A Chat with Chris Pilkerton, Keynote Speaker at our 17th Business Appreciation Summit and Community Impact Awards

Business Appreciation Summit - Chris Pilkerton

Chris Pilkerton, former acting administrator and general legal counsel for the U.S. Small Business Administration will headline the 17th Talbot County Business Appreciation Summit on Thursday, May 2, 2024.

We recently sat down with Chris in preparation for the Summit to learn more about his work with small businesses and his take on why Talbot County works as a great place to live and grow a business.

Tell us about your career and how you ended up focusing on small businesses.

I have had the great fortune to have been closely impacted by so many amazing entrepreneurs. From my father, to my brother, to my wife, my personal exposure to the successes and challenges of small businesses has been an integral part of my life.

As a prosecutor at the Manhattan District Attorney’s Office, I saw the importance of a safe community to these companies; during my time working at both the SEC and JP Morgan Chase, I saw the critical needs around regulatory clarity and access to capital; and as a practicing lawyer, I have served as an advisor to many small businesses and always marvel at their ingenuity, passion, and commitment. My time at the SBA, and my ongoing research on small business policy issues have allowed me to put all this experience into work that I truly love.    

What was your role with the SBA and what are you working on since leaving the agency?

I served as the General Counsel for the SBA from 2017 to 2020. In that role, I oversaw about 150 legal personnel, which included engagement with all of the program offices and cases across the agency, including standard and disaster loans, government contracting, entrepreneurial development initiatives, investment companies, and the various innovation programs.

From 2019-2020, I was asked to take on the role of Acting SBA Administrator, which included representing the agency across the country and as part of the President’s Cabinet. Since leaving the agency, I have continued working on small business policy issues, including serving as the head of legal and regulatory matters for Accion Opportunity Fund, the leading community development financial institution focused on small business lending; conducting research on the Paycheck Protection Program at the Harvard Kennedy School; and serving as adjunct faculty/executive in residence at Johns Hopkins and Georgetown business schools.

At Georgetown, we have developed something called the Small Business Corps – which has allowed business school students to work directly with small businesses in the DMV on specific business needs.

What attracted you to Talbot County to make your home?

Talbot County is a very special place. My wife and I had lived in both New York City and Washington, DC just prior to coming to visit the Eastern Shore. We stayed with friends in Easton and eventually took a short trip out to Tilghman Island. We literally woke up and started looking for real estate the next day. The history, the spirit and the people make this just a wonderful community to be a part of, and I will be a resident of Talbot County for the rest of my life!

Underserved Chris Pilkerton Summit

Where did you find your inspiration for writing UNDERSERVED: Harnessing the Principles of Lincoln’s Reconstruction for Today’s Forgotten Communities?

The inspiration that my coauthor and I had in writing the book was to show the reader that while so much of Reconstruction failed to meet its objectives, there is now an occasion in this country where we can pick up the mantle of Lincoln’s original intention to provide meaningful opportunities for underserved communities, particularly through entrepreneurship and workforce development.

What do you think are the biggest takeaways from your book, regarding Ulysses Grant and Abraham Lincoln?

While there are so many lessons to be learned from the Civil War and the Reconstruction era, but in the context of small business, President Lincoln’s vision of opportunity for all underserved communities was very personal, and he wanted to ensure that the forgotten men and women of this country would have the chance to succeed.  

This is probably best put by him when he talked about his goal “to lift artificial weights from all shoulders — to clear the paths of laudable pursuit for all — to afford all, an unfettered start, and a fair chance, in the race of life.”

Frederick Douglass is Talbot County’s native son. Is he included in your book, and how?

It is impossible to talk about the Civil War and Reconstruction without discussing Frederick Douglass. He is a unique American hero whose brilliance, determination and advocacy were critical to moving our country forward. While he is most notably known for his part in ending the inhumanity of slavery, his ability to play such an important role as an abolitionist and civil rights leader was due in part to his foundational success as a small business owner, including newspaper publishing, and also serving as the President of the Freedman’s Bank, which provided financial services to many former slaves.     

How does the SBA best help businesses from your perspective of being inside the agency?

The best thing about the SBA is the people. These folks are so committed to helping entrepreneurs in a variety of ways and truly want you to succeed! While there are innumerable resources online, if your schedule permits, I always encourage folks to set up an office/virtual appointment with an SBA staff member, as the menu of support capabilities is very long, and they can help tailor a plan to your specific needs.

What advice would you give small businesses to support their ongoing success?

I am always hesitant to provide advice to small business owners as I usually learn so much from them. However, in this instance, along with the support services within Talbot County, I do often encourage folks to look at all of the small business support that the federal government can provide, including access to nearly a quarter of its government contracts.

Of course, there is the SBA, but there are also very valuable offerings at the Department of Commerce through its Minority Business Development Agency and Economic Development Administration, as well as the state workforce boards through the Department of Labor.  

Why do you think Talbot County is a great place for businesses?

I have had the opportunity to travel through many states and many counties throughout the country and meet directly with local economic development officials. In my experience, the team within this county is uniquely supportive of their small businesses and is accessible to help with so many topics as they come up.

The other great trait that I have seen first-hand here is that the small business community actively seeks out ways to work together to support each other and their businesses. That type of environment creates real opportunities for new and existing companies. And finally, Talbot County is the home of my wife’s company, Tilghman Island Baking Company, which is of course my favorite small business!  

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About Talbot County Department of Economic Development and Tourism

The Talbot County Department of Economic Development and Tourism’s mission is to enhance and promote a business-friendly environment for current and prospective enterprises and to advocate for policies that support and strengthen the economic vitality of Talbot County. The department’s vision for Talbot County is built on the principles of strong communities, empowered businesses, and innovative solutions.

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