AI
19 posts
MAY 21, 2026
The cheapest way to fix an AI project is before it starts. The most expensive way is after it ships. The honest version of "de-risk your first AI project" is a list of seven things to lock down…
MAY 18, 2026
Vendor quotes for SMB AI projects routinely miss 20 to 50% of the actual cost. The missing pieces aren't hidden in the sense of dishonest. They're missing because the quote was scoped to what the…
MAY 16, 2026
Most SMB AI pilots fail. The published failure rates I've seen put it at 60 to 80% [verify], which is roughly consistent with what I've watched in the field. But the failure rate isn't the…
MAY 13, 2026
Professional services firms have a different relationship with AI than product businesses. The product is hours of expert judgement. The thing AI is good at, repetitive task execution, doesn't…
MAY 11, 2026
E-commerce is the SMB category where the AI landscape has fragmented most aggressively. Every Shopify or BigCommerce store I look at has 6 to 12 AI-enabled apps installed, half of which are barely…
MAY 9, 2026
Back-office operations is the most underrated category for SMB AI investment. The vendor pitches focus on customer-facing flashy stuff. The real ROI sits in the unglamorous workflows: invoices,…
MAY 6, 2026
Sales ops is one of the easiest AI categories to oversell and one of the easiest to ship well. The disconnect between the marketing pitch (AI handles your whole pipeline, replaces your SDRs,…
MAY 4, 2026
Customer support is the most over-pitched and most under-shipped category in SMB AI. Every vendor wants to sell you a chatbot that "handles" 80% of tickets. Most of the chatbots SMBs deploy this way…
MAY 2, 2026
The custom-vs-off-the-shelf question is the most common confusion I see in SMB AI conversations. Owners default to one side or the other based on temperament. Builders want custom. Frugal owners want…
APR 29, 2026
The cost to build a custom AI agent is the question SMB owners ask earliest and get the most varied answers on. I've seen quotes for "the same" agent range from $8,000 to $120,000 depending on who's…
APR 27, 2026
The first AI agent works. The team trusts it. The numbers add up. The owner is asking what's next, and the answer is usually "the second agent". Then the third. Then the fourth.
APR 25, 2026
Choosing the wrong AI partner has cost the SMBs I've watched more money than choosing the wrong technology. The mistake is hard to see at the time, because vendors are good at sounding credible in…
APR 22, 2026
The ROI of AI for small business is one of the most lied-about numbers in the current vendor pitch landscape. Every vendor deck has a chart showing 5x or 10x return in the first year. Most of them…
APR 20, 2026
The build vs buy decision is older than AI. Every IT shop has had this conversation about every internal system since the 1990s. The AI version has a few new wrinkles but most of the framework is…
APR 17, 2026
Every consultant has a maturity model. Most of them are nonsense. Five-stage transformation journeys with quadrants that take three months to fill in and produce a report nobody acts on.
APR 15, 2026
The question "where to start with AI in your business" is asked badly more often than it's asked well. I've heard it phrased as "what AI tool should we buy", "should we hire an AI person", "what's…
APR 14, 2026
I've been on the receiving end of more failed AI projects than I'd like to admit. Some I ran. Some I inherited and tried to save. Some I was asked to do a post-mortem on after the original team had…
APR 11, 2026
When SMB owners ask me about AI agents, the first thing I usually have to do is unscramble the word "agent". The term is used to mean five different things in five different vendor pitches, and most…
APR 8, 2026
Most small business owners I talk to are stuck in the same place with AI. They've watched ChatGPT do something impressive. They've signed up for two or three SaaS products with "AI" in the name.…