Jason Phillips

Contractor Freedom Podcast

Business EN ↓ 22 episodes

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 y...

Author

Jason Phillips

Episodes

The AI Trap Contractors Need to Avoid 07.07.2026 12:20

The central thesis of this episode revolves around the perilous inclination of contractors to employ automation as a means of evading fundamental business challenges, rather than addressing the underlying issues directly. I elucidate how many contractors, beset by a meager closing rate or ineffective follow-up mechanisms, resort to developing elaborate technological solutions, such as chatbots, in...

How Contractors Can Stop Hiring the Wrong People 30.06.2026 53:43

In this episode of the Contractor Freedom Podcast , Jason W. Phillips sits down with Jennifer Smith , HR manager and culture champion at Phillips Home Improvements, to unpack why most contractor hiring problems are not really people problems. They are clarity problems. Jason and Jennifer talk through what has to happen before a job posting ever goes live: defining the role, knowing your core value...

From Panic to Profit: A Contractor's Guide to Managing Lead Droughts 23.06.2026 21:44

The primary focus of this podcast episode is to elucidate the crucial steps contractors should undertake when experiencing a downturn in lead generation, emphasizing the necessity of refraining from hastily investing in additional advertising to rectify a problem that may stem from internal inefficiencies. I expound upon the common tendency of contractors to panic and flood the market with ads, wh...

From Addiction and Cancer to Contractor Freedom: Joe Carfagno’s Story 16.06.2026 24:40

In this episode of the Contractor Freedom Podcast , Jason W. Phillips sits down with Joe Carfagno of Carfagno Professional Painting to unpack how Joe went from addiction, cancer, relapse, and starting over to building a growing painting business with real systems, team culture, and purpose. Joe shares how his company grew to 10 painters, 3 office team members, and $1.8M last year. He also talks ab...

From 30% to 62% GP: How 605 Painting Built a Real Freedom Machine 09.06.2026 36:03

In this episode of the Contractor Freedom Podcast, Jason W. Phillips sits down with Kyle Schuh of 605 Painting to unpack how their company moved from owner-operator chaos to a more scalable, profitable business. Kyle shares the behind-the-scenes story of how 605 Painting improved gross profit from around 30% to 62%, hit $1M in a quarter, and began building the systems, sales process, and team alig...

He Rebuilt His Life and Built a $1.8M Painting Business 02.06.2026 39:24

In this episode of the Contractor Freedom Podcast, Jason Phillips sits down with Konrad Derheim of Derheim Painting for a powerful conversation about rebuilding, refocusing, and growing a painting business through one of the hardest seasons of his life. Konrad shares how he went from feeling overwhelmed and stuck to building a $1.8M painting company by getting clear on the right work, making hard...

How To Buy Back Your Time & Make More Money 03.07.2024 47:32

Jason Phillips: [00:00:00] Welcome to the Contractor Freedom Podcast. I'm your host, Jason Phillips. This show exists to help small business owners like you escape the tyranny of contractor prison and enter the bliss of contractor freedom so you can have the time, money, and freedom to live your life with purpose beyond your business. As a certified human behavior consultant in DISC personality st...

This Is Why You're Not Closing Sales feat. Joe Covarrubias 17.04.2024 42:24

Jason Phillips: [00:00:00] Welcome to the Contractor Freedom Podcast. I'm your host, Jason Phillips. This show exists to help small business owners like you escape the tyranny of Contractor Freedom and enter the bliss of Contractor Freedom so you can have the Time, Money, and Freedom to Live Your Life With Purpose Beyond Your Business. As a certified human behavior consultant in DISC personality s...

Master the Art of Connection: Best Kept Secrets Reveal w/ Janell Roedl 06.03.2024 25:17

Jason Phillips: [00:00:00] Welcome to the Contractor Freedom Podcast. I'm your host, Jason Phillips. This show exists to help small business owners like you escape the tyranny of Contractor Freedom and enter the bliss of Contractor Freedom so you can have the Time, Money, and Freedom to Live Your Life With Purpose Beyond Your Business. As a certified human behavior consultant in DISC personality s...

The #1 Strategy for Selling More Painting Jobs w/ Tanner Mullen 17.01.2024 40:47

Jason Phillips: [00:00:00] Welcome to the Contractor Freedom Podcast. I'm your host, Jason Phillips. This show exists to help small business owners like you escape the tyranny of Contractor Freedom and enter the bliss of Contractor Freedom so you can have the Time, Money, and Freedom to Live Your Life With Purpose Beyond Your Business. As a certified human behavior consultant in DISC personality s...

From Soldier to 7-Figure CEO: How a Veteran Entrepreneur Built a Million-Dollar Painting Company 03.01.2024 46:42

Jason Phillips: [00:00:00] Welcome to the Contractor Freedom Podcast. I'm your host, Jason Phillips. This show exists to help small business owners like you escape the tyranny of Contractor Freedom and enter the bliss of Contractor Freedom so you can have the Time, Money, and Freedom to Live Your Life With Purpose Beyond Your Business. As a certified human behavior consultant in DISC personality s...

How This CEO's Software is Driving MASSIVE Profits for Contractors 20.12.2023 35:21

Jason Phillips: [00:00:00] Welcome to the Contractor Freedom Podcast. I'm your host, Jason Phillips. This show exists to help small business owners like you escape the tyranny of Contractor Freedom and enter the bliss of Contractor Freedom so you can have the Time, Money, and Freedom to Live Your Life With Purpose Beyond Your Business. As a certified human behavior consultant in DISC personality s...

How Ignoring Cash Flow Is Draining Profits 06.12.2023 37:19

Jason Phillips: [00:00:00] Welcome to the Contractor Freedom Podcast. I'm your host, Jason Phillips. This show exists to help small business owners like you escape the tyranny of Contractor Freedom and enter the bliss of Contractor Freedom so you can have the Time, Money, and Freedom to Live Your Life With Purpose Beyond Your Business. As a certified human behavior consultant in DISC personality s...

Reducing setbacks and empowering collaboration in business with Brandon Lewis 22.11.2023 47:36

Jason Phillips: [00:00:00] Welcome to the Contractor Freedom Podcast. I'm your host, Jason Phillips. This show exists to help small business owners like you escape the tyranny of Contractor Freedom and enter the bliss of Contractor Freedom so you can have the Time, Money, and Freedom to Live Your Life With Purpose Beyond Your Business. As a certified human behavior consultant in DISC personality s...

Contractor Freedom: Turning your Contractor Business into passive income with Jason Paris 08.11.2023 45:17

Jason: [00:00:00] Welcome to the Contractor Freedom Podcast. I'm your host, Jason Phillips. This show exists to help small business owners like you escape the tyranny of Contractor Freedom and enter the bliss of Contractor Freedom so you can have the Time, Money, and Freedom to Live Your Life With Purpose Beyond Your Business. As a certified human behavior consultant in DISC personality styles and...

Why Networking and Learning from Peers Are Essential for Contractors w/ Will Reyes 11.10.2023 46:19

[00:00:00] Welcome to the Contractor Freedom Podcast. I'm your host, Jason Phillips. This show exists to help small business owners like you escape the tyranny of Contractor Freedom and enter the bliss of Contractor Freedom so you can have the Time, Money, and Freedom to Live Your Life With Purpose Beyond Your Business. As a certified human behavior consultant in DISC personality styles and motiva...

Contractor Success Secrets: BBB's Role in Home Services 27.09.2023 44:57

From Surviving to Thriving: How to Build a Customer-Centric and Profitable Painting Business w/ Mark DeFrancesco 13.09.2023 52:42

From Vision to Victory: Building Contractor Freedom with Integrity featuring Jason Humrichous 30.08.2023 49:30

Guiding Your Business to Success: The Importance of Establishing Core Values with Jennifer Smith 16.08.2023 37:20

Jason Phillips: [00:00:00] Welcome to the Contractor Freedom Podcast. I'm your host, Jason Phillips. This show exists to help small business owners like you escape tyranny of Contractor Prison and enter the bliss of Contractor Freedom so that you can have the time, money, and Freedom to live your life with purpose beyond your business. As the owner of a multi million dollar home improvement compan...

Contractor Freedom: How to Pay for New Hires and Boost Your Bottom Line by making Strategic Decisions with Annie Newton 02.08.2023 31:35

In this episode, join host Jason Phillips as he delves into the world of financial management in supporting small businesses. Our special guest, Annie Newton, hailing from Walla Walla, Washington, brings her expertise as a fractional CFO to the table. Together, Jason and Annie explore the various indicators or pain points that small business owners often encounter. They discuss crucial aspects suc...

Contractor Freedom Podcast Trailer 31.07.2023 0:52

[00:00:00] Welcome to the contractor freedom podcast. I'm your host, Jason Phillips. This show exists to help small business owners like you escape the tyranny of contractor prison and enter the bliss of contractor freedom so that you can have the time, money, and freedom to live your life with purpose beyond your business. As the owner of a multimillion dollar home improvement company and certifi...