No Assholes, Just Anglers: How David Lord Is Building a Tech Legacy for Outdoor Guides

When David Lord decided to launch his next startup, he had just one rule: no assholes allowed.

After decades of building and selling companies—from pioneering e-commerce with ToySmart to revolutionizing online ticketing and educational gaming—Lord had earned every accolade from Microsoft Innovator of the Year to Ernst & Young Entrepreneur of the Year. But none of it mattered anymore. He’d built his fortune. Now he wanted to build something that mattered.

“I love fishing. I love the outdoors. I love guides,” he said. “And I hate assholes. So I decided to fund a company myself and build something for the people I love—with none of the people I don’t.”

That company is Guidesly, a platform that’s quietly transforming the guiding industry—one trip, one photo, and one smart piece of software at a time.

From the Boardroom to the Boat Ramp

Lord’s career began far from the water. A Bostonian by birth and an accountant by training, he worked his way up to CFO before catching the entrepreneurial bug during the early internet boom. He founded ToySmart in 1996, sold it to Disney, and kept building from there—through online ticketing, gaming, and tech turnarounds that generated hundreds of millions in revenue.

But somewhere between the boardrooms and business plans, he found himself drawn back to the stream. A lifelong fly fisherman, Lord started wondering why so many guides—experts on the water—struggled to run their businesses off of it.

“I’d fish with these incredible guides,” he recalled. “And over dinner, they’d ask, ‘Hey, you’re a tech guy—why doesn’t my website work? Why am I paying someone half my revenue to send me customers?’ I knew the problem. I just couldn’t solve it—yet.”

Building a Platform for the People Who Make It Happen

Guidesly was born out of that frustration. It’s the first vertical SaaS platform built for outdoor guides, outfitters, and charter captains—helping them do everything from booking and billing to marketing and client communication.

In Lord’s words: “They do the fishing. We do everything else.”

For many guides, that means no more wrestling with websites or trying to figure out search algorithms. Guidesly manages all of it—CRM, accounting, Google reviews, local search, and customer follow-ups—so that guides can focus on the work they love most: being outdoors with clients.

It’s a distinctly blue-collar approach to technology. “If our code isn’t working, no one’s going home,” Lord said. “The difference between a good day and a bad day for our guides might mean food on the table. Everything matters.”

That philosophy led to a company culture focused not just on customer service, but what Lord calls “Guide Success.” The team’s goal isn’t to fix problems after they happen—it’s to build best practices that make guides successful from the start.

“We changed the name from customer service to Guide Success because that’s the job,” he said. “We’re here to make them successful.”

Meet JackAI: The Smartest Deckhand in the Business

The most innovative piece of Guidesly’s toolkit might be JackAI—an AI assistant that handles the parts of the job most guides simply don’t have time for.

When a guide finishes a trip, JackAI automatically processes every photo taken that day, identifies species and locations, and drafts fishing reports. It posts to social media, updates Google Business pages, and even emails the guest a link to their trip gallery—all without the guide lifting a finger.

“Every fish becomes an asset,” Lord explained. “We tell our guides—take a picture of everything. You don’t have to edit or post it; Jack does that. That photo might be the one someone’s searching for next week.”

The results speak for themselves. Early beta guides saw their traffic double year-over-year, with open rates over 55% and click-throughs around 10%.

Guidesly’s latest addition, JackBot, takes it one step further—a voice and text AI assistant that answers calls or chats when a guide is out on the water. It speaks in the guide’s voice, can handle common FAQs, and even books trips in real time.

“Almost 30% of searches now are people saying, ‘fishing charters near me,’” Lord said. “They’re on their phone, they see someone fishing, and they just want to call. JackBot lets them do that—and the guide never misses an opportunity.”

Family, Legacy, and Leadership

Lord isn’t building this company alone. His daughter serves as Guidesly’s Chief Product Officer—his “right-hand person.”

“It’s one of my proudest things,” he said. “The hardest part is learning to stand beside her, not in front of her—to stop being the coach and start being the bystander cheering her on.”

His leadership philosophy mirrors his company’s mission: leave something lasting. “I just want to build a great company and leave a legacy,” he said. “For the industry. For my team. For my daughter.”

A New Era for RecTech

As Lord and LandTrust’s Nic De Castro discussed, the two companies share a similar mission: using technology to make people’s time outdoors more effective and meaningful.

“Our customers are blue collar,” De Castro noted. “They’ve got jobs, families, responsibilities—and not enough days outdoors. When they do get that time, it needs to count.”

Lord agreed. “That’s what Guidesly does,” he said. “We help guides save time and make money so their clients can have better experiences on the water. It’s all connected.”

Both leaders see RecTech—the emerging category of recreation technology—as a growing force. While traditional venture capital often overlooks outdoor businesses, both LandTrust and Guidesly are proving there’s a massive market in connecting passionate people to the land and water they love.

“I think AI will be the reason this industry breaks through,” Lord said. “Legacy companies are slow to adapt—but passion-driven ones like ours? We’re just getting started.”

Passion Over Profit

After a career spent building, scaling, and selling companies, David Lord has finally found his sweet spot: creating something that blends his professional expertise with his personal passion.

“This isn’t just another startup,” he said. “It’s a community, a legacy, and a way to give back to the people who make the outdoors what it is.”

And for the guides out there—those who wake up before dawn, who work weekends, who live by the tides and the seasons—Guidesly isn’t just software. It’s a partner that helps them do what they do best.

No venture capital jargon. No Silicon Valley fluff.
Just anglers helping anglers—and building something that lasts.

Learn more about Guidesly and its tools for outdoor guides at Guidesly.com or visit the new pro platform at GuideslyPro.com.

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