Taylor was born in Springfield, Minnesota, and grew up on a farm in Comfrey, Minnesota. He graduated from Comfrey High School in 1959, and received a bachelor of science in mathematics, physics and social studies from Minnesota State University, Mankato, in 1962. In 1978 he received an executive MBA from Harvard Business School.

During and after college, Taylor worked at Carlson Wedding Service (later Carlson Craft), a Mankato print shop specializing in formal invitations. In 1975, company owner Bill Carlson wanted to retire, and Taylor offered to pay $2 million over the course of 10 years for the company. The purchase (which he paid off early) formed the basis for the Taylor Corporation, a privately held multinational printing and electronics company with more than 15,000 employees and based in North Mankato, Minnesota. Taylor continues to serve as chairman and CEO.

Taylor purchased majority ownership of the Minnesota Timberwolves NBA basketball team in 1994 and purchased the Minnesota Lynx WNBA basketball team in 1999. Taylor was in talks to buy the Minnesota Twins but nothing came of it.

In 2000, he was banned for nearly a year for signing Joe Smith to a secret contract in violation of the league’s salary cap rules. Before Donald Sterling, Glen Taylor was the only NBA owner to be suspended for more than a couple of games.

In 2014, he purchased the Star Tribune for about $100 million. He told MinnPost that the famously liberal Star Tribune would be decidedly less liberal under his watch, but noted that the paper had already been shifting more to the center in recent years.

In 2015, Taylor had a falling out with NBA legend, Kevin Garnett, over a miscommunicated agreement. Garnett had been under the impression that after his retirement from the NBA he would be able to take over ownership of the Minnesota Timberwolves. However, after some discrepancies that was not the case. Taylor and Garnett are no longer on talking terms and Garnett also refuses to have his jersey retired by the Timberwolves after spending 14 seasons of his career there.

In 2017, Taylor purchased the Iowa Energy of the NBA Development League (later called NBA G League) and renamed the team the Iowa Wolves as the developmental affiliate of the Timberwolves.