Forty Women Over 40: Jill Smallwood Helps Turn Dirt into Diamonds


We often hear about the success of women much younger than the encore entrepreneurs over 40. We created this 40 Over 40 feature to celebrate seasoned sisters striking out on their own after 40. If you know someone that we should know about please contact us at

Jill Smallwood is our first of 40 women that we are profiling. Jill tries to do tons of work. 

Maneuvering her triaxle dump truck through the area’s hilly and narrow landscape with ease, the owner and operator of J KoKo Hauling LLC, moves mountains of dirt, stone, gravel and construction debris. 

For three years, she’s been beautifying the area and aiding in local efforts to help create retail and office buildings, a college dormitory and green spaces. 

“Some of the places I’ve hauled to are special…serene and peaceful farmlands,” the real-estate enthusiast said. “I get to see the beginning of construction sites by hauling away dirt and debris to begin the next phase. Months later, I’ll drive by and think ‘oh, look at that building.”

Smallwood, a former Port Authority bus operator, was inspired by a fellow employee who also owned a hauling company. Selling a rental property provided much-needed money for working capital and equipment, enabling Smallwood to transfer her skills transporting passengers into a full-time hauling service. Her efforts aiding in creating both jobs and amenities in the region and for her small business. “I can’t believe I helped turn a hole in the ground into a beautiful nine-story beautiful glass-and-brick grocery store and office complex,” she said of the Whole Foods project. “I also made good on a promise to myself and recently hired a driver, allowing me to focus more on managing my business.”

Before hauling her first truckload, Smallwood made stops at the Chatham University Center for Womens Entrepreneurship Women’s Business Center (WBC) and the University of Pittsburgh Small Business Development Center (SBDC) seeking assistance.

“Jill knew what she wanted to do and had work lined up through networking and connections even before starting her business in a traditionally male-dominated field, and now businesses are contacting her to provide services,” said Meghan Hillegas, Pitt SBDC business consultant. “We helped her fine-tune her business plan while also providing financial projections.”

SBDCs and WBCs are a national network of U.S. Small Business Administration (SBA) centers also funded by state entities and private organizations helping small businesses in every phase of development. In Western Pennsylvania, eight SBDCs and one WBC offer free counseling, as well as low-cost training to help both startups and established businesses. Many entrepreneurs elect to remain clients long after they’ve rung up that first sale – helping their company weather the ebbs and flows of small business ownership.

Smallwood is one such client initiating quarterly check-in calls with Hillegas.

“We discuss federal contracting set asides for women-owned small businesses and the certification process, as well as equipment and managing her business,” explained Hillegas.


Navigating a new business through a pandemic can prove difficult. But Smallwood, a former Army Reservist and city police detective, admits she hasn’t failed much in her 59 years.

“I think I was the oldest person in my training class to drive a bus and obtain a commercial driver’s license,” she said. “When I studied, I pushed myself — concentrating by shutting off the phone and locking the door. I do the same when driving — focusing on the enormous responsibilities that leave no room for error.”

She credits her military background as being a cornerstone for success, citing discipline along with setting and achieving goals. 

According to SBA Western Pa. District Director Dr. Kelly Hunt, veterans often possess entrepreneurial skills ranging from physical and emotional stamina to decision-making and planning. “The SBA offers an array of services for entrepreneurial veterans, like Jill, designed to help them turn that idea into small business ownership,” she added. “I’m impressed with her efforts to better the area and her business while using the SBA’s free services.”

Taking enormous pride turning gravel into gems, Smallwood routinely drives past projects she helped create. Her favorite remains the Liberty Green site. “I was hauling dirt from a demolished housing area only to learn it was going to become a park in the East Liberty neighborhood,” she added. “I’m so happy for the children and families in that community.”

About the U.S. Small Business Administration

The U.S. Small Business Administration makes the American dream of business ownership a reality. As the only go-to resource and voice for small businesses backed by the strength of the federal government, the SBA empowers entrepreneurs and small business owners with the resources and support they need to start, grow or expand their businesses, or recover from a declared disaster. It delivers services through an extensive network of SBA field offices and partnerships with public and private organizations. To learn more, visit

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