Entrepreneur Lessons That I Learned the Hard Way


Entrepreneur lessons  – At times we need to give a little more thought to our actions as business owners especially when it involves clients. Here are a few of the hardest lessons I’ve learned over the years. I hope they can save you a lot of time and misery.

Entrepreneur Lessons That I Learned the Hard Way

Entrepreneur Lessons That I Learned the Hard Way – Be careful who you surround yourself with in front of your clients

I had a situation a few years back where I took a “friend” to an event because she was out of work and I knew there would be people there that could help her get back into her field. The VP of the company wanted me to ride with him to the event and I sat in the lobby with her while he got dressed. When the VP came downstairs and was ready to go, she complained that her feet were hurting and we were walking too fast. FIRST WARNING! We get to the event after the VP and I slow down for her and she speaks to everybody and she had a drink which leads to another drink and another drink.  She gets drunk and I can hear her slurring her words and speaking loudly while I’m talking to colleagues on the balcony. SECOND WARNING. I pull her to the side and tell her “You are drunk and you are talking too loud bring it down a few notches. She agrees and 10 minutes later she is even louder. THIRD WARNING. I am HUMILIATED and EMBARRASSED and my client is being cordial but I can tell he is not impressed.

I opt to leave the event early just to get her out of there. As we leave she goes for the final coup-de-gras and asks several people for their cards. I was MORTIFIED as they all lied and said they didn’t bring any cards. FORTH WARNING. We leave and she takes off her shoes and is complaining about her feet again as we end up in a coffee shop and she is now fully drunk. I can’t believe I invited her and I KNEW she had a drinking problem but I was trying to help her get a job. The next day at another event, I had one glass of wine to try to relax after the mishap the night before and I got tipsy myself. I usually don’t drink. Now I have made my OWN impression.  While the client still does business with me, they have not invited me to any of their events since and its been 3 years.  I mentioned to her that she made a fool of herself and I was trying to help her and she did what people like her do, she told me I was over thinking it and that I should not care what the client thinks. I should have never expected an alcoholic to take responsibility especially when she then stated she was not that drunk.

LESSON LEARNED: I have a bad habit of always looking out for others even to the detriment of myself.  I should have escorted her back to her car and sent her BACK home when she complained about her feet and wanted the client to wait while she tried to maneuver in high heels that she could not wear. All of this could have been avoided if I had stopped everything right there or not invited her at all-knowing her history, which I did. I have to take full responsibility for this grave error for trying to help a “friend” out. I put the word friend in quotes because we have to KNOW who our true friends are as black entrepreneurs. There are some people who ACT like they are your friend to go along for the ride, to reap some of the benefits of your hard work, to pick your brain and drain you. My uncle told me when I was a boy that you must always make sure you deal with people in just about every circumstance, who have as much to lose AS YOU DO.

That’s how you establish trust. He was right, another black entrepreneur who was in the same field as me would have thought twice about doing what this woman did. I had to realize that most people are in the situations they are in by CHOICE. They don’t want to make the necessary moves to get out of a rut and we are not their babysitter. Some of us have been there too. You can’t lay your burdens on other people if YOU are not willing to do the work FIRST. Truth be told this woman is an alcoholic and people who have addictions put the addiction ahead of everything else. Being her friend was too much weight on me so I had to let her go after a couple of other really negative experiences with her. When it comes to doing businesses make sure you surround yourself with people who have YOUR best interest in mind along with theirs and not just theirs. CLICK “NEXT” ABOVE OR BELOW TO SEE THE NEXT TIP

Entrepreneur lessons – Consistently Develop a Relationship with Clients

Entrepreneur Lessons That I Learned the Hard Way

In my field, people call clients only when they want something. In the interest of their time, I have done the same. I have been told early on by a client that I only call when I want something. I was dumbfounded by that because I thought what the hell else would I call for? Then I realized that in the true art of selling you SHOULD reach out to your clients every now and then to have a regular conversation. There is always room at the end to do a quick pitch but you never want your clients to avoid your calls. I make sure I KNOW my clients and I KNOW things about them that we can talk about besides sales. In the long run they greatly appreciate that. They know that you are there for business but going the extra mile will put you miles ahead of your greedy competitors.

Entrepreneur lessons – Take a Vacation

I RARELY do this but it is SO important. The more you work the harder it is to leave your business in the hands of others. You fear that they will destroy your business but that’s rarely the case. Your business can survive for a few days without you and the benefit is that when you get back you are ready to take on your job with a new perspective fresh eyes and new energy. You can even take a mini vacation in a nicer resort part of your city for a few days or somewhere close.

©2012 Red Square, Inc.


Entrepreneur lessons – Treat Yourself

Take yourself to lunch, a movie or the museum once a week. If you are over 50 AARP has AMAZING coupon deals where you can try different restaurants and various entertainment functions. Whatever it is you like to do pick a day to do it and do it alone or with another POSITIVE black entrepreneur.



Entrepreneur lessons – Watch your Accounting and Taxes

VERY IMPORTANT. Make sure your finances are on point. Nuff said



Step away to create Your Growth

Take a day off a couple of times a month to attend seminars of meetings that can help your business grow. The time away will do you good.



Entrepreneur lessons – Competitors can be Dirty

When you are on top, it’s very hard to stay there and there are people who don’t want to see you there. Always be cordial, handle your business and know your enemies and what they are up to. Clients are a great source for this kind of information. When they like you they will look out for you and give you valuable information about competitors as well as your employees.



Entrepreneur lessons – Make appearances but never isolate

There was a time when I was content to do the work, hide and just collect the money. That’s a mistake. This is your opportunity for growth. Hire someone temporarily to do some of your work while you play the politician on occasion. Never stay until the end of an event and never be the first one there. Whisk through, make sure you speak to the VIPs, leave a great impression and allow the guests to wonder where you went.



Entrepreneur lessons – Spend your day wisely

Stay off social nets unless it’s Linkedin. FaceBook is a HORRIBLE way to spend anytime during the day as well as Twitter unless you are marketing your product. I don’t even watch TV. I don’t like wasting time.



Entrepreneur lessons – Take care of yourself/Work out

Hire a QUALIFIED trainer and go to the gym I say qualified because there are a TON of fake trainers out there who don’t know what they are doing and you will get injured. Spend the money and the time on what actually works. Being an black entrepreneur in great shape opens MANY more doors for you. I’ve seen it firsthand. Appearance IS everything. Don’t be fooled and spend money on chain gym trainers, they suck and they lack the qualifications. Real trainers balk at chains because they don’t pay enough and so they don’t work for them. My best in business… Kev


Entrepreneur lessons – Build a New Side Business from another Hobby

This one is self-explanatory but it’s a backup plan and believe me, you will need it. Not only do I do this and one other blog. I’m also a real estate agent.

black-owned, black black entrepreneurs, gig, side hustles

Entrepreneur lessons – When it’s no longer fun … STOP DOING IT

Not only will you waste your time but your energy levels will tank and you will sleep a lot, gain weight and not look forward to the day. Remember when you started how you felt? You almost could not sleep in anticipation of the day when that feeling is gone don’t waiver and hope it will come back TRUST ME it’s GONE. Start doing your backup career until you get your next idea. It’s better to leave on your own terms than to be kicked out. KNOW when the leave.

black-owned, black black entrepreneurs, gig, side hustles

Leave a Reply