At 11:59, we're focused on helping mid-market companies navigate the complexity of AI adoption with clarity, speed, and confidence. Today, we're excited to announce a new resource designed to further that mission — a LinkedIn newsletter written by our founder and CEO, Alex Castro, called The Mid-Market AI Navigator.

This newsletter is designed specifically for executives, operators, and change-makers in mid-sized organizations who are looking to transition from AI curiosity to AI execution. Each issue is practical, strategic, and written to help you accelerate transformation without unnecessary risk or wasted effort.

Why a Newsletter for Mid-Market AI?

AI isn't just for tech giants anymore, but the path to meaningful adoption looks different for mid-market companies. These organizations often face unique constraints, including limited resources, leaner teams, and increased pressure to demonstrate short-term ROI. That's where The Mid-Market AI Navigator comes in.

Rather than chasing trends, the newsletter focuses on what works in the real world, offering proven frameworks and actionable insights that help companies make better decisions more quickly.

A Preview of the First Two Issues

Issue #1: AI That Grows With You: Why Mid-Market Success Starts with a Keyhole Strategy

In the debut issue, Alex introduces the concept of the Keyhole Strategy — a focused, entry-point approach to AI implementation that drives measurable results without overextending your organization. Rather than going "all in" too soon, he advises starting with narrow, high-impact use cases that provide quick wins and valuable internal learning.

"The real opportunity isn't chasing AI — it's leveraging it to accelerate what your business already does best."

Issue #2: The Hidden Cost of AI Hesitation

In this follow-up, Alex tackles a common and costly pitfall: hesitation. For many mid-market leaders, the instinct to "wait and see" feels safe, but it often leads to lost time, talent, and momentum. This issue breaks down the actual opportunity cost of inaction and outlines how businesses can build momentum through focused experimentation.

"Waiting is no longer neutral. It's a strategic disadvantage."

Subscribe and Start Navigating AI with Confidence

Whether you're just beginning your AI journey or working to scale early efforts, The Mid-Market AI Navigator offers guidance that's grounded in experience and optimized for execution. Each issue contains tools, language, and clarity to empower you to make AI a lever, not a landmine.

➡️ Subscribe to the newsletter on LinkedIn
➡️ Follow Alex Castro on LinkedIn for more insights and conversations
➡️ Learn more about how 11:59 makes companies AI-enabled in weeks, not months. 

Let's start with a small, scalable project that can be rolled out quickly and safely, with measurable outcomes.