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.

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