The Napkin Business Plan: How the Best Deals Really Get Done

Complexity Is the Enemy of Execution

I've negotiated multimillion-dollar real estate deals, acquired restaurants, launched software platforms, and partnered with national vendors like SpotOn and QuickBooks. Want to know what the worst deals had in common?

Too many lawyers in the first meeting. Too many slide decks. Fifty pages of financial models pretending to predict what's going to happen three years from Tuesday.

The deals that actually made money, built lasting friendships, and changed lives? Almost every single one was sketched out on a waffle house napkin or a coffee shop table.

The Three Napkin Questions

Whenever I sit down with an entrepreneur or potential partner, I only care about three things:

1. What is the real problem we are solving, and does anyone actually care enough to pay for it?

2. Can both of us make money without either party feeling taken advantage of?

3. Can we look each other in the eye and shake hands knowing we'll honor our word when things get messy?

If you can't answer those three questions on a single napkin, no 40-page pitch deck is going to save you.

Keep It Simple, Keep It Real

Don't let consultants convince you that business has to be complicated. Clarity wins. Character wins. Keep your word, do what you said you would do, and leave room for the other guy to win too.