What does the first year of building a roofing company actually look like when there is no guaranteed pipeline, massive team, or proven playbook?

In this episode of The Roofing Millionaires Podcast, Muhammad Faiz sits down with Tyler Addison, founder and general manager of Big League Roofing in Northeast Georgia.

Tyler started Big League Roofing in June 2025 after learning the industry as a roofing sales representative. Before roofing, he played professional baseball, worked in law enforcement for nearly ten years, and built a successful baseball-training business.

That background shaped how Tyler now approaches leadership, pressure, failure, and building a team.

Tyler explains why he still knocks doors, climbs roofs, handles customer conversations, and trains new representatives beside him. He believes roofing owners cannot expect their salespeople to face rejection and generate opportunities if they are unwilling to do the same work themselves.

He also discusses his biggest first-year hiring lesson. After initially trying to fill canvassing positions with whoever was available, Tyler realized that more bodies did not automatically create a stronger company. He now prioritizes quality over quantity and wants representatives who can build homeowner relationships from the first knock through completion.

The conversation also explores the financial decisions involved in building a young roofing company. When choosing between a newer wrapped truck and a dump trailer, Tyler invested in the equipment that could improve jobsite control, reduce operating expenses, and strengthen margins.

Tyler shares why a roofing company must prepare its production and operations before chasing more volume, why he does not teach rigid door-knocking scripts, and how genuine human connection helped him sell before he had yard signs, door hangers, or complete company uniforms.

They also discuss lead-generation services, choosing mentors carefully, the “snake oil” sold to new roofing owners, learning from a failed business partnership, operating through fear, and remaining resilient when the pipeline becomes uncertain.

This is not a conversation with someone claiming to have roofing completely figured out. It is an honest look at an owner still building, learning, correcting mistakes, and showing up every day.

In this episode:

* Tyler’s journey from professional baseball to roofing

* How law enforcement shaped his leadership

* Starting Big League Roofing in June 2025

* Competing against larger and cheaper roofing contractors

* Why Tyler does not teach sales scripts

* Building genuine connections at the door

* Why roofing owners must lead from the front

* Training inexperienced roofing representatives

* Allowing employees to fail forward

* Preparing a company before pursuing more volume

* Choosing a dump trailer over a newer truck

* Tyler’s experience with lead-generation services

* The snake-oil problem in the roofing industry

* Choosing the right mentors

* What a failed business partnership taught him

* Why the canvasser model did not work for his company

* Choosing quality over quantity when hiring

* Operating through pressure and uncertainty

* Building something meaningful instead of chasing a title

Learn more about Big League Roofing:

https://www.bigleagueroofs.com/

Subscribe to The Roofing Millionaires Podcast for honest conversations about roofing sales, leadership, company culture, marketing, and building a contracting business.

#RoofingBusiness #RoofingPodcast #RoofingContractors

Roofing contractors are making costly mistakes that can destroy a growing roofing business—even when the company has plenty of work.

In this episode of Roofing Millionaires, Ryan Holliday shares the biggest lessons he has learned from years in the roofing, insurance, payments, and technology industries. We discuss why contractors need to answer the phone, manage cash flow, track the right numbers, maintain financial reserves, and stay open to new technology. Ryan also explains how AI is transforming insurance claim analysis and why contractors who refuse to change could fall behind.

You’ll learn why taking on too many roofing jobs can create a cash-flow crisis, why 3–6 months of runway can matter, and how AI may change the future of insurance claims.

If you own, manage, sell for, or work in a roofing company, this conversation is packed with practical lessons for growing a stronger business.

Connect with Muhammad Faiz:

https://www.facebook.com/muhammadfaiz99/

theroofingmillionaires@gmail.com

Subscribe to The Roofing Millionaires Podcast for direct conversations about roofing, insurance claims, business growth, technology, leadership, and the realities of running a contracting company.

⏱️ YOUTUBE CHAPTERS:

00:00 The Roofing Mistakes Contractors Ignore

02:06 Welcome to Roofing Millionaires

02:58 Meet Ryan Holiday

04:07 From Roofing Sales to Entrepreneurship

08:22 Why Contractors Resist Technology

09:44 The Contractor's Math Problem

12:40 How AI Is Changing Claim Audits

15:19 AI vs. Humans: Who Wins?

17:27 The Biggest Mistakes Roofing Contractors Make

20:20 Why Answering the Phone Matters

22:04 The Cash-Flow Problem

23:32 Why Contractors Need 3–6 Months of Runway

26:07 The Danger of Taking Too Many Claims

27:22 Building Inc. From the Ground Up

33:10 How to Create Demand for New Technology

41:15 Are Roofing Conferences Worth It?

45:30 Ryan Holiday's Definition of Success

51:07 How Health Changed His Perspective

53:00 Final Lessons on Business & Life

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Is FORTIFIED roofing being oversold, or does the roofing industry’s resistance have more to do with cost, change, and accountability?

After our first conversation generated both support and pushback from roofing contractors, Muhammad Faiz sits down again with Fred Malik from @IBHS_org FORTIFIED. This time, Muhammad brings Fred the objections and difficult questions roofers have raised about the program.

They discuss whether FORTIFIED is simply another certification layer, whether strong building codes should already be enough, and why homeowners should pay more for third-party verification when their contractor claims to be following every required standard.

Fred also addresses questions about the long-term performance of sealed roof decks, tapes, membranes, and adhesives under heat and moisture. He explains the different sealed-roof-deck methods permitted under FORTIFIED and what contractors must do when a FORTIFIED roof reaches its next replacement cycle.

Finally, Muhammad asks Fred for a practical example of a homeowner who should not invest in FORTIFIED and whether contractor resistance may ultimately be resistance to greater accountability.

This is not a FORTIFIED sales presentation or a roofing-contractor takedown. It is a direct conversation about roof performance, building codes, third-party verification, insurance incentives, installation quality, and what homeowners are actually paying for.

In this episode:

* Is FORTIFIED roofing being oversold?

* Why some contractors see it as unnecessary certification

* Whether homeowners will pay more for roof resilience

* Why FORTIFIED matters outside coastal hurricane markets

* How wind, hail, and wind-driven rain affect roof systems

* Whether sealed-roof-deck tapes and adhesives last

* What the available long-term field evidence shows

* Code-compliant roofing versus third-party verification

* Whether homeowners are paying for better roofs or better paperwork

* Insurance incentives and FORTIFIED grant programs

* Who homeowners should trust when contractors disagree

* FORTIFIED’s positioning problem within the roofing industry

* What happens during the next roof-replacement cycle

* Whether FORTIFIED benefits IBHS more than homeowners

* The most common objections Fred hears from contractors

* Who should—and should not—invest in a FORTIFIED roof

* Accountability and the future of roofing standards

Chapters:

00:00 Highlights

02:03 Introduction

02:51 FORTIFIED reaches 100,000 designated homes

05:32 Is FORTIFIED being oversold?

08:46 Sealed roof decks and hurricane zones

19:55 Strong building codes versus FORTIFIED

29:01 Who should the homeowner trust?

36:27 What happens during the next roof replacement?

41:59 Who benefits most from FORTIFIED?

50:37 Who should not invest in FORTIFIED?

Learn more about FORTIFIED and IBHS:

https://fortifiedhome.org/

https://ibhs.org/

Connect with Muhammad Faiz:

https://www.facebook.com/muhammadfaiz99/

theroofingmillionaires@gmail.com

#FORTIFIED #RoofingPodcast #RoofingContractors