Five biggest mistakes I’ve made as an entrepreneur

biggest mistakes I've made as an entrepreneur

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.

100 percent human contentBy 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.

The darn thing worked. We were ready to take the system to the world.

An entrepreneur wears many hats, and the hat I hate most of all is sales. I’m terrible at sales because I’m impatient.

Literally, every company that saw our demonstration was interested in the product. But the sales process exhausted me. For example, the day I was going to sign a contract with Oracle, I was informed that the procurement manager had left the company and I needed to start the process all over again. At every account, I faced an endless string of delays …

  • Unexpected budget cuts
  • Departments being disbanded
  • Bosses getting fired

This was not bad luck. This is simply the typical B2B sales process, which requires endless patience! And I hated it. Every minute I spent time spinning my wheels on sales, I thought about everything I would prefer to be doing … which was pretty much anything other than this big waste of time.

So after about a year and a half, I pulled the plug. I lost a ton of money on this experiment and learned the painful lesson that when it came to selling, I sucked. One of the biggest mistakes I’ve made as an entrepreneur was pinning my success on an activity that I didn’t enjoy. I’ll never put myself in that position again. Don’t do the work you despise.

2. Marketing to the wrong audience

biggest mistakes I’ve made as an entrepreneur

Early in my “second career,” I was known as a go-to guy for social media tips and tactics. I wrote bestselling books on Twitter, blogging, and social media strategy, for example.

But I grew out of this. After a few years, I was making most of my money from consulting about strategy, teaching about marketing, and public speaking.

I had outgrown my audience but only realized this when I read Evelyn Starr’s book Teenage Waste Brand. This book examines the lull that occurs in brand adolescence, and that is exactly what had happened to me.

I had to re-align my message with a different audience, and that is still a work in progress!

3. Complacency

The first quarter of 2020 was the most successful of my career. And then, we all know that happened in March of that year. When the pandemic hit, my entire business crashed to zero in about 48 hours.

I was lamenting to a friend how sad I was that this rewarding and profitable career so easily went “poof!” and he asked me, “when you were having that great success, were you innovating?”

The answer was “no.” Business was coming in to me so easily that almost every phase of my business had stagnated. I wasn’t building new products, my website was outdated, and I overlooked basic marketing fundamentals like an email strategy.

I had failed to look up from my entrenched practices and adjust to the changing world. Success had made me complacent.

I’m still rebuilding and moving forward, but about one-third of my income now derives from revenue streams that did not exist before the pandemic.

4. Following my heart instead of my head

biggest mistakes I’ve made as an entrepreneur

Several years ago, I invested time and resources in a start-up. This relationship had more red flags than a parade in Moscow. I knew deep down that success was unlikely, but I liked this entrepreneurial partner so much that I followed my heart.

I ignored the accumulated wisdom of my life and wasted a lot of energy on a venture that was probably doomed from the start.

Sometimes, it’s OK in business to follow your heart. At least for me, that’s where the fun and creativity occur. But it’s not OK to ignore your own intellect and take your business down the wrong path. This was a gigantic waste of time that should have been avoided.

5. Becoming undisciplined

This is my most recent challenge.

From the outside, many people marvel at how much I accomplish. I’m speaking, teaching, consulting, and I just published my tenth book.

The key to this success is discipline. I have three core activities in my business, and if I’m asked to stray outside those boundaries, I either say no or find a way to delegate it to somebody.

Over the past year or so, I’ve been crushed by not following this practice.

Part of this is because I’m a nice guy, and I want to personally say yes to every request for help. But it’s just become too much, and I’ve been dragged into activities that have zero benefits for me or the business.

An example: I receive several books each week from an author wanting me to promote it for them. The book comes with a sweet personal note and an appeal for help. I’m sympathetic because not long ago, I was a new author looking for support. But just the act of creating and posting videos is a distraction, and I can’t delegate to somebody until there is a Mark Bot ™.

Stress doesn’t come from being busy. Stress comes from devoting too much time to activities that don’t make you come alive.

The next biggest mistakes!

I suppose five years from now, I’ll be writing a new post with five more mistakes I’ve made as an entrepreneur!

My teacher and mentor Peter Drucker used to say that it’s OK to make mistakes as long as you don’t dig yourself into a hole so big that you can’t get out.

So far, I’ve succeeded in following Dr. Drucker’s advice! I’ve been able to recover from every mistake.

As I reflect on the biggest mistakes I’ve made as an entrepreneur (so far), it’s disappointing that they all could have been avoided if I had just used common sense. Perhaps part of the entrepreneurial journey is discovering your own common sense!

Mark Schaefer is the executive director of Schaefer Marketing Solutions. He is the author of some of the world’s bestselling marketing books and is an acclaimed keynote speaker, college educator, and business consultant.  The Marketing Companion podcast is among the top business podcasts in the world. Contact Mark to have him speak at your company event or conference soon.

Follow Mark on TwitterLinkedInYouTube, and Instagram.

Illustrations courtesy MidJourney. 

All posts

The Marketing Companion Podcast

Why not tune into the world’s most entertaining marketing podcast!

View details

Let's plot a strategy together

Want to solve big marketing problems for a little bit of money? Sign up for an hour of Mark’s time and put your business on the fast-track.

View details

Share via