Blog Post

A tale of two cities: Brothers and champions in Brooklyn and Chicago

— Josh Haywood and his mentee Leo in Chicago (left), and Sean Haywood and his mentee Kerwin in NYC (right).

Last summer, Sean Haywood, a New York City mentor who works for Ernst and Young, sent an email to his brother Josh, who lives in Chicago and works at a startup community-based health organization. In the email, Sean let his brother know that iMentor had expanded to Chicago and urged him to volunteer. “There was no hesitation,” Sean says, “I knew how hard iMentor worked to recruit male mentors. I was always telling my male friends and colleagues in NYC to apply. So when I heard iMentor was launching in Chicago, the first thing I did was recruit my brother.” Josh wasted no time getting involved. 

Sean has always appreciated the mentors in his own life, and he counts his high school teachers as having filled that role for him. For Josh, his experience as a summer camp counselor for middle school students from Trenton, Newark, and Baltimore helped him realize that while “every student deserves a champion”, in many communities, too few students actually have them. “That experience really opened my eyes to just how fortunate my brother and I were,” Josh noted. “Our students were overcoming challenges that neither of us had ever even considered.”

Now, the brothers share the experience of mentoring in their respective cities. Sean’s mentee, Kerwin, is a senior at the High School for Innovation in Advertising and Media in Canarsie, Brooklyn. They have worked together since Kerwin’s freshman year, and he is now on track to matriculate at the College of Staten Island in the fall. Josh’s mentee, Leo, a creative and energetic teen, just completed his junior year at Chicago’s North Grand High School. Leo has his sights set on several colleges, including the University of Illinois at Chicago.  

Sean and Kerwin are already making plans to continue their mentoring relationship as Kerwin heads off to college in the fall. For Josh, who will be heading to medical school next year, and Leo, a rising senior, the next step is the college application process, but the two couldn’t be more ready to take it on.