As a farm boy growing up in Belle Plaine, Iowa, Henry Tippie started his education in a one-room schoolhouse. After graduation from Belle Plaine High School in 1944, Henry enlisted in the Army Air Force at the age of 17. After his service in the 20th Air Force in the western Pacific, he was able to attend the University of Iowa thanks to the G.I. Bill. He received his BSC in accounting in 1949 after 24 consecutive months of study.

Henry Tippie began his professional career as a junior accountant in the Des Moines area. He passed the CPA exam in 1951 and was a member of the Iowa Society of CPAs (CPA #276) and the American Institute of CPAs for more than 65 years.

Henry Tippie brought innovative ideas to the world of business through his work with John and Wayne Rollins. While at Rollins, he was an instrumental part of the team that put together the company's purchase of Orkin Exterminating Company. This was one of the first large leveraged buyouts of its kind in U.S. corporate history. Tippie's hard work, thoroughness, and dedication led to a number of successes where he helped build and turn unprofitable projects around by following solid business practices.

Today, five Rollins companies trade on the NYSE. He served as the lead director for Rollins Inc., RPC Inc., and Marine Products Corporation. He also served as a co-trustee for the O. Wayne Rollins Foundation, Rollins Children's Trust, and the managing director of the RMT Trust. He was the chairman of the board for Dover Motorsports Inc. and former chairman of Dover Downs Entertainment Inc.

Tippie was an original member of the college's Board of Visitors (now called the Tippie Advisory Board). During the campaign to raise funds for the Pappajohn Business Building, he donated funds to build a 175-seat auditorium, a student lounge, and Pat's Diner, named for his wife, Patricia.

In February 1999, Tippie made a significant contribution to the College of Business to support its students and faculty. The college was renamed the Henry B. Tippie College of Business in his honor. This gift supports student scholarships and faculty research including two endowed chairs as well as several professorships and fellowships. His scholarships have benefited a large number of business students as well as students from his native Belle Plaine. His legacy of support for the college includes six Tippie-related faculty chairs, as well as numerous professorships and fellowships. 

Henry B. Tippie will continue to have a tremendous impact on the University of Iowa, its students and faculty, his hometown of Belle Plaine, and the business world at large. For his numerous contributions, Tippie received the University of Iowa's Distinguished Service Alumni Award, the Hancher Finkbine Medallion, and Outstanding Accounting Alumni Award. In 1996, he was a recipient of the nationally prestigious Horatio Alger Award. He was named to the Junior Achievement Eastern Iowa Hall of Fame in 2004. In addition, he received an Honorary Doctorate of Humane Letters from the University of Iowa in 2009 and from Allegheny College in 2011. In 2018, he became the 17th member of the NYSE Wall of Innovators, better known as the NYSE Wall of Fame.