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Last week I went to The Newsletter Conference, my first-ever industry event outside the journalism world. It was a bit of a culture shock.

I expected to walk away with tips on audience growth and monetization. I did. But I also left feeling like I’d stepped into a parallel universe: one where newsletters are treated almost exclusively as business assets, not as tools for service, trust or community. The emphasis was on scaling fast, slicing audiences into ever-nicher segments, and automating everything possible. Not bad advice — and the most valuable insights came from conference emcee and Inbox Collective founder Dan Oshinsky. (more below)

Attempts to weave journalism into the programming didn’t quite land. The Ankler’s Janice Min and Semafor co-founder Ben Smith offered tales from the elite media world that felt far removed from the experiences of the solopreneurs and indie producers in the room. (Min on Substack: “Our experience isn’t the same as anyone else. We have direct access to Hamish and there is a best-sellers team.”)

TL;DR: The conference spotlighted big-name success stories, but offered less for solo operators trying to build sustainable, values-driven businesses — as opposed to launching media startups built to scale.

There were valuable takeaways — like the warning that AI-enabled inboxes might soon reroute your newsletter into a “promotions” tab unless you seriously up your engagement game. Or that “if you’re still calling yourself a newsletter business a year from now, you might be in trouble,” as Jacob Cohen Donnelly from A Media Operator said. (He was moving fast into video and community platforms.) And there was a lot of love for Substack — though even that came with caveats about whether creators are building their own brands or simply building Substack’s.

But some moments were downright surreal — like a panel on Making Local News Profitable that began with 6AM City co-founder Ryan Heafy mocking nonprofit journalism as a failed model. It was jarring to see public service news treated like a naïve experiment instead of a lifeline for underserved communities. Luckily, Capital B’s Akoto Ofori-Atta was on that panel too and deftly, resoundingly made just that point to a burst of spontaneous applause from the audience.

So, what’s the takeaway?

There’s a ton we can learn from outside our industry — especially about business modeling, growth strategy and diversifying revenue. But not everything needs to be absorbed. Creator journalists are navigating a different path: one that blends public mission with personal brand, revenue with values, audience with community. And while it might not scale like Workweek or go viral like MrBeast, it matters.

Would I go again? Probably. And I’d love to talk with the organizers about how future programming could better reflect the needs of journalism creators building sustainable, mission-driven work.

In the spirit of sharing what was useful, here are a few of the most actionable tips I took away:

the latest

• The New Yorker’s Kyle Chayka writes a surprisingly cynical take on creator-model journalism… in his own private, creator-style Substack. He dismisses the shift toward independent media and laments the decline of prestige institutions, but misses the deeper reasons why so many journalists are choosing to build something of their own.

• Because balance in all things is nice: Dick Tofel makes the case for why legacy newsrooms should take creator journalists seriously – not just as curiosities, but as colleagues in a smart, generous read that urges collaboration over gatekeeping.

• Liz Plank takes us inside Trending Up, a D.C. gathering where progressive creators, organizers – and even folks like Pete Buttigieg and Elizabeth Warren – talked about building progressive media ecosystem to match the right’s sprawling universe.

• Dear Media is becoming the estrogen-fueled answer to the podcast manosphere, now operating the largest network of podcasts for women with a slate of 100+ “girlboss and therapy speak” heavy shows, writes Jessica Testa for the NYT.

• Twitch star Kai Cenat announced Streamer University — a free, weekend-long content bootcamp aimed at helping aspiring creators break into the business. Within hours, 6 million people tried to sign up. It’s a striking example of how creator-led education is scaling fast – and a reminder that journalism has its own opportunity to meet this moment with training rooted in public service and credibility.

• Tween podcasters are taking over the internet! 😱 This conversation between Taylor Lorenz and New York Mag’s EJ Dickson is a must listen. (And no, Desmond - my 14-year-old son - does not have a podcast. At least that I know of. 🤔 )

  

platform stuff

• Gen Z is “always on” and deeply social-first, according to a study from Toluma. They average 7–8 digital activities per daypart, with 74% using social media at any time of day. Vertical video DOMINATES: 81% watch it weekly, with TikTok, Instagram Reels and YouTube Shorts leading the way. So if you had any questions about why WaPo’s Carmela Boykin is such a ⭐️ , now you know – she’s serving up awesome algorithm friendly vertical video to the audience of the future.

• Teen Vogue adds another layer: nearly 40% of young people now get news from influencers, not traditional outlets — and many say it feels more trustworthy. For creator journalists, the takeaway is clear: don’t just chase reach. Build relationship.

• If you’re one of the few people on Substack who didn’t migrate there from broadcast TV, have they got a feature for you: The platform just launched an audio-only livestream feature, giving writers a way to go live without video.

• Hey podcast friends, Spotify just launched Plays, a new stat showing how many people actually listen to (or watch) your podcast episodes in real time. It’s available now in Spotify for Creators and could help indie journalists fine-tune what’s resonating — especially for those experimenting with video or multi-format storytelling.

• LinkedIn isn’t just for job hunting anymore – it’s becoming a legit space for creators to position themselves as high-value B2B voices. This Digiday piece shows how creators are landing brand deals by showing up as experts. For journalism creators especially, it’s a reminder: if your work helps people do something (understand, decide, act) LinkedIn might be worth your time as you build your brand.

• Prediction: TikTok will not be banned in the U.S. (Yes, you also likely made this prediction.)

do something cool

• Build your media kit: If you’re selling sponsorships or going after funding of almost any kind, you need a media kit. Last week, fellow Going Solo instructor Blair Hickman and I taught media kit fundamentals to Medill’s Local News Accelerator cohort. More to come soon in this space. In the meantime, Nathan May put together a collection of the best newsletter media kits he’s found out there. Worth a scan.

• Set a goal: Join Lex Roman for the free Your Next Milestone session on Tuesday, May 13 at 2 p.m. ET and learn more about how to set and reach your revenue goals.

• Go to SRC CON: It’s not too late to apply to participate in the 2025 conference where Lex and I will be leading a session titled, cheekily, “I’m not an influencer, but I play one on the internet.” Join us in Minneapolis. We can hit Paisley Park. 💜 

🎉 👏 🚀 A HUGE congrats to Going Solo cohort 1 grad K Kaufmann for the launch of her new newsletter E/lectrify and to cohort 2’s Bryan Vance whose Stumptown Savings continues to take off and led to this recent appearance on Portland TV!