I had the pleasure of interviewing Demetrius Gray, Founder and CEO of WeatherCheck, a company that helps property owners and managers respond to forecasted and observed insured losses through machine learning.
Thank you so much for doing this with us! What is your backstory?
I grew up in a small town in Kentucky, not quite carefree but I had a lot of freedom and friends. I’ve always been a hard worker. I’m one of those kids who sold gum to you on the playground, for a profit. My dad once took me into the oilfields of Kentucky and showed me where money comes right out of the earth, from hard work. I started my first company at 20, replacing roofs after storms. I drove all over the country, knocking on doors, finding roofs to fix, and being frustrated that there wasn’t an easier way to know who really needed a new roof, that insurance would pay for. I knew there had to be an easier way. Turns out I was right. I ended up selling my roofing company to start my current company, WeatherCheck. Today, we can tell you exactly which addresses across the country have been damaged by weather in the past 24 hours, and we can help you take the steps to recover.
Can you share the funniest or most interesting story that happened since you’ve been leading your company?
I think this story is amusing, and it illustrates how well suited my co-founder, Jermaine Watkins, and I are to be partners. Personal taste says so much about a man. The first time we met, we were wearing the same exact pair of Cole Haan shoes.
What do you think makes your company stand out?
I think our company stands out by the way people react to it, that kind of wow-why-didn’t-I-think-of-that reaction. When we meet with a new potential investor, or customer, I am always blown away by the almost instant ownership they take to our work! It never gets old, when you start explaining what your data can do, and you see their eyes light up, and they go, “So, can you……?” And when the answer is yes, which it almost always is, you can watch the wheels turn. Our company has its own gravity, it pulls people to us.
Are you working on any new or exciting projects now?
We’re the only company tracking hail damage nationwide, by address, and notifying customers to take specific actions. Our hail-damage algorithm, driven by AI and ML, is already 90%+ accurate, so we are adding tracking for several other perils, including fire, flood, and storm surge. We’re also working with FEMA to use those capabilities to track and triage peril victims for emergency response. People die during storms because 911 gets overwhelmed. Our application can help with that. To know we’re helping to save lives and homes, well, it doesn’t get much more exciting than that. That’s what pushes us every day.
What advice would you give other founders to help their employees to thrive?
From day one we set up a transparent, flat company that empowers everyone to participate in the entire corporate process. We are all responsible for each other, and we are all answerable to each other. Our culture sets very high expectations of productivity and quality. I’d advise founders to be as open, honest, and humble as we expect our employees to be.
None of us is able to succeed without some help along the way. Is there a particular person who you are grateful toward, who help you get where you are?
My mother: she stayed out of my way. That may sound odd, but I have always been very headstrong, going my own way. I appreciate that she didn’t sit on top of me or predict what my life would be like. She let me go my own way, make my own mistakes, and face the consequences or reap the reward. I gained a lot of self-confidence from that.
How have you used your success to bring goodness to the world?
Currently, I’d say in two main ways. Our company protects owners from out-of-pocket costs for weather repairs on their home. We offer our services at cost or for free to community development and low-income housing efforts. If anyone is interested in enrolling their Habitat for Humanity home, for example, please send them our way. Also, we are working to develop an app that will instantly track and triage peril victims for emergency response. Using cloud computing and our app, we can quickly know the exact addresses where people need the most help.
Can you share the top five lessons you have learned from your experiences as a “Black Man in Tech”?
1. Persist. I’ve been laughed at my whole life, and definitely around this work, as someone with big “pipe dreams.” But what I’ve realized, at age 30, is that each of those experiences builds who you become. Now, I am almost invincible. There’s no way we won’t succeed. Every nay-sayer added to my resolve. I remember once a teacher demanding a lot of me, and I felt kind of singled out. The truth is, she knew I was capable of more. All those people along the way helped me learn the value of persistence.
2. Don’t judge books by the cover. It sounds hokey, but we have a wildly diverse workforce, and it makes our company better every day. We like to give people a chance to get ten times better at what they do, so when and if they leave us, they’re better off having been with us.
3. Provinciality is everywhere. Growing up in the south, I expected to see it around here. But I’ve learned that old ways of thinking are still everywhere. They might be subtler, but they’re there. It takes time for new ideas to take root. Be ready to explain things, many times, and listen with respect.
4. Have fun! We were in the middle of some very intense planning, that days-long kind of planning that can numb your mind. Progress was stalling. One of our advisors brought some toys the third day and you’d have thought we were a kindergarten class. We played and laughed like kids, and it felt like fresh air had entered the room. Now, having fun is a key value for our company.
5. Stay true to yourself. We’re in a turbulent social period, for sure, but we’re realizing that profit is still what really matters. What I mean by that is, businesses are being judged more on the verifiable truth of their premise. That’s positive social movement. No one can afford to leave a good idea on the table because the founder doesn’t fit the expected look. Profit is an equalizer on many levels.
Can you please give us your favorite “life lesson” quote?
My go-to is Batman, who said “People need dramatic examples to shake them out of apathy.” To me, that means people are settled, comfortable with certain ways of thinking, and to get to them to think or do anything different, you have to be compelling. We waited until we had a real story to tell, and a product that is truly valuable in unique ways.
Who would you like to have lunch with, and why?
I’d love to meet Robert F. Smith, of Vista Partners. We have a lot in common. He’s a ninth-generation Coloradoan, I’m a sixth-generation Kentuckian. Clearly, family paved both our paths. As an infant, his mother took him to the March on Washington, when Dr. Martin Luther King Jr. delivered his “I Have a Dream Speech,” the same speech I delivered year after year in elementary school, as I portrayed Dr. King in an annual event. Mr. Smith is hugely generous and inspires me to always question whether I am giving back enough. As one of the smartest people in the world about technology, and as the wealthiest African American in the country, he’d be great to have in our corner! Mr. Smith say when. I’m buying!