Digital Sportsman: Guide-First Booking, AI Tools, and Community
With his new tech platform, Digital Sportsman, Anthony Hamilton blends modern tools with old-school values to support the next generation of anglers.
When Anthony Hamilton, a seasoned tech executive with experience leading companies in more than 35 countries, stepped away from enterprise software, he didn’t trade his career for a boardroom—instead, he headed back to the woods and waters of his North Carolina upbringing.
“I grew up in North Carolina, surrounded by the outdoors—fishing, hunting, all of it,” Hamilton says. “As my corporate career wound down, I knew I didn’t want to spend the next chapter behind a desk. I wanted to build something that let me enjoy the outdoors with my family—and give back to the community that shaped me.”
That’s what led the entrepreneur, Army veteran, and lifelong builder to launch Digital Sportsman, a tech platform designed to revolutionize the way anglers, guides, and outdoor businesses connect, grow, and thrive. Hamilton’s vision is to dominate the outdoor tech landscape through advanced platforms while building a brand that reflects American ingenuity, family values, and the spirit of the wild. “We’re creating something that goes far beyond ones and zeroes,” he says. “This is about culture, freedom, and the future of the outdoors.”
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What Digital Sportsman Does (for guides, anglers, and outfitters)
At first glance, Digital Sportsman might seem like one more tech platform in a world already crowded with apps. But it’s far more than that. For guides and captains, it’s a tool to reduce back-office headaches and get them back on the water. For anglers, especially those new to the sport or vacationers looking to book a trip, it makes getting out on a boat as easy as clicking “Book Now.”
“Too often, guides are stuck fielding calls or managing their schedules when they should be fishing,” Hamilton explains. “We give them the tools to automate the business side—online booking, email reminders, even AI assistance—so they can focus on what they do best.”
Tailored specifically for guides and outfitters, Digital Sportsman’s upcoming platform, Ahoy, introduces a user-friendly booking system that replaces the old “Contact Us” online forms with seamless scheduling options, saving time and simplifying logistics. “If you want to make a booking in the middle of the night, you can just click ‘Book Now’ rather than fill out a form or wait until the following day to make a phone call,” Hamilton points out.
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Keeping Tradition Alive Innovatively
Fishing and boating are built on tradition, and Hamilton is deeply aware of the tension between honoring those roots and introducing innovation. “We’re not here to replace the way things have always been done,” he says. “We’re here to support it—to bridge the gap between generations.”
As part of that objective, Digital Sportsman has introduced a new Partner Program to keep money in the community by connecting outfitters, retailers, tour guides, property managers, and other outdoor professionals with consumers. The program offers a no-cost opportunity for partners to monetize their network or donate proceeds back to guides or participating charities, increasing loyalty and exposure for their own brand. Those who join receive a personalized brand page on the Digital Sportsman Marketplace showcasing their own curated selection of outdoor experiences and earn commission directly from Digital Sportsman on net revenue generated through their referrals.
AI Tools: Voice Booking, Reminders, Forecasts, Inbox Help
The company is also building AI-powered tools to streamline operations. A virtual assistant for charter captains can respond to voice prompts—“Book me for next Thursday,” for instance—and instantly handle the rest, from scheduling to confirmation emails. Another upcoming feature predicts weekly bookings and revenue, giving outfitters new ways to plan and grow.
And it’s not all backend tech. After receiving overwhelmingly positive feedback from female captains, the company is rolling out Digital Sportswoman, a toggle in the app that changes branding to better resonate with women anglers. “We want everyone to feel seen and supported on the water,” Hamilton says.
Built by Family, Powered by Community
Hamilton didn’t build Digital Sportsman alone. His three sons, Devin, Trevor, and Ethan, have been along for the ride, and that family-first approach has shaped the company’s culture from day one. It’s also informed their grassroots strategy—connecting with local fishing communities through events, open discussions, and shared stories.
“We’ve hosted events with local guides, retailers, and influencers like Danny Pruitt of Reel American Road Trip and Captain Danny Allen from the fishing show Beyond the Surface,” says Michelle Faul, Digital Sportsman’s head of marketing. “It’s about being present and proving that technology can be a fabric of the community, not a threat to it.”
In that vein, Digital Sportsman has made it a mission to listen first, build second. “Many of the existing platforms weren’t made with guides in mind,” Hamilton says. “We sat down, asked what they needed, and built from there.”
That includes offering full functionality from mobile devices—a feature often overlooked in legacy platforms. Whether it’s managing bookings, sending invoices, or communicating with clients, guides can now do it all from the dock, without having to return home or to the office to their computer.
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Roadmap: 10 AI Features, City-by-City Rollout
With 10 AI-powered features in development and a growing network of strategic partnerships—including some created to help elevate women in fishing—the Digital Sportsman team isn’t slowing down. Hamilton hints at several upcoming announcements and expanded tools that will help guides grow their businesses, connect with their communities, and get more people outside.
“We’re just getting started,” he says. “This is a grassroots effort. Like Uber, we’re focusing on specific markets, building trust, and creating something truly useful. Our goal isn’t just to digitize the outdoors—it’s to preserve what’s great about it and make it more accessible for the next generation.”
For a company born in the backwaters of North Carolina and built by a father and his sons, that mission feels right at home.
-by Lori Capullo
FAQ - People Also Ask
What is Digital Sportsman?
A guide-first platform that simplifies booking, communication, and growth for fishing guides and outfitters, while making it easy for anglers to book trips.How does Ahoy help?
It replaces slow contact forms with real-time scheduling so customers can click Book Now anytime.What AI features are coming?
Voice booking, automated reminders, smart inbox help, and weekly booking/revenue forecasts.What is Digital Sportswoman?
An optional branding toggle designed with feedback from female captains to help more women feel represented.How does the Partner Program work?
Partners get a branded page to curate experiences; they earn commissions on net revenue or donate proceeds to guides/charities.
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