Boyle is one of three children born to Joseph Cornelius "Neal" Boyle, an Irish Catholic and Gertrude Lamfrom. His mother was Jewish and fled as a teenager from Nazi Germany and immigrated to Portland, Oregon; she converted to Catholicism after marrying her husband. He has two sisters: Kathy Boyle (born 1952) and Sally Boyle (born 1958).
His grandfather purchased the Rosenfeld Hat Company and changed its name to the Columbia Hat Company (after the river). His Father became President of Columbia hat after his grandfather died and then Diversified the hat Business into outerwear for Hunters, fishermen, and skiers. In 1960, his mother designed the first fishing vest (his Father was an avid fisherman) and the name of the company was changed to Columbia Sportswear.
Boyle was still at university when his Father died in 1970 at the age of 47 and joined his mother - who had become President of Columbia - then with $800,000 in annual sales. The company struggled and teetered on bankruptcy until in the 1970s when he and his mother refocused the Business on outdoor clothing and Casual wear which paralleled a general trend away from formal work attire. In 1975, they were the first company to introduce Gore-Tex parkas. In 1986, Columbia released the Bugaboo, a jacket with a zip out Li Ning which became quite trendy and further propelled the company's growth. Columbia was unique among specialty clothing manufacturers in that it would sell its products to any Retail shop or chain. In 1987, Columbia had $18.8 million in sales and by 1997 it had grown to $353.5 million. The company went public in 1998. In the early 2010s, Boyle refocused Columbia away from top line products and more towards the mid-range, moderately priced products; he also continued to align sales with changes happening in the Retail industry, shifting the company more toward internet sales.
In 2007, he and his wife Mary donated $5 million to the University of Oregon.
Boyle's 41% ownership interest in Columbia Sportswear was worth over $1.0 billion in 2013.
In 2016, he donated $10 million to the University of Oregon's aquatic animal care facility.