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Last Update: Thursday July 29, 2021

Key Idea: Leave a Bad Boss

Cheryl Womack had the courage to leave a bad boss and then she went on to build a multi-million dollar operation.

Key Question:


For Cheryl a bad boss was the motivation for her to leave a job and start her own business. she said her goal was to be able to control her own destiny.

Q: Is this a good reason to start a business? 

A: Yes. Cheryl's experience working for someone else was positive in many ways, yet in the end, negative. She was working hard but that hard work was not recognized. Another person was brought in to be President of the company and Cheryl was asked to train that person. Did you know the same thing happened to Mary Kay Ash? For the same reason, she started Mary Kay Cosmetics and sheevolved to have 350,000 sales representatives throughout the world.

Have you ever had a job where you felt your efforts were not recognized? Many supervisors, owners, or bosses are insensitive and fail to simply say thank you and pat people on the back. If you ever supervise the work of others, learn the communication skills needed to keep people satisfied in their work.

All of life's experiences can be applied to a new business venture. Cheryl worked for a large insurance company, then moved to a small insurance business. While working for the big company she learned industry standards, had state-of-the-art technology, and watched how seasoned executives closed deals. In the small company she was given broad responsibilities and was able to make decisions and move quickly to build the business.

Q: Is it good to work for someone before you start a business?

A: In Cheryl's case, she never would have started an insurance company had she not learned the business as an employee. Thousands of business are started by people who are disgruntled with their situation. They stay in the same industry because the learning curve would be too steep to change and perhaps also because they enjoy the business.  I learned from the founders of Cross Timbers Oil to, "Do what you know with whom you know."

You should not feel stuck though. If you don't enjoy the industry, if you want to re-invent yourself, great. Just know that it may take years for you to hit your stride in an entirely new field.

Think about it

What have you done in the past when you were stuck?  If you are stuck now, what actions can you take to move toward where you want to be 3-5 years from now?

Clip from: VCW- National Association Independent Truckers

Kansas City:  In this episode of the show you meet Cheryl Womack.  Way back in the 1980 she became unhappy  with her job when her boss  hired a person for Cheryl to train to become her new boss. She left that company both sad and exasperated because she felt she deserved the promotion.

Cheryl spotted a niche to serve.  That was 1981 when she started a company dedicated to providing insurance to the owners of the 18-wheeler trucks moving cargo up and down our highways. She worked for the first year out of the basement of her home with one phone line that had call waiting and no computer.  She barely had enough to eat and admitted that she would go on dates just to get a decent meal.  At the time of this taping, she had 75 employees and was doing $45 million in annual sales.

In 2002, when her annual revenues had reached $100 million, she sold her National Independent Truckers Association and now focuses almost entirely on encouraging women.  She launched a non-profit called, Leading Women, to recognize women in business.

National Association of Independent Truckers

Cheryl Womack, Founder

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Leave a Bad Boss

HATTIE: Hi. And welcome back. If you have a business and want to grow it, or if you're thinking about starting a business, the next 30 minutes could be invaluable to you. Most business stay small.

But now you're going to meet a woman who is growing a business and growing it fast. Also, Jim Schell is here, our veteran entrepreneur. Jim has started and sold four businesses, and today he writes about his experience as a small-business owner. He will convince you that a written plan of action is well worth the time invested.

If you've been watching this series every week, you know the small business Master Class follows. For those of you who have not been with us, a Master Class is not taught by a teacher or an academic -- you will find no gurus or journalists in this session -- what you'll find is a professional small-business owner explaining exactly how they do what they do. Finding the master small-business owner is not easy, and I wouldn't want to waste your time and bring you someone who doesn't have a lot to say.

So let me warn you right now, grab a pencil. Cheryl Womack talks fast, and she's has a lot to teach us.

CHERYL WOMACK: The whole reason I started a business was to be in control of my destiny. You can't end up worse than even. I have never, ever gotten caught up on a pride issue because if they're going to pay me, it's money in the bank. And I'll cash my pride in at the bank.

HATTIE: In 1981, in her basement with one telephone and call waiting, Cheryl Womack started an association. Today she has 75 employees and will see $45 million in revenues this year. And the name of the company is VCW.

CHERYL: Stands for Very Cute Women.

HATTIE: That's great.. On the NAFTA Highway between Minneapolis and Laredo, we met some of her customers at Carl's Corner, a one-of-a-kind truck stop.

Unidentified Man #1: An owner-operator, an independent truck driver--he is a businessman. If he does not have good business sense, he's not gonna make it.

Unidentified Man #2: They don't make the money they used to make. The people out there that's running up and down the interstate used to could drive four, five days a week and make a good living. Now they've got to drive seven.

Unidentified Man #3: It takes a certain kind of breed to be a truck driver.

HATTIE: Cheryl has over 8,000 truck drivers in her National Association of Independent Truckers. In addition, many of the country's large motor carriers who hire independent truck drivers are her customers. She offers cost-effective insurance coverages, retirement benefit plans, low-interest credit cards and more to her members. Cheryl's customers move the world. I mean, they move everything we use every day. There are about 300,000 independent truck drivers in the US. In 1994, 353 billion miles were logged by all trucks used for business purposes. Man #3: We're running the United States. We run it. All we got to do is stop, and so do you.

CHERYL: I worked for a gentleman here in Kansas City who actually was the founder of the idea of putting insurance on independent contractors, separate from employees. And he developed the concept and idea, and I came on board and worked for him for about five and a half years. And after five and a half years, he decided to bring a gentleman in (that I started in business with at Firemens Fund) and asked me to train him to be his boss. And I did all the money, so he was paying him twice my pay and giving him a company car.

And I said, `Well, OK. I guess I'd better go.' And I didn't know what I was going to do, but the more I thought about it. I took six weeks off, the only six weeks I've probably ever taken in my life off since about 12. And my husband promised he'd keep a roof over my head and keep me fed, and I could do what I wanted to do.

So I found myself just migrating back toward this line of work, found a market in about four months that would write the business and started my own agency.

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