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

Framework

March 10, 2026

The PE Operating Partner's AI Playbook

The complete playbook for PE operating partners looking to drive AI-powered value creation across their portfolio. Strategy, execution, and measurement.

Azure AICopilot StudioMicrosoft Fabric+2

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 18 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

AI Agent ROI: Real Numbers from Real Deployments

Data

August 20, 2025

AI Agent ROI: Real Numbers from Real Deployments

Forget the hype. Here are actual ROI numbers from 8 AI agent deployments across PE portfolio companies.

Copilot StudioPower AutomateAzure OpenAI+1

Building a Multi-Tenant SaaS Portal for PE Firms

Case Study

June 10, 2025

Building a Multi-Tenant SaaS Portal for PE Firms

How I built The Hub — a multi-tenant client portal that gives PE operating partners real-time visibility into portfolio technology health.

Microsoft Entra IDAzurePower BI Embedded+1

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

How I Built an AI Leadership Simulation Game

Case Study

November 22, 2024

How I Built an AI Leadership Simulation Game

The story behind theboardiswatching.com — an interactive AI transformation simulator where you play the CEO navigating disruption.

Azure OpenAITypeScriptGitHub Copilot+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 $600B 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 software as SasbenJr, 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 diligence across PE-backed acquisitions, the patterns 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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