Podcast Summary: TheUPside Podcast

Episode: Build a Freedom Machine: The SOS Framework for Business Growth with Jason Phillips
Date: January 20, 2026
Host: Theresa Flood
Guest: Jason Phillips (Phillips Home Improvements / Contractor Freedom)

Episode Overview

In this episode, Theresa Flood sits down with Jason Phillips, a decorated entrepreneur and founder of Phillips Home Improvements, to discuss building a "freedom machine"—a business that enables its owner and team to thrive with both purpose and freedom. The conversation traces Jason’s journey from humble beginnings to business success, his pivotal mindset shifts, and the creation of his SOS Framework for business growth. The episode is packed with practical wisdom on leadership, team building, systems, and how personal faith and personal growth fuel lasting business significance.

Key Discussion Points & Insights

1. Jason’s Entrepreneurial Origin Story

• Initial Motivation: Jason started his company out of necessity after being laid off, with the goal to "put food on the table."
  “I never intended to actually start a company…” (02:28)
• Sensed a compelling need to improve the industry's treatment of employees, homeowners, and workers (03:01).

Memorable Quote:
"What was probably one of the most difficult times in my entire life bloomed into a blessing for me and even for others that I never dreamed of." – Jason (04:29)

2. The Grit Years and Effort Ceiling

• Early growth built through “grit, prayer, and hours.” (05:35)
• Jason quickly hit a point where he was "bankrupt on time," and his business controlled him (05:55).
• Pivotal Moment: Hearing "Cats in the Cradle" forced him to reassess his priorities (07:05–08:40).

Notable Story:
"Tears were streaming down my face ... I slammed my hand on the desk and stood up and threw my hands in the air. I just said, 'God, I need help.'" – Jason (08:15)

• Realized building a team was the only way to reclaim time and sanity (08:34).

3. The First Team, Leadership Growth, and Rebuilding

• Initial team built “came for a paycheck, not a purpose” (09:18).
• Leadership lesson: The only way for the business to grow was for Jason to grow as a leader (09:36).
• Invested in self-education, seminars, and books (“devouring books”) (10:00).
• Rebuilt the company with core values and vision—tore it down by 70% to start anew (11:18).

Quote:
"The only way the company was going to get better was if I got better, if I grew as a leader." – Jason (09:35)

4. The SOS Framework Explained (12:13)

• S = Self:
  • Integrity, vision, and leadership start with personal growth.
  • Utilizing DISC assessments transformed his leadership, marriage, and fatherhood.
  • "That's the S: starting with self." (12:14)
• O = Others:
  • Building a team aligned to vision and values.
  • “You can buy their hands with a paycheck, but only leadership burns their hearts.” (13:55)
  • Hire for vision and values alignment, not just skills or compensation.
• S = Systems:
  • Simple, repeatable, scalable systems make high performance possible.
  • “If you're too busy to build systems, you'll always be too busy.” (18:57, quoted by Theresa)
  • Systems create owner independence and bring predictability and scalability.

5. Leadership, Integrity, and Team Dynamics

• Integrity: Team watches leaders’ choices; cutting corners erodes trust even if nobody else notices (15:43).
• Hiring: Hire people for purpose, not just tasks or compensation (14:39–15:43).
• DISC Profiles:
  • Understanding natural behavior and stress responses helps align people to the right roles.
  • “Experience is great, but if you have the right alignment … the right person can figure it out.” (28:05–28:32)
• Wrong person in a role drains both the employee and the company (28:41).

6. Personal Faith and Business

• Faith is Jason’s core value at work (“Faith in God. Another word for faith is trust.”) (23:39–24:05)
• Business reflects the strengths, weaknesses, and values of its owner (24:12).
• Strives for balance: "People over profit," but also maintaining accountability and numbers to sustain both (25:36).

7. Letting Go & Scaling with Trust

• Limiting beliefs (e.g., “no one can do it as well as me”) can bottleneck growth (30:06).
• Giving people real responsibility—not just tasks—lets them (and the business) grow (31:14).
• Resist over-delivering quality that the customer doesn’t perceive or value; align with client expectations (31:26–32:25).

8. Building Family Legacy & Contractor Freedom

• Jason’s son now runs the primary business; Jason mentors other contractors full time (32:59).
• Contractor Freedom provides coaching, sales bootcamps, and systems training for business owners (33:08–34:42).
• Message for entrepreneurs:
  • Time and freedom matter most.
  • Get a mentor who’s done what you’re trying to do to shortcut your learning curve (34:57).

Quote:
"You can shortcut decades of trial and error and iterations. If you can do that, so good." – Jason (35:46)

9. Key Takeaways and Advice

What would you do differently?

• Learn DISC (personality framework) much sooner; it's had far-reaching impact (36:00).
• Dream bigger; set ambitious goals even at risk of failing (36:54).

Book Recommendations (37:12–39:13)

• Who Not How by Dan Sullivan & Benjamin Hardy (37:12)
• Crucial Conversations (37:17)
• Chase the Lion by Mark Batterson (38:13)
• Anything (21 Irrefutable Laws of Leadership, 5 Levels of Leadership) by John Maxwell (38:21)
• Atomic Habits by James Clear and Tiny Habits by BJ Fogg (38:42)

Notable Quotes & Timestamps

• "What was probably one of the most difficult times in my entire life bloomed into a blessing..." – Jason (04:29)
• "The only way the company was going to get better was if I got better, if I grew as a leader." – Jason (09:35)
• "You can buy their hands with a paycheck, but only leadership burns their hearts." – Jason (13:55)
• “If you're too busy to build systems, you'll always be too busy.” – Theresa quoting a favorite adage (18:57)
• "My business was getting the best of me. And the worst part is I was letting it happen. I had to make a change." – Jason (30:06)
• "Freedom is designed … Get a mentor, get a coach… shortcut decades of trial and error" – Jason (34:57)

Timestamps of Key Segments

• Jason’s Origin & Motivation: 02:28–04:56
• Hitting Effort Ceiling/Cats in the Cradle Moment: 06:06–08:40
• Building & Rebuilding Team; Leadership Growth: 09:00–11:22
• SOS Framework Introduction & Breakdown: 12:13–19:25
• Integrity & Team Culture Examples: 14:52–16:50
• Faith in Business: 23:37–25:36
• Letting Go & Empowering Others: 30:06–32:25
• Contractor Freedom and Coaching: 33:08–34:42
• Advice to Entrepreneurs & Book Picks: 34:57–39:13

Conclusion & Where to Connect

Jason wraps up with encouragement for business owners to dream bigger, invest in themselves, and become leaders who serve both people and purpose. For those in the DFW area, his company is Phillips Home Improvement; find him online at Contractor Freedom (Facebook) and @contractorfreedomlive (Instagram).

Contact:

• Facebook: Contractor Freedom
• Instagram: contractorfreedomlive