Kalan Haywood Sr. is no stranger to success as the founder of the Haywood Group real estate development, investment and consulting firm, which is making a mark on the city. Neither is his son. Kalan Haywood II, or K2 as his dad calls him, became the youngest elected official in the state in January, after winning the 16th District seat in the Wisconsin State Assembly. At age 19, he defeated four rival candidates while studying business and finance at Cardinal Stritch University. Do you have feedback on Milwaukee NNS's reporting? Take our survey to let us know how we're doing! The Milwaukee Neighborhood News Service talked with the two about their paths to success in Haywood Sr.’s office at the historic Germania Building, 135 W. Wells St., which he redeveloped in 2014. Alike and different, the Haywoods exude drive and a serious commitment to bringing improvements, each in his own way, to Milwaukee and Wisconsin, especially to the African American community where they live. “What are we waiting for to fix our city?” asked Haywood Sr. Both were born, grew up and still live in the Brewers Hill neighborhood. Haywood Sr., now in his mid-40s, was one of three children in a family headed by a single mother. Her extended family helped raise him, he said, but in most ways he faced the same challenges as the majority of his low-income central city peers. Haywood II grew up with a successful father as an important role model and was inspired to see Barack Obama elected president when he was in fourth grade. Haywood Sr. attributes his success to the help of many, but two men in particular guided his path from a young age and diverted him from the dangers of the city streets. “My being here today is really a collaboration and summation of people helping me out, people believing in me, people giving me exposure when I didn’t know certain things existed, people who showed me the way and gave me advice,” he said. The first, Kevin Ingram, then an Upward Bound recruiter, met the older Haywood at Morse Middle School when he was in eighth grade. The program provided four years of tutoring and supplemental courses on the Marquette campus to prepare selected high school students from underserved communities for college. It ran after school, Saturday mornings and in the summer, said Ingram, who now works as an educational consultant at the Wisconsin Department of Public Instruction. At age 13, “that didn’t really sound too attractive to me — to go to school year-round,” said Haywood Sr. But Ingram saw that he had demonstrated enough interest to apply and sit for an interview, and when Haywood failed to act on the offer to enroll, Ingram visited his mother to discuss the program. Ingram “wouldn’t give up, and lo and behold, I got involved in Marquette’s program,” said Haywood Sr. It was Tyrone Dumas, a graduate of the UW Milwaukee School of Architecture and Urban Planning, who sparked Haywood’s interest in architecture, a field he said he didn’t know existed. Dumas spoke to the Upward Bound students about his background and about making mistakes when he was a teenager that resonated with Haywood Sr. Dumas became his first mentor, he said. “If you had asked me the day before I met Tyrone, what did I want to do when I grew up, I would have told you I didn’t know. If you had asked me what did I want to do the day after I met Tyrone, I would have told you I want to be an architect,” said Haywood. Possessing a love of math and drawing, architecture turned out to be a good fit for Haywood. With Ingram’s help, Haywood Sr. got an internship under Dumas at the City of Milwaukee Department of Bridges and Building Services, where Ingram was the director. Haywood learned about how city government works in relation to building issues and practiced drawing, he said. Dumas later helped him get a college internship at the Eppstein Ulen architecture firm, now the largest in the state, Haywood Sr. said. He was a rambunctious teenager but always a deep thinker, Dumas said. He asked a lot of questions; he listened to a lot of good people and thought about how to move his life forward. “I wouldn’t say anybody made him. He made himself,” Dumas said. At the same time he was learning, the redevelopment of Brewers Hill was happening. “You had a lot of people I was raised with moving out or being pushed out and a lot of white people moving in,” Haywood said. “I arrived at this idea of how can I use development, how can I use brick and mortar to change my neighborhood to provide a housing product that can benefit the community,” he said.