Field notes for operators making AI bets
Dispatches from the Summit
Insights on AI, technology, and building a smarter business — from someone who's actually shipped it.
July 23, 2026
AI Search and Your Small Business: How to Stay Visible When AI Answers First
AI Overviews and answer engines like ChatGPT are ending searches before customers ever reach your site. What changed, why local businesses still have runway, and how to be the source the AI quotes.
July 16, 2026
The Silent Guest in Your Meetings: What to Know Before AI Records Everything
Your team already runs AI note-takers in every meeting. Where those recordings live, why Florida's consent law matters, and the fifteen-minute fix that keeps a useful tool from becoming a liability.
July 9, 2026
AI Phone Agents for Small Business: What to Automate on the Phone (and What Not To)
AI receptionists crossed from novelty to genuinely useful in 2026. Where they win back missed calls, where they backfire, and how to pilot one without embarrassing yourself in front of a customer.
July 2, 2026
Before the Storm: A Hurricane-Season Systems Check for Florida Businesses
A below-average 2026 forecast still means storms — and your business doesn't experience the season, it experiences the one that hits. The systems check that keeps you running when the power's out.
June 25, 2026
What Is Go-Live Assurance? A Plain-English Guide to System Cutover QA
Switching your POS, CRM, or billing system is where small businesses get burned. What go-live assurance is, why launches fail, and the five-part process that makes launch day a non-event.
June 23, 2026
How Much Does a Fractional CTO Cost in 2026?
Real pricing for fractional technology leadership — typical monthly ranges, what drives the number up or down, and how it compares to a full-time CTO hire.
June 20, 2026
How to Choose an AI Consultant for Your Small Business (7 Questions to Ask)
Seven questions that separate AI consultants who ship real results from the ones selling tools you don't need.
June 18, 2026
What Does Business Process Automation Cost for a Small Business?
The real cost of automation — tool subscriptions, the build, and maintenance — what drives the number, and the ROI math that tells you whether it's worth it.
June 16, 2026
The Small-Business System Go-Live Checklist
Switching a POS, CRM, billing, or ERP system? The four-phase checklist — prep, go/no-go, cutover, and validation — that turns a risky launch into a non-event.
June 13, 2026
Zapier vs. Make vs. Custom Automation: Which Is Right for Your Business?
A practical comparison of the three ways to automate — when each one fits, what it costs, and how to choose workflow by workflow.
April 6, 2026
The Hidden Cost of Bad Software Decisions
Most growing businesses lose $10K–$30K/year to tooling decisions that looked fine at signup. Five questions worth asking before the next purchase.
April 4, 2026
AI Agents Are Here — What Small Businesses Need to Know
Agents take action, not just answer questions. The practical implications for an SMB stack — and where to start without overcommitting.
April 2, 2026
Your Business Has Experimented With AI — Now What?
Experimenting with AI isn't the same as adopting it. The structural moves that turn pilots into operational tools.
March 28, 2026
5 Signs Your Small Business Is Ready for AI
A practical diagnostic for AI readiness — well before the conversation about which model to use.
March 22, 2026
How Workflow Automation Can Save Your Business 20+ Hours a Week
The math behind automation savings — and the operational redesign that has to happen for the savings to actually compound.
March 15, 2026
What Is a Fractional CTO — and Does Your Business Need One?
Fractional technology leadership, broken down — when it works, when it doesn't, and what the alternatives look like.
March 8, 2026
What Enterprise Delivery Discipline Looks Like in a 25-Person Company
Five enterprise practices that translate cleanly to small business — and three that don't.
March 1, 2026
How to Connect Your CRM, Invoicing, and Scheduling Without Hiring a Developer
No-code platforms have caught up. The integration patterns most SMBs miss because they assume connection requires code.
February 20, 2026
How Much Does Technology Consulting Actually Cost?
A pricing model breakdown — discovery, working sessions, sprints, projects — and how each anchors expectations.
February 5, 2026
5 Signs Your Operations Are Too Manual to Scale
The admin-vs-real-work test — and the operational tells that show up before the financials do.
January 15, 2026
The Best Software Stack for a Growing Contractor Business
Core tools every growing contractor needs — and the criteria for picking between options when each looks the same in a demo.
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Field notes for operators making AI bets.
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