‘What are we waiting for?’ Service is a family affair for Haywoods | Milwaukee Neighborhood News Service
Andrea Waxman
July 25, 2019
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.
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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.
In 1999, Haywood founded the Haywood Group real estate development firm with an eye for advancing economic equity and building community.He is working on a plan to redevelop the old Sears building, which later became the Milwaukee Mall, into a hotel and convention center at North Fond Du Lac and North avenues in Lindsay Heights.
“Kalan Haywood Sr. is certainly a community-minded visionary,” said Joanne Sabir, a Lindsay Heights business owner and developer. She hopes his success will inspire residents to get engaged and become owners.
Rep. Kalan Haywood II has carved out his own path to success but cites his father as his most important role model and mentor.
When he was a kid, Haywood II said, he thought, “‘My daddy, he’s a dad. He’s old and he doesn’t really get it,’ but now when I think about the advice he gave me and how he was trying to help guide me and support me, I’m like, ‘You know what? This old guy kind of knew what he was talking about.’”
Growing up watching his father, Haywood II said, he learned the importance of working hard.
“Even though I was a procrastinator in high school, if I knew there was work to be done, I couldn’t sleep at night.” Though he enjoys bowling and movies, he said, “I have more fun when the work is done.”
Another important lesson his parents taught him, he said, was to treat everyone with respect, be they the janitor or the president.
Haywood Sr. said his son was “abnormal” in that he knew he wanted to run for political office from an early age. The younger Haywood said he understood his dream was possible when, at age 9, he watched Obama’s presidential inauguration on TV at Golda Meir School.
He got some early lobbying experience when he and his father disagreed about where he would attend high school. Haywood Sr. wanted his son to go to his alma mater, Riverside University High School, but Haywood II was set on going to Rufus King International High School, ranked No. 1 in the state.
“I was doing research. I was calling his friends and asking ‘Can you talk to my dad and convince him that King is a great school?’” Eventually Haywood Sr. gave in. The Riverside-King rivalry regularly emerges between them — in a joking manner.
The younger Haywood juggles his work in Madison — traveling there on Mondays and Fridays during the school year.
In his six-plus months in the Wisconsin Assembly, Haywood II said he’s learned a lot by talking to representatives from outside of Milwaukee and traveling to correctional facilities around the state. Though the atmosphere in Madison is hyper-partisan, he said, he’s begun to get to know his fellow representatives and to find common ground with them.
He said it’s important for his colleagues and himself to understand the difficulties that each area faces and for him to support his own district and as well as theirs.
Like his father, who said he recharges his batteries by being around young people who may not be sure what they want to do, or what the first step is, or believe in themselves wholly, Haywood II likes to share his success with younger people, in his case, by speaking at schools and youth organizations.
“I always tell young people when I go to schools and talk to students, ‘Find out what your end game is, what your final goal is and then work backwards. If it’s a big race and the finish line is where you want to be, you’ve got to figure out the milestones until you get to the finish line.”
His end game was to be elected, he said. In high school doing well academically, joining the Milwaukee Youth Council and becoming president, getting internships with elected officials and working on political campaigns were the steps he determined he needed to take.
We focus in on the moment and on what we’re doing today and tomorrow, he said, but we have to plan for the long game. “People who play the long game are the ones that win.”
Whether his future will be shaped by more politics or a business career, Haywood II is not yet sure but he figures that understanding how business and finance work will be fundamental to his success in either field.
Haywood II’s work ethic is one of his most exceptional qualities, say Ald. Milele Coggs and Rep. David Bowen, mentors and fellow elected officials.
Working hard comes out of K2’s passion and commitment to the community, said Bowen. It started with the youth leadership opportunities he had at Urban Underground and in the Milwaukee Youth Council, Bowen said.
There are so many decisions that are made for young people without their input and once K2 made it his goal to engage in activism and leadership, he went out front and got involved, not waiting for the chance to contribute, Bowen said.
K2’s optimism is what most impresses Bowen about his younger colleague, he said.
“He has always demonstrated an ability to be innovative and committed to the goals he sets but also be wise enough to seek and accept counsel from others who have more knowledge that can aid him,” Coggs said.
This may be a lesson he learned from his father who is a proponent of having mentors.
“It’s like football. People blocked for me when I needed someone to block for me, people coached me when I needed coaching, people sat me on the bench when I needed a time out, but they never gave up,” said Haywood Sr.
Affable, immaculately dressed and thoughtful in their comments, this father and son complement and mirror many qualities of the other — sometimes in almost the same words.
“No matter who it is — it can be a 5-year-old; it can be a 50-year-old; it can be the janitor in the building; it can be a CEO of a Fortune 500 company. You can learn something from everyone,” said Haywood II.
Haywood Sr said, “I learn something from everybody I come in contact with. It may just be over a cup of tea or it may be with a stranger making jam.”
But, he often wonders, “how do I take my life lessons and how do I implement what I’ve learned to benefit others? That’s my fun thing. I know it’s a dull fun thing.”