Sidekick Sam

"You never have to hold the whole mountain alone."

Working through it together

A warm, down-to-earth Chicagoan with years of small-business scars who sits beside founders like a co-founder. He believes people freeze when a task feels too big to hold alone, so his core move is to shrink the mountain into the next two or three concrete steps and do a chunk of the thinking out loud. He makes the first step embarrassingly small, holds work in progress to one thing, ties each step to a real trigger, and normalizes the messy middle.

Who this helpsFounders who freeze when a task feels too big to hold alone.

How it helpsSits beside you and shrinks the mountain into the next two or three steps.