Dr. Ken Knapton is the Chief Information Officer at Win Brands, the parent company of Costa Vida Fresh Mexican Grill and FatCats Entertainment. With more than 30 years of experience in technology strategy and digital transformation, Ken was hired to bring together two very different brands under a single IT vision. Costa Vida operates nearly 100 fast-casual Mexican restaurants, while FatCats runs large family entertainment centers that include bowling, arcades, mini golf, and cinemas.
At Win Brands, Ken’s goal is to align the technology infrastructure across both companies to create operational efficiency and shared services while preserving what makes each brand unique. His leadership focuses on connecting systems, improving data management, and implementing innovation that drives measurable growth across the organization.
Here’s a glimpse of what you’ll learn:
- How Win Brands connects Costa Vida and FatCats under one IT strategy
- Why identifying similarities between distinct businesses creates efficiency
- How consolidating networks and MSPs builds stronger operational control
- The importance of defining, measuring, and managing technical debt
- How clean, unified data supports successful AI implementation
- What “tech debt leverage” means for executive decision-making
- Why machine bias requires human oversight in AI-driven environments
- How to turn IT into a proactive, strategic part of business leadership
In this episode…
Dr. Ken Knapton explains what it takes to merge the IT environments of two completely different businesses, Costa Vida and FatCats Entertainment, under one parent organization, Win Brands. Each company had its own systems, vendors, and operational culture, which made integration complex. Ken began by identifying shared priorities such as Microsoft 365 consolidation and finance alignment. “They each had different MSPs,” he recalls. “So we chose one and started migrating everything to a shared network.” His goal was to eliminate duplication, standardize systems, and create a stronger foundation for both brands to grow together.
One of the most valuable lessons in the conversation is Ken’s approach to technical debt, the silent barrier that limits innovation. He defines it as anything within your systems that prevents progress toward business goals. Drawing on insights from his book Unveiling Tech Debt, Ken introduces a structured way to measure and manage it. “You can’t improve what you can’t measure,” he explains. “So I created a model that looks at how stable, sustainable, and supportable each technology is.” This metric-driven approach helps business leaders quantify their risks and make informed decisions about modernization.
Ken also explores how AI and data quality are deeply connected. “One of the biggest challenges with implementing AI is that most companies don’t have clean data,” he says. Poor data quality often becomes a hidden form of technical debt, undermining the reliability of insights and predictions. For Win Brands, AI tools are being used for operations such as staff scheduling, order accuracy, and customer experience analytics. Even so, Ken emphasizes that AI should always complement human judgment. “Everything that comes out of AI still has to pass the sniff test,” he says. “We should not make business decisions solely based on what AI tells us.”
The episode ends with practical guidance for IT leaders. Ken encourages them to document their systems, measure their risks, and remember that technology is only as effective as the people who use it. His work at Win Brands demonstrates how two vastly different companies can share one digital strategy built on structure, clarity, and accountability.
Resources mentioned in this episode:
Matthew Connor on LinkedIn
CyberLynx Website
Dr. Ken Knapton on LinkedIn
FatCats Entertainment Website
Costa Vida Mexican Grill Website
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