Doing business in Metro Charleston

Stanfield Gray is the head of Dig South. File/Provided

Stanfield Gray founded DIG SOUTH, an annual conference showcasing the technology and entrepreneurship sector in the Southeast, four years ago. This year’s three-day event starts Tuesday at the Gaillard Center in downtown Charleston.

Previsouly, Gray was music editor at Charleston Magazine and was once employed by the College of Charleston, where he worked in media relations and strategic communications. He has a bachelor’s degree in English literature from the University of South Carolina Honors College and a master’s degree in Southern studies from the University of Mississippi.

Q: Who is your favorite business leader and why?

A: Aside from my father — who steered the Gray family ship through fair winds and stormy seas — Patagonia founder Yvon Chouinard is my favorite business leader. Chouinard built an incredibly successful, socially conscious brand. He leads with integrity, living out his vision as an avid outdoorsman and environmentalist.

Q: Who is your favorite leader of any kind and why?

A: Dr. Martin Luther King, Jr. is certainly ranked among the finest. Dr. King shared a vision of freedom and equality for everyone and offered actionable plans for how we might get there together. He also remained hopeful and positive despite long odds and a hostile political climate.

Q: What is the best leadership advice you’ve received?

A: Whenever I’m considering a new challenge, my mother loves to say, “Go for it. You can do it.” And it’s not what she says, but how she says it — with conviction and absolute certitude – that inspires me.

Q: What is the best leadership advice you could give?

A: I’m a strong believer in situational awareness paired with preparation. In other words, opportunities are all around us if we listen and look closely, and prepare for the unexpected.

Q: What is the best book on business or leadership that you’ve read and why?

A: Isaac Asimov’s Foundation trilogy is a fascinating science fiction take on leadership. Using mathematical sociology (yes, I had to look it up again), the lead character, Hari Seldon, puts together a foundation of artists and engineers to document and expand mankind’s collective knowledge and build a new empire. It’s not “Winning” or “The Art of the Deal,” but it’s far more creative and sounds like something Elon Musk might attempt today.

Q: What other business publications do you regularly read?

A: I read the Wall Street Journal, N.Y. Times, Fast Company, Wired, Inc., Harvard Business Review, TechCrunch, VOX, Mashable, The Post and Courier plus a slew of articles forwarded to me via social media. It’s an avalanche of information.

Q: What are the most important decisions you make as a leader at your business?

A: Every day I think about how the team is doing professionally and personally. Are we learning, growing and improving together? I also think deeply about how our business impacts the culture around us and what that will mean for the future of my two kids. Are we doing our best to create a South full of opportunity and the same advantages found in other regions of the U.S. and globally? Can we harness creativity and technology to build a better society and not leave any group behind?

Q: What is the biggest challenge facing business leaders today?

A: I think it’s very difficult to balance profitability and social good. Every choice we make has an impact locally and globally, and prioritizing those decisions is a constant struggle. It’s also an exciting opportunity to reframe the bigger challenges and approach them with 21st-century solutions.

Q: What was your biggest mistake as a leader and what did it teach you?

A: Hiring the right talent for the job at hand is tough, and I’ve made mistakes. But I’ve learned that it’s seldom the candidate or partner’s fault. It’s often the way that I’ve approached the hiring process that has derailed the plan. I’m learning to ask the right questions and think more carefully about those strategic alignments.

Q: What was your biggest success as a leader and what did it teach you?

A: Outside of marrying Sunny Gray and having two amazing kids, launching DIG SOUTH is my biggest success. And it would not have been possible without an incredibly talented team, first-rate sponsors and presenters, and a wildly supportive community. I’ve learned that a well-designed vision can only succeed if you are able to sell it to the right audience and deliver on your promises. I’ve also learned to appreciate each daily success, no matter how small. It can sound cliche, but it really is about the journey and the experiences you have along the way that matter. Personal success is not defined by the destination, a shelf full of hardware or a financial benchmark; it’s living in the moment.

Q: What are you doing to grow the next leader in your company?

A: I’m working on becoming a better listener and learning to focus on each team member’s unique skill set to help them grow. We have plans to travel more in 2016 for professional development and share what we’re learning inside of our industry and from compelling outside sources. We’re also on-boarding high-level freelancers who are bringing new energy to the core DIG Team and keeping us up to speed on the latest market trends. I’m stoked about the brilliant young talent reaching out to help us.

Q: How do you define a great business?

A: To me, a great business contributes positively to the world, builds an incredible employee culture where people are excited to go to work, and is profitable.

Q: What’s your favorite thing about doing business in this region?

A: Doing business on a boat in a deep water creek. Metro Charleston is the perfect intersection of quality of life and business opportunity.

Q: What is your least favorite thing about doing business in this region?

A: It can be challenging to get some folks to see the bigger picture. We have to manage growth smartly without pretending it will suddenly stop and Charleston will return to the 20th century. We can grow responsibly while supporting noble conservation efforts like the Lowcountry Land Trust and the S.C. Conservation Bank, for example. But, these are the normal growing pains of an engage citizenry and we’re all the better for waging great public debates.

Q: Name one thing government could do to help your business.

A: By helping fast-growth, scalable startups that participate in DIG SOUTH succeed. We need more favorable tax incentives for high-wage, digital economy businesses, statewide gigabit bandwidth and a vision for transportation that includes multimodal options, particularly self-driving cars and walkable, connected neighborhoods.

Q: Name one thing government could stop doing to help your business.

A: Government could start thinking more about the future and less about the past.

Q: What are some of the biggest issues facing the local tech industry?

A: Affordable housing options close to work, and better connected neighborhoods are big issues facing the local tech industry – and everyone. We need more venture capital. And we need to support regional, talent-attraction efforts like Charleston Open Source to fill high-wage knowledge economy jobs. The digital wave is coming, get ready.