The First-Time Founder Playbook: 20 Entrepreneurship Rules To Live By

Nicolas Cole Twitter

In addition to writing, I love bootstrapping companies.

Over the past 5 years, I have built multiple 6-figure side-hustle businesses and two 7-figure businesses, including:

• Category Pirates: a paid business newsletter on Category Design & Category Creation.
• Digital Press: a ghostwriting agency exclusively for founders, executives, investors, Grammy-winning musicians, professional athletes, and more.
• Ship 30 for 30: a cohort-based digital writing program for people who want to learn how to start writing online.

However, I remember what it was like being a first-time founder.

It’s hard.

You don’t know what you don’t know, and finding your way forward is a bit like being blindfolded drunk in a pitch-black forest and being asked to find your way out.

Which is why I wanted to assemble a short playbook for other first-time founders.

These are 20 rules you should live by—if you want to make it out alive:

1. Build in public

Too many founders want to build “in stealth” — so they can do a grand reveal to the world.