Cheryl Womack
A self-made mogul who built a $100 million empire by insuring America's independent truckers, then turned her focus to philanthropy.
Born 1950 (age 76)·Birthday: December 31·Baby Boomers
Biography
Cheryl Womack saw opportunity where others saw risk. In the 1970s, she identified a gap in the market: independent truckers, the backbone of American freight, struggled to get affordable insurance. From her base in Kansas City, she founded VCW and the National Association of Independent Truckers, Inc., creating a tailored service that offered them coverage and advocacy. She grew the venture into a powerhouse, eventually selling it for a fortune. Womack then pivoted seamlessly from business to benevolence, becoming a transformative philanthropist in the Kansas City region. Her giving is personal and strategic, often honoring her family, like the $2 million donation to name the University of Kansas's Arrocha Ballpark after her father. Her story is one of sharp commercial insight followed by a deep commitment to community.
Baby Boomers
1946–1964
The largest generation in history at the time. Shaped by postwar prosperity, the Vietnam War, the sexual revolution, and Watergate. They questioned every institution their parents built — then ran them.
Cheryl was born in 1950, placing them squarely in the Baby Boomers. The events that shaped this generation — postwar prosperity, civil rights, Vietnam, and the counterculture — shaped the world they entered and the choices available to them.
#1 When Cheryl Was Born
The biggest hits of 1950
#1 Movie
Cinderella
Best Picture
All About Eve
#1 TV Show
Texaco Star Theatre
Cheryl's Life & Times
The world at every milestone
1950Born
Korean War begins
Gas: $0.27/galHome: $7,354Min wage: $0.75/hrPresident: Harry S. Truman"Goodnight Irene" — Gordon Jenkins & The WeaversBest Picture: All About Eve
1955Started school
Rosa Parks refuses to give up her bus seat
Gas: $0.29/galHome: $9,550Min wage: $0.75/hrPresident: Dwight D. Eisenhower"Rock Around the Clock" — Bill Haley & His CometsBest Picture: Marty
1963Became a teenager
JFK assassinated in Dallas; Martin Luther King's 'I Have a Dream' speech
Gas: $0.31/galHome: $13,100Min wage: $1.25/hrPresident: Lyndon B. Johnson"Sugar Shack" — Jimmy Gilmer & The FireballsBest Picture: Tom Jones
1966Could drive
Star Trek premieres on television
Gas: $0.32/galHome: $14,200Min wage: $1.25/hrPresident: Lyndon B. Johnson"The Ballad of the Green Berets" — SSgt Barry SadlerBest Picture: A Man for All Seasons
1968Could vote
Martin Luther King Jr. and Robert Kennedy assassinated
Gas: $0.34/galHome: $14,950Min wage: $1.60/hrPresident: Lyndon B. Johnson"Hey Jude" — The BeatlesBest Picture: Oliver!
1971Turned 21
Voting age lowered to 18 in the US
Gas: $0.36/galHome: $18,100Min wage: $1.60/hrPresident: Richard Nixon"Joy to the World" — Three Dog NightBest Picture: The French Connection
1980Turned 30
John Lennon shot and killed in New York
Gas: $1.19/galHome: $47,200Min wage: $3.10/hrPresident: Jimmy Carter"Call Me" — BlondieBest Picture: Ordinary People
1990Turned 40
Hubble Space Telescope launched; Germany reunifies
Gas: $1.15/galHome: $79,100Min wage: $3.80/hrPresident: George H.W. Bush"Hold On" — Wilson PhillipsBest Picture: Dances with Wolves
2000Turned 50
Y2K passes without incident; contested Bush-Gore election
Gas: $1.51/galHome: $119,600Min wage: $5.15/hrPresident: Bill Clinton"Breathe" — Faith HillBest Picture: Gladiator
2010Turned 60
Deepwater Horizon oil spill; iPad launched
Gas: $2.79/galHome: $147,800Min wage: $7.25/hrPresident: Barack Obama"Tik Tok" — KeshaBest Picture: The King's Speech
2020Turned 70
COVID-19 pandemic shuts down the world
Gas: $2.17/galHome: $248,800Min wage: $7.25/hrPresident: Donald Trump"Blinding Lights" — The WeekndBest Picture: Nomadland
2026Age 76 today
Gas: $3.91/galPresident: Donald Trump
Key Achievements
- Founded and scaled VCW/NAIT into a $100-million-a-year business serving independent truckers.
- Successfully sold her insurance companies to the private equity firm Clayton, Dubilier & Rice.
- Became a major philanthropic force in Kansas City, supporting education and community projects.
- Donated $2 million to the University of Kansas for Arrocha Ballpark, named for her father.
Did You Know?
Her father, Demostenes Arrocha, was a Panamanian baseball player, inspiring her gift for the ballpark.
She is known for her private nature despite her significant public business and philanthropic impact.
Her success came in the male-dominated industries of trucking and insurance.
“I built a company by solving a real problem for the man with the rig.”
