Blog

Insights from 20+ years in enterprise architecture, 75+ M&A transactions, and a growing obsession with AI agents. Microsoft tech, PE value creation, and building in public.

The Journey

Two years of frameworks, tools, and lessons — mapped chronologically

March 8, 2024

All Posts

How I Built an AI Leadership Simulation Game

Case Study

February 18, 2026

How I Built an AI Leadership Simulation Game

The story behind theboardiswatching.com — an interactive AI transformation simulator where you navigate disruption.

Azure OpenAITypeScriptGitHub Copilot+1

500+ GenAI Case Studies: What Companies Actually Ship

Research

January 22, 2026

500+ GenAI Case Studies: What Companies Actually Ship

I curated 500+ real-world GenAI deployments across industries. The patterns are surprising — and most have nothing to do with chatbots.

Azure AICopilotMicrosoft Fabric+1

From Consultant to Builder: My Open Source Journey

Personal

December 14, 2025

From Consultant to Builder: My Open Source Journey

How shipping 15+ open source projects in 2 months changed the way I think about consulting, credibility, and building in public.

GitHubVS CodeGitHub Copilot+1

Agentic Design Patterns Every Developer Should Know

Technical

October 8, 2025

Agentic Design Patterns Every Developer Should Know

The patterns behind effective AI agents are not new — they are borrowed from distributed systems, game theory, and workflow engines. Here are the ones that matter.

Azure AIGitHub CopilotSemantic Kernel+1

Data

August 20, 2025

AI Agent ROI: What the Data Actually Shows

Everyone claims AI agents deliver ROI. But what do the real numbers look like? I dug into the research, the case studies, and my own experience to find out.

CopilotPower AutomateAzure AI+1

What I Would Build: A Multi-Tenant Portal for PE Technology Oversight

Thought Leadership

June 10, 2025

What I Would Build: A Multi-Tenant Portal for PE Technology Oversight

What would a purpose-built technology oversight portal for PE operating partners look like? Here is how I would approach it — the architecture, the trade-offs, and the decisions that matter.

Microsoft Entra IDAzure

Playbook

March 28, 2025

The Fractional CTO Playbook for PE-Backed Companies

The 90-day playbook I run at every new PE portfolio company. Discovery, stabilization, and value creation — in that order.

AzureMicrosoft 365Microsoft Fabric+1

The SaaS Displacement Calculator: Quantifying the Reset

Product

January 15, 2025

The SaaS Displacement Calculator: Quantifying the Reset

I built an interactive tool that shows companies exactly how much they could save by replacing legacy SaaS with AI-powered alternatives.

Power BIAzureCopilot Studio+1

From 150K Subscribers to Enterprise Exit: The Hupit Gaming Story

Case Study

December 5, 2024

From 150K Subscribers to Enterprise Exit: The Hupit Gaming Story

I co-founded Hupit Gaming as a hobby YouTube channel, grew it to 150K+ subscribers across combined channels, and sold it to an enterprise company. Here is how it happened.

Azure Media ServicesMicrosoft StreamGitHub+1

Why Every CTO Should Understand Blockchain Accounting

Thought Leadership

October 10, 2024

Why Every CTO Should Understand Blockchain Accounting

Blockchain is not just for crypto. It is transforming how enterprises handle audit trails, reconciliation, and financial transparency. Here is what CTOs need to know.

Microsoft FabricPower BIAzure+1

Framework

September 5, 2024

AI Readiness Assessment: A Scoring Framework for PE Portfolios

A structured framework for evaluating AI readiness across PE portfolio companies. Six dimensions, weighted scoring, and a clear action plan.

Azure AICopilotMicrosoft Fabric+1

Co-Authoring the Bitcoin Private Whitepaper: Lessons from the Crypto Frontier

Case Study

August 15, 2024

Co-Authoring the Bitcoin Private Whitepaper: Lessons from the Crypto Frontier

In 2018, I co-authored the Bitcoin Private (BTCP) whitepaper — a first-of-its-kind fork-merge of Bitcoin and Zclassic. Here is what that experience taught me about blockchain, privacy, and building in public.

Azure BlockchainAzure Confidential ComputingGitHub+1

The SaaSpocalypse: Why Per-Seat SaaS Is Dying

Thought Leadership

July 12, 2024

The SaaSpocalypse: Why Per-Seat SaaS Is Dying

The SaaS market is about to get disrupted by the same forces that built it. AI agents are replacing seats—and the economics are brutal.

Power PlatformCopilot StudioAzure AI+1

From BBS to Boardroom: What the Cracking Scene Taught Me About Enterprise IT

Personal

May 22, 2024

From BBS to Boardroom: What the Cracking Scene Taught Me About Enterprise IT

I ran a BBS at 14, cracked, I mean, reverse engineered, software, and trained newcomers in Mexelite. Those skills became the foundation of a 20-year enterprise IT career.

Windows NTMicrosoft DefenderAzure Security+1

What 75+ M&A Transactions Taught Me About Technology Debt

M&A

April 18, 2024

What 75+ M&A Transactions Taught Me About Technology Debt

After two decades of transformation for businesses, diligence and execution across PE-backed acquisitions, generate similar patterns that are unmistakable. Here is what I learned about the real cost of technology debt.

Azure DevOpsMicrosoft 365Azure Migrate+1

40 Years of Computing: From Apple IIe to AI Agents

Personal

March 8, 2024

40 Years of Computing: From Apple IIe to AI Agents

My tech journey started in 1984 with an Apple IIe and BASIC. Four decades later, I am building AI agents. Here is every inflection point along the way.

Windows NTMicrosoft 365Azure+1

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