This week in Field Notes, a product designer building an e-commerce chatbot confessed she doesn't think shoppers want to chat, a Safari update blocking The Trade Desk turned into a fight over whether ad tech was a failure, and members argued over whether we'll end up with one personal agent or five. Join Field Notes.
This week:
A conversation with The Lever’s Daid Sirota on his beef with “corporate” media
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.
These days, corporate media can’t win. The right believes they’re a bunch of aggrieved liberal arts majors with declining cultural power, envy at tech riches and power, and fueled by resentment that media is a handmaiden to tech. The mood can be just as frosty from the left, which sees legacy media as a tool of the ownership class that controls the major institutions of society at the expense of regular people.
David Sirota, founder of independent news outlet The Lever, is a critic from the left. He’s a veteran journalist who was also a speechwriter for Bernie Sanders. He sees publications like The Atlantic and The New York Times as liberal bastions that ultimately serve corporate interests by making progressives feel smart and informed rather than mobilize them to challenge entrenched power structures.
“If you read most “corporate” mainstream news, you’re reading a perspective,” David told me on this week’s The Rebooting Show. “And the perspective is from the big corporations and establishment that essentially owns those media outlets. And it’s not to say that good journalism and good reporting can’t happen inside of that. It certainly can. It’s just to say that that is the dominant perspective put forward by the media machine, the big media outlets.”
The remedy is outlets like The Lever, a reader-supported publication that explicitly challenges corporate power. The Lever has delved into the regulatory regime’s role with regards to AI safety; the role Democrats have played in opposing corporate concentration like the recent Paramount takeover of Warner Bros; and taken a critical view of the role Wall Street has played in Barack Obama’s fundraising for his presidential center in Chicago.
Critical coverage of Obama and other Democratic stalwarts doesn’t win David many friends in progressive circles. These pieces end up losing subscribers, he told me. The Lever looks to achieve a balance between reader subscriptions, foundation grants and select sponsorships.
“The ideal is certainly don’t be captured by any one piece of funding,” he said.
The goal is to assemble an audience that values a sense of learning and discovery, so the journalism must deliver that experience while questioning establishment assumptions. It also has to make structural issues compelling enough to compete with cultural conflict.
“People on the left, center left, etc perceive themselves to be open-minded,” David said. “They want to feel like the media experience is a learning experience, that they’re being exposed and made smarter by their media consumption.”
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The explosive popularity of Muse, Instinct and a raft of AI personal assistants like ChatGPT’s Dots is pointing to a massive interface shift coming to the entire digital economy. My belief is this will put the most pressure on retailers and any business that relies on complexity to create a moat. Basically, lots of others are going to face the compression publishers have undergone for a generation. My current hypotheses:
Liquid publishing is here. Sometimes called headless content, the new approach to media is to be multimodal and have a business model that doesn’t depend on people coming to you.
Outcomes are the new performance. Platforms excelled at direct marketing, which they rebranded performance marketing. Now they’re about to do the same to affiliate marketing, as these assistant coalesce around a business model that takes a cut of transactions.
Convenience is the marketing. Silicon Valley is obsessed with booking flights, for some reason. The real breakthrough of these assistants is likely in disentangling school apps and offloading customer service. Every business will need to have their own agents to deal with the flood of customer service calls.
Privacy is a massive unknown. These agents are betting on being proactive rather than becoming a toy that’s played with a couple times and put away. That will challenge privacy boundaries, as seen by Muse accessing iMessages. Muse sent me a message as I was driving by a hospital because I’d inquired about changing primary care doctors. The creepy line is fuzzy, and tech people regularly cross it.
This isn’t a winner-takes-all market. Search was unique in being a market that had one winner. I don’t see that happening with these agents, which will have their own use cases. Silicon Valley loves the idea of superapps, probably because it concentrates power, but the market has shown time and again that people like to separate out different aspects of their lives. Otherwise there wouldn’t be an Instagram and a LinkedIn.
Send me a note with your feedback by hitting reply. For sponsorship information, contact Richard Jamieson at [email protected].