Billy Penn celebrated its 10th anniversary with fans, cake and the return of the Billies awards. (Heather Chin/Billy Penn)

More than 200 Billy Penn readers and fans gathered at WHYY Wednesday night to celebrate 10 years of the news website and hear from seven winners of the publication’s Billies Awards. 

Launched as a startup in 2014 and acquired by WHYY in 2019, the nonprofit news website strives to cover Philadelphia “like a friend who happens to be really knowledgeable” about the city. Its journalists guide readers through the latest on elections, sports, transportation, development, arts and culture, and the city’s food and drink scene. 

“I always viewed Billy Penn as more independent journalism, and I’m attracted to that,” said Brian Smith, who relied on the publication’s early coverage of city government and politics to learn about Philly after he moved to the city 10 years ago. 

In the decade since, Billy Penn has covered the wacky and wonderful parts of Philly, as well as the serious

“Billy Penn has really been a gem for us in telling city stories,” said WHYY Vice President of News & Civic Dialogue Sarah Glover.  The current staff includes investigative reporter Meir Rinde, deputy editor Heather Chin and spot-news reporter Nick Kariuki, as well as editor Kevin Donahue.

Albert Lee of @urphillypal poses with his photo ahead of receiving a Billie award at the 10th anniversary celebration at WHYY on October 23, 2024. (Heather Chin/Billy Penn)

Wednesday’s event was a celebration of notable Philadelphians profiled by Billy Penn. They included Chinatown business booster Albert Lee, social media sensation Terrill Haigler, aka Ya Fav Trashman, artist entrepreneur Conrad Benner, coworking pioneer Alex Hillman, the man who took to eating entire rotisserie chickens for sport on an abandoned pier, Nancy Schure Olivieri (one of the leading women of Philly’s cheesesteak scene), and Dave Cline, the single West Philly guy who rented a billboard this summer to find a date.  

“I think I’m the first person ever to win an award for being single,” Cline said. “If I made you smile, then this was all worth it.”

Conrad Benner, Philadelphia artist, accepts a Billie award at the 10th anniversary celebration at WHYY on October 23, 2024. (Kimberly Paynter/WHYY)

Billy Penn was the first media outlet to interview Cline about his billboard, he said. Other outlets, including the New York Times and Washington Post, later picked up the story. 

“The press has just been overall, super positive,” he said. “It seems that everyone who is dating right now is having a similar experience, which is, it’s very hard to date. And the articles always seem to reflect that.”

Billy Penn editor Kevin Donahue (right) presents Dave Cline (left) with a Billie award at the 10th anniversary of WHYY’s Billy Penn on October 23, 2024. (Kimberly Paynter/WHYY)

Billy Penn’s coverage also helped raise Terrill Haigler’s profile. The former sanitation worker, professional dancer and City Council candidate is currently working to hire returning citizens and young people to clean up their own neighborhoods, he said Wednesday. 

“No matter your ZIP code, you deserve to live on a clean street,” he said. “Billy Penn was very instrumental in me launching and getting recognized nationally.”

Terrill Haigler, aka Ya Fav Trashman, accepts a Billie award at the 10th anniversary celebration at WHYY on October 23, 2024. (Kimberly Paynter/WHYY)

Donahue, who joined the publication in June with a background in news and service journalism, says the Billies Awards exemplify the kind of journalism Billy Penn does well. 

“It reflects back people you don’t know, but that you kind of wish you did, after you read the story,” Donahue said.

When Spirited Media first launched Billy Penn in 2014, the company targeted its content toward millennials. 

“We had this idea for trying to reach younger city dwellers via mobile phones primarily, and using a voice and an attitude and an energy that was not prevalent at the time in the traditional media sources,” said co-founder Jim Brady in a video played at the event. 

A few years later, WHYY saw purchasing Billy Penn as an opportunity to cultivate a new generation of public media consumers, said WHYY President and CEO Bill Marrazzo. 

“It’s been fascinating and satisfying to see over the last 10 years that, while millennials do traffic Billy Penn, anybody at any age that’s interested in the community they live in are also participating in the consumption of Billy Penn,” he said.

Billy Penn celebrated its 10th anniversary Wednesday, October 23, 2024. (Heather Chin/Billy Penn)

Retired teacher Jane Roosa is one example of a loyal reader who’s not a millennial. She remembers finding Billy Penn’s Chicken Man coverage hilarious and turns to the news site to learn about upcoming events, too. 

“It tells us what we can do in the city … things that we didn’t know about to go visit — parks, shows,” she said. “It’s our social life.”

The Billy Penn team also sneak-previewed its annual DIY Halloween costumes (see the 2023 lineup!), which are an irreverent look at the previous year. The costumes and a video will be available in the next few days.

Billy Penn reporters Meir Rinde (left) and Nick Kariuki (right) preview the 2024 Billy Penn Philadelphia Halloween costumes at the 10th anniversary of Billy Penn celebration at WHYY on October 23, 2024. (Kimberly Paynter/WHYY)

Sophia Schmidt covers the environment for WHYY’s PlanPhilly. Before coming to Philadelphia in 2021, Sophia reported on her home state of Delaware for Delaware Public Media and produced interviews for...