Thinking

Blog

Lessons from 20 years in the trenches — building systems, scaling companies, and figuring out what actually works.

AI & StrategyAI & LeadershipAI & SecurityAI & ArchitectureAI & OperationsAI & Systems ArchitectureAI & EngineeringAI & MarketsSales & AutomationCRM & AutomationAI & InfrastructureAI & AutomationMarkets & AIERP & SystemsStrategyeCommerceAccounting & FinanceData & AnalyticsCybersecurityOperationsLeadership
The Iceberg Below the Code: Everyone Can Write Code Now. Almost Nobody Knows What to Write.
March 2026·AI & Strategy·10 min

The Iceberg Below the Code: Everyone Can Write Code Now. Almost Nobody Knows What to Write.

90% of CEOs See No AI Productivity Gains. That Is a Choice.
March 2026·AI & Leadership·9 min

90% of CEOs See No AI Productivity Gains. That Is a Choice.

Microsoft Just Put an Autonomous AI Agent in Every Office. Nobody Asked If It's Safe.
March 2026·AI & Security·11 min

Microsoft Just Put an Autonomous AI Agent in Every Office. Nobody Asked If It's Safe.

Your AI Is Lying to You. And Math Says It Always Will.
March 2026·AI & Architecture·9 min

Your AI Is Lying to You. And Math Says It Always Will.

The Operator's Playbook: Deploying an AI Agent Workforce That Actually Works
March 2026·AI & Operations·12 min

The Operator's Playbook: Deploying an AI Agent Workforce That Actually Works

Observability: The Practice That Makes Everything Else Survivable
March 2026·AI & Operations·9 min

Observability: The Practice That Makes Everything Else Survivable

Trust Architecture: Designing AI Systems That Assume Every Agent Lies
March 2026·AI & Security·10 min

Trust Architecture: Designing AI Systems That Assume Every Agent Lies

The Graduation Thesis: Why Your Best AI Agents Should Build Themselves Out of a Job
March 2026·AI & Architecture·11 min

The Graduation Thesis: Why Your Best AI Agents Should Build Themselves Out of a Job

Your AI Agents Will Fail the Same Way Databases Did in 1978
March 2026·AI & Systems Architecture·14 min

Your AI Agents Will Fail the Same Way Databases Did in 1978

Software Entropy Is Inevitable. Rebuilding Is Now Free.
March 2026·AI & Engineering·10 min

Software Entropy Is Inevitable. Rebuilding Is Now Free.

The Byzantine Generals Problem Is Solved. You Just Won't Like the Answer.
March 2026·AI & Architecture·11 min

The Byzantine Generals Problem Is Solved. You Just Won't Like the Answer.

AI Companies Will Fail. Your AI Agents Won't.
March 2026·AI & Strategy·9 min

AI Companies Will Fail. Your AI Agents Won't.

Jack Dorsey Cut 4,000 Jobs. Developer Employment Went Up. Both Are True.
March 2026·AI & Markets·10 min

Jack Dorsey Cut 4,000 Jobs. Developer Employment Went Up. Both Are True.

The Dopamine Call: Why Your Rep Should Ring the Moment the Package Lands
March 2026·Sales & Automation·8 min

The Dopamine Call: Why Your Rep Should Ring the Moment the Package Lands

Every Missed Call Is a Missed Sale: How to Auto-Log VoIP Calls to Your CRM
March 2026·CRM & Automation·9 min

Every Missed Call Is a Missed Sale: How to Auto-Log VoIP Calls to Your CRM

The iPhone Moment: Why Local AI Agents Are the Biggest Leap Since Smartphones
March 2026·AI & Strategy·12 min

The iPhone Moment: Why Local AI Agents Are the Biggest Leap Since Smartphones

Secrets Management for Autonomous Agents: The Attack Surface Nobody Talks About
March 2026·AI & Security·10 min

Secrets Management for Autonomous Agents: The Attack Surface Nobody Talks About

What a Full AI Agent Team Looks Like in a Real Company
March 2026·AI & Operations·12 min

What a Full AI Agent Team Looks Like in a Real Company

Every AI Has a Weakness. Here's What Happens When You Stop Choosing.
March 2026·AI & Strategy·14 min

Every AI Has a Weakness. Here's What Happens When You Stop Choosing.

Local AI Models vs Cloud APIs: The Math Nobody Shows You
March 2026·AI & Infrastructure·11 min

Local AI Models vs Cloud APIs: The Math Nobody Shows You

The Layered Model Architecture: Why One AI Model Is Never Enough
March 2026·AI & Automation·9 min

The Layered Model Architecture: Why One AI Model Is Never Enough

Token Optimization for AI Agents: A Practical Guide That Saved Us 70%
March 2026·AI & Automation·10 min

Token Optimization for AI Agents: A Practical Guide That Saved Us 70%

Memory Optimization for Local AI Agents: A Six-Layer Architecture That Actually Works
March 2026·AI & Automation·12 min

Memory Optimization for Local AI Agents: A Six-Layer Architecture That Actually Works

The SaaS Apocalypse Is Here. AI Coding Did It.
March 2026·Markets & AI·9 min

The SaaS Apocalypse Is Here. AI Coding Did It.

Is AI Safe for Business? You Are Asking the Wrong Question.
March 2026·AI & Strategy·7 min

Is AI Safe for Business? You Are Asking the Wrong Question.

Why Milwaukee Businesses Keep Getting ERP Wrong
March 2026·ERP & Systems·7 min

Why Milwaukee Businesses Keep Getting ERP Wrong

The Case for a Fractional CTO in Milwaukee
March 2026·Strategy·6 min

The Case for a Fractional CTO in Milwaukee

eCommerce in Milwaukee: Why Your Online Store Is Underperforming
March 2026·eCommerce·7 min

eCommerce in Milwaukee: Why Your Online Store Is Underperforming

AI Agents Are Not Chatbots: Building Systems That Actually Work
March 2026·AI & Automation·8 min

AI Agents Are Not Chatbots: Building Systems That Actually Work

The ERP Trap: Why Small Businesses Overpay and Underdeliver
March 2026·ERP & Systems·6 min

The ERP Trap: Why Small Businesses Overpay and Underdeliver

The eBay Profit Illusion: What Your Reports Are Not Telling You
March 2026·Accounting & Finance·10 min

The eBay Profit Illusion: What Your Reports Are Not Telling You

What CEOs Get Wrong About AI in 2026
February 2026·AI & Leadership·8 min

What CEOs Get Wrong About AI in 2026

The Vendor Trap: Why Your Tech Stack Is Costing You More Than You Think
January 2026·Strategy·9 min

The Vendor Trap: Why Your Tech Stack Is Costing You More Than You Think

Stop Building Dashboards Nobody Looks At
December 2025·Data & Analytics·8 min

Stop Building Dashboards Nobody Looks At

Cybersecurity Is Not an IT Problem. It Is a Business Survival Problem.
November 2025·Cybersecurity·7 min

Cybersecurity Is Not an IT Problem. It Is a Business Survival Problem.

The Multi-Channel Playbook: How to Sell Everywhere Without Losing Your Mind
October 2025·eCommerce·10 min

The Multi-Channel Playbook: How to Sell Everywhere Without Losing Your Mind

AI Will Not Replace You. A Person Using AI Will.
September 2025·AI & Automation·8 min

AI Will Not Replace You. A Person Using AI Will.

Why Your ERP Migration Failed (And How to Make the Next One Stick)
August 2025·ERP & Systems·9 min

Why Your ERP Migration Failed (And How to Make the Next One Stick)

Everyone Says Data-Driven. Nobody Means It.
July 2025·Strategy·7 min

Everyone Says Data-Driven. Nobody Means It.

The Ops Person Problem: Why Your Most Important Hire Does Not Exist Yet
June 2025·Operations·8 min

The Ops Person Problem: Why Your Most Important Hire Does Not Exist Yet

What I Learned Scaling a Company from $1.4M to $14M
May 2025·Leadership·12 min

What I Learned Scaling a Company from $1.4M to $14M