Outworking Your Imposter Syndrome with Jesmond Riggins

Brian chats with long-time friend and fellow lawyer-turned-entrepreneur Jesmond Riggins. Jesmond founded Legislative Logistics, a legislative consulting company for small and medium-sized businesses. On the episode, Jesmond tells his inspiring story from graduating high school near the bottom of his class to graduating from law school and now starting his own business. He also provides insight into the motivational mindset that helps him to continue to achieve success.

Episode Highlights

Who you were does not determine who you will be.

By the time Jesmond reached high school, he was entirely disinterested in school except for playing football. In a pivotal conversation, his football coach convinced him to not quit the team, which he now attributes as a key factor for why he stayed in school and eventually graduated. However, he graduated with a GPA of 1.3 on a 4.0 scale and a rank of 443 out of 459 students.

“Graduating from high school I felt lost,” Jesmond said. “I remember thinking to myself, ‘I’m going nowhere. I’m left behind.’”

While his friends went off to college, Jesmond joined the military. After his time in the service, he worked full-time and attended community college while sleeping in the living room of his mother’s apartment. Because of his poor high school performance, he had a lot of catching up to do and took several remedial classes.

Despite the difficulty, Jesmond kept pushing and landed a scholarship to continue his education at St. John’s University in Queens, NY, where he decided to study government and politics. His professors saw a brilliance in him that they cultivated, which led him to attend Rutgers University law school and land a job after graduation in the Department of Justice.

“I was lucky enough to find myself in the Civil Rights Division,” he said. “I was the only Black male civil rights analyst who implemented and enforced section five of the Voting Rights Act.”

Outwork your imposter syndrome.

Even as Jesmond worked toward a future he wanted, he struggled with self-doubt and imposter syndrome. To overcome those feelings, he gave his studies his best effort and gained confidence as the effort he put in reflected in his grades.

“I was deathly afraid that people would find out that I was stupid, that I’m not supposed to be there,” he said. “So I worked hard. I studied every single day. And when I got my first report card back, it was straight As.”

Create a business that solves a problem.

Desmond’s law career spanned a variety of government and politics-related roles, where he noticed that many people from organizations didn’t know how the political system worked and how to best influence it.

“I had no idea that what I was observing would turn into a business idea," he said. "It was just something that I noticed and all of us complained about.”

Once he realized he could create a business to help small and midsize businesses that can't afford lobbyists, he came up with the dollar amount he needed to save to cover the essentials for himself and his family while he got his business off the ground. Then, he saved as if his life depended on it.

"If you wait for the right moment, you may never do something," he said.

Resources + Links

• Jesmond’s Social Media: LinkedIn

• Brian’s Social Media: Twitter, Instagram, Facebook

About Brian and the Mission Driven Business Podcast 

Brian Thompson, JD/CFP, is a tax attorney and certified financial planner who specializes in providing comprehensive financial planning to LGBTQ+ entrepreneurs who run mission-driven businesses. The Mission Driven Business podcast was born out of his passion for helping social entrepreneurs create businesses with purpose and profit.

On the podcast, Brian talks with diverse entrepreneurs and the people who support them. Listeners hear stories of experiences, strength, and hope and get practical advice to help them build businesses that might just change the world, too.