Richmond Griner of Wag Works chats with Alan Wieder in Part Two of this series, exploring the evolution of Crappily Drawn Pets and how a simple idea turned into a growing, highly personal art business.

Building on the shift explored in Part One, Alan shares how offering to poorly draw pets on Instagram quickly revealed real demand. What started as a lighthearted concept turned into something much bigger, as pet owners connected with the humor, personality, and individuality behind each piece. He walks through how the idea took shape and began gaining traction.

The conversation explores the realities of building a creative business rooted entirely in custom work. Each drawing is unique, requiring detailed communication, reference photos, and thoughtful decisions around composition and captions. Alan breaks down his process from initial concept to finished piece, along with the time, energy, and attention that go into every commission.

As demand increases, the discussion also touches on the challenges of scaling. Alan reflects on pricing adjustments, managing workload, and the possibility of bringing on help in the future, all while maintaining the style and quality that define the work.

At its core, Crappily Drawn Pets blends humor, storytelling, and a genuine love for animals, creating something that resonates well beyond the drawing itself. As the business continues to grow, Alan’s journey highlights how leaning into authenticity and connection can turn a creative outlet into a sustainable business.