hats turned into a passion where he then turned it into a business. Being a serial entrepreneur, he realized that he could make a living by doing something he loved. He named his business Nathan Mason Hats, after the names of his sons, Nathaniel, Jordan and RJ Mason.

He wanted to create something that he could pass onto his children if they so choose to become hat makers. Reginald describes his hat making style as a combination of "modern and classic" as he uses both vintage and 3D printed tools to bring the imagination of the customer to life.