The First Conversation I Have With Anyone Starting a Dream Business

Published on August 7, 2026 at 3:18 PM

Almost everyone who comes to me with a dream business starts the conversation the same way — talking about the idea, the passion, the thing they're good at. I let them finish, and then I ask a question that usually catches them off guard: “Who is this for, and what will they actually pay you for it?”

It's not meant to deflate anyone. It's meant to move the conversation from a dream to a business, because those are two different things that require two different kinds of planning. A dream needs enthusiasm. A business needs a customer, a price, and a way to keep the lights on while it grows.

Once we've answered that question honestly, the rest of the conversation gets easier — entity structure, startup costs, systems, pricing. But it all builds on that first, unglamorous question. Skip it, and you're building on excitement instead of a foundation.