Ask Me Anything: Contractor Edition

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In this Q&A episode, Dmitry Lipinskiy answers questions directly from roofers and entrepreneurs about branding, hiring, and the future of the roofing industry.

He starts by tackling a simple but common question — should you put your phone number on your truck? From there, he dives into deeper topics like where the industry is headed over the next decade, the impact of private equity, and why companies like Erie and Best Choice Roofing are thriving even when they ignore typical “influencer” advice.

Dmitry also shares what he would do differently if he were starting over in 2025, how to build brand trust faster, and the single most important factor that’s kept him successful over the years.

For small contractors, he explains how to make your first hire, the balance between personal and company branding, and how to combine your business name with a stronger brand identity. He wraps up with timeless advice for anyone dreaming of starting their own roofing company.