Cheryl Womack

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Verna Cheryl Womack (born December 31, 1950) is an entrepreneur who founded Kansas City, Missouri-based VCW and National Association of Independent Truckers, Inc. which became a $100 million a year business selling insurance to independent truckers before selling the companies to private equity investors Clayton, Dubilier & Rice.[1]

File:Cheryl Womack - headshot.jpg
Cheryl Womack - headshot

She has since became a major philanthropist in the Kansas City area. Among her donations was $2 million to the University of Kansas to build Arrocha Ballpark which is named for her father Demostenes Arrocha.

Early life

Womack was born in Kansas City, Kansas. She was the third of 11 children to her Panama-immigrant father and American mother. She attended Wyandotte High School and received a bachelor in education from the University of Kansas in 1975.[2] Following graduation she taught elementary school for a year and worked at a trucking insurance company.

After failing to be promoted, she started the National Association of Independent Truckers in the basement of her home in 1981. She started the National Association of Independent Truckers to fill a niche need for the independent contractors.[3] Truckers who paid a membership got discounts on various products. In 1983 and more lucratively she created VCW to sell customized insurance policies to truckers. "I listened to what the independent truckers complained about, and I solved their problems," she said. "I created something and said, 'Here's what you asked for.'[4]

Sale of SIRVA

By the time she sold the companies, there were 12,000 members. She was 100 percent owner. The sale to SIRVA was reported to have been for $100 million.[5] (although SEC filings indicate the price was closer to $40 million).[6] SIRVA would sell the insurance business along with Transguard Insurance Company of America, Inc. and Vanguard Insurance Agency, Inc. to IAT Reinsurance Company Ltd. in 2005.[7]

Since the sale, her new VCW Holding investments include The Star Group team in program and partnership development for annual events recognizing and honoring the, Leading Women Entrepreneurs of the World and participates in mentoring programs sponsored by The Kauffman Foundation for Entrepreneurial Leadership, The Committee of 200, Harvard University's John F. Kennedy School of Government, and the Women's Leadership Board.

Business Interests

  • President & CEO, The Star Group
  • Chair, The Leading Women Entrepreneurs of the World, Inc. – 501 (c) 3
  • President & CEO, VCW Holding Company, L.L.C.
  • CEO, R&A Properties, L.L.C.
  • Member, W & P Development, L.L.C.

Awards and Achievements

  • Avon Women of Enterprise Award for Small Business Administration – 1991 Nominee
  • Blue Chip Enterprise Initiative, 1991 State Designee (Missouri)
  • Business Women’s Network, Honorary Committee.
  • Council of Growing Companies’ National “Bootstrap” Award, “In recognition of her achievements as an entrepreneur who started with minimum resources, pursued the opportunity, took the risks, faced the challenges, cared for her employees, provided quality to her clients and built a successful enterprise.”
  • Dun and Bradstreet’s Best of America competition – named only semi-finalist from Missouri
  • Greater Kansas City Chamber of Commerce, 1992 Small Business of the Year finalist
  • Greater Kansas City Insurance Association, 1996
  • “Insurance Industry Leader of the Year” Inc. 1992
  • Entrepreneur of the Year, Western Missouri/Kansas Finalist
  • Ingram’s 1996 Corporate Report 100, Greater Kansas City area’s fastest-growing companies
  • Junior Achievement of Middle America, 1991-92 Banner Year Award
  • Kansas City Business Journal 1997 Top 25 Women-Owned Businesses - Listed #2
  • Kansas City Business Journal 1997 Top 150 Area Private Companies - Listed #71
  • Kansas City Business Journal 1995 Who’s Who in Insurance
  • Leading Women Entrepreneurs of the World, 2002 Honoree, Paris, France
  • National Association of Women Business Owners, Industry Leadership Award
  • National Conference for College Women Student Leaders, 1995
  • “Woman ofbbbbb Distinction” Award “Who’s Who Among Rising Young Americans,” 1992 Edition
  • Women’s Intersport Network for Kansas City WOW (WIN Outstanding Women) Award, 2003
  • Women Impacting Public Policy (WIPP) Entrepreneur of the Year Award, 2002
  • Women Who Mean Business Award, Kansas City Business Journal; July, 2006
  • Working Woman Top 500 Women-Owned Businesses
  • Working Mother “100 Best Companies for Working Mothers”
  • YWCA of Kansas City, Kansas, 1997 Hearts of Gold Award
  • Honorary Doctorate Degree from William Woods University 2003
  • “A Reason To Believe” Award, KCK, 2004 alumni
  • Ziggs Profile Award; 2005

Civic and Business Affiliations - Past and Present

  • American Movers Conference
  • American Trucking Associations
  • Arrocha Ball Park, University of Kansas (in her father’s name); $2 million contribution; 2002 – provided the funds to build the new women’s softball field.
  • Chamber of Commerce of Greater Kansas City
  • Chamber of Commerce of Greater Kansas City, 1992 Small Business Week Chair
  • Commission for the Future of Worker/Management Relations, sponsored by the U.S. Departments of Labor and Commerce. Testified before the Dunlop Commission and singularly represented small businesses at the hearing.
  • Committee of 200 – Group of just over 300 women, mostly in the US, who have business of 10 million or more or manage budgets of 20 million or more. Member since 1992.
  • Committee of 200 Mentoring Program –Committee of members agreeing to mentor smaller businesses.
  • Council of Growing Companies. National Executive Committee & Local Chapter Co-Founder & Chair
  • “Developing Entrepreneurial Opportunities,” sponsored by Kauffman Foundation’s Center for Entrepreneurial Leadership – panel participant.
  • Economic Development Corporation of Kansas City, Director
  • Entrepreneur’s Exchange, Co-Founder & Board Member
  • Entrepreneur’s Exchange, Founding Member, Executive Board & Chair for the first 3 years
  • Garth Brooks Steering Committee; 2006
  • Grass Roots Impact, Inc., Founding Member
  • Harvard University, John F. Kennedy School of Government Women’s Leadership Board & Mentoring Committee
  • Heart of America Council, Boy Scouts of America, Board of Directors & Executive Committee International Truckload Carriers Conference
  • Junior Achievement of Middle America, Board of Directors & Executive Committee
  • Junior Achievement, National President and Chief Executive Officer Search Advisory Committee Kansas City Chamber Orchestra, Host annual fundraiser
  • Kansas City Symphony, Steering Committee
  • Kansas City’s 25 “Up and Comers” – Judge for 1st year’s selection
  • Kauffman Foundation for Entrepreneurial Leadership Mentoring Program
  • Lyric Opera of Kansas City, Board of Directors, Executive Committee & Lyric Opera Circle
  • Metropolitan Entrepreneurs Council, Board of Directors
  • Metropolitan Organization Combating Sexual Abuse (MOCSA)
  • Missouri Collegiate Entrepreneur Award sponsored by St. Louis University- served on selection panel
  • National Association of Independent Truckers, Member Advisory Board & Motor Carrier Advisory Board, Chairperson
  • National Women’s Business Council
  • Rockhurst High School, Auction Committee 2001 - Served on committee that raised $500,000, an increase of more than $200,000 over previous years.
  • Search Advisory Committee to select Junior Achievement’s National President and Chief Executive Officer.
  • Starlight Theater, 1994 Gala Chair
  • St. Vincent’s Operation Breakthrough Inner City Daycare; nearly $400,000 contribution for new building construction; 2004
  • Treads & Threads, Gala benefiting KU Med Center Breast Cancer Center, Founding Committee and Event Committee Chair
  • U.S. Chamber of Commerce, Board of Directors
  • U.S. Chamber of Commerce, Transportation Infrastructure Task Force.
  • University of Kansas School of Business, Board of Advisers
  • University of Kansas School of Business, Institute for Entrepreneurship & Business Ventures,Founding Member & Advisory Board
  • University of Missouri Kansas City Bloch School of Business, Advisory Board Women Impacting Public Policy, Inc., Founding Member

Press and Media

  • American Express Corporate Card 1993 national media print ad campaign
  • Australian Financial Review, May 2004
  • The Australian, May 2004
  • Australian Broadcasting Commission – Talkback radio ‘mentoring’, May, 2004
  • Bangkok Today – Bangkok To Be Host City, September 30, 2005
  • Bangkok Post – Thailand to Host Awards Next Year, September 28, 2005
  • BBC Interview in NYC about LWEW (Leading Women Entrepreneurs of the World), December 28, 2005
  • BCB/USB Communicator – Vancouver Hosts Ninth Annual Conference,November 1, 2005
  • Brand Age/ Sydney, Australia – Tycoons from Venus, August 1, 2005
  • Business Week Online – Cheryl Womack - Tips for Entrepreneurs, May 13, 2006
  • What Do Businesswomen Want?, January 30, 2006
  • Capital Romania – LWEW Organization Featured in Bucharest, July 29, 2005
  • CIE Asia Pacific, September 2006City Press, South Africa to Host Top Business Women, March, 2006
  • Czech Business Weekly – Dr. V. Cheryl Womack Interview – On the Record, August 1, 2005
  • Daily News, Thailand – World Award for Women Entrepreneurs, September 30, 2005
  • El Universal (Spanish version), V. Cheryl Womack – A Woman Leader in a Man’s World, January 9, 2006 (Mexico)
  • Entrepreneur Magazine - “Today’s Hottest Young Entrepreneurs!”
  • ESPN - “Nation’s Business Today”
  • Flourish! Magazine – Ask a Leading Woman, October/November 2006
  • Fortune Magazine– “Succeeding With Tough Love”
  • Hlavni stranka – Chairperson Featured in Business Section of Prague Newspaper, July 26, 2005 – First woman ever profiled in this section.
  • Ingram’s – “Up and Comer”
  • Kansas City Business Journal - “Who’s Who in Women-Owned Businesses.”
  • Kansas City Business Journal – Focus on Insurance
  • Kansas City Business Journal – Women Who Mean Business, July 2006
  • Kansas City Star, Business Section – Her Vision Embraces the World, June 27, 2006
  • Kansas City Star Columns; Your Enemy Has a Familiar Look, 8/15/06; Every New Day Brings Wonder, 6/13/06
  • Manager Weekly – Take The Next Step Grants – Announced Thailand, October 3, 2005
  • Nation’s Business
  • Neaw-na, Thailand Organizing Committee held Press Conference on September 27, 2005
  • NN – Leading Women – Thailand, September 24, 2005
  • Oprah Magazine – Your First $1,000,000 “The Truck Stops Here” – September 2005
  • Pink Magazine – The Best Revenge is a Great Life, June 1, 2006
  • Pink Magazine – Dress It Up and Move It Out, October 2006
  • Prague Daily Monitor – Prague Wants to Host the World’s Women Entrepreneurs Congress in2007, July 26, 2005
  • Profit – Chairperson & Executive Director Meet with Czech Republic Deputy Prime Minister,August 1, 2005
  • Scarlett Magazine, Creative Outtakes July 2004
  • Success
  • Sydney Weekly Courier, Some Amazing International Business Women, May 19, 2004
  • Thailand Official News Online – Promoting the Role Models for Working Women from the Office of the Prime Minister for Thailand, January 26, 2006
  • Thailand Post –Nominate an Outstanding Woman for 2006 Leading Women Entrepreneurs of the World™, October 4, 2005; Women Forum May Be Held In Thailand, March 10, 2005
  • Thai Rat, LWEW Press Conference, December 14, 2005; Siam Paragon Official Opening –Chairperson and Bangkok Governor, December 12, 2005; Thailand Organizing Committee Featured, September 29, 2005; Leading Women Entrepreneurs’ Submission, September 28, 2005
  • The Sun-Herald, Australia – Amazing Grace of the Filthy Rich, May 16, 2004
  • "The Tom Peters Seminar and Book: Crazy Times Call for Crazy Organizations,"
  • Transport Topics
  • USA Today
  • Voice of America, Organization Recognizes Successful International Businesswomen, February 2, 2006
  • What AM on the Exchange with Elmer Smith – Interview, July 2006
  • Working Woman Magazine
  • Working Mother Magazine


On December 12, 2013, she was indicted for allegedly using numerous foreign trusts and secret Cayman Island bank accounts as part of a scheme to avoid paying more than $7 million in income taxes and for lying to federal authorities concerning her Cayman Island interests.[8]


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  3. "Star Female Entrepreneurs Bask in Global Showcase - Womens eNews".<templatestyles src="Module:Citation/CS1/styles.css"></templatestyles>
  4. Her Vision Embraces the World: After Succeeding on Her Own, She Now Owns a Nonprofit That Honors Businesswomen Around the Globe - June 27, 2006 -
  6. "SIRVA INC - Annual Report (10-K) BALANCE SHEET".<templatestyles src="Module:Citation/CS1/styles.css"></templatestyles>
  7. "Trucking Driving & Trucking Information - BubbaJunk".<templatestyles src="Module:Citation/CS1/styles.css"></templatestyles>
  8. "Mission Hills Woman Indicted in Cayman Island Tax Scheme and for Lying to Federal Authorities". December 12, 2013. External link in |publisher= (help)<templatestyles src="Module:Citation/CS1/styles.css"></templatestyles>

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