There's a version of success in roofing that looks great on paper and feels completely empty in real life. Corey Combes lived it.

Corey is the owner of Southshore Roofing and Exteriors in Tampa, Florida, a contractor with 30 years in construction who built his company to $22 million and then watched the thing he loved about his business quietly disappear.

In this episode, we don't talk about tactics. We don't talk about lead generation or closing ratios. We talk about what happens when a roofing business owner gets everything they chased and realizes that was the wrong thing to be chasing.

Corey gets honest about the spending trap that exposed itself when revenue dropped, why stepping away from customers was the beginning of losing his company's identity, what the transition from $22M back toward $8M actually felt like, and why he's now convinced that $8M at 15-20% net profit means more than $22M with a fractional CFO spending a month cutting expenses just to survive.

We also get into the Uncle Bill idea, that a roofing business in your community is more like the local farm everyone trusts than a corporation trying to scale. And what happens to that identity when you start running it like a machine that shouldn't need you.

This is one of the most honest conversations we've had on The Roofing Millionaires. If you've ever felt like growth was pulling you away from the reason you started - this one is for you.

What we cover:

- The spending trap that hits when revenue suddenly drops

- Why removing yourself from customer interactions kills your business's identity

- The difference between a business that can run without you vs. one you've abandoned

- What Corey actually lost when he scaled from $8M to $22M

- Why "run it like a machine" is incomplete advice and what the coaches selling it get wrong

- Redefining what scaling actually means for a roofing business

- The Uncle Bill principle, and why roofing was never meant to be Amazon

- Purpose vs. revenue as the metric that matters

- Financial discipline, fear, and the anxiety that comes from being over-leveraged

- The Florida market right now, consumer confidence, insurance, and what's coming

- Private equity - the good, the predatory, and what it's actually done to the industry

- Diversification as survival: why being a one-trick pony is dangerous right now

- The version of Corey that comes out the other side of this chapter

🎙️ Guest: Corey Combes | Owner, Southshore Roofing and Exteriors | Tampa, Florida

Timestamps

0:00 Highlights

01:33 How much have you changed since we last met?

08:02 A business should run like a machine?

16:37 A business that connects with customers

32:32 The role of purpose in a business

37:15 Future of the roofing industry and consumer behaviour

47:57 Is private equity a trap?

Subscribe to The Roofing Millionaires for weekly conversations with the contractors, leaders, and industry veterans who are building something that lasts.

-Website: https://www.theroofingmillionaires.com

-Instagram: https://www.instagram.com/theroofingmillionaires/

-Facebook: https://www.facebook.com/theroofingmillionaires/

#businessguide #roofingwork #theroofingmillionaires

In this episode of The Roofing Millionaires, I sit down with Rick Ringer - a 46-year roofing industry veteran, former sales team manager, supply-side expert, and author of the upcoming book Beating the Curve, for one of the most honest and experience-rich conversations we've ever had on this show.

Rick breaks down the concept of the learning curve, why contractors fall off it, why success itself is often what pulls them away from the basics, and what it actually takes to get back on track.

We go deep on why most roofing marketing fails, the 55 Mile Rule for yard signs, the real difference between sales and marketing, and why Rick believes one-call closing creates more tension than it closes. He makes the case for connection-based roofing over transaction-based roofing — and explains why going back to the basics might be the most sophisticated business strategy in today's market.

If you're a roofing contractor trying to figure out why growth feels harder than it used to or why the new things you're trying aren't working, this episode was made for you.

What we cover:

- The learning curve: what it is, why you fall off it, how to get back

- Why people leave what made them successful and what that costs them

- The 55 Mile Rule and visibility basics most contractors are ignoring

- The difference between sales and marketing — and why most marketing fails

- How to build a sales system that actually fits your business

- Why you should stop trying to sell everyone

- Pressure selling vs. multiple touchpoints — which actually converts

- Transaction-based vs. connection-based roofing companies

- Surviving price hikes, market shifts, and economic uncertainty

- Private equity's impact on the roofing industry

- How Rick plans to give back after 46 years in the game

Timestamps:

0:00 Highlights

01:31 Brief Intro

05:36 What has kept you going?

07:57 What is the learning curve?

18:06 Business owners only care about price?

29:37 The perfect sales system

41:55 Real function of marketing

48:35 Scaling a business

52:57 Transactions vs Connections

55:46 Advice for roofing contractors

🎙️ Guest: Rick Ringer | Ethical Building Solutions | Author of Beating the Curve (Coming Soon)

Subscribe to The Roofing Millionaires for weekly conversations with the contractors, leaders, and industry veterans who are building something that lasts.

-Website: https://www.theroofingmillionaires.com

-Instagram: https://www.instagram.com/theroofingmillionaires/

-Facebook: https://www.facebook.com/theroofingmillionaires/

#roofingcontractor #roofingwork #theroofingmillionaires

In this episode of The Roofing Millionaires Podcast, I sat down with Joe Stephens, owner of Sure Claims, to break down what’s actually happening behind the scenes when roofers handle insurance claims, supplements, and appraisals.

We talked about:

- Why supplement companies are often seen as “middlemen” — and when that’s true

- The 3 types of supplement companies (and why most roofers choose the wrong one)

- What really changes financially, operationally, and emotionally when you outsource

- When you should keep claims in-house vs bring in a supplement partner

- The moment your business starts breaking because of claims overload

- How poor systems and CRM usage silently kill your operations

- Real scenarios where roofers leave money on the table without realizing it

- The role of appraisals and where most contractors misunderstand them

🎯 Who This Episode Is For:

Roofing owners handling their own claims and feeling overwhelmed

Companies scaling past $1M–$5M and hitting operational bottlenecks

Sales managers stuck managing supplements instead of closing deals

Roofers trying to decide between in-house vs outsourced claims

Timestamps

0:00 Highlights

01:30 Brief introduction

02:31 Importance of supplement companies in roofing

08:39 Effect of supplement companies on revenue

16:59 Factors to consider before choosing a supplement company

23:08 Mistakes to avoid as a contractor

29:41 Quality Control and expectations from supplement companies

39:16 Appraisal process for claims

43:52 Strategies for customer coaching and CRM

📌 Key Question to Ask Yourself:

Are you running your claims process…Or is your claims process running your business?

If this shifts your perspective, share it with another roofer who needs to see this.

🔗 Connect with Joe Stephens:

Website: https://sureclaims.com/

🔔 Subscribe to The Roofing Millionaires Podcast for more practical, experience-based episodes that help roofers build better companies and stronger teams.

-Website: https://www.theroofingmillionaires.com

-Instagram: https://www.instagram.com/theroofingmillionaires/

-Facebook: https://www.facebook.com/theroofingmillionaires/

#insurancesupport #supplements #homeinsurance