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The Hardest Decisions Every Contractor Has to Make

Published on: July 23, 2026

Author: The Better Contractor

What should you do when you’re booked months in advance but customers keep calling? Are you experienced enough to start charging for your work? Should you lower your price to keep a longtime customer?

In Episode 86 of The Better Contractor Podcast, Brent and Alex answer three real questions submitted by members of The Better Contractor Facebook group.

They discuss when contractors should hire more employees, rent or purchase additional equipment, raise their prices, turn down unprofitable work, and walk away from customers who only care about receiving the lowest bid.

Brent also shares advice for newer contractors who are still building their skills and confidence. You do not need to know how to handle every possible project before starting a business—but you need to understand your current capabilities, price your work appropriately, manage your liability, and continue improving.

In this episode:

00:00 Introduction
00:33 What to Do When You’re Booked Months in Advance
01:23 Hiring More Employees and Adding Equipment
01:48 When It’s Time to Raise Your Prices
02:32 Using a Premium “I Don’t Want the Job” Price
03:07 Turning Demand Into Business Growth
03:44 Starting a Contracting Business With Limited Experience
04:29 Managing Risk and Liability as a New Contractor
05:18 Choosing the Right Services to Offer
06:19 Building Confidence and Charging for Your Work
06:39 How New Contractors Should Set Their Rates
07:44 Starting Small and Growing Into Better Work
08:39 How Brent Started Lanracorp
10:00 Gateway Dealer Network Sponsor Message
10:52 Should You Match a Competitor’s Lower Price?
11:37 When to Walk Away From a Longtime Customer
12:14 Why Contractors Get Stuck at Break-Even
13:17 The Problem With Low-Barrier Competition
14:13 Becoming More Specialized and Valuable
15:17 The “Low-Low-Low Bid” Process
16:04 Lowest Price vs. Best Value Customers
16:42 Why Some Customers Come Back After Choosing the Cheapest Bid
17:18 Join The Better Contractor Facebook Group

JOIN THE BETTER CONTRACTOR COMMUNITY

Website:
https://thebettercontractor.com/

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https://www.facebook.com/share/g/1D7WETCTXG/

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FREE TRAINING & ONBOARDING VIDEOS

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LISTEN TO THE PODCAST

Spotify:
https://open.spotify.com/show/1tjPd8zKXx2oXT8WpjTwir

Apple Podcasts:
https://podcasts.apple.com/us/podcast/the-better-contractor-podcast/id1728924279

CONNECT WITH BRENT OBERLINK

Website:
https://brentoberlink.com/

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https://www.facebook.com/brent.oberlink.9

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https://www.instagram.com/brentoberlink/

LinkedIn:
https://www.linkedin.com/in/brent-oberlink-0a70b3161/

ABOUT THE BETTER CONTRACTOR PODCAST

The Better Contractor Podcast features real conversations about growing a contracting business, developing strong leaders, hiring and retaining employees, improving company culture, managing operations, and building a business that can succeed for the long term.

Subscribe to the channel and share this episode with another contractor who is working through these same decisions.

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