Episode 13

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Published on:

25th Aug 2026

The 5 Questions Contractors Keep Asking Me

Jason W. Phillips went through four months of coaching calls and conversations with contractors across the country to identify the five questions owners ask him most.

In this episode of the Contractor Freedom Podcast, Jason answers those questions using lessons from nearly three decades of building and leading an 8-figure contracting company.

He covers when to make your next hire, choosing between sales and production, managing project capacity, finding the right people, and gaining financial clarity inside your company.

These aren’t theoretical answers. They’re practical lessons about leadership, systems, team development, profitability, and building a contracting business that can grow beyond the owner.

Topics Covered: contractor business growth, leadership, team building, project management, sales systems, recruiting, operational capacity, bookkeeping, financial clarity and scaling

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About the Podcast

Contractor Freedom Podcast
Escape Contractor Prison and Live With Greater Freedom and Purpose
Contractor Freedom is the podcast for growth-minded contractors who are tired of chaos, overwhelm, and feeling trapped by the very business they built.

Hosted by Jason Phillips, owner of the multimillion-dollar Phillips Home Improvements and founder of Contractor Freedom, this show helps contractors break free from “Contractor Prison” through leadership, people, systems, and personal growth.

Each episode delivers real-world insights on building winning teams, creating scalable systems, increasing profitability, improving leadership, strengthening culture, and designing a business that serves your life instead of stealing it.

Whether you’re trying to grow your company, reclaim your time, develop leaders, or simply rediscover your purpose, Contractor Freedom will equip and challenge you to lead at a higher level and live with greater freedom and purpose.

About your host

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Jason Phillips

Meet Jason Phillips, a visionary entrepreneur who transformed his one-man show into a thriving empire. His journey from struggle to success with a move into roofing and gutters, his company skyrocketed, earning a spot on the Inc 5000 list five years in a row. Overcoming roadblocks, he reinvented the business, achieving astonishing results. Now, he's dedicated to helping other small business owners to break free by helping them foster a team built on trust, faith, teamwork, and excellence. Join him to create "ABLE-Systems" for scalable, repeatable success and customer satisfaction. Don't let mistakes drain you; let Jason guide you to new heights!