Believing in herself is Womack's key to success

About ten years ago my boyfriend, now husband, was “cellaring” some chardonnays worth about fifteen bucks each at his friend’s place. When I met him I had sort of gotten into wine, and had a nice bottle of Chateau Mouton Rothschild, from one of the top chateaus in France. To make a long story short, this bottle of Mouton has grown my husband’s interest in wine over the last decade to become a major hobby for him to collect and cellar top wines. The wine industry is big business – there’s all the paraphernalia associated with wine collecting, like owning or renting wine cellar space, buying wine guides like Wine Spectator magazine, special glasses for each wine type, wine cellar organization software, etc. While reading the latest issue of Wine Spectator, I found an article about the first woman to sell her personal wine cellar via Sotheby’s auction. V. Cheryl Womack, from Kansas City, MO, recently sold about 5000 bottles from her collection, bringing in a whopping $1.7 million. This auction represented half her collection.

Womack was the third born of eleven children in an impoverished Panamanian immigrant family. Her father worked 18 hour days in a fiberglass company. He raised Cheryl with the attitude of taking responsibility for her actions, to believe in herself, and know that change is available to everyone. In the 1980s, Womack was making only $17,000/year at her insurance job. She was sick of watching men be promoted above her, so in 1981 she founded the National Association of Independent Truckers, providing business services for truck drivers. A couple years later, out of her basement, she founded VCW, an insurance agency to cover the needs of truck drivers. After that, she founded another company called Preferred Administrative Services, a third party claims administration company. Womack created several innovative insurance products, including an alternative to workers’ compensation for independent contractors that has become a model for the industry.

Womack sold all of her companies in 2002 at the age of 51, for around $100 million. She had over 90 employees and was insuring over 14,000 people.

Cheryl is an inspiration to business people in general, but particularly women, who she gives motivational speeches to and sponsors mentoring programs. Since selling VCW, Womack now spends much of her time advising budding entrepreneurs through her nonprofit organization, Leading Women Entrepreneurs of the World.