If you want to play the game on hard mode… randomly pick an industry and hope it works.

In this episode of Owned and Operated, John Wilson and Jack Carr break down exactly how they’d build a home service business in 2026—and why the old 2016–2020 playbook is dead. They go deep on research-first market selection, avoiding late-stage consolidation traps, picking “boring” services with clean SKUs, and building a business that can win even when weather, competition, and ad platforms don’t cooperate.

In this episode, we cover:

• Research, Research, Research: Why “randomly picking a trade” is hard mode—and how to find unmet demand in a specific market.
• The 2016–2020 Playbook Is Irrelevant: Why advice from the late 2010s doesn’t match today’s competitive reality.
• Consolidation & Multiples: How consolidation changes outcomes—and why “gold mine” industries can cool off before you’re big enough.
• Pick the Right Industry (Fragmented + Big TAM): What to look for in a winning service category in 2026.
• Boring Businesses Win: Drain cleaning, duct cleaning, leak detection, jetting, water filtration, septic, turf—simple offerings, repeatable operations.

🔥 What You’ll Learn:

• How to choose a home service niche in 2026 using market demand + consolidation timing, not vibes.
• The fastest path to “easy leads” (and why competing in stacked markets is an uphill fight).
• A practical framework for building a saleable business—even if you don’t plan to sell.
• Why multi-location forces better systems (and reduces dependence on a few A-players).
• Where the next marketing edge is coming from as attention shifts and platforms evolve.

Shout Out to FieldPulse 🚀

FieldPulse is an incredible Field Service Management platform that helps you save hours each week while keeping your operations running smoothly. If you're looking to streamline your processes, stay competitive, and focus on what truly matters, FieldPulse is a game-changer!

📅 Book your demo


💼 Extra Special Thanks to Service Scalers!

We’ve been partnering with Service Scalers to maximize our Local Service Ads (LSAs) and optimize our Google My Business profiles, and the results have been incredible. With hundreds of thousands in sales and 900+ calls in a single week, GMBs are now our top-performing organic lead channel.

Want to learn how Service Scalers can do the same for you?

🔗Check Them Out Here


💼 Big Reputation — Stop chasing reviews and watching competitors outrank you. B

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• John's YouTube Channel
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• Owned and Operated

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John Wilson, CEO of Wilson Companies
Jack Carr, CEO of Rapid HVAC

📌 Disclaimer: Some links may include UTM parameters or affiliate relationships, meaning we may earn a commission if you make a purchase. Episodes may feature sponsors, but all opinions expressed are our own.

Most security & life-safety companies don’t get stuck because they lack hustle—they get stuck because they lack measurement.

In this special feed drop of Entry & Exit, Stephen Olmon and Collin Trimble (Alarm Masters, Houston) walk through their 2026 planning process: how they set revenue/RMR/EBITDA goals, translate them into departmental KPIs, and use actuals vs. budget to decide when to invest, when to cut, and how to avoid “hope-based” growth.

They unpack why so many firms stall around $3M in revenue (comfort + underinvestment), why “Talent Wins” became a non-negotiable, and how to think about emerging trends like AI the right way—starting with a solid tech foundation and the right people before chasing shiny tools.

You’ll also hear the core scorecard metrics they track across sales, marketing, finance, operations, and M&A, plus practical homework you can apply immediately in your own business.

🔗 Connect

Stephen Olmon
Collin Trimble

Check out more from Entry & Exit

Send Us Mail!

More Ways To Connect with O&O

• John's YouTube Channel
• Weekly Newsletter
• Owned and Operated

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John Wilson, CEO of Wilson Companies
Jack Carr, CEO of Rapid HVAC

📌 Disclaimer: Some links may include UTM parameters or affiliate relationships, meaning we may earn a commission if you make a purchase. Episodes may feature sponsors, but all opinions expressed are our own.

Insurance claims, storm chasers, and broken incentives — welcome to the dark side of roofing.

In this episode, John Wilson sits down (again) with Adam Cherup to unpack what really happens behind the scenes in roofing — from “deny, delay, defend” insurance tactics to the storm-chasing playbook that leaves homeowners stuck holding the warranty bag. They also get practical: seasonality, lead gen, cash flow, and what it actually takes to start a roofing business (especially in Florida).

In this episode, we cover:

• The Insurance Game: “Deny, delay, defend” — and why carriers aren’t your friend.
• Retail vs. Insurance Strategy: Why some roofers push retail first, then litigate the claim after.
• How to Win Insurance Work: Xactimate, codes, the paperwork game, and why payouts can double when done right.

🔥 What You’ll Learn:

• How contractors can guide homeowners through insurance without waiting months for approvals.
• The biggest red flags of storm-chasing contractors (and how people get burned).
• Why roofing cash flow can get brutal — and how seasonality + claim delays compound it.
• What makes roofing “easy” vs. “hard” depending on your model (subbed installs vs. controlled labor).

💼 Extra Special Thanks to Service Scalers!

We’ve been partnering with Service Scalers to maximize our Local Service Ads (LSAs) and optimize our Google My Business profiles, and the results have been incredible. With hundreds of thousands in sales and 900+ calls in a single week, GMBs are now our top-performing organic lead channel.
Want to learn how Service Scalers can do the same for you?

🔗Check Them Out Here

💼 Shoutout to Quick Staffers LLC

Need trained HVAC & plumbing CSRs at a fraction of the cost? Quick Staffers LLC specializes in placing top-tier global talent with the best SOPs and scripts.

🔥 Get $1,000 off your first placement HERE

💸Sponsored by CFO Made Easy

Built a strong trades business? Let’s take it to $10M and beyond. CFO Made Easy offers part-time CFO services for home and trade service businesses—helping you boost cash flow, maximize profit per tech, and make clear growth decisions.

📈 Free Offer: Book a 45-min Financial Insight Session to uncover growth blockers.

🔗 Connect

John Wilson

Adam Cherup

Send Us Mail!

More Ways To Connect with O&O

• John's YouTube Channel
• Weekly Newsletter
• Owned and Operated

Leave a Review

John Wilson, CEO of Wilson Companies
Jack Carr, CEO of Rapid HVAC

📌 Disclaimer: Some links may include UTM parameters or affiliate relationships, meaning we may earn a commission if you make a purchase. Episodes may feature sponsors, but all opinions expressed are our own.