BLOG

The Caddy blog.

Straight answers on putting AI to work in a mid-market business: what it's worth, who should build it, and what discovery should actually find.

What a construction office actually spends on admin

What admin really costs a construction office: verified numbers on overhead, invoicing, and lost hours, and what recovered payroll is worth when you sell.

Read the article

The operator tax, the magic five, and handing you the keys: Tucker on the Board of Advisors Podcast

Tucker joins host Dillon England for sixteen minutes on the operator tax, a 14 person admin team going down to 4, and why you own the system at the end instead of renting it forever.

Watch the episode

The state of AI in mid-market operations 2026: what the numbers actually say

Verified public data from the Census Bureau, Stanford, MIT, and Gartner: mid-market AI is stalling, and the gap is leadership, not technology.

Read the article

The AI multiple: what a digital workforce does to your company's value

How a digital workforce raises both your earnings and your exit multiple, from a founder who sold his family business to private equity.

Read the article

How mid-market companies actually deploy AI in 2026: fractional CAIO vs. agency vs. in-house hire vs. build-it-yourself

The four real ways a mid-market company deploys AI in 2026, when each is the right call, and the questions to ask before you sign.

Read the article

The 21-metric framework: how to measure what AI is actually worth in your business

21 metrics, five buckets, and a worked example: how mid-market operators put a defensible dollar figure on AI before buying anything.

Read the article

AI executive, AI agency, or figure it out yourself: how mid-market companies should decide

A fair decision guide for mid-market owners: when to hire an AI executive, when to use an agency, when to DIY, and the questions to ask before signing.

Read the article

What AI discovery should actually uncover in your business

What a serious AI discovery process examines, the signs your AI assessment is shallow, and what should exist in writing before anyone builds anything.

Read the article

Get the next playbook

One useful piece on putting digital labor to work, straight to your inbox. No spam, unsubscribe anytime.

Book a Call