The Contractor Fight with Tom Reber

In this episode, Tim and Derek dive deep into the uncomfortable moments that test contractors daily—both in business and life. From tech frustrations to difficult sales conversations, they highlight how discomfort is a necessary catalyst for growth and success. If you’re stuck in a rut, it’s likely because you’re avoiding the uncomfortable steps that push you forward.

In this episode Tim and Derek discuss:

• The real reason most contractors struggle: a lack of willingness to get uncomfortable
• Their own tech struggles as a metaphor for business challenges
• Why embracing discomfort in sales, communication, and leadership is essential
• The danger of getting too comfortable and stagnant in business practices
• How fear of looking foolish prevents growth and improvement
• The role your significant other plays in your journey and how to bring them along
• The impact of changing personal habits and how they affect your relationships
• Why consistent communication with your partner is crucial when you're growing your business
• Overcoming the fear of role-playing and uncomfortable conversations in sales
• Understanding that discomfort is often the gateway to breakthrough

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☎️ Sick of spinning your wheels and wondering where the money’s going?

If your business is already over $200K, you don’t need another “tip”, you need a plan.

Book a 15-minute Growth Call with our team and we’ll cut the bullsh*t, look at where you’re bleeding, and show you what’s possible when you take control.

→ Book your call here: https://go.thecontractorfight.com/15min-free-call

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In this episode of The Contractor Fight, Tom breaks down real contractor truck wraps submitted by fighters just like you. He exposes the good, the bad, and the downright embarrassing mistakes contractors make when they slap their name on a vehicle.

You’ll hear:

Why your truck is a moving billboard (and how most of you waste it)

Tom’s 5-point checklist for evaluating a wrap design

Real-life examples of what works and what fails at 60mph

How your wrap, website, and branding must all connect

👉 Want to stop looking like an amateur and start standing out as the premium contractor in your market? This episode will show you where you’re blowing it.

📌 Chapters

0:26 Why Truck Wraps Matter

0:55 Two Trucks, Big Impact

1:21 My Biggest Regret on Truck Wraps

1:52 The 5-Point Truck Wrap Checklist

2:20 Example #1: Cheyenne Home Services

5:08 Example #2: Legacy Fence

7:58 Example #3: Maine Outdoor Spaces

10:15 Example #4: Hernandez Essence Renovations

15:29 Example #5: Superior Ponds

18:25 Why Branding Must Match Your Quality of Work

19:16 Rebranding Success Stories

19:43 The $4/Day Marketing Investment That Works

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☎️ Sick of spinning your wheels and wondering where the money’s going?

If your business is already over $200K, you don’t need another “tip”, you need a plan.

Book a 15-minute Growth Call with our team and we’ll cut the bullsh*t, look at where you’re bleeding, and show you what’s possible when you take control.

→ Book your call here: https://go.thecontractorfight.com/15min-free-call

============================================================

== Rate the Podcast ==

Help your fellow contractors find the podcast! Please leave a rating/review.

Apple Podcasts

Spotify

Tim and Derek dive into a real-world sales story that illustrates the power of connection, emotional intelligence, and proper communication. Tim shares how a routine consultation for pond maintenance turned into an unforgettable sales experience—one that highlights the importance of trust, empathy, and being fully prepared through training.

In this episode Tim and Derek discuss:

• How a simple pond consultation evolved into a deep emotional connection with the client
• The critical moment when trust was lost with the previous contractor—and how Tim seized the opportunity
• How understanding and labeling client emotions can open doors in sales conversations
• Why consultation fees and in-person visits matter when diagnosing problems and building relationships
• The bizarre yet powerful moment the client realized Tim looked just like her late father—and how it sealed the deal
• The importance of training, role-playing, and continuously sharpening your sales skills
• How preparation and consistency helped Tim confidently close the deal and land a long-term client

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🛡️ Join us in BATTLEGROUND

Everything your contracting business needs in one comprehensive program. Three main focus areas: Leadership, Communication, and Numbers. For more info visit:

https://thecontractorfight.com/battleground

💰 You didn’t become a contractor to struggle financially.

Download our worksheet and start calculating a 50% gross profit on every job. It’s time to get your shit together!

https://thecontractorfight.com/50/

🎥 Explore over 1,400 free videos on Contractor Fight TV:

https://www.youtube.com/c/TomReber

💬 Join over 18,000 contractors in the free Facebook group:

https://thecontractorfight.com/facebook

== Rate the Podcast ==

Help your fellow contractors find the podcast! Please leave a rating/review.

Apple Podcasts

Spotify

Benji Carlson has spent his life building movements in the trades. From the franchise painting world to Breakthrough Academy to now helping lead Leanscaper, an AI-powered platform for landscapers. In this deep-dive with Tom, they tackle the real reasons the trades lost their shine, and what it’s going to take to make them cool again.

They talk content, culture, recruiting, money, and what separates struggling contractors from thriving ones. This episode is pure 🔥 for anyone serious about growing a blue-collar business with pride and purpose.

👇 CHAPTERS

00:00 - Intro

01:13 - Who is Benji Carlson?

03:00 - Why Startups Are His Sweet Spot

06:00 - Biggest Mistakes Contractors Make With Content

12:00 - The “It’s Not About You” Content Rule

14:30 - What Does It Mean to “Make the Trades Cool Again”?

17:00 - Why the College-First Narrative Failed

20:00 - The Death of Shop Class

23:00 - Being Blue-Collar and Broke Ain’t Cool

28:00 - Why the Trades Are Primed for a Renaissance

30:00 - AI’s Impact on the White-Collar Workforce

32:30 - How Contractors Must Shift Their Culture

35:00 - Using Social Media to Attract Top Talent

39:00 - Leadership vs. Managing: Be the Grandfather

41:00 - Get Young: Benji’s Mindset Shift for Building Culture

43:00 - Branding, Swag & the Piecework Future

46:00 - Rapid Fire: Benji’s Top Advice

53:00 - AI Tools That Are Changing the Game

57:00 - What Every Contractor Should Do This Week

59:00 - What Is LANA? The AI Tool Built for Landscapers

1:00:00 - Final Thoughts + Where to Find Benji

 Follow Benji Carlson & Leanscaper

Website: leanscaper.com

Instagram: @leanscaper

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🧰 CONTRACTOR BUSINESS SCHOOL

If you’re serious about building a profitable, structured contracting business without the chaos, this is your shot. Get the tools, insights, and mentorship you need to level up—on YOUR time, at YOUR pace.

https://contractorbusinessschool.com/

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== Rate the Podcast ==

Help your fellow contractors find the podcast! Please leave a rating/review.

Apple Podcasts

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In this episode, Tim and Derek break away from the usual sales-focused content to explore deeper, more personal aspects of life as a contractor. They reflect on the evolving direction of the podcast, emphasizing the importance of authenticity, vulnerability, and addressing the challenges that affect both business and personal life. From parenting and emotional triggers to frustrating bank experiences, this episode dives into how life’s realities shape us as leaders and business owners.

In this episode, Tim and Derek discuss:

• Reframing the podcast to encompass more than just sales – diving into life, leadership, and personal growth
• How self-perception and emotional baggage, like feelings of abandonment or laziness, impact business performance
• The importance of acknowledging personal struggles and their ripple effect on professional success
• A powerful story about Tim’s emotional response to his kids' first day of school and the realization of past wounds
• How tribe and community, like Battleground, can help contractors feel less alone
• Tim’s frustrating banking ordeal and how his daughter’s advice changed his approach
• The importance of grace – for others and ourselves – in handling mistakes and miscommunications
• Respecting different perspectives and the value of empathy in both business and relationships

Links from the episode:

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🛡️ Join us in BATTLEGROUND

Everything your contracting business needs in one comprehensive program. Three main focus areas: Leadership, Communication, and Numbers. For more info visit:

https://thecontractorfight.com/battleground

💰 You didn’t become a contractor to struggle financially.

Download our worksheet and start calculating a 50% gross profit on every job. It’s time to get your shit together!

https://thecontractorfight.com/50/

🎥 Explore over 1,400 free videos on Contractor Fight TV:

https://www.youtube.com/c/TomReber

💬 Join over 18,000 contractors in the free Facebook group:

https://thecontractorfight.com/facebook

== Rate the Podcast ==

Help your fellow contractors find the podcast! Please leave a rating/review.

Apple Podcasts

Spotify