How I Discovered The Importance Of Persistence And Learned To Annoy The Heck Out Of Everyone.
My nature is somewhere in between an introvert and extrovert. As a kid I was very shy, but I could also be a loud mouth and a leader amongst my friends. I guess when I was comfortable, I was an extrovert and when uncomfortable, I was an introvert. I was also very laid back, something I used to think of as a great quality. My motto was live and let live–you do what you need to do, and I will do what I need to do. This was a great motto for life, but when I started my own business, The Fresh Diet, I soon discovered that this attitude was counter-productive.
Although I am not a believer of micro-managing, I came to the realization that a laid back CEO isn’t going to cut it. As my business quickly expanded, I needed to expand with it. Staying away from the office because I didn’t like telling people what to do was no ingredient for success. I had to begin teaching myself how to become more persistent and annoying with my employees, customers and potential partners.
As an entrepreneur and eventually the CEO of 300 employees, I had to quickly learn how to speak up and get my message out. Whether that meant picking up the phone to try and get a customer to renew their meal delivery service, or cold emailing a reporter to pitch a story on our business, I had to teach myself to do whatever was needed even if I didn’t like it. Comfort is a luxury I used to tell myself, and it was a luxury I couldn’t afford. Unfortunately, looking back there is more I wish I had done if only I could have taken myself out of my comfort zone more often.
One of my biggest mistakes as an entrepreneur and CEO was not being around the office enough because I didn’t want to get involved in the office politics that come with the territory of a large organization. I would create out of town meetings just to avoid going into the office. This became detrimental to the growth of our business and management team and was a large part of why we eventually stopped growing. A CEO with his head in the sand can never see what is right in front of him or what is coming.
As I realized these personal failure traits I began to make changes and took a look deep inside myself for answers. Luckily I surrounded myself with great people, and one close friend in particular really made me understand what an entrepreneur needs to do. David Schottenstein, who successfully launched and sold his clothier company Astor & Black, was a shining example of a very important trait every entrepreneur needs in order to achieve real success. The key ingredient for him was to annoy the heck out of everyone.
After spending some time with David during working hours, I wasn’t surprised at how successful he was, but I was surprised that no one had put out a restraining order against him yet. His new start-up, the app ViewABill, allows small business owners to see their legal bills in real time — great for entrepreneurs but not as welcomed by law firms. Watching David get on the phone convincing lawyers to use his service for their clients gave me a quick education on Annoying 101. If the firm didn’t pick up his call because they already recognized his number, David would quickly ask me for my cell-phone to use since they would never recognize my number. What I learned from David was annoy, annoy and annoy some more.
I took this and put it into action in my daily routine. I decided that my passive personality was old news and the new me would be more aggressive. This was something I continue work on everyday and although I am out of my comfort zone, the more I do it the more comfortable I become with it. Unfortunately there is no switch you can just turn on to change your habits but the trick I learned was the more I do it the easier it becomes.
This has paid off already, helping me land an advisory position with a new start-up I was pursuing. Instead of sending an email to the founder and sitting back to wait for a response, I followed up countlessly by “annoying” him every day until he realized the value of having me on his team. Of course sometimes this approach can backfire as not everyone has the appetite for dealing with annoying people, but I believe the pros greatly outweigh the cons.
As entrepreneurs we all have different personality traits, some are good for business and some are bad. The best thing one can do for themselves and their business is to quickly understand their weaknesses so they can begin to change or bring in people that can do the “dirty” work for them. The first step to making that change is to identify the problem. For me that may have come too late for my first business, but now that I have made that change it is doing wonders for my future.
Originally published at www.forbes.com on April 24, 2015.