Kristi Whitfield: Helping D.C. Businesses Find ‘Every Opportunity to Rise’

Start-up entrepreneurs and business owners often deride big government, but one D.C. official with local business experience of her own — Kristi C. Whitfield, director of the Department of Small and Local Business Development — has dedicated herself to supporting local small business owners and the District’s socioeconomically diverse neighborhoods, especially during the pandemic.

According to a 2019 U.S. Small Business Administration report, over 76,000 small businesses, employing over 245,000 employees, contribute to the District’s economy. Supervising just over 50 employees, Whitfield made the point that her “small and nimble” agency, with only a $14-million budget, is able to experiment with innovative approaches.

Just keeping track of the volume of DSLBD’s programs is a challenge. Harnessing web-based solutions, the DC Capital Connector is a “free, online matchmaking tool that connects small businesses to Community Development Financial Institution lenders and bonding agents with the push of a button.” The program has verified the local credentials of over 1,900 Certified Business Enterprises in the District and helped direct close to $1 billion in contract procurements their way through Procurement Technical Assistance Centers. “That’s local dollars going back into local companies who are hiring local people,” Whitfield noted.

The listings of all government contracts — known as “The Green Book” — have been moved online for the first time, enabling CBEs to connect more readily to contracting opportunities across every field and industry. Each of the District’s Business Improvement Districts has been certified for tax purposes. And DSLBD provides a clearinghouse for information and support services, not only from the Small Business Administration, but from other financial, accounting, business, technical support and marketing entities.

Whitfield has worked side by side with Mayor Muriel Bowser to enhance the DC Main Streets program, dedicated to developing the city’s 26 commercial corridors. The number of Main Streets — which employ significant numbers of D.C. residents at a “livable wage” on Clean Teams — has doubled since the mayor first came to office in 2014. In 2020, DSLBD “celebrated over 300 loans totaling more than $1.5 million to local small businesses” and “over 65 Robust Retail grants totaling $1 million.”

Whitfield is not at all your stereotypical government bureaucrat. With a master’s degree in city planning from M.I.T., she worked as an advocate for affordable housing, inspired by her activist parents, as well as by her upbringing in the racially integrated planned community of Columbia, Maryland.

“So, my dad was Black and my mom was White and they fell in love in the ’60s and got married,” she recounted. “They worked at Job Corps and did housing rights and my mom would go in and try to rent an apartment and see if anything was available and then my dad would go in separately and try to rent an apartment” — documenting the racial discrimination of the time. Whitfield’s upbringing drove her to thinking about how society could be structured to create opportunities for others, rather than hold them back.

“So, my dad was Black and my mom was White and they fell in love in the ’60s and got married,”

In 2009, however, after a “full career” in planning and housing advocacy, she and her then-boyfriend (now her husband) took the plunge to become entrepreneurs. Finding a toehold in D.C.’s burgeoning food truck industry, they established Curbside Cupcakes, the idea being: New York loves cupcakes and L.A. loves food trucks, so why not fuse the two concepts?

Soon, their business took off. “We had three trucks. We had a brick-and-mortar location … and then we had a temporary kiosk at Pentagon City, and then we were one of the first vendors in the cohort that went into Union Market. We had quite a little distribution system going at one point,” she said with pride.

After a few years, as Whitfield was advocating for D.C.’s 17-member food truck association, word hit the street that the District Council was contemplating shutting down the food truck industry downtown.

She quickly arranged a meeting at the Wilson Building with her Ward 4 Council member at the time, Muriel Bowser.

“Hi, would you shake my hand before you regulate me out of existence?” were Whitfield’s first words to Bowser. During an intense back-and-forth, she eventually used a deft maneuver to win an understanding. “I picked up my phone and said, ‘If you do that, we’re going to tweet it out to 65,000 people,’” Whitfield recalled.

Eight years later, when she applied for the position of DSLBD director, Mayor Bowser was heard to say: “Cupcakes, right?” Ever since their first meeting, the two have demonstrated mutual respect and admiration; the mayor knew she had hired a fierce advocate for D.C.’s small businesses, with whom she could work closely.

Whitfield helped set up a “first-of-itskind” pilot project, the Made in DC kiosk at Reagan National Airport. Designed to “connect makers with the market” for D.C. crafts, “It was one of the most profitable kiosks in the entire airport and I was really excited because their first customer was Cory Booker, who — for a halfsecond — was almost going to be the president,” she said with a smile. The Made in DC movement has since taken off with Shop: Made in DC stores in Georgetown, at the Wharf, in Dupont Circle and on Pennsylvania Avenue NW.

When the COVID pandemic hit the District in early 2020, Whitfield turned her entrepreneurial skills and bright sense of humor toward savvy media outreach. She hosted the mayor’s podcast, “Every Opportunity to Rise,” featuring local start-ups such as and She made sure DSLBD staff made phone calls to all 1,900 CBEs to ask them what sort of support they needed during the pandemic. And she helped Mayor Bowser, along with the Main Streets and the BIDs, to deliver almost 3,000 care packages with PPE to local small businesses.

Over the holidays, Whitfield launched the #iBuyDC Challenge, encouraging shoppers to post photos of their local purchases to allow “residents and businesses to showcase how they support the local economy every day while highlighting the local businesses they love to visit.” To make the online campaign go viral, she encouraged supporters to challenge their friends and family to do the same. In one post, Whitfield challenged local radio talk-show host Kojo Nnamdi to join the effort. On Small Business Saturday, the campaign drew national attention when Vice President-elect (at the time) Kamala Harris and her husband, Douglas Emhoff, took up the challenge and posted photos of their shopping visit to the Downtown BID’s Holiday Market.

Using the tools of “distance virtual learning,” Whitfield helped DSLBD post webinars under the Build Back Better program and enhance the website’s “Business Toolkit” to provide answers to every question entrepreneurs and small business owners might ask at each phase of their business trajectory. Whitfield helped the Main Streets redirect $750,000 in their budgets toward direct grants to local businesses. She also steered local business owners towards millions of dollars of federal COVID-19 stimulus funds as they became available through the SBA. In a recent press conference, Whitfield drew attention to the Latino Economic Development Center and its services as a CDFI, in both Spanish and English.

In Georgetown, high rents and retail vacancies are of concern to Whitfield. But she believes Georgetown is “lucky” to have an “amazing BID” under the leadership of Joe Sternlieb, who was an M.I.T. classmate of hers.

As a former entrepreneur, Whitfield most of all wants D.C.’s local small business owners to know that DSLBD is approachable and there to help. During the pandemic, she said, business owners have “been through a crucible.” She emphasized: “It’s okay to not be okay. And you don’t have to bring some social media version of your perfect self to DSLBD when you ask for help, because we deal with actual, real people whose credit is shot and who are exhausted, and who are really at their wits’ end.” Mainly, she said, “DSLBD is here to help you, so please call us.”

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