Kewaan Drayton, a Savannah native and recognized Entrepreneur of the Year by the Savannah Area Chamber of Commerce, is deeply rooted in his hometown’s business community.
As Startup Savannah’s Director of Operations, he champions mentorship and community-building while continuously finding new ways to support local entrepreneurs and foster growth. We met with Kewaan at Mailbox Café, a generationally Black-owned property–turned café and shipping center that he helped launch in 2021.
On The Malin Journal, he shares his insights on his professional journey, Savannah’s entrepreneurial ecosystem, and the impact he hopes to make on his hometown.
You wear a lot of hats—entrepreneur, consultant, operations leader, and you’re also engaged in continued education. Can you walk us through your professional journey and how these endeavors connect?
It might look like I’m juggling a lot of different roles, but to me, everything is connected. My brother and I started Red Eye Film Productions back in high school, and that’s where I got my first taste of entrepreneurship. Over time, I realized I had a passion not just for creating content, but for the entrepreneurial side of things—like networking, learning how businesses grow, and figuring out how to leverage social capital.
For me, being an operations leader at Startup Savannah, mentoring entrepreneurs, and being involved in community organizations like the Savannah Downtown Business Association and the Greater Savannah Black Chamber of Commerce all comes from the same place. It’s about being a lifelong learner and seeing how all these pieces fit together—entrepreneurship, community work, and economic development are all intertwined. Continuing my education with an MBA at Georgia Southern is just another layer, helping me bring fresh ideas and academic insights back to the real world. So in my mind, it’s all one hat, just with a lot of layers.
Looking back on your own journey, what professional milestones or achievements are you most proud of, and why?
If I had to sum it up, my biggest accomplishment is positioning myself in the community as the entrepreneur’s entrepreneur. I want to be that person people can count on to get help, resources, and connections. That’s what I’m most proud of—more than any title or award. There’s still a lot of work to do, a lot of entrepreneurs to help, and other markets and communities I want to reach. So I see these milestones as seeds being planted for the bigger impact I hope to make.
Through your work as a Truist Fellowship Fellow, you launched the Big Ambition Guild (BAG). Can you explain what BAG is, and how it seeks to transform funding for minority entrepreneurs?
BAG is about creating programs where we educate and train entrepreneurs on key principles, and then we showcase their ventures to the community. The idea is that people who live in that community can invest small amounts into these businesses. It’s like a hyper-local, community-driven stock market, where instead of just going to a traditional lender, entrepreneurs get buy-in directly from their neighbors.
It’s a way to break down those funding barriers and also get the community involved in local entrepreneurship. And I’m using what I learn in my MBA program to refine this model, with the hope of one day taking it global.
What does it mean to you to bring innovation like BAG to Savannah, and how does it connect to your broader vision for the city?
Bringing the Big Ambition Guild framework to Savannah means a lot to me personally because it’s all about creating that bridge between local entrepreneurs and the community. For example, through Startup Savannah, we created unique spotlight videos showcasing entrepreneurs from the Spark Savannah program. That got the community excited and helped founders get real support—like one founder who needed space for her writing labs and ended up getting offers from community members who wanted to help.
So, for me, it’s about building these platforms where local entrepreneurs can launch, grow, and get that community buy-in. I hope it’ll transform how we fund and support minority entrepreneurs right here in Savannah and eventually create a model that can grow even bigger.
You’re also deeply involved beyond your own ventures—board roles, mentorship, consulting, and advocacy through programs like Right to Start. How does that advocacy work inform your day-to-day, and what does it mean for Savannah’s growth?
One thing I’ve learned is that advocacy is a huge part of being a successful entrepreneur. Day in and day out, I see that when you notice things that aren’t right—like barriers that keep certain groups from getting what they need—you have an obligation as an entrepreneur to help break those barriers down.
Serving on boards and advocating for other entrepreneurs isn’t just about policy—it’s about making sure that the business community knows someone’s out there fighting for them.
All of that advocacy informs my day-to-day work and it means a lot for Savannah’s growth. It’s like a mission—you do the hard work on behalf of others so that everyone has a better shot at success.
What does it feel like to support Savannah-based businesses, and why is it important to you?
It feels good to serve no matter how hard the work can be. I truly love what I do. Supporting Savannah-based businesses is all about making sure that entrepreneurship here doesn’t get overlooked. Our economy really needs that kind of grassroots growth, and I think it’s important that people who just want to add value to their community have the support they need. Not everyone wants to be the next big tech giant—some folks just want to open a neighborhood café or a local bookstore. And they deserve a place and a person they can rely on to help them move from just an idea to taking that first real step. That’s why it’s so important to me. I want to be that dependable resource in Savannah for entrepreneurs at every stage.
Tell us about your connection to Mailbox Café.
Mailbox Café definitely holds a special place in my heart. Back in 2021, I got to partner with Mr. Sheldon [Sheldon Kelly] and his son Leafy [Khalief Kelly] to revitalize the café side of it. The concept is basically if a Starbucks and a UPS had a baby—you can grab a coffee and ship a package all in one stop. It’s a really welcoming space, and it naturally became this centralized hub for small business owners.
From the moment I walked in, I knew I wanted to be part of it in some way. Even though I’m not there as much now, I love the owners, the customers, and the vibe. Plus, there’s this iconic, vintage type mural on the side of building that says “Small Business Headquarters,” which is like a perfect symbol of what it represents in Savannah. It’s just a great legacy to be part of.
Tell us about your connection to Mailbox Café.
Mailbox Café definitely holds a special place in my heart. Back in 2021, I got to partner with Mr. Sheldon [Sheldon Kelly] and his son Leafy [Khalief Kelly] to revitalize the café side of it. The concept is basically if a Starbucks and a UPS had a baby—you can grab a coffee and ship a package all in one stop. It’s a really welcoming space, and it naturally became this centralized hub for small business owners.
From the moment I walked in, I knew I wanted to be part of it in some way. Even though I’m not there as much now, I love the owners, the customers, and the vibe. Plus, there’s this iconic, vintage type mural on the side of building that says “Small Business Headquarters,” which is like a perfect symbol of what it represents in Savannah. It’s just a great legacy to be part of.
From your viewpoint, how has Savannah’s entrepreneurial ecosystem evolved over the years, and what’s remained constant?
In my view, Savannah has always had a strong entrepreneurial spirit. That’s something that’s been part of the city’s culture for a long time, so that’s the constant. What’s changed—and what I’ve sometimes disliked—is how gatekeeper-y it could be. For a long time, people did business mainly with those they already knew, forming cliques and circles that weren’t always easy for new entrepreneurs to break into.
Now, I think the evolution we’re seeing is a push toward a more community-focused ecosystem. We’re building spaces where any entrepreneur can come in, get their questions answered, and feel supported from the ground up. That grassroots effort is what I believe will help the ecosystem grow and become as inviting to locals as Savannah already is to its many visitors.
What’s surprising about Savannah as a place to do business?
Something outsiders might not expect is just how unique networking is here. In Savannah, it’s not just about what you can do business-wise. People really want to know you as a person before diving into any transactions. It’s a very human-level approach to business, and that’s something I always emphasize to anyone coming into our community.
And what’s next for you, personally—as a leader, innovator, and advocate?
I’m focused on leveling up the work we do at Startup Savannah, helping to build a truly inclusive entrepreneurial ecosystem. That means always looking for opportunities to add value and support others in the community. I’ve also been expanding my work into the Atlanta area, and now being locked in the Malin, I’m able to start forming deeper relationships in NYC.
On a personal level, I’m eager to finish my MBA and possibly explore law school in the future—just continuing to learn and grow. And with Red Eye Film Productions evolving into the Red Eye Collective, I’m excited to blend media, podcasting, and entrepreneurship under one roof. I’ll always be the entrepreneur’s entrepreneur and keep advocating for others, staying Savannah strong through it all.
Looking ahead, what legacy would you like to leave on Savannah, as someone born and raised here who’s giving back and building forward?
Looking forward, the legacy I want to leave on Savannah is one where entrepreneurship is seen not just as a way to build businesses, but as a path to transforming lives and communities. I want people to know that you don’t have to fit into a traditional box or choose just one lane. You can blend your passions, create your own path, and find real fulfillment.
And if people remember me as someone who was a big advocate, a supporter, and a true community leader who believed in them, then I’ll have done my part.
Looking ahead, what legacy would you like to leave on Savannah, as someone born and raised here who’s giving back and building forward?
Looking forward, the legacy I want to leave on Savannah is one where entrepreneurship is seen not just as a way to build businesses, but as a path to transforming lives and communities. I want people to know that you don’t have to fit into a traditional box or choose just one lane. You can blend your passions, create your own path, and find real fulfillment.
And if people remember me as someone who was a big advocate, a supporter, and a true community leader who believed in them, then I’ll have done my part.
