$1.8M in Year One: The Roofing Playbook No One Explains

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Most people want the upside of entrepreneurship… but they don’t want the loneliness, the pressure, or the discipline it demands.

In this episode, I sit down with Andrew Matson, owner of Homecourt Roofing, and we break down how his team did $1.8M+ in revenue in year one — plus the real mindset and operating decisions behind it.

We talk about the truth behind W2 “security,” why 1099 sales creates a totally different kind of person, what roofing margins actually look like, and why most people stay stuck because they’re just comfortable enough to not change.

We also get into the part people don’t say out loud: entrepreneurship can feel isolating — because your identity changes, your habits change, and sometimes your relationships change too.

If you’re in sales, building a service business, or trying to level up your income and discipline, this one will hit.

TIMESTAMPS
00:02 – The lonely part of entrepreneurship nobody talks about
00:07 – Why W2 “security” is tempting… and why it traps people
02:05 – “Six figures is nothing now” (why the math doesn’t math anymore)
02:23 – How I almost hit $1M my first year… then scaled past it
03:01 – Real roofing margins: gross profit vs real EBITDA
04:02 – 1099 vs W2 sales: the model that creates killers (and why)
06:13 – The real reason I’ll never go back to W2 (vacations + promotion)
10:19 – Why I spend on travel instead of flashy cars (and why it matters)
18:34 – How I build confidence in reps: vision + stacking small wins
31:09 – Identity death + why entrepreneurship feels lonely (and how I fixed it)

👉 If you want to connect with Andrew:
HomecourtRoofing.com
Instagram: @Homecourt_Roofing
Andrew: @Andrew_matson_KY