One of the biggest mistakes roofing contractors make happens early — their first hire.

In this episode, I break down who you should hire first in your roofing business, who you should absolutely avoid hiring too early, and why getting this decision wrong creates years of stress, wasted money, and stalled growth.

If your business still depends heavily on you for sales, phones, scheduling, or finances, this episode will help you make a smarter move and build a company that doesn’t fall apart when you step away.

Hiring your first employee is one of the most important decisions you’ll ever make as a roofing contractor — and it’s also where many contractors go wrong.

In this episode, Dave Sullivan explains why hiring a salesperson too early is usually a mistake, and why your first hire should focus on removing you from the day-to-day chaos, not adding more volume you can’t support.

Dave walks through real-world examples from his own business and from contractors he coaches, showing how the wrong first hire leads to confusion, poor cash flow, and burnout. He explains how outsourcing and administrative support can often be a smarter first step than hiring full-time sales or production roles.

This episode gives you a clear framework to decide when you’re ready to hire, who to hire first, and how to build systems that support growth instead of magnifying problems.

• Your first hire should buy back your time, not add complexity
• Hiring sales too early usually creates more problems than profit
• Systems must come before scaling
• Administrative and operational support often delivers the fastest ROI
• Clear roles and expectations prevent hiring regret
• The goal is a business that runs without you

00:00 – Introduction

04:17 – Why the First Hire Matters So Much

13:51 – The Mistake of Hiring Sales Too Early

24:21 – Outsourcing vs Full-Time Hiring

31:36 – Financial Clarity Before Growth

42:07 – Transitioning from Chaos to Structure

50:30 – Building a Business That Doesn’t Rely on You

https://theroofercoach.com

https://theroofercoach.com/resources

https://smasupport.us

https://useproline.com

Ruby Receptionists

SMA Support

Proline

👉 Download free tools and resources at

theroofercoach.com/resources

In this episode of The Roofer Show, Dave Sullivan sits down with Brian Huff, the guy behind Modern Roofing Group in Denver and Littleton, CO. Brian dives into his story of how he got into the roofing world and even started his own business right in the middle of the COVID-19 pandemic! He discusses how crucial it is to build a solid reputation and tackle financial hurdles, and how mastermind groups can be a game-changer for contractors. They chat about how Brian uses CRM systems to make things run smoother, keep up with follow-ups, and improve how they interact with customers. Plus, Brian shares some cool marketing strategies and why keeping an eye on ROI is so important. This episode is packed with great tips for contractors looking to grow their business and boost customer service, so tune in!

What you’ll hear in this episode:

• Importance of having a reliable Customer Relationship Management (CRM) system for roofing contractors
• Brian Huff's journey into the roofing industry and his experiences working for various companies
• Challenges of starting a roofing business during the COVID-19 pandemic with limited financial resources
• Significance of maintaining a strong reputation in a competitive market
• Value of networking and being part of a mastermind group for contractors
• Innovative strategies for business growth through technology and automation
• Lead generation techniques and the importance of quality leads over quantity
• Tracking return on investment (ROI) for marketing strategies and adapting to regional market conditions
• Use of automation in managing customer interactions and streamlining operations
• Importance of continuous learning and adaptation in the roofing industry for sustained success

Resources:

Connect with Brian Huff and Modern Roofing Group!

Modern Roofing Group, 

Call Brian! (720) 334-3449

Check out this episode on our Youtube channel at @DaveSullivanRooferShow" or use this link - https://youtu.be/N7F2wJVbfwk

Be sure to subscribe, like, and comment!

Set up a FREE strategy call with Dave and get a few tips on how you can improve your business: https://davesullivan.as.me/free-strategy-call

Interested in learning more about our 1-on-1 coaching, mastermind groups, or fractional CFO services? Email me or send me a text at (510) 612-1450.

No Plan? No problem. Download our FREE 1-Page Business Plan For Roofing Contractors: https://theroofershow.com/plan

The Roofer Show’s Vetted Sponsors

Check out this episode on our YouTube channel at @DaveSullivanRooferShow. 

Have RUBY answer your phones and tee up the sale by leaving a great first impression. Use this link to get up to $150 off your first month’s service: theroofercoach.com/ruby.          

Automate your follow-up process and close more sales with ProLine. Get started for FREE at https://useproline.com/. Use promo code “DAVE50” to get 50% off your first month’s service.

Most roofing contractors work hard, stay busy, and still feel like they’re stuck.

The problem usually isn’t effort — it’s clarity.

In this episode, I walk you through the Roofing Business Success Audit, a simple framework designed to help contractors identify what’s actually holding their business back. We cover the key areas that most roofing companies struggle with, including finances, leadership, systems, and personal decision-making.

This isn’t about adding more tools or chasing more leads. It’s about understanding where your foundation is weak so you can fix the right things, in the right order, and build a business that’s profitable, sustainable, and doesn’t depend entirely on you.

Running a roofing business without regularly auditing it is like driving without a dashboard — you might be moving fast, but you don’t really know where you’re headed.

In this episode, Dave Sullivan breaks down the Roofing Business Success Audit, a practical tool built specifically for roofing contractors and home service business owners. The audit helps you evaluate where your business stands today across several critical areas, including financial management, leadership structure, operations, marketing, and personal clarity.

Dave explains why so many contractors stay busy but never feel in control, and how a lack of clear systems and financial understanding often leads to stress, cash flow problems, and burnout. The audit uses simple yes/no questions to expose blind spots and spark honest conversations about what needs attention.

The goal isn’t perfection — it’s awareness. Once you know what’s broken or missing, you can prioritize fixes that actually move the needle instead of guessing or reacting.

This episode is a starting point for contractors who want more profit, more freedom, and a business that works without constant firefighting.

• You can’t fix what you don’t measure — clarity starts with honest assessment
• Profit problems usually come from system problems, not lack of work
• Understanding your financials is essential to making good decisions
• Clear roles and structure improve leadership and accountability
• Simple systems create smoother operations and better customer experience
• Knowing your key numbers helps you focus on what really matters

00:00 – Introduction to The Roofer Show

06:18 – Understanding Business Profitability

06:57 – Building a Strong Foundation for Business Success

15:10 – Starting Point: Understanding Your Business Today

19:43 – Personal Finance Education and Training

31:28 – Transitioning to Effective Business Leadership

33:45 – Financial Management Essentials

37:55 – Understanding Cash Flow and Financial Management

44:35 – Understanding Financial Statements and Marketing Budgets

49:02 – Optimizing Your Website for Sales

58:41 – Operations and Customer Engagement Strategies

01:03:20 – Analyzing Budget Versus Actual Results

• https://theroofercoach.com
• https://theroofercoach.com/resources
• https://smasupport.us
• https://useproline.com

• Ruby Receptionists
• SMA Support
• Proline

👉 Download the Roofing Business Success Audit at theroofercoach.com/resources

Today, host Dave Sullivan speaks with Emily May, the owner of M&M Roofing in Texas. Emily opens up about her inspiring journey, how she went from working as an ICU nurse to becoming a roofing entrepreneur. She discusses what it was like to acquire and grow an existing company, the hurdles she faced in breaking into the industry, and why educating customers is so important to her.

Emily also shares how she’s built a strong team and found ways to balance work and life. She emphasizes the need for strategic, sustainable growth, creative branding, and consistently prioritizing quality and integrity. Her story is packed with practical advice for contractors who want to grow their businesses while staying true to their values and supporting their teams.

What you’ll hear in this episode:

• Transition from nursing to roofing entrepreneurship
• Acquisition of an existing roofing company through seller financing
• Importance of marketing, branding, and technology in the roofing industry
• Strategies for business growth and expansion
• Challenges of hiring, training, and retaining quality employees
• Emphasis on customer education and transparency in roofing sales
• The role of networking and learning from industry peers
• Balancing work-life commitments and setting boundaries
• Importance of building a strong company culture and team investment
• Insights on maintaining quality and integrity in business practices

Resources:

Connect with Emily May

M&M Roofing

Get in touch with M&M Roofing.

M&M Roofing YouTube

Instagram

Facebook

Connect with Dave

Check out this episode on our YouTube channel at @DaveSullivanRooferShow or use this link - https://www.youtube.com/@DaveSullivanRooferShow

Be sure to subscribe, like, and comment!

Set up a FREE strategy call with Dave and get a few tips on how you can improve your business: https://davesullivan.as.me/free-strategy-call.

Interested in learning more about our 1-on-1 coaching, mastermind groups, or fractional CFO services? Email me or send me a text at (510) 612-1450.

No Plan? No problem. Download our FREE 1-Page Business Plan For Roofing Contractors: https://theroofershow.com/plan

The Roofer Show’s Vetted Sponsors

Automate your follow-up process and close more sales with ProLine. Get started for FREE at https://useproline.com/?via=roofercoach. Use promo code DAVE50 for $50 off your first month’s service!

Have RUBY answer your phones and tee up the sale by leaving a great first impression. Use this link to get up to $150 off your first month’s service: theroofershow.com/ruby.

SMA Support Services fills a need by empowering contractors to simplify and optimize their operational processes with virtual assistant services. Explore what a virtual assistant can do for your contracting business. Let SMA do the hiring, training, and onboarding. Check out SMAsupport.us (Tell them Dave sent you.)

For many roofing contractors, labor compliance is one of the most stressful — and misunderstood — parts of the business.

In this episode, I’m joined by labor and employment attorney Philip Siegel to talk about what really happens when ICE shows up at a roofing job site, what your rights are as a business owner, and how to protect yourself before a problem ever arises.

This is a must-listen for contractors who want to reduce risk, stay compliant, and avoid mistakes that can shut down a business overnight.

Labor shortages and immigration enforcement are realities every roofing contractor must take seriously.

In this episode, Dave Sullivan sits down with Philip Siegel, a labor attorney who specializes in the construction and roofing industries, to break down exactly what contractors need to know about ICE audits, I-9 compliance, and employment verification.

Philip explains the difference between a job-site visit and a formal audit, what contractors are legally required to do (and not do), and the common mistakes that turn manageable situations into costly disasters. The conversation also covers misclassification issues, documentation best practices, and how proactive self-audits can significantly reduce fines and liability.

This episode isn’t about fear — it’s about preparation. Contractors who have systems, documentation, and legal guidance in place sleep better at night and protect the long-term value of their businesses.

• ICE audits are increasing in construction and roofing
• Knowing your rights prevents costly mistakes during inspections
• Proper I-9 documentation is critical to business survival
• Self-audits can significantly reduce penalties and risk
• Misclassification issues often trigger deeper investigations
• Strong systems protect both profitability and peace of mind

00:10 – The Reality of Labor Challenges in Roofing

07:24 – Understanding I-9 Audits

11:23 – Common Compliance Mistakes

23:12 – Misclassification and Worker Status

27:22 – What Happens During an ICE Audit

32:44 – Protecting Your Business Proactively

41:42 – From Compliance to Stronger Systems

https://theroofercoach.com

https://smasupport.us

https://useproline.com

https://pjslaw.com

Ruby Receptionists

SMA Support

Proline

👉 Download free tools and resources at

theroofercoach.com/resources

Getting paid shouldn’t be the hardest part of running a roofing business — but for many contractors, it is.

In this episode, I sit down with construction attorney Alex Barthet to break down the legal and contractual mistakes that cause roofers to wait too long (or never get paid at all). We cover lien rights, contracts, payment timelines, and the systems contractors need in place to protect their cash flow.

If you’re tired of chasing checks and dealing with payment delays, this episode will give you practical steps to tighten things up and get paid faster.

Cash flow problems are one of the top reasons roofing contractors struggle — even when sales are strong.

In this episode, Dave Sullivan talks with Alex Barthet, a construction attorney who works extensively with roofing and home service contractors. Alex explains why many contractors unknowingly give up leverage before a job even starts and how simple contract language, lien rights, and documentation can dramatically improve payment speed and certainty.

The conversation covers how and when to send notices, why understanding lien laws matters even if you never plan to file one, and how contractors can protect themselves from stalled payments, scope disputes, and legal surprises. Alex also explains why having systems — not just good intentions — is critical when it comes to getting paid consistently.

This episode is about prevention, not conflict. Contractors who understand the rules and use them properly avoid stress, protect profit, and keep their businesses healthy.

• Getting paid starts with the contract, not the invoice
• Understanding lien rights gives contractors leverage — even if never used
• Clear documentation prevents payment disputes
• Delayed payments often come from weak systems, not bad customers
• Legal knowledge protects cash flow and long-term profitability
• Strong processes reduce stress and financial uncertainty

00:00 – Introduction to The Roofer Show

05:18 – Why Contractors Struggle to Get Paid

15:34 – Understanding Lien Rights and Notices

29:16 – Contract Language That Protects You

43:25 – Subcontractor and Payment Pitfalls

51:24 – Legal Systems That Improve Cash Flow

59:14 – Avoiding Litigation Through Preparation

https://theroofercoach.com

https://contractdetective.com

https://smasupport.us

https://useproline.com

Ruby Receptionists

SMA Support

Proline

👉 Download free tools and resources at

theroofercoach.com/resources

SEO is changing fast — and roofing contractors who don’t adapt are going to get left behind.

In this episode, I sit down with Aaron Hockel, SEO expert and founder of Roofing SEO Webmasters, to talk about how search is evolving from traditional Google results to AI-driven platforms like ChatGPT. We break down what actually matters for roofers in 2025 and beyond, what hasn’t changed, and where contractors are wasting time and money.

If you want more leads without chasing every new marketing trend, this episode will help you focus on the fundamentals that still drive visibility, trust, and sales.

The way homeowners search for roofing contractors is changing — but the fundamentals of SEO still matter more than ever.

In this episode, Dave Sullivan is joined by Aaron Hockel, a long-time SEO expert in the roofing industry, to discuss how contractors should think about search engines, AI tools like ChatGPT, and long-term visibility. Aaron explains why SEO isn’t about tricks or hacks, but about building authority, credibility, and clear messaging that both humans and algorithms understand.

The conversation covers how Google, AI search, and voice search are influencing buying behavior, why reviews and content matter more than ever, and how roofing contractors can position themselves as the obvious local expert. Dave and Aaron also discuss common SEO mistakes contractors make — including chasing rankings without tracking leads or ROI.

This episode is about clarity, not complexity. Contractors who focus on strong foundations, consistent messaging, and systems will win no matter how search technology evolves.

• SEO is evolving, but fundamentals like trust and authority still matter
• AI tools reward clear, helpful, expert-driven content
• Reviews and reputation are critical for visibility and conversions
• Contractors must track leads — not just rankings
• Strong branding improves both SEO and close rates
• Long-term strategy beats short-term SEO tactics

00:00 – Introduction to The Roofer Show

06:46 – How Search Is Changing for Contractors

15:40 – AI, ChatGPT, and the Future of SEO

22:23 – Topical Authority and Content Strategy

29:09 – Google Maps and Local SEO

37:08 – Reviews, Reputation, and Trust

44:22 – Branding and First Impressions

54:15 – Tracking Leads and SEO ROI

01:12:26 – Video, YouTube, and Visibility

https://theroofercoach.com

https://roofingseowebmasters.com

https://smasupport.us

https://callruby.com

Ruby Receptionists

SMA Support

Roofing SEO Webmasters

👉 Download free tools and resources at

theroofercoach.com/resources

Most roofing contractors think they’re making money — until they look at the numbers.

In this episode, I sit down with Michael Stone, one of the most respected voices in construction financial education, to break down one of the most misunderstood topics in roofing: markup vs. margin. We explain why confusing the two destroys profit, how contractors accidentally underprice jobs, and what it really takes to price work correctly.

If you want consistent profit instead of riding the gross profit roller coaster, this episode is required listening.

Pricing mistakes are one of the biggest reasons roofing contractors struggle — even when sales are strong.

In this episode, Dave Sullivan talks with Michael Stone about the financial fundamentals every roofing contractor must understand to stay profitable. The conversation centers on the critical difference between markup and margin, and why confusing these two concepts leads to chronic underpricing and cash flow problems.

Michael explains how overhead, job costing, and pricing discipline all work together — and why “industry averages” are dangerous if you don’t know your own numbers. Dave and Michael also discuss warning signs contractors miss, how profit fade happens over time, and why many businesses look busy on the outside but are bleeding internally.

This episode is about clarity. When contractors understand their numbers, they gain control — and control leads to profit, stability, and freedom.

• Markup and margin are not the same — confusing them kills profit
• Accurate job costing is essential for pricing correctly
• Overhead must be included in every pricing decision
• Gross profit should be consistent, not a guessing game
• Cash flow problems often start with pricing errors
• Knowing your numbers gives you control and confidence

00:00 – Introduction to The Roofer Show

05:37 – Why Contractors Fail Financially

12:37 – Understanding Markup vs. Margin

18:33 – Overhead and True Job Costs

30:22 – Accounting Red Flags and Embezzlement

36:35 – Gross Profit Margins Explained

45:51 – Job Costing and Financial Discipline

55:22 – Coaching, Mentorship, and Accountability

https://theroofercoach.com

https://markupandprofit.com

https://smasupport.us

https://useproline.com

Ruby Receptionists

SMA Support

Proline

Markup & Profit

👉 Download free tools and resources at

theroofercoach.com/resources

In this episode of "The Roofer Show," host Dave Sullivan interviews Jon Starry, owner of Steadfast Roofing in Tampa Bay, FL. Jon shares his journey from IT to roofing, highlighting the company’s rapid growth, the importance of in-house crews for consistent quality, and leveraging technology like CRM systems and virtual assistants. He discusses effective lead generation, job costing, and building a strong company culture. Jon also offers practical advice on cash flow management, sales incentives, and continuous learning, providing valuable insights for contractors aiming to grow and improve their roofing businesses. Tune in to hear more!

What you’ll hear in this episode:

• Transition from IT to the roofing industry
• Importance of customer service in business growth
• Lead generation strategies and techniques
• Building a strong online presence and utilizing SEO
• Significance of having a robust CRM system
• Managing cash flow and financial planning
• Tracking key performance indicators (KPIs) for marketing effectiveness
• Creating a positive company culture to retain talent
• Implementing effective project management and communication strategies
• Emphasizing quality control and consistency in work standards

Resources:

Steadfast Roofing

Check out this episode on our YouTube channel at @DaveSullivanRooferShow or use this link - https://www.youtube.com/@DaveSullivanRooferShow

Be sure to subscribe, like, and comment!

Set up a FREE strategy call with Dave and get a few tips on how you can improve your business: https://davesullivan.as.me/free-strategy-call.

Interested in learning more about our 1-on-1 coaching, mastermind groups, or fractional CFO services? Email me or send me a text at (510) 612-1450.

No Plan? No problem. Download our FREE 1-Page Business Plan For Roofing Contractors: https://theroofershow.com/plan

The Roofer Show’s Vetted Sponsors

Automate your follow-up process and close more sales with ProLine. Get started for FREE at https://useproline.com/?via=roofercoach. Use promo code DAVE50 for $50 off your first month’s service!

Have RUBY answer your phones and tee up the sale by leaving a great first impression. Use this link to get up to $150 off your first month’s service: ruby.com/roofershow.

SMA Support Services fills a need by empowering contractors to simplify and optimize their operational processes with virtual assistant services. Explore what a virtual assistant can do for your contracting business. Let SMA do the hiring, training, and onboarding. Check out SMAsupport.us (Tell them Dave sent you.)

Most roofing companies look the same — and that’s a problem.

In this episode, we talk about why being “just another roofer” is killing your close rate and driving your marketing costs up. Homeowners don’t remember average, and they definitely don’t trust it.

We break down what branding really means for roofing contractors, why brand isn’t a logo or a truck wrap, and how the right brand positioning helps you book more jobs without racing to the bottom on price.

If your roofing business relies only on leads and price to win jobs, your brand is probably forgettable — even if your work is solid.

In this episode, Dave Sullivan explains why branding matters more than ever in the roofing and home services world. With increased competition and rising advertising costs, contractors who fail to differentiate themselves blend into the noise and struggle to convert leads into signed contracts.

Dave walks through the real purpose of branding: trust, clarity, and confidence. He explains how homeowners make decisions, why familiarity beats features, and how consistent messaging across your website, trucks, proposals, and sales process creates credibility before you ever show up at the house.

This episode challenges contractors to stop thinking like tradespeople and start thinking like business owners — building a brand that attracts the right customers, supports premium pricing, and makes sales easier.

• If you look like every other roofer, homeowners will shop you on price
• Branding is about trust and clarity, not just logos
• Strong brands shorten the sales cycle and improve close rates
• Consistency across marketing and sales builds confidence
• Being memorable helps you compete without racing to the bottom
• A clear message attracts better customers and better jobs

00:00 – Introduction to The Roofer Show

05:10 – Why Most Roofing Brands Blend Together

12:45 – How Homeowners Choose Contractors

20:18 – Branding vs. Marketing: What’s the Difference

28:40 – Consistency Across Website, Trucks, and Proposals

36:22 – Pricing Power and Brand Trust

44:05 – How to Position Yourself in Your Market

https://theroofercoach.com

https://theroofercoach.com/resources

https://useproline.com

https://smasupport.us

Ruby Receptionists

SMA Support

Proline

👉 Download free tools and resources at

theroofercoach.com/resources