Michael Blackshear

You are a Brooklynite.

Born, raised, and I still claim! Tell me about growing up in Crown Heights, Brooklyn.

Tell me about growing up in Crown Heights, Brooklyn.

I lived not too far from the former site of Ebbets Field, the old Dodgers’ stadium. I attended Bishop Ford Central Catholic High School. Brooklyn, my family, and my community laid the foundation of who I am today.

Who were your childhood heroes?

My father. What was amazing about my father is that he raised the family while going to John Jay [College of Criminal Justice] at night, and he was a police officer. When he finished his studies, he decided to go to law school at night. And so today, when I look at who my hero was, it was my father, because he provided lessons, going back 30, 40 years, that I apply today.

You got your degree in finance from Syracuse University, then an MBA from St. John’s, and then you went to Fordham Law School, as did your father. Did he encourage you to go to law school?

Yes, he did. I never saw myself going to law school. I was done when I obtained my MBA, and my father challenged me to attend law school to sharpen and enhance my professional skill sets. He said it would enhance my problem-solving skills, which it has.

Your father, Cornelius Blackshear, was a longtime U.S. bankruptcy judge for the Southern District of New York. You spent time with him in his chambers. That must have been an education.

That was a master class. There were times where he would try to mediate a conflict between two parties. If he couldn’t resolve it in the courtroom, he would bring both parties back to his chambers to indulge in a glass of Johnnie Walker Blue, a blended Scotch Whisky. I always remember this, because it is one of my go-to whiskeys. More importantly, I observed in real time the art of conflict resolution.

What are your favorite things to do in Chicago on your days off?

I love, particularly in the summertime, the ability to do so many outdoor activities, whether that’s walking, biking, being on the water. I’m also a foodie, so I love exploring different types of foods.

Mets, Yankees, Dodgers, White Sox, or Cubs?

My heart bleeds New York. I’ve always been a Yankees fan.

You lead the diversity, equity, and inclusion initiative at Ryan Specialty. How will the current administration’s opposition to DEI affect what you and Ryan Specialty are trying to do?

At Ryan Specialty, we embrace our values, as they set the foundations for what our firm represents. We are and will continue to be committed to building, growing, and sustaining a diverse workforce reflective of society throughout the entirety of the organization and insurance industry. We harness our differences and commonalities to better serve our trading partners, workforce, and communities. This has not changed.

What three words would your co-workers use to describe your management style?

Democratic—I believe in getting consensus. Transformational—There are times we have to take risk to change the status quo. Servant-leadership—How can I support the interest of others for the greater good?

If you could change one thing about the insurance industry, what would it be?

I would like to see our industry become even more intentional and deliberate with creating a more inclusive industry. If we all do that, that would create a better equitable society, a better world, but also a thriving insurance industry.

What gives you your leader’s edge?

When I started back in 1991, it was my intent to be learned in the scope of the insurance transaction. What makes me lean forward is the time I took to understand our business. I know my industry, and I know the players in it. I think that’s what gives me my strength.