Robert “Bob” Cummings passed away peacefully at the age of 63 in St. Petersburg, Florida, surrounded by loved ones. Born in Milwaukee, Wisconsin, in 1962 to Lowell and Nancy Cummings, Bob developed a deep appreciation for the idea that life should be lived with intention and joy. After graduating from Greendale High School in 1981, then first in his class from the College of Business at the University of Wisconsin-Milwaukee, Bob worked for 15 years as an executive in the printing industry. True to the words he encouraged others to live by—“Don’t live where you have to work; live where you want to live, and start a life there”—Bob chose to build his family’s life in Door County, Wisconsin, a place whose natural beauty and community reflected what mattered most to him. Prior to retirement, Bob spent the last 20 years in the financial services industry at Baird and Merrill Lynch, where he dedicated his life to helping countless others live their best lives. He was the embodiment of the American Dream, a man who seemed to be able to shape the world around him through sheer tenacity and will. When you were in his presence, you believed he could do it. And he had a way of making you believe you could do it, too. He was larger than life, both in presence and in heart, devoted to his family, and deeply invested in their happiness and self-fulfillment. He is preceded in death by his parents, Lowell and Nancy. He is survived by his six children, Luke, Sam, Ali, Taylor, Macki, and Jake; their mother, Terry; his brothers, Mike and Tom; his wife, Paula; and his fourteen grandchildren, to whom he was, and will always be, “Grandbob.” Bob Cummings may be gone, but his legacy lives on.