Robert Jeremiah Gallivan Jr.

Robert “Bob” Jeremiah Gallivan, Jr., of Naples, Florida, passed away peacefully on December 11, 2024, at the age of 89. Born on October 1, 1935, in St. Paul, Minnesota, Bob’s life was a remarkable journey filled with generosity, optimism, and love.

The consummate optimist, Bob often introduced himself with a smile, saying, “My name is Bob—spell it backwards!” He was a steadfast believer in PMA (Positive Mental Attitude). His infectious positivity inspired everyone fortunate enough to know him. Throughout his 89 years, Bob made a lasting impression on countless lives, leaving behind a legacy of motivation, resilience, and connection.

Bob was the eldest of four siblings and son of Robert Gallivan, Sr., owner of Gallivan’s restaurant and a co-founder of the St. Patrick’s Day Parade in St. Paul. He attended Nativity Elementary School, St. Thomas Academy, and later graduated from the University of St. Thomas. A talented athlete, Bob excelled in both baseball and basketball, and his sports career included brief stints with the Minnesota Lakers and the Milwaukee Braves before he turned his focus to the business world.

For 50 years, Bob devoted his career to guiding others through life insurance and financial planning, helping individuals secure their futures and protect their families. He championed his “Three D’s” philosophy: while no one can control Death or Disability, they can, to a large extent, shape their Destiny through thoughtful investment planning. Bob, the bestselling author of How I Started Earning $50,000 a Year in Sales at the Age of 26 (published in 1963), received numerous accolades and awards throughout his career. Following the release of his book, he was invited as a guest on popular shows such as What’s My Line?, To Tell the Truth, and I’ve Got a Secret. One particularly memorable moment came when a helicopter was sent to retrieve Bob from a cruise ship where he was making a public appearance. He was flown directly to the Oval Office at the White House, where he met President John F. Kennedy, who personally signed his book. In 1970, Bob was named one of the “Ten Outstanding Young Men of Minnesota” by the Minnesota Jaycees. Bob was named “Producer of the Year” for Alexander Hamilton numerous times, in addition to many years on the President’s Council, recipient of the Hamilton Award in 1983, and President’s Agency Award in various years. He is a Life and Qualifying member of The Million Dollar Roundtable, a global association of the world’s leading life insurance and financial services professionals. Over his 47 years of membership, Bob achieved Court of the Table 18 times and Top of the Table 4 times.

Later in his tenure, Bob and his firm specialized in the design and delivery of non-qualified incentive and key man plans exclusively for financial institutions. A pioneer in the Bank Owned Life Insurance space, his team worked with successful financial institutions to provide security and protection for bank owners, executives, and directors. Bob participated as a director on over 30 public and private Boards where he used his experience to consult in the areas of compensation, employment contracts, venture capital, and mergers and acquisitions.

Bob’s personal life was equally rich and fulfilling. Father of 9 children (18 grandchildren and 11 great grandchildren), Bob loved to spend time with his family and shared many passions with his kids including golfing, duck hunting, and traveling. Married to the love of his life, Barbara Gallivan, for nearly 50 years, the couple built a life grounded in love, shared adventures, and unwavering support. In 1995, Bob and Barbara relocated from Minnesota to San Diego, California, where they lived for 27 years before moving to Naples, Florida, in 2019. Bob’s love of travel led him to visit 112 countries, with a special fondness for Ireland’s golf courses and green landscapes. One of Bob’s most cherished memories was celebrating a career milestone at the top of the Eiffel Tower, where he was honored with a gold diamond ring commemorating his 10th year on the Presidents Council. Surrounded by Barbara and his industry peers, the moment was a highlight of his professional journey.

Although Bob’s passing is a profound loss for his friends and family, his children take comfort in the lasting impact he had on shaping them into the individuals they are today. They know he would encourage them to focus on the positive and carry forward his unwavering optimism. As he entered the pearly gates of Heaven, they imagine he was giving high-fives, undoubtedly asking, ‘How’s your PMA?’ and reminding everyone, ‘Attitude, Aptitude, Action.’

Bob’s incredible journey will be celebrated as he wished, with his ashes scattered in several of his favorite places around the world. A celebration of life will be held in Minnesota in early 2025.

In lieu of flowers, the family kindly asks for donations to the St. Thomas Academy scholarship program in Bob’s honor.

To leave online condolences or share memories, please visit https://www.dignitymemorial.com/obituaries/naples-fl/robert-gallivan-12126532.