INSIGHTS

Thinking out loud.

Perspectives on AI strategy, implementation, and leadership. Written for the people making the decisions.

LONG READ·STRATEGY· 11 min read

AI Governance Mid-Market: How to Protect the Business Without Slowing It Down

Most mid-market companies treat AI governance as a compliance layer. The fastest adopters embed it into workflows and use it to move faster with confidence.

Issy · May 29, 2026

Q&A·STRATEGY· 9 min read

Why Value Pricing AI Consulting Matters More Than You Think

Value pricing in AI consulting aligns incentives: builders own outcomes, clients pay for results. Why developers beat traditional consultants at this game.

Issy · May 29, 2026

LONG READ·STRATEGY· 11 min read

AI Consulting for Mid-Market Companies: What to Look For Before You Sign

91% of mid-market companies use AI, but 70% need outside help to maximize value. Here's the 5-point due-diligence checklist before signing any engagement.

Issy · May 24, 2026

LONG READ·STRATEGY· 15 min read

AI ROI for Mid-Market: Separating Real Returns from Consultant Theater

AI ROI for mid-market needs workflow redesign and error accounting. 56% see zero return. Here's the formula separating real outcomes from theater.

Issy · May 18, 2026

LONG READ·STRATEGY· 9 min read

5-Day AI Sprint vs. 90-Day AI Pilot: How Mid-Market CEOs Should Choose

Most mid-market companies mismatch readiness to format. A 5-day AI sprint surfaces ambiguity; a 90-day pilot proves capability. Here is how to choose.

Issy · May 16, 2026

Q&A·STRATEGY· 10 min read

AI Alignment for Leadership Teams: A Practical Governance Framework for Mid-Market CEOs

AI alignment for leadership teams is a governance discipline for mid-market CEOs. Learn the RICE principles and NIST framework that prevent costly missteps.

Issy · May 13, 2026

LONG READ·AI STRATEGY· 14 min read

Claude vs GPT-4o for Enterprise Teams: A CEO's Framework for Switching or Staying

Most enterprise teams evaluate AI platforms like consumer software. A CEO's decision framework for staying with Claude, switching to GPT-4o, or running a bounded pilot.

Aspiro AI Studio · May 8, 2026

LONG READ·STRATEGY· 6 min read

The Reason Manufacturers Can't Stop Inventory Bleed Has Nothing to Do with Their ERP

Inventory bleed persists despite a working ERP because ERPs record the past. Here's how predictive AI reads the future and what that means for your margins.

Issy · Apr 20, 2026

LONG READ·STRATEGY· 1 min read

Running a Business With AI Agents: Real Lessons From Q1

After 90 days of agentic operations, we share what worked, what didn't, and the real tradeoffs of building an AI-first venture studio.

Issy · Mar 29, 2026

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