Five Questions For … WatchHerWork Founder and CEO Denise Hamilton

Xconomy Texas — 

Houston—Technological innovation is sometimes rightly criticized for how it automates work, creating uncertain economic futures for many people.

Denise Hamilton has decided to focus on how, as she puts it, technology can instead “inject people” into processes, amplifying their efforts. That ethos underpins the work she’s done recently to help victims of Hurricane Harvey, for whom she helped create the my.haveyneeds.org website. That site is designed to connect those in need of assistance with those who can provide it.

That philosophy could also be applied to her startup, WatchHerWork, a website that features women offering testimonials of their experiences navigating a variety of workplace issues. It’s a way to help women expand their network by finding mentors they would not otherwise meet.

After a three-week hiatus due to Hurricanes Harvey and Irma, we are resuming our regular Friday feature, “Five Questions For.” This week, the spotlight is on Hamilton, who speaks about making sure she’s not her startup’s weakest link, the three-fifths compromise, and being on the “Arsenio Hall” television show. Here is a lightly edited transcript of our conversation.

Xconomy: Who do you admire and why?

Denise Hamilton: I really admire—this feels so cliché—Oprah Winfrey, in a couple of different ways. She’s kind of the unlikely hero. She didn’t look or sound the part of somebody who should have been successful in media—she was even fired early in her career. You can take strength in the idea that, if you’ve got a level of giftedness and you’re willing to share it with the world, and have the courage to extend yourself, the universe comes up to meet you. She’s just a gleaming beacon and example of that. And I would also extend that idea to the formulation of OWN [the Oprah Winfrey Network on cable television.] I remember how many people were saying, ‘This is going to fail. Who do you think you are? You, as a black woman, can’t start a TV network.’ The channel is thriving.

Whenever I get that question or energy from people, that’s the example I have in the back in my head. I’m Denise Hamilton and I can do whatever my giftedness allows me to.

X: What’s your biggest fear?

DH: This would have been a different answer last week. Right now, from a small business startup perspective, when you’re in a natural disaster like this, [you ask yourself], ‘How do you survive and get on the other side of this?’

My biggest fear is that I will be a cap on my business. I believe that an organization doesn’t grow past its leader so I’m constantly learning and growing. I don’t want to be the reason my business doesn’t succeed because I make decisions 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.

Denise Hamilton with her mother, Penelope Allen. (Photo courtesy: Denise Hamilton.)

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.