out of fear or lack of information. That fear of being a cap drives me to constantly research, innovate, ideate, and grow.
X: If you could go back in time and get five minutes with any major historical figure, who would it be, and what would you want to say to him or her?
DH: It’s not one person. It’s the Continental Congress. What I’m fascinated by is the three-fifths compromise. How did you get these two groups that had such incredibly diverse processes and personal goals and how did you get to a compromise? We look at history—and the compromise was ridiculous—I mean, how do you get to three-fifths of a person? But to me, it’s the perfect example of creativity in solving problems and moving the ball forward.
You couldn’t do it today. People are so entrenched in their personal positions and they can’t meet in the middle. That was the ultimate meeting of the minds in the middle. How did you get there? If you’re creative and problem-solving people with widely divergent thought processes and goals, that’s the ultimate genius.
X: What’s your most impressive or most quirky skill that has nothing to do with your day job?
DH: I am a singer. I used to actually sing backup for El DeBarge, Stevie Wonder, and Vogue. It was me on “Arsenio Hall” singing backup with El DeBarge. [Editor’s note: Hamilton claims to not have any photos of these gigs on hand.] I get called on for specific [singing gigs] from time to time. I’m retired. I think Stevie Wonder is just a genius. It was amazing getting to meet him, let alone sing with him.
X: Tell me about your early influences.
DH: I’m Jamaican. We came here when I was in Kindergarten, first grade. And I am absolutely mystified by the strength and courage of my mother. She has a high school education. She worked at the phone company and I can’t imagine the courage that it took to get up and move to another country, to leave this warm, beautiful tropical island and move to New York City in January and it’s 15 degrees. And so for me my whole life it’s, ‘How did you do that? Why did you think to do that?’
I’ve seen that example of someone taking nothing and making it into something, and why would I think I couldn’t do that? Her example was so incredibly powerful. There’s no excuse, just execute and just get it done. I try to bring that to my life and my business every day. When people say to me, ‘Oh I don’t know how to do something.’ Well, guess what? There’s a book, a YouTube video; figure it out. You can solve literally any problem. If people can come to this country and navigate the culture and differences, I feel like you can watch a video and learn how to set up MailChimp.
It’s how I handle my team. It’s the driving belief system in my life: People with far less have done far more.
