Henry Tippie, former Dover Motorsports chair, dies at 95

DOVER —  Henry B. Tippie, a businessman who started a long career in corporate leadership on the sands of Delaware’s beaches and was one of the forces behind the former Dover Motorsports, bringing NASCAR to Kent County, died Sunday at age 95.

Henry B. Tippie | PHOTO COURTESY OF DOVER MOTORSPORTS

An Iowan who took a chance on an advertisement in a trade journal, Tippie was well-known for being one of the longest-serving executives of Rollins Inc., a global consumer and commercial services company that is valued at $2 billion today. He served as chairman of the board for Dover Motorsports Inc. and Dover Downs Gaming and Entertainment Inc., both known as Dover Downs Entertainment Inc. until 2002. Tippie served for 25 years on the board, only stepping down once Dover Motorsports was acquired by Speedway Motorsports in December.

“Dover Motorsports wouldn’t have been the organization it became without Henry Tippie,” Denis McGlynn, the longtime president and CEO of Dover Motorsports, said in a statement. “His leadership and guidance over the last several decades made the company a cornerstone of the entertainment and recreational offerings in the Mid-Atlantic region.”

He was also one of 16 men and women honored on the Wall of Leaders at the New York Stock Exchange.

Jeff Rollins, the son of Tippie’s longtime business associate and founder of Rollins, Inc. John Rollins, best remembers Tippie as a constant force in his life and a great teacher in business.

“I can’t remember a time I didn’t know Henry, and I started working with him about 37 years ago. He was a quiet, powerful and positive force in my life. He was known for being humble, his consistency, and above all, doing the right thing for the people you work with, no matter what,” Jeff Rollins told the Delaware Business Times. “He was family, and his family is part of our family.”

Tippie was born and raised on a farm in Belle Plaine, Iowa, and, after graduating high school, enlisted in the U.S. Army Air Force in the Pacific Theater during World War II. Once his service was completed, he graduated with a degree in accounting from University of Iowa. Two years after receiving his diploma, Tippie placed an ad in an accounting trade magazine to see what opportunities lie out there.

John Rollins, a rising business magnate who opened a Ford dealership in Lewes a few years earlier, and his brother Wayne, saw the ad and sent an inquiry. Tippie flew into Washington, D.C., and took the bus to Rehoboth Beach and started work in early 1953.

The Rollins brothers founded Rollins Broadcasting and had bought a radio station in Virginia, and took advantage of the falling radio station prices. In turn, the brothers launched programs geared to the Black community. The venture paid off, and within a decade, the company branched into television.

Come 1961, the brothers took the company public, marking the foundation of Rollins Inc. As the revenue grew, Tippie spearheaded buying out Orkin Exterminating Company for $60 million in 1964. In corporate lore, it was the first American leveraged buyout. At the time, Rollins Inc. was seeing more than $9 million in annual revenue.

Tippie continued his work with Rollins Inc., serving as a director when the company was listed on the stock exchange in 1968. He held that role for longer than anyone in the company, including John and Wayne, for roughly 56 years. He also served as the company’s  longest chief financial officer for 17 years.

“He had a mind like a steel trap. He knew risk and he knew how to manage it. It was deeper than having a great mind for finances, it was having the foresight about what was ahead and planning for it,” Jeff Rollins said. “He had this incredible stamina, and he wasn’t afraid of work. It would get to the point where I would think I couldn’t do anymore, and he’d be there right beside me, with his sleeves rolled up to keep going.”

While Tippie and the Rollins brothers were building the premiere global company, Delaware leaders and businesses were dreaming of something that would put Dover on the map. Then-Delaware Attorney General David Buckson hoped to create a speedway, and Melvin L. Joseph Construction Company agreed to build it in what was a 204-acre farm and airfield. Rollins would finance the venture, and the first NASCAR event was held in July 1969.

Jeff Rollins said that while his father and uncle were often dreaming of new business ideas, Tippie often served as the voice of reason to ensure that business remained on track.

“That’s what made them great partners. My dad would often joke that Henry was Dr. No, because he’d say no to whatever they thought they wanted to do. But the three of them worked so well together,” Jeff Rollins said.

Tens of thousands of fans attended the Monster Energy NASCAR Cup Series Drydene 400 at Dover International Speedway on Oct. 6, 2019, in Dover. | PHOTO COURTESY OF NASCAR/MATT SULLIVAN/GETTY

The sport continued to grow to two race weekends in 1971, but it was a struggle until the 1990s when ESPN and other broadcast networks began to pick up the races. By 2010, the racetrack had a capacity of 135,000 fans. Though attendance has since fallen in recent years, TV broadcast rights were valued at $34.2 million as of 2019.

“It wasn’t an easy business to be in at times, but I always remember what he’d say, ‘the sun will come up tomorrow,’ just that it was a new day and to keep moving forward,” McGlynn said. “He was a product of the depression, so very conservative in leadership – which was perfect for the company at the time.”

Tippie joined the Dover Motorsports board of directors in 1996, when the company was first publicly offered on the New York Stock Exchange. He later became chairman after John Rollins died in 2000, after serving as vice chairman at the time.

“I remember a couple days after it happened, Henry called me and asked me whether it was OK with me if he became chairman. That spoke volumes to me, because I just assumed Henry would take the position, but to call and ask showed me the kind of person he was,” McGlynn said.

Tippie could be a hard taskmaster, to colleagues who he thought did not appreciate the work he and others put in. Rollins mentioned in his early years working in the family business, he would be afraid of calling him, “because he’d always ask about follow-ups to what needed to be done.” Other times, he would not be afraid to mince words about the sloppy work.

But underneath was a heart of gold, and on very rare occasions would be able to crack – and take – a joke. On his way out of the office one night, he told McGlynn to tell everyone that the jerk was going home. So McGlynn did, turning immediately on his heel and loudly announcing it in the office.

“He started laughing, and I think it was the only time I saw him crack up at the office. He had a rare sense of humor, and it took a lot to get him to laugh at anyone or anything,” McGlynn said.

After living in Delaware for more than a decade, he and his wife, Patricia, moved to Austin, Texas, where he owned a 33,000-acre ranch. He would still visit Delaware throughout the years for NASCAR races and Dover Motorsport board meetings. He enjoyed the cattle on his ranch, following Iowan football and basketball teams, and traveling with his family. Tippie had a map filled with pushpins marking where he and his wife had traveled in their spare time.

Most importantly, Tippie loved big band music — specifically the Glenn Miller Band. 

“It lit his fire, and we’d have the Glenn Miller band come to the casino once a year. He and Patricia loved come to the casino and dance the night away,” Jeff Rollins said.

“Don’t ask me how, he managed to become friends with the band leader,” McGlynn said in a separate interview. “He was comfortable with a microphone he would almost emcee the events, and the room would be filled with people of his time, just rocking to the music.”

Last April, Tippie retired from Rollins Inc. after working with the Rollins family for 68 years.

“Without the financial knowledge and leadership Henry provided, Rollins Inc. would not be where it is today,” Rollins Inc. Chairman Gary W. Rollins said at the time. “His expertise and meticulous eye for detail has allowed Rollins Inc. to become the largest pest control company in the world. We are appreciative of Henry and for everything he has done for our company. We will continue to honor his legacy and the example he provided of hard work and dedication as we continue to grow and succeed.”

Tippie was also known for his generosity when it came to his alma mater, the University of Iowa. He donated $30 million in 1999, marking it the largest individual contribution to a university of its time. UI renamed its business college Tippie College of Business in his honor. He and his wife matched $15 million to UI’s fundraising campaign in 2016 and his efforts also awarded 900 students scholarships.

Tippie died at his home in Austin. He and his wife Patricia, had three children: Henry II, Linda and Helen.