Technology

#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

#25 Five Things I Stopped Doing That Made Me a Better CEO

This edition covers the discipline of subtraction -- what I stopped doing that made me a better CEO, and why the gap between a marketing tactic and a business model decision is worth understanding before it costs you a decade. We go honest on AI: what it actually means to say "people first" when the technology requires fewer people, and what fourteen months of real implementation looks like when the pitch deck version runs out. And for roofing operators, the insurance market is shifting faster than most sales processes have adjusted -- this one has the data and the argument for why financing is no longer optional.

Jun 16, 2026

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20 min read

#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

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

#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

#17 Our $500K Mistake. A 10% Conversion Lift. One Big Lesson.

This week’s issue is all about turning operational discipline into competitive advantage — from uncovering a hidden $500,000 filter expense to leveraging AI call scoring, smarter financing with GreenSky, and more rigorous ServiceTitan reviews. If you’re serious about scaling profitably, mastering your data, tightening execution, and pulling the right growth levers, this one’s for you. Plus: a teaser on mastering YOUR data and a few favorite tweets from the week.

Feb 16, 2026

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20 min read

#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

#9 Profit vs Purpose. You Don't Have to Compromise.

Profitability and purpose aren’t opposing forces—they’re mutually reinforcing. In this edition, I share why strong financial results are what enable us to invest in our people, pursue growth, and stay independent. Purpose without profit is fragile—but when the two work together, that’s when a company becomes unstoppable.

Oct 6, 2025

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18 min read

#8 What Smart Operators Are Tracking in 2025 (That Most Aren't)

From AI risks to financing blind spots, here’s what you need to know to protect your margins and grow smarter. Tactical insights for contractors, operators, and acquirers who want to win in 2025—without taking their eye off the ball.

Sep 16, 2025

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17 min read

#6 My Secret Weapon for Business Growth: Outside Voices

How I continuously learn & grow while leading our $200 million business. Financing and the future of service companies: inside our 2025 playbook.

Aug 18, 2025

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19 min read

#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.

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

#2 Home Services, Rewritten: The Privately Held Playbook

No fluff. No PE funds. Just field-tested leadership, strategy, and growth from a $200M business that bets on itself.

Jun 17, 2025

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16 min read

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

Jun 3, 2025

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6 min read

Technology

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

#25 Five Things I Stopped Doing That Made Me a Better CEO

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

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

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

#17 Our $500K Mistake. A 10% Conversion Lift. One Big Lesson.

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

#9 Profit vs Purpose. You Don't Have to Compromise.

#8 What Smart Operators Are Tracking in 2025 (That Most Aren't)

#6 My Secret Weapon for Business Growth: Outside Voices

#5 How much money should I pay my team?

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

#2 Home Services, Rewritten: The Privately Held Playbook

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

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