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

Nicolas Cole
8 min readMar 7, 2022
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.

Unfortunately, stealth =

  • Slower
  • Very expensive
  • Harder to iterate
  • More pressure to make it “perfect”

When you Build In Public, however, you get to iterate as you go. There is no need for a “grand reveal.” You’re building your product/service with your customers, together. You’re learning what works and what doesn’t in real time. And you are freeing yourself from the pressure of needing to emerge from the darkness with “the greatest product the world has ever seen.”

Don’t set yourself up for failure like that.

2. Always be “in beta”

Don’t ever think your startup will reach an end.

Don’t strive for “done.”

Even at 600,000 employees and $1.5 trillion in market cap, Amazon still operates as “it’s always Day 1.”



Nicolas Cole

100M+ Views | 5x Author | Co-founder of Ship 30 for 30 | Want to start writing online? Get the Ultimate Guide: