Ingaged | The Contractors Who Win Will Be the Ones AI Can Find

Jared built a ~$10M siding, windows, and exterior-painting company from scratch in 2010 by refusing to run leads on evenings and weekends — proving the old-school 'two-legger' model wrong.

His edge was doing what nobody else did — advertising on Google 15 years ago when older owners rejected the internet; now that everyone has copied it, cost-per-lead has risen and margins have compressed.

The new frontier is AI discovery — buyers want ChatGPT or Google AI to simply name the top three companies, so the goal is to be one of those three before competitors catch up.

Measure technology by investing and tracking hard — asking every caller 'how did you hear about us?' alongside CallRail over a 90-day window tells him whether the spend paid off.

As a small business with independent-contractor reps, you can't mandate tools — you buy it, deploy it, and 'beg and plead'; adoption is the constant challenge (his cores: know your product and tell the truth).

His biggest tech lesson: a new CRM turned out far more complex and time-consuming than promised — a small business without someone dedicated to own the build gets stuck deep in sunk cost.

Vet realistic expectations and bandwidth before you buy — AI is only as good as the context you give it, and honest dialogue (even telling a homeowner not to buy) beats being sold a dream that can't be delivered.