10 things I’ve learned about independent publishing since launching Billy Penn in 2014

Ten years ago, I was preparing to launch a local, independent online news business aimed at a target audience that wasn’t served by traditional media.

The site we launched, Billy Penn, would win national praise, and our parent company, Spirited Media, would raise money and encompass branches in two other cities before we sold our three sites to new owners — after confronting the hard reality that our organization was not independently sustainable.

Yes, once upon a time, I was a LION Publishers member. My CEO at the time, Jim Brady — who’s now vice president of journalism for Knight Foundation — spoke at a LION gathering held in Philadelphia a year after our launch.

It’s been 10 years, and hundreds of other publishers have launched since then; most have a similar backstory: Former legacy newsroom veterans in a hurry to cover their communities and building businesses along the way. Here are 10 lessons for today, looking back on that launch a decade ago.

Lesson 1: The site needed more time to become sustainable.

The Spirited Media sites sold in 2019, nearly five years after we launched. Billy Penn landed at Philadelphia’s largest public media station, WHYY. Two years later, in 2021, it broke even for the first time.

Lesson 2: Focusing on where our audiences were paid off.

Billy Penn was built to be viewed — and shared! — on your phone, and in 2014, that was not the way most of the Internet worked, especially for news. Some legacy news brands’ websites took a full minute or more to load on that era’s iPhones and Androids; most of those newsrooms also actively avoided social media. We built an audience quickly by leaning into the mobile platform.

Lesson 3: It’s cheaper and easier to launch a LION site today.

In order to gain a first-mover advantage for phone viewing, we poured dollars into a custom WordPress theme — bringing on a short-term team of three developers, a designer, and a project manager. At the time, it was revolutionary; today, between Substack, Beehiiv, Ghost through the Tiny News Collective, and Newspack, there are better, faster, and cheaper options. Saving those dollars could have allowed us to focus on building our audience and growing our revenue.

Lesson 4: Philly needed Billy Penn-style journalism.

Alumni of Billy Penn now work for other Philly-based publications. Early hire (and later BP editor) Danya Henninger is now editorial director at Technically, a startup technology-focused newsroom. The type of reader-centered explainers and quirky lifestyle stories that were a hallmark of early Billy Penn now routinely grace the Inquirer’s pages, thanks in no small part to their smart hire of founding BP reporter/curator Anna Orso. 

Lesson 5: Competing for ads with a very small team was really hard.

While Billy Penn and Spirited Media were on a growth trajectory, explaining the value of digital advertising in large markets crowded with much bigger newsrooms proved hugely challenging. In our earliest days, it was far easier to sell ads in a pamphlet for an event than an ad on our site, which reached exponentially more folks but never as many as even the smallest TV newsroom’s web operation, with its emphasis on mugshot-driven crime news. Philadelphia is the nation’s fourth-largest TV market, so there is a ton of competition for media adjacencies. Advertising is a key revenue stream for LION members; some 70 percent of for-profit members sold it in 2024, per our membership data. 

Lesson 6: We were too slow on membership revenue.

I was stepping out of the newsroom in 2017 when the newly combined organization of three contracted with the News Revenue Hub to launch a membership program across our sites. In the beginning, we weren’t sure what the most important measure of our success was — was it a unique visitor? A page view? A follow on Twitter, a fan on Facebook? The Hub helped us understand why gathering emails was the best predictor because that was the first step to directly monetizing our audience through a membership program. Today, one in five LION members lists membership as a piece of their revenue pie.

Lesson 7: ‘In a relationship’ to ‘It’s complicated’: Our changing relationship with Facebook.

In Billy Penn’s early days, the platforms were not only receptive to news — they were optimizing for it. Every year in the run-up to New Year’s Day, this Billy Penn post on a traditional PA Dutch recipe got hundreds of thousands of views because other people started sharing it, year after year. And then, well, the algorithm cared much less about news — what went up came down.

Lesson 8: Everybody needs a lawyer.

Billy Penn worked closely with several legal experts along its path, but not in the ways that journalists-turned-publishers normally think about legal help. That is, we weren’t enlisting help on the whole to FOIA documents or vet stories, but more locking down our corporate incorporation documents. We paid for those services; years later, the nonprofit Lawyers for Reporters would be created, helping future news startups find pro bono help to handle those kinds of costly legal interventions. There’s also the Local Legal Initiative from the Reporters Committee for Freedom of the Press, for help when reporting stories requires an attorney, and ProJourn, from Microsoft and Knight Foundation, aimed at unblocking legal hurdles in reporting.

Lesson 9: In retrospect, we needed intermediaries.

It’s tough to cast my mind back a decade, but here are a few efforts by journalism support organizations that could have benefited Billy Penn and have benefited hundreds of other nascent digital publishers in the intervening years: INN’s NewsMatch; Report for America’s hundreds of fellows (Billy Penn did, actually, get one of those!); the Local Media Association’s NewsFuel to find grants; the American Journalism Project’s big, important projects in dozens of communities; the Lenfest Institute for Journalism; vendors like Blue Lena, state-level efforts like the North Carolina Local News Workshop and Lab Fund; the New Mexico Local News Fund; the Tiny News Collective…. And, quite frankly, our experience a decade ago drove the thinking behind every single program LION has done in my five-plus years here, from the Revenue Growth Fellowship to our Google News Initiative Startups Playbook, Startups and Sustainability Labs to the Sustainability Audits and Funding program supported by the Google News Initiative and Knight Foundation.

Lesson 10: We still have work to do.

I mentioned at the jump that Billy Penn, a decade ago, was a good idea but that the business took more years than we, as owners, could give it. This is borne out in the data that LION collects from its members; in 2024’s data, as we’ve just published, our longer-term members have a median revenue of $147,000 —  and that’s an increase over past years. I’m hopeful, though — the $500 million Press Forward effort, which will help build and grow even more infrastructure, has the potential to build on the progress we’ve made so far, continuing to drive down costs. And hopefully it will inspire even more giving at the local level.

Our experiences in Philadelphia ten years ago are why I took the job at LION more than five years ago, and are at the root of the work today from our team and those of other organizations working to grow this part of the local news ecosystem. It’s why we at LION think news entrepreneurs are the future of local news — and that by empowering them, a renewed independent press can better inform the communities they serve.