Five biggest mistakes I’ve made as an entrepreneur

Mark Schaefer
6 min readMar 21

This year I’m trying to get a little more personal on this blog and peel back the curtain on some things going on in my business and life that might be relevant to you. A few weeks ago, I talked about the biggest success of my career. Today I’ll balance that out with five mistakes I’ve made as an entrepreneur.

I fail a lot. Everybody does. But the failures I’m highlighting today are special because I should have known better. Today I present to you my five dumbest mistakes.

Setting the stage

First, a little background.

I’ve had two distinct careers. For the first half of my career, I was a marketing executive for a Fortune 100 company. But more likely, you know me as an entrepreneur, speaker, consultant, teacher, and author — and that career started about 15 years ago.

As I look back on my life, the biggest flubs I made in my corporate career were probably political. Sometimes I had difficulty following corporate norms when it led to waste and non-productive work. I guess that was the entrepreneur in me trying to get out. That drive also led to my biggest successes in the corporate world, by the way!

The biggest mistakes I’ve made as an entrepreneur come from straying from my core competence. Here they are:

1. Doing work that I despise

In 2015, I wrote a book called The Content Code, which provided a map on how to create content that was actually seen and shared (most corporate content just sits on a website and is never even viewed … a big waste of money!). By the way, this book still holds up today. I would change very little.

By cobbling together research, systems, and content patterns I described in the book, I developed an algorithm that could predict the viral potential of content. By applying this assessment to your content and your competitors, you could devise a framework for content marketing success and a leading indicator for sales.

I pulled together a team to support a new company that would bring this idea to the world. We beta-tested this algorithm with IBM, a London media company, a boutique wealth management firm, and a massive data processing company.

Mark Schaefer

Keynote speaker, marketing strategy consultant, Rutgers U faculty and author of 10 books including KNOWN, Marketing Rebellion, and Belonging to the Brand!