On the long and winding road of entrepreneurship…


Being an entrepreneur is not for the faint of heart. It is a constant barrage of stress, issues, fires and losses, balanced (only sometimes) with flickers of greatness and short-term wins along the way. I have heard it often compared to jumping out of an airplane and only first starting to build the parachute mid-air. I think that visual is a fair one.

We are living in a time, where it seems kind of cool to run your own business and I think it is seen as the easier option when compared to being an employee at someone else’s business. It is not, this I can promise you. Sure, calling yourself a founder and hanging out and not working all day is very easy. Actually creating an enterprise that is built to last and showing continuous growth year over year, is a very different task. If you want to win in that game you need to know that:

1. The buck stops with you: You are now responsible for all of the decisions. Entrepreneurs have an incredible opportunity to create something from nothing, which you cannot generally accomplish when working for someone else. With this upside, comes the downside of making all of the big decisions about what must be done, when and how. You can’t wait for things to happen, or for someone to tell you what to do, you must make them happen for yourself.

2. You must always be working on “the now” and “the later”: You need to execute efficiently on the day to day work, while also planning and prospecting for the future. As an entrepreneur, you have to project your mind forward and think about next month, quarter, year etc. Nobody else is out there bringing you new business, managing your renewals and developing the brand. It is grounding to know that what you do, or don’t do, today, will have an impact on your business down the line. This creates a sense of urgency and forces the winner to constantly put in the “extra reps” to produce better gains.

3. You have to have thick skin and be able to endure rejection: When you try and sell your products or services you are certain to hear a lot of no’s. It never feels good, but it is much more personal and harder to take when it is your own baby. You have to be able to set (and then stay) the course, despite the many rough water days that lie in your path.

4. You have to constantly be learning and tweaking: You can never have a “set it and forget it” mentality.  I think a lot of entrepreneurs want to set up their business, get it to a point where it is humming and then work less and enjoy the fruits of their labor. While that might be the case for some very lucky ones, that is definitely an outlier. For most of us, you need to be iterating, researching and modifying processes each and every day. You cannot get comfortable and can never put your feet up and relax. It is a constant uphill climb, and while it is ok to look down and be proud of what you have built from time to time, you do need to look upward nearly all of the time.

5. You must know your numbers:  While this is admittedly not my strongest skill, it is such an important element of success.  Meaning, if you aren’t watching cash flow and managing your pipeline religiously, it can be game over, real quick. You need to set substantial “reach goals” and drive towards hitting them from an offense POV constantly.  On the defensive side of the ball, you need to plan for potential puddles along the path and manage your overhead each month. I personally lean towards being more aggressive and investing in my people (compensation, perks, food, and fun) and marketing (website, collaterals, video), so I need to make sure I score a ton of points on offense to win my games.

8. You are always on: As an entrepreneur, especially one with employees and paying clients, it is an all the time thing. While you definitely have more control over your hours and location, you will always be thinking about the business. Usually, those thoughts are about what can go wrong and/or what you are not doing well. It is an interesting feeling of never being good enough, which is an uncomfortable and sometimes defeating view for most.  There is no reprieve, it is always there.

At the end of the day, you have to be totally focused and committed, super gritty and the kind of person who is ok with constantly being consumed by your brand and it’s success.  Plenty of people are in this role without these traits, and they will not make it long term. It doesn’t make anyone better or worse, it is just the way it is. It might take a very long time to build, and you might never feel as though you have truly succeeded. I can say that the road is long and winding, but beautiful and exciting too. I wouldn’t have it any other way…