- The Path Less Traveled
- Topics
- Technology
#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.
#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.
#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.
#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.
#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.
#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.
#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.
#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.
