← All Insights
Insights · Sales & Competition

How I Beat the Biggest Brand in the Room

Draft — pending Dean's review before publishing.

Let me tell you how I ended up in a room full of presidents and CEOs, as one of only two people there who wasn't even a contractor for the dominant brand — and why they wanted to know what I was doing.

First, context: I'm not a roofer. I never was. My background is commercial construction and real estate development. I built houses. I taught people how to buy houses as investments. Then I went bankrupt, and I had nothing to do but go out and sell. My brother gave me a shot selling roofing for a brand almost nobody had heard of — Elk — and I sold it like my life depended on it, because it did.

I closed 70% of what I pitched. Selling the underdog. Against the giant.

The giant isn't the only option — that's just marketing

The dominant shingle brand spent years making everyone believe they're the only game in town. "North America's largest shingle manufacturer." Great. Big deal. Largest doesn't mean best — it means they out-marketed everyone into thinking they're the safe, obvious, only choice. And most contractors just believe it. They sell what they're told to sell and never question the story.

That belief is the opening. When the whole market has decided there's only one option, anybody willing to make a real case for a better-value alternative has room to win — because the customer has never actually heard the other side. I wasn't beating the giant on brand recognition. I was beating them on the fact that nobody else was even trying.

Why they wanted me in the room

Eventually the giant's own people brought me in — with my brother — because they couldn't figure out how a couple of guys selling a brand nobody knew were taking their business. My brother pointed at me: "I don't know what he did. Talk to him." What I told that room is the same thing I'll tell you: stop believing the market leader is the only choice, for you or for your customers. They're marketing to make you think that. It isn't true.

The real lesson isn't about roofing

I figured it out because I came at it as a business guy, not a tradesman. I didn't inherit the industry's assumptions, so I didn't respect the ones that were wrong. That's the actual edge — being willing to look at a "settled" market and ask why everyone's so sure.

Whatever business you're in, there's a dominant player everyone treats as inevitable, and a story the market accepted without checking. Find it, challenge it, and make the case nobody else is making. That's how the unknown brand wins the room.

Selling against a giant in your market? Schedule a conversation →