For Leslie Winston III, it was a case of the third time is the charm when his company, Monocle, was named HBCU Grand Prize Winner at the 3rd Annual Black Ambition Demo Day on Nov. 9 at Spring Studios in New York.

It was a win that earned the company $200,000 in funding. Black Ambition is a nonprofit initiative founded in 2020 by record producer, singer/songwriter and Virginia native Pharrell Williams to empower and support Black and Hispanic entrepreneurs. To date, it has mentored nearly 1,000 entrepreneurs and given $10 million in funding to over 100 prize winners.

“I knew about Black Ambition because I am a big fan of Pharrell Williams and N.E.R.D.,” Mr. Winston said in a recent telephone interview.

“I saw the posts on social media when he launched it three years ago and I entered the first time partially for the chance to meet Pharrell.”

The idea for Monocle—a social e-reading app that would allow any reader’s thoughts to be embedded within any book—occurred to him the previous year during the pandemic. Everyone was reading more said Mr. Winston, including himself. His read was “History of the Black Dollar” by Angel Rich.

“It was right after George Floyd was murdered and there was what seemed to be a collective effort to understand policing in America, race in America and people were very openly sharing their thoughts and reactions,” Mr. Winston shared.

As he read, he came to a page about Black Codes, laws enacted in D.C. and other states after emancipation that governed the conduct of Black people and severely limited their rights, and decided to share it with his thoughts on Instagram to engage friends in conversation.

“People post so often online that it was really only relevant for like 30 minutes before people moved on to the next thing on their timeline,” Mr. Winston explained.

But while his post only garnered a few comments, it was the impetus for Monocle. He designed a quick prototype, asked friends and family for their reaction, and was thrilled when they shared his excitement for the idea.

The graduate of North Carolina A&T State University was buoyed further when he was selected in March 2021 to participate in Nex Cubed’s inaugural HBCU Founder’s Summer Acceleration Program, an initiative that helped him to develop his idea and provided him with $10,000 in capital.

When his application to Black Ambition didn’t advance in 2021, Mr. Winston tried again the following year with the same result. For this year, the Richmond native and current Brooklynite said his thoughts of entering for the third time were “on the back burner,” but he submitted his application at the last minute, becoming one of more than 2,000 to apply.

He advanced through the competition, eventually being selected as one of the top eight finalists who were invited to present their pitches on Demo Day, supported in spirit by his family.

“It was great. I shared a livestream link with them and they watched the whole program,” Mr. Winston said, adding with a laugh, “We were texting throughout and they told me my presentation was the best so far, even though I pitched second.”

Back in Henrico County, his parents, Leslie and Betty Winston, were watching on the edge of their seats. While younger brother Daniel and older sister Lauren weren’t able to be at the house, his eldest sibling Christopher also was there cheering for his brother.

Calling her son a “natural born engineer,” Mrs. Winston said by phone that he would “break apart the vacuum and then put it back together,” and loved building with LEGO growing up.

“When the emcee said he’d be announcing the HBCU winner, I just had the feeling Leslie was going to win so I videotaped it on my phone,” she added. “We’re just so proud of him, of his app and of the way he pitched. He’s just a wonderful human being.”

Mr. Winston said the success Monocle had at Black Ambition earned the company more than double what had been raised in funding thus far.

“This win is just a huge signal to me and my team that there’s something real here that deserves our time and attention,” he added.

Now the team is working on updates and improvements identified by a private Beta testing group earlier in the year.

Mr. Winston hopes to have Monocle ready for a public launch next year and dreams of a platform where people can go for meaningful human connection and conversation that can help improve their own life and the lives of those around them.

“I think books are the most compelling piece of content we look to to shape the world,” Mr. Winston said. “If books can be the foundation of connection, I think we can appreciate learning more about each other and the world.”