AI INSIGHTS

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Cutting-edge perspectives on artificial intelligence and automation

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Is It an AI Agent or a ChatGPT Wrapper? One Test, and What It Takes to Build on the Right Side of the Line
October 12, 2026
AI AgentsCustom AI

Is It an AI Agent or a ChatGPT Wrapper? One Test, and What It Takes to Build on the Right Side of the Line

Most AI products are a UI on top of a frontier model, dressed up as an agent. Here's the test: if the model provider adds this feature next quarter, does your product still exist? What I told Sam Dey on DataScienceWithSam about building things a business can run on every day.

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Why Your Team Won't Update the CRM (and the Step to Remove Instead of Reminding Them)
September 29, 2026
CRMWorkflow Automation

Why Your Team Won't Update the CRM (and the Step to Remove Instead of Reminding Them)

One person told me their team relies on the CRM for everything. Another said phone messages still get written on sticky notes. Both are true. Before you send another "please update the CRM" reminder, ask whether the update is recording or copying.

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You Don't Replace, You Wrap: What We Showed Denver Business Owners at Colorado Startup Week 2026
September 24, 2026
Colorado Startup WeekAI adoption

You Don't Replace, You Wrap: What We Showed Denver Business Owners at Colorado Startup Week 2026

On September 17, Joey and I stood on the Grand Stair at Denver Place and showed a room of business owners how we actually run our companies with AI. Two live demos, one assignment, and a first look at HumCrew.

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The Four Cash Questions No Owner Can Answer Without Opening Something (and the AI CFO Agent That Answers Them)
September 15, 2026
AI CFOFinance Automation

The Four Cash Questions No Owner Can Answer Without Opening Something (and the AI CFO Agent That Answers Them)

What's coming in this week, what's going out, what's owed to you, what you owe. Could you answer that right now, out loud, without opening anything? Most owners can't. Here's how I run it with an agent connected to my bank, Stripe and QuickBooks.

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AI for the Business You Already Have: How to Add AI Without a Migration
September 1, 2026
AI StrategySmall Business

AI for the Business You Already Have: How to Add AI Without a Migration

Every week I talk to an owner who wants AI and is dreading the same conversation. They think saying yes means tearing out systems their team just finished learning. It doesn't. AI doesn't replace your stack. It wraps around it.

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Build vs Buy Software in 2026: The Math Changed and Most Companies Haven't Redone It
August 19, 2026
Build vs BuyCustom Software

Build vs Buy Software in 2026: The Math Changed and Most Companies Haven't Redone It

Three buyers asked me the same question this month: can you build this so we own it? Five years ago I'd have talked them out of it. Here's what changed, a five-minute test for your next renewal, and the three kinds of software I'd renew every time.

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AI Automation Pricing: How Much Does It Cost in 2026?
August 7, 2026
AI Automation CostPricing Guide

AI Automation Pricing: How Much Does It Cost in 2026?

Compare AI automation pricing for chatbots, voice agents, customer support automation, workflow automation, and private ChatGPT. See realistic 2026 setup fees, monthly ranges, vendor questions, and budget factors before you buy.

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Adopting AI Faster Than We Can Master It: Why the Judgment Is the Hard Part
August 4, 2026
AI AdoptionSmall Business

Adopting AI Faster Than We Can Master It: Why the Judgment Is the Hard Part

66% of small and midsize businesses now use AI. 70% say they need more training to use it well. The tools got easy. The judgment didn't. A client story about an assistant that went looking for problems, and a twenty-minute software-bill exercise.

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Where to Start With AI in Your Business: Don't Start With a Tool
July 21, 2026
AI StrategySmall Business

Where to Start With AI in Your Business: Don't Start With a Tool

The companies that get burned on AI pick a technology, then hunt for a problem. The companies that win start with the pain. Two field examples, a one-hour exercise, and the three tests for an automatable task.

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Blog | AI Automation Insights & Best Practices | Humming Agent