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#29 The Cost of Not Looking: problems that compound because nobody checked

#29 The Cost of Not Looking: problems that compound because nobody checked

Problems that grow quietly until you go looking: a field manager ratio that caps growth without anyone noticing, a price book that drifted off target with no bad actor involved, and a first 90 days that quietly decides whether a new hire sticks. We also cover what AI search means for how homeowners find a contractor, and why we'd rather lose a financing sale than let a customer get surprised by a bill.

Aug 25, 2026

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15 min read

#27 What You're Not Selling, Not Watching, and Not Showing Up For

#27 What You're Not Selling, Not Watching, and Not Showing Up For

This issue is about the stuff that doesn't make the highlight reel, at home and in the business. I share a leadership takeaway from Sun Valley on being present for the routine and not just the fun parts, how we're using AI to win back cancelled and dropped bookings, and why duct cleaning, appliance repair and insulation deserve more attention than most operators give them. I also break down what financing on smaller tickets can do for your close rate, and what I'm watching for at ServiceTitan's Pantheon 2026.

Jul 20, 2026

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9 min read

#24 Why We Stopped Buying Our Trucks (And What the Numbers Taught Us)

#24 Why We Stopped Buying Our Trucks (And What the Numbers Taught Us)

This issue of The Path Less Traveled covers two decisions that look simple on the surface but carry real strategic weight as you scale: how you manage your data infrastructure and how you finance your fleet. In both cases, the lesson is the same — what felt right when you were smaller may no longer serve where you are going, and the discipline is in being willing to question the assumptions your operation was built on before they become the thing holding you back.

Jun 3, 2026

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13 min read

#22 Build vs. Buy: A Framework for Thinking About AI

#22 Build vs. Buy: A Framework for Thinking About AI

This issue covers the build vs. buy decision in AI — a framework from venture investor Mike Volpi that cuts through the noise: only build if it creates a real competitive advantage, buy everything else, and never confuse a prototype with a production-ready tool. We also go deep on the service wrapper — the six-step system around the technical work that our customers actually write reviews about.

May 4, 2026

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10 min read

#20 I Spent $4.2 Million on Google Last Year.  Here's What I Actually Know About Whether It Worked.

#20 I Spent $4.2 Million on Google Last Year. Here's What I Actually Know About Whether It Worked.

Most home service operators can tell you what they spent on Google. Very few can tell you what they actually got for it. The companies that win long-term aren't just the ones who spend the most on marketing — they're the ones who convert that spend into lasting relationships, and then build a membership base that makes the next call free.

Apr 1, 2026

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10 min read

#19 The Most Important System in Your Business That Nobody Sees.

#19 The Most Important System in Your Business That Nobody Sees.

This week’s TPLT dives into a simple idea: the best operators win by mastering the fundamentals. From using “old-school” marketing like equipment stickering and cross-trade awareness, to building a reliable financial foundation, to leveraging tools like Netic and GreenSky to drive efficiency and close more deals—we explore practical ways to grow smarter, not just bigger. The common thread? Systems that remove friction, increase visibility, and help great teams execute at a higher level.

Mar 17, 2026

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20 min read

#13 Measure THIS in your AI-first Call Center...

#13 Measure THIS in your AI-first Call Center...

In this edition, I break down the two KPIs that matter most in an AI-powered call center: speed to answer and speed to resolution. These metrics are shaping how we blend AI automation with human responsiveness—and ensuring customer experience doesn’t get lost in the tech.

Dec 5, 2025

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14 min read

#5 How much money should I pay my team?

#5 How much money should I pay my team?

Being intentional about your compensation philosophy, overcoming the aversion to "sales" in home services, and the financing programs our customers love.

Jul 31, 2025

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17 min read

#4 To own, or lease? Real estate strategies + your business.

#4 To own, or lease? Real estate strategies + your business.

Re-imagining our marketing function, leading through change, and building a real estate portfolio alongside your operating business

Jul 15, 2025

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16 min read

How we grew our Residential Service Plan Memberships to 20,000+ (TPLT Full Access)

How we grew our Residential Service Plan Memberships to 20,000+ (TPLT Full Access)

A full break down of our program design, marketing, fulfillment, pricing, features, benefits, and more

LockSimple

Jun 3, 2025

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6 min read

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