top of page


Back when I was in elementary school, we use to read the Weekly Reader. 1992 was an election cycle, so it focused on the two primary candidates, George H. W. Bush and Bill Clinton. My teacher asked us if we could vote who would we vote for and why. Being poor black kids living in South Memphis, all of us chose Bill Clinton, and all of them said because that's who their parents like. I also chose Bill Clinton, but I took it a step further. I explained how the Bush tax plan only benefited people who made over $150,000 and how my parents made nowhere near that. I said that Bush does not seem like a bad guy, but his plan did not appear to help my family at all. That probably represented just about all of us that lived in South Memphis. My teacher went "holy crap" while my fellow students had that "what is he talking about" look on their face. Here's the thing, I didn't care what was said about me because I was in my element and I was strong in my conviction. My teacher asked how I knew this and I told her because my mom allowed me to stay up late at night to watch both national conventions. When you are an entrepreneur you have to just "let it fly" and let the chips fall where they may. Going the extra mile and doing the unexpected will unearth new opportunities for you and your business. How do you do that exactly? Here are a few ideas.

Set Clear Priorities

When in a business setting a roadmap is so important. From writing a business plan to a daily agenda, these activities put you on the path to success. As Tony Robbins would say, " clarity is power." When you are clear about what you have to do it is very easy to be bold. When you have clarity, you will not fall victim to doing things that are not in the best interest of the business. It will also allow you to know when something is the right opportunity for your business or when something may not be a good fit. When entrepreneurs lack clarity, they try to service the entire market. Clarity forces you to do one or maybe a few things very well. Remember this very important rule in business: BEING EVERYTHING = DOING NOTHING. This practice can lead to your customers being confused about what purpose your business serves and a loss of credibility. When a business loses credibility, it often leads to losing business.

Make Your Presence Known
Let me clarify something: I am not saying dominate conversations and takeover events. What I am saying, is to be confident, assertive, and decisive. I see too often when I go to business seminars and conferences that people are afraid to ask questions or speak up in a crowd full of people. However, they give great monologues under their breath. (you can't help but hear them). As entrepreneurs, you have to be willing to sacrifice a few moments of being uncomfortable to accomplish something bigger. Doing this establishes you as credible in that subject, industry, or whatever. People may come to you afterwards and want to talk more. Now you are establishing a new relationship simply by being bold for what? Maybe 30 seconds. When we started OWLS, people told us we could not get into one of the largest school districts in the nation for our services (if you know anything about our company, you know we love a challenge). So once at a business seminar, the topic of literacy came up. In the company, I am the business mind and not the educator. However, I had been in enough conversations to feel confident I could hold my own on this topic. I got up, and I said my piece. Some agreed, and some did not. Afterwards, someone came up to me and asked a little bit more OWLS and our focus. By the end of it, that person gave me her card and said "we need an OWL." Her business card was from the school district people said we would never be able to do business with. We now have a deep relationship with that school district...and it came from just 30 seconds of boldness.
Take Calculated Risks

This topic relates to my first point about clarity. When you are clear about your path and vision as an entrepreneur it allows you to make great choices and mitigate risks. To be clear, starting a business is full of risk and no plan is full proof but you can greatly reduce your chances of failure by thinking about the risks you take. One example of this is a client who once told me that she wanted to open a restaurant in our initial consultation. Anyone who has run a restaurant will tell that it is a hard business to turn a profit in because there are so many moving parts. I asked her why she wanted to open one and; she told me that her family has always loved to cook. I'm thinking we are off to a great start because I always ask about a person's passion. Then I asked if she or someone on their staff had restaurant management experience or at least had working knowledge of a restaurant's margins (which are extremely volatile by the way). She said no. I told her at that moment that she should not open a restaurant without one. She decided to go against that logic. The restaurant, which had a terrible name to begin with, was closed within 3 months. That was a terrible risk to take. The calculated risk would be to hire a restaurant manager. It would have been tough but, at least you would have expertise on your side in order to help combat the risk. Also hiring that restaurant manager would have gone a long way in securing the funding she so desperately needed.

Cherish The Small Wins

Entrepreneurs know that every day will not be a home run which is why you must appreciate the base hits. The small victories can go a long way to building confidence. When I interact with someone new, whether it be online or in person, my goal is not to sell them something. That can be extremely off-putting to anyone if they feel like they are being sold something after meeting someone for five minutes. No, my goal is to provide them some type of value and make a connection. So when we first talk I tend to give them no more than two pieces of advice. If they ask for my card, then I know they found value and a connection is made. That is my small victory. The small victories are important because they build confidence. They remind you that you are on the right track and if your are anything like us at OWLS, they create the need to get more small victories. Trust me, when you tally small wins they lead to the big ones. It's up to you to find out what they look like to you and your business. A small victory can be the share of a Facebook post or hearts on Periscope. Whatever they may be, cherish those moments and never take them for granted.

One More Thing......

Networking is a huge part of being part of being bold in your business. Many entrepreneurs shy away from this only to find out later that it's just as important as the very thing you are selling. The crazy thing is, and this is true, a great networker can keep a terrible business afloat for awhile. Now think if you combined a great business with networking how much your business would thrive. Just remember people tend to do business with individuals they know. If they don't know you, then your business won't know success.

What's The Bottom Line?

Have confidence in the business, the process, and, more importantly, yourself to find the success you seek. Don’t be afraid to go “all in” and never look back. Clarity provides you with the roadmap to the vision you want to come to life. Refraining from being timid makes your customers listen to you, and your competitors respect you. Risks that are accompanied with a plan of action are likely to be successful and not feel like a rudderless ship. The small victories will give you life on days when you might want to quit. So go forth my entrepreneurs and be bold in your business. Don't get caught being sheepish because as Gordon Gecko would tell you, "sheep get slaughtered" #AnOwlInYourCorner

Featured Posts
Recent Posts
Search By Tags
Follow Us
  • Facebook Basic Square
  • Twitter Basic Square
  • LinkedIn Social Icon
  • Instagram Social Icon
  • Snapchat Social Icon
bottom of page