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Strategy

Browse all articles in the Strategy category

The Likability Trap: AI Benchmarks Reward Charm, Not Value
Strategy

The Likability Trap: AI Benchmarks Reward Charm, Not Value

The most popular AI benchmarks measure which model people like most, not which one is most useful. This has created a sycophancy epidemic, broken evaluation incentives, and a generation of teams picking AI tools the way we pick Instagram filters. Here's what actually matters, and how I use multiple models to get real work done.

6 min read
Your AI Is an Ivy League Grad With No Textbook
Strategy

Your AI Is an Ivy League Grad With No Textbook

AI is the smartest hire you've ever made. It's also the most clueless about your business. Here's why your data isn't ready, what happens when you ignore that, and how to fix it.

4 min read
The Fabric of Work Has Changed. Most Companies Haven't Noticed.
Strategy

The Fabric of Work Has Changed. Most Companies Haven't Noticed.

Your customers are becoming AI agents, your teams need to become architects, and your internal workflows are now your most defensible IP. Three structural shifts every leader needs to internalize.

5 min read
The Real AI Risk Isn't Incremental Progress. It's a Step Function.
Strategy

The Real AI Risk Isn't Incremental Progress. It's a Step Function.

Jason Lemkin's warning about 'jaspering' reveals why workflow integration isn't a moat when AI models make a step function leap. The real risk: leaders who don't use AI daily can't see the existential threat coming.

5 min read
The System Prompt Revolution
Strategy

The System Prompt Revolution

Why exposing system prompts to users isn't just good UX—it's a competitive advantage that turns your most advanced customers into your R&D team.

4 min read
Featured
Context Rot: A Contrarian Take on the Million-Token Race
strategy

Context Rot: A Contrarian Take on the Million-Token Race

LLM performance degrades as context grows — even on simple tasks. The million-token race might be solving the wrong problem entirely.

5 min read
MIT's AI Report: What the Headlines Got Wrong
strategy

MIT's AI Report: What the Headlines Got Wrong

95% of enterprise AI investments are 'failing'? MIT's 2025 report reveals a growing divide between flashy demos and real ROI.

4 min read
Lead, Follow, or GTFO: The AI-Native Mandate
Strategy

Lead, Follow, or GTFO: The AI-Native Mandate

The 'lead, follow, or get out of the way' framework isn't just a suggestion for AI-native teams—it's an existential mandate.

4 min read
Evolve or Die: Why Every Startup Must Become AI-First
Strategy

Evolve or Die: Why Every Startup Must Become AI-First

Evolving to become AI-first is crucial for startups to stay competitive and innovative in a rapidly changing tech landscape.

3 min read
Vibe Coding Isn't About Code—It's About Solving Problems
Strategy

Vibe Coding Isn't About Code—It's About Solving Problems

Demystifying 'vibe coding' for leaders: why it's the most important trend in building, and what it means for the future of software.

2 min read
Unlocking Executive Potential: Using ChatGPT for your 1 on 1
Strategy

Unlocking Executive Potential: Using ChatGPT for your 1 on 1

Explore how tech executives can leverage ChatGPT to gain clarity and focused decision-making.

4 min read