Reminder: Check out The Rebooting’s latest research project, which examines email's strategic role in sustainable publishing strategies.
My first job in media was in distribution. I delivered the Philadelphia Inquirer on my bike in Avalon, NJ, and then sold it outside Orlando’s Bakery. Local news is in a tough spot, so it’s encouraging to see signs of a sustainable model emerging at the Inquirer, which has shrunk for years. Inquirer CEO Lisa Hughes joined me on The Rebooting Show to discuss the turnaround.
Rally Rd. is a marketplace where investors buy shares in rare collectible assets. Inside the app, compliance rules limit what they can say. So the real selling happens in their newsletter, Shiny Things, a weekly long-form essay that runs on beehiiv and never actually asks readers to open the app.
The strategy, when paired with beehiiv’s all-in-one growth platform, is clearly working: newsletter subscribers convert at 3X the rate of standard users, with a 20%+ lift in investment behavior and stronger portfolio retention.
And between Q4 2025 and Q1 2026, two major institutional partnerships opened tens of millions of dollars in tier-one supply, both attributed directly to the newsletter.
Owned audience, built right, doesn't just drive engagement. It drives businesses to new levels of success.
Last Thursday, we held the the first NYC edition of the TRB Media Mixer at Dear Irving. We had a great group from companies like People Inc, Semafor, Business Insider, The Financial Times, The Onion, Yahoo, The New York Post and more. Thanks to Beehiiv for the partnership in making the event possible.
We have a series of gatherings coming up;
On April 9, in NYC, we’re holding the TRB Audience Strategies Salon, where we’ll have candid conversations about what’s working in developing direct audience connections and building audience-first products. Thank you to Omeda and ViaFoura for sponsoring the salon.
From April 15-18, I’ll be at the International Journalism Festival in Perugia, Italy. We’re holding an informal dinner there on April 16.
We’ll be at Possible in Miami Beach from April 27-29. We’re doing a series of video podcasts at the event, and I’m looking for a spot to do a casual meetup for anyone in town. Thanks to EX.CO for its sponsorship. We are a media partner of Possible; look for my conversation with Possible creator Christian Muche about what makes for great events.
On May 13, in NYC, we’re holding an AI x Media Salon, where we’ll discuss what’s working in using AI not just for efficiency but to create new products. Thanks to Beehiiv for its sponsorship.
On May 20, also in NYC, we’re holding the third edition of the Media Product Forum, a collaboration between The Rebooting and Wordpress VIP. We are mixing stage conversations of what to build now with roundtable discussions on specific topics, focused again on what’s working.
I’ll be making what could be my 20th pilgrimage to the Cannes Lions from June 22-26. We’re doing a series of video podcasts, private dinners, conversational gatherings, and hopefully a Mixer. Thanks to EX.CO, Beehiiv, Omeda for sponsoring.
All of our events are by invitation only. Please register your interest here.
Get in touch to discuss sponsorship opportunities for TRB gatherings: [email protected].
The Philadelphia Inquirer is a typical big city newspaper that’s been in retreat for a generation. Now under a unique non-profit ownership structure with the Inquirer operating as a for-profit entity with an independent board, the Inquirer grew revenue last year for the first time in 20 years and turned an “operating profit of several million.”
Lisa Hughes, the former New Yorker chief business officer who was named Inquirer CEO in 2020, has focused on shifting the newspaper to a consumer revenue model. It now generates 70% of its revenue from consumer revenue, with the rest coming from advertising, distribution partnerships and philanthropy.
"We are the paper of record,” she told me on The Rebooting Show. “We have been there almost as long as Philadelphia. And you want Philly? We don't need New York telling us about Philly. We don't need New York telling us where to eat in Philly. We need Philly telling us where to eat in Philly."
Notes from the discussion:
AI to power hyperlocal news expansion. Philadelphia has a massive population in the suburbs surrounding the city. The Inquirer is building a network of hyperlocal newsletters covering suburbs by using an in-house tool called Scribe that monitors school board meetings, flags noteworthy moments and surfaces leads for reporters (the human kind). The plan is to grow from four newsletters to 14 by the end of the year and over 30 in 2027.
Adopt B2B moves. The Inquirer has launched a branded content studio that’s produced its “Changemaker” series, which is sponsored profiles of Philadelpia business leaders. It’s similar to how B2B media often run awards and honorifics – with added similarities to DC-based corporate social responsibility advertising.
Useful, revealing and responsive. Local news is a utility. It needs to be useful to people’s everyday lives. The Inquirers’s content strategy was overhauled to de-emphasize the “enterprise to nowhere” stories that were expensive to produce and often failed to have much impact. Now, stories are evaluated against three pillars: useful, revealing, responsive. A useful story: best dive bars. A revealing story: a cop bar with DUIs that are covered up. Responsive: mass-transit outages.
Expanding the TAM. Philadelphia has a population of 1.5 million, down from a peak of 2 million in 1950. The surrounding suburbs that make up the Delaware Valley have 6.5 million people. South Jersey is a big opportunity. It is closer to Philadelphia culturally (translation: they root for the Eagles) and without many strong news outlets. The Inquirer has beefed up its Trenton presence. Lisa said another region is to come, which I suspect is Delaware.
My working assumption of the AI-and-jobs debate is that companies will take a “burn the boats” approach, cut a bunch of jobs and force the Left Behind to fully embrace using these technologies to do more with far less. That will prove in sufficient, more will be hired back and then the economy will go into a tailspin and more layoffs will ensue. On this week’s episode, we discuss why we are still skeptical of AI doom scenarios and more.
I debuted my Tech Mount Rushmore, with slots for The Wizard (Dario Amodei), The Builder (Elon Musk), The Hustler (Travis Kalanick) and more.
We also do show and tell with our vibe coding projects. Troy has tried to create a news aggregator, while I shamelessly tried to rip off CJ Gustafson’s CFO Tech Guide.
AI continues to have a brand problem. One reason I added Steve Jobs in memorium to my Tech Mount Rushmore as The Product Marketer is he’d never have presented this tech as a job-killer at best and world ender at worst. This is first-principles thinking gone awry.
A Canadian billionaire bought a 27% stake in The Economist. More evidence that billionaires will always love to be in the media business for its cachet and access. The trick is to not try to meddle too much. No need to be a Jerry Jones. The Economist’s structure keeps that from happening.
Who lost BuzzFeed? The demise of BuzzFeed has been ongoing for years. For its many pivots, it never settled on a sustainable strategy. It had pieces of many growth areas – creators, the makings of a Substack-like news platform, commerce – but never properly executed.
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