The Journey from Entrepreneur to CEO

by | Jun 5, 2015

Every now and again, I enjoy spending a little time reflecting on where I am and where I have come from.

For me, one of the most major changes has been from entrepreneur to chief executive officer. As an entrepreneur, over the last several years I’ve been very interested in growth – and not just any growth, but fast growth. From 2011-2014 The Newsletter Pro has grown by just under 3,000 percent. As the saying goes, “I feel the need … the need for speed” (Maverick and Goose, Top Gun).

About a year ago my team (and my entrepreneurial self) made the decision that we wanted to be the largest print newsletter company in the world. We did a bit of research and estimated if we were mailing 1 million pieces of mail per month, we would easily hit our goal. That BHAG (Big Hairy Audacious Goal) set us down a path that has been one of the most challenging in my professional career.

I didn’t know this at the time, but to hit our goal, I was going to have to make major changes to who I am and the way I manage and run a business. I was going to have to adjust some of my thinking and leadership style from a “shoot from the hip” entrepreneur to a CEO and manager of managers. On this journey (of which I am still firmly in the middle) I have had to realize my shortcomings and adjust a ton. Here is a brief list of my findings:

  • I am likely the reason for the delay.
  • I can’t do it all.
  • I can’t approve it all.
  • I don’t know it all.
  • There are people who can do it better than I can.
  • There is a give and take with all relationships.
  • Sometimes others have to win (or at a minimum, be heard).
  • I need to take on tasks and projects others can do.
  • I do not have to be the last person to leave the office.
  • My team wants us to succeed, and if I get out of the way and trust them, they can do great things.
  • The mission and vision are bigger than any single person (including me).
  • Systems rule!
  • Slow and steady changes win the race. And the bigger you get, the more that is true.
  • I am the investor in this business and need to operate as such.
  • Culture matters.
  • Your team matters.
  • When I first started out, the business revolved around me, but as we have grown, I have had to realize that there is no “I” in The Newsletter Pro.

Not too long ago, I sat down by myself and looked at all the changes the company and I were going through. I then considered all the changes we likely will have to go through in the future. The purpose of this was to decide if all this change was what I wanted for my business and my life.

I feel it is a question not enough people ask.

The decision wasn’t easy, mainly because changing is hard. Ultimately I decided that growing and changing is exactly what I want. I want to grow as an entrepreneur and ultimately into a successful CEO.

A word of caution for those who don’t want to change:

I have watched a few companies – clients of The Newsletter Pro – come and go because the entrepreneurs have decided to fight against being CEOs. These entrepreneurs either don’t realize they need to change or they simply don’t want to.

There comes a point where you MUST make the change or you will have to be okay with and happy with your business where it is presently. A good rule of thumb is between the 2-million and 4-million mark in sales. If you don’t start to transition from entrepreneur to CEO, but still insist on growing, as with the majority of businesses, yours will likely turn from something that is fun and exciting to something that is a constant struggle and not enjoyable.

I’m watching a Red Alert Client (our code name for someone who is likely going to cancel our service) right now. This client is super smart and successful. From what I can tell, he is an amazing provider for his service. My guess is he is doing between 2.5 million and 3 million in revenue, but he can’t let go. Because of that, his business is likely in some of degree of stagnation, decline, or at a minimum, he is (or soon will be) miserable. This client must stamp his approval on everything at every turn. He doesn’t even trust his own team. My guess is he won’t be a client much longer. Of course we have identified that he is in our “danger zone” and will work to help him, but my experience tells me that it is a 50/50 chance he survives as a client. There just is no way he can stamp his approval on every area of his business, as well as the newsletter, given how busy he is. Ultimately he will decide to let it go or he will quit. If he quits, it will be both our loss and his.

As an entrepreneur or CEO, our job is to make the hard decisions; our job is to improve and change both ourselves and our business. There will be a point where you have to decide if the sacrifice is worth it or not. For me and my team, I have decided that even though the journey is and has been difficult, the destination is worth the sacrifice.


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