3 Unpopular Habits of Truly Successful Entrepreneurs

by / ⠀Startup Advice / March 13, 2013

Saying No and Other Skills of EntrepreneursI love listening to interviews with successful entrepreneurs.The nuggets and stories they share are like motivational crack. I can pop in a Mixergy or Mitch Joel interview on the way to a meeting and I’ll be bouncing off the walls once I get there!

What I really love is hearing about the habits these successful men and women developed out of necessity to reach their goals. Sure they innovated and adapted over time but it’s always the things they relentlessly stick to that always give credit to over any lucky break or chance encounter.

There are several popular habits that we hear over and over again but I don’t want talk about those. In this post I highlight three of the less glamorous habits that you just don’t hear about as much. These aren’t bad habits, they’re just tough and they’re some of the most essential habits to an entrepreneur’s success.


When I started my marketing company, I thought I was doing a disservice to my clients if every piece of every project wasn’t customized. It didn’t seem right that things got easier and I was charging the same rate.

I know, I know, stupid right? That’s the goal for most of us. But chances are your probably doing it in a part of your business as well and you just don’t realize it.

Most entrepreneurs can step back and identify the line between busy and productive but what happens when you’re in the thick of it and the line gets blurry? Take the amount of time you spend per week. For new business owners spending 60 to 70 hours a week feels like a rite of passage to becoming a true entrepreneur.

When I first brought on my business partner John, we easily put in 60+ hours a week. It was like a competition to spur us on. But that’s not a business, that’s not even a life! When we discovered that our model wasn’t scalable and we were doing the same things over and over that we could decide one once, establish a baseline and improve on from there, it blew our minds. We  literally took six months off to focus on building systems for every part of our business. From accounting to sales to client management, we examined every part of our business through this new lense.

See also  Challenges that Young Entrepreneurs Face

We started with zero knowledge of systemizing but scraped up every piece of information we could to create them. And then while doing that something crazy happened. Our focus started shifting from working in the business to working on the business. If we did something new, we wrote it down. We stopped guessing what to do next because we had already recorded it and instead of reinventing the wheel, we improved on what we did the last time.

The time it took to run our daily operations was literally cut in half. We were able to look at the big picture and immediately zoom in on different parts of the business with the perspectives we need to make the best decisions and zoom out again to see how those decisions affected each part of the business.

Saying “No”

During college, I discovered one of the most ineffective ways of communicating known to mankind: Powerpoint. Professors would paste chunks of the textbook into PowerPoint slides with clipart and call it class.  It drove me nuts! I tried to get the professors to talk about what might be a better way to communicate but that literally got me kicked out of class.

I knew there had to be a better way to communicate through presentations and became obsessed trying to find it. Thankfully I stumbled onto Garr Reynolds, Nancy Duarte  and several others presentation masters. I soaked up their strategies and immediately tried to apply my new-found skills! I offered it as a service and started creating presentations for local businesses. I was convinced that my passion would make up for my complete lack of design skills.


Even though my presentations were better than what most clients had, it was at that time I discovered what was to become my favorite book from Seth Godin, The Dip:  The little book that teaches you when to quit. In it he talks about the dip that every entrepreneur goes through. You start at the exciting point at the top of the dip where everything is new and exciting. You’ve just begun a project, a business or a new skill which is smooth sailing on the downhill part of the dip.

See also  5 Entrepreneurial lessons from Facebook CEO Mark Zuckerberg

But then you continue up the other side. That’s the part that separates the pros from everyone else. If it’s not something you plan on focusing all of your time and energy at becoming the best at, it’s useless to make the climb up the other side. Before reading that I felt like a failure for quitting presentations but in hindsight I’m so glad I did!

“Strategic quitting is the secret of successful organizations.” ~Seth Godin, The Dip

The best way to start with a great idea and turn it into a mediocre service is to do too many things for too many people. If that stings a little, it’s time to take inventory of where your time is going and if each piece is essential to your objectives.

BUT Saying no doesn’t have to feel like you are failing.

Here’s why:

It’s very simple to turn a “NO” into an opportunity. While in the process of discovering I needed to quit website design (another service I discovered wasn’t the best use of my time and talent), I didn’t just want to turn prospects away for coming to me to ask for a website. After all they were referred and deserved to be taken care of. So I decided to get a hold of every website designer and developer in my area and buy them coffee so I could have a quality list of people I could refer these prospects to.

During that time, I met dozens of awesome designers and developers that were able to do a far better job than I could ever do. Instead of sending them on their way, I was able to update prospects on what I was currently offering refer them to services I wasn’t offering. This gave me leverage and helped build my brand. It not only made it easier to say no but many of those people to this day are some of my best referral sources!


Before learning what it really meant, I associated the word mindset with a hokey self-help term that you used if something was wrong with someone. I know now that couldn’t be further from the truth.

See also  Developing Natural Audience – Lessons from the Creative World

The more I learn about mindset and the more I study great entrepreneurs I found one thing increasingly in common: They spent more time on their mindset than anything else.

I put off hiring my first employee for a year longer than I should have. Even though I had managed large projects with several freelancers it was completely different than an employee in my mind. I stressed, reasoned and justified why I wasn’t ready to hire yet. And I was right. I wasn’t ready.

But one day at the prodding of my business partner I wrote down all the reasons I wasn’t ready. It boiled down to a fear of committing to a full-time employee and not knowing how to train them. After talking through it, I got over the commitment issue by starting the person part-time and based on performance. And I found someone to teach me how to train them. Now that I had no excuses left,  the next day I had posted a job description and the next week I had hired my first employee. It took a week to actually do but a year to shift my perspective.

There are so many demands on our time and mental energy that if you don’t take the time to fill your mind back up with good stuff you’ll inevitably burn out. I learned a very simple but effective way of doing from my buddy John Morgan. He taught me to start every morning with something positive that helps set the tone for the entire day. Whether it’s a book, devotion or podcast, just 15 minutes can be the difference between an insanely productive day and a miserable one.

My goal isn’t to break the code of these three habits for you but rather explore them to the point you’ll think about how they can be applied or improved in your business.

So what about you? Which of these habits have made the biggest impact on your business?

Joel Widmer helps businesses make their marketing outcomes more predictable through content marketing strategies that fit their culture. He also enjoys longboarding and is on a search for the perfect hamburger. 

Image Credit: Shutterstock.com

About The Author

Matt Wilson

Matt Wilson is Co-Founder of Under30Experiences, a travel company for young people ages 21-35. He is the original Co-founder of Under30CEO (Acquired 2016). Matt is the Host of the Live Different Podcast and has 50+ Five Star iTunes Ratings on Health, Fitness, Business and Travel. He brings a unique, uncensored approach to his interviews and writing. His work is published on Under30CEO.com, Forbes, Inc. Magazine, Huffington Post, Reuters, and many others. Matt hosts yoga and fitness retreats in his free time and buys all his food from an organic farm in the jungle of Costa Rica where he lives. He is a shareholder of the Green Bay Packers.


Get Funded Faster!

Proven Pitch Deck

Signup for our newsletter to get access to our proven pitch deck template.