Unfortunately, Don Lemon was roasted on Twitter once again last night. He opened up a CNN newscast with two large cards in front of him; one with me Confederate flag the other with a sign that spelled “Nigger.” He asked if each one was offensive. He was trying to create shock value, based on a podcast that President Obama had done where he said the word “Nigger’ and the current controversy over the Confederate flag and what it means. Truth be told, the two are not synonymous in this instance. The segment was poorly executed and received. What was his point? A firestorm erupted but not in Don’s favor. The general consensus, was it is too soon after the Charleston shootings to play this game, this was just not the time.

It seems that Don is constantly trying to find himself on the worst possible platform, national TV. I feel bad for him, it makes one curious as to who is behind the curtain at CNN directing him, or worse is he directing himself? He seems to take pride in knowing that he offends people on both sides but one is left to wonder if that is just a response to yet another futile effort instead.

It’s very easy to feel sorry for Don, because underneath it all, it appears he is desperately seeking acceptance and attention. Worst yet, from places he may never get it. Television news is getting more and more dated as millennial’s rely on online methods to get their news and information. Times have drastically changed and you can see how commercial TV news is trying desperately to capture the audience by becoming more and more like Entertainment Tonight, or like Entertainment Tonight was, which is also dated. More and more people are tired of being depressed and sparked by sensationalism. The audience prefers comedy or opinion based news coming from the people who are actually passionate about it. Passion cannot be faked. I, like Don L Lemon, am a last generation baby boomer and even I hate watching TV for the same reasons.

Desperation is ugly and if once you become desperate it is best to pull out and rethink your strategy instead of humiliating yourself in front of everyone. How does this relate to entrepreneurs? Because it’s about passion, sales and marketing. There are some very valuable lessons to be learned from Don Lemon starting with…

Know your target

Knowing your target means that you’re not afraid to speak to them, eat with them, live with them, spend time with them, accept them, love them and get to know more of them. One of the worst things that you can do is tell people how to behave when you rarely have anything to do with them. (Click “NEXT” above or below)

Don’t fake the funk

Don is constantly talking about black issues and black people, but when you look at his social networks he is often surrounded by white and Latin men and women. Recently he’s been called “Uncle Tom” a lot. When this happens, it is always when a black person is playing both sides of the coin. It is painfully evident that Don is not connected to the black community but at the same time he’s making a futile effort to act like he is. You don’t make a sale this way because it does not go over well with the customer. It is no different than when an entrepreneur thinks of money first when starting a business. He or she will almost always fail. Passion wins, Money follows! When you are passionate about something people know it, when you are only trying to make money or fulfill an agenda people also know that.

Surround yourself with the right people

Without even being sure, I can almost guarantee you that Don Lemon is not surrounded by black people at CNN. It is evident with his on air delivery and antics. The best candidates win elections when they’re surrounded with the right team and understands the target! If CNN is asking him to go out and represent himself as a spokesperson for the black community, it would behoove him at best to ask for the right team?

Plan Strategies

It appears that a lot of Don’s strategies are not well thought out. This can be very costly. As a late Maya Angelou once pointed out, “People may forget what you said but they never forget how you make them feel.” In many instances you will not get a second chance to make a first impression. Don started out as a very straight forward news guy then CNN wanted to turn him into a controversial figure which is working, but not to Don’s advantage. It’s no different than the person who is friendly with all of his coworkers and all of a sudden gets promoted to their boss. If he’s a good boss, he will adapt to his new environment or he plays both sides which will lead to an inevitable overall loss. Once Don got into mainstream news, without question, he had to forego a lot of what he learned or knew as a black man in order to compete. Now he’s being asked to circle back and it’s too late. As entrepreneurs we should not adapt to a new environment our job is to create it!

Don’t try to be who you are not

There is an incredibly high price to pay on a platform like national TV when you are asked to change who you are to be a different person in the same arena. The audience has come to know you one way and now you are trying to become someone else in the same space. In a situation like this, it’s best to start over by creating another platform altogether. As entrepreneurs it’s okay to add an ancillary product but it’s not okay to completely change the entire business when your audience has come to know you in one way. Either Don Lemon is insecure or he’s very arrogant and it’s evident. In addition there is a thin line between insecurity and arrogance. It’s okay to be afraid, but only when you can the admit it, a sense of humor also helps. When you fake it, it comes off as arrogant. People are more sympathetic to those who admit shortcomings an/or can laugh at themselves.

Connect with the audience

When it comes to the black community, it is crucial not to hide in plain sight. People pay very close attention to social networks these days, beware of what you post on your social networks. When it is evident that you are not actually friends with the people you target or claim to be connected to on TV it doesn’t do much to serve your purpose. Contrary to the beliefs of other races, just because you’re black doesn’t mean you’re connected to the culture. When you act like you are, you look like and become a token which can result in being called an “Uncle Tom.”  You are basically saying I’m one thing on TV and another thing in my personal life as if people are so stupid they can’t make that connection. As entrepreneurs, we cannot allow other people to tell us who we are. That is why we are entrepreneurs, we already know that!

Capitalize on your strengths

If you want to be successful in business, you must capitalize on your strengths. Unfortunately Don’s greatest strength has become dated. He is intelligent and an excellent reporter on world news and issues but unfortunately he loses all of that when he tries to connect with the black community.  His years of training as a focused professional newsperson make him less personable when connecting with the black community.

Admit your shortcomings

If you’re not the right person for the job  admit it or stop doing it and give the right person the chance to do it before you are asked to leave. At that point what do you have left but a negative reputation? If Don we’re in business for himself, he callwould be broke at this point and forced to leave the business.