My latest: How investment newsletter The Daily Upside reached 300,000 subscribers

How do you go from zero to over 300,000 newsletter subscribers in a little over two years? For The Daily Upside, it certainly helped to form a partnership with an already-established financial news publication.

Reader mailbag

Hello there! This is the latest edition of my Q&A series where readers ask me questions and I do my best to answer them.

But there’s a catch: while the answers are free to read, only the paying subscribers get to ask the questions. If you’re a paying subscriber who wants to ask a question for the next edition, you can leave it in this thread over here.

And if you want to subscribe, the link below will get you 10% off for your first year. Not only will you be able to participate in these Q&A sessions, but you’ll be supporting the work I do for my newsletter and podcast.

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Ok, let’s jump into it…

Why media companies don’t partner up on bundled subscriptions very often

The first question comes from Taegan Goddard

Do you know any instances of publications owned by different companies offering a bundled subscription? How do the mechanics and economics work — especially if the publications are on different subscription management platforms?

I can certainly think of a few examples where media companies teamed up to offer bundled subscriptions. For instance, Bloomberg and The Information offered one back in 2020, though I think it’s since been discontinued. There was also the Everything Bundle, a Substack experiment where several writers teamed up to distribute their paid newsletters through a shared account.

But you’re right, Taegan, these kinds of partnerships are rare, even though the benefits seem obvious. Not only can two publishers share the marketing burden, but a discounted bundle would presumably produce more value for a subscriber.

So why don’t we see more bundled subscriptions? It really all comes down to logistics. Let’s run through some of the challenges you’d need to overcome:

• As you hinted at in your question, you would need to get the subscription management platforms to play well together, which can be a huge hurdle in and of itself.

• You’d need to find a publisher who’s of equal size and influence to you. Otherwise, you’d end up driving 80% of subscriptions while only taking home 50% of the revenue.

• There’d be little recourse if the partner didn’t hold up their end of the bargain. Let’s say you team up with another newsletter and then the writer starts to publish only sporadically. Are they continuing to earn their 50%, or whatever fixed rate you agreed upon?

• Even if you decide to end the bundle, then you’re stuck servicing those legacy subscribers in perpetuity. At the very least, you would have to transfer them back over to your subscription management program and comp them for a year’s subscription to make up for the fact that they’re no longer benefiting from the bundle.

These hurdles aren’t insurmountable, but they’re large enough to deter many publishers from even bothering with a subscription partnership.

That’s not to say there aren’t cool ways that publishers are teaming up to help grow each other’s subscription products. One of my favorite examples was Sidechannel, a shared Discord community that you could join if you became a paid subscriber of one of the participating newsletters. What I loved about this is that it added an additional subscriber benefit and allowed these newsletters to cross promote each other, but at the same time they could continue to operate their subscriptions independently, which meant that nobody was harmed if one of the participating newsletters pulled out of the arrangement. 

I’ve also seen examples where creators team up to launch a subscription product that’s separate from their main offering. A great example of this is Dithering, the joint podcast run by Ben Thompson and John Gruber. It publishes two 15-minute episodes per week and costs $50 a year. It’s a fantastic way for Gruber and Thompson to cross pollinate their audiences, yet if they decide to walk away, then their individual businesses aren’t affected. I think this is a great way to capitalize on the benefits of a subscription bundle without dealing with the downsides that I listed above.

Building a media company with the goal to exit one day?

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They Got Acquired shares stories of companies that sell for 6, 7, and low-8 figures, including media companies like:

• The Charlotte Agenda, a local publication with $2 million in revenue that was acquired by Axios

• Hot Pod, a newsletter about the podcasting industry with 25,000+ subscribers that sold to Vox

• The Write Life, a niche website for writers that saw nearly 500,000 monthly pageviews and sold for mid-6 figures

For more stories like these and resources for selling your company, subscribe to They Got Acquired’s newsletter.

Who are my favorite creators right now?

The next question comes from Leslie Bradshaw:

Who is doing some of the most original thinking and writing these days?

My newsletter is so narrowly focused that I rarely get to zoom out and spotlight my favorite creators, so thank you for asking this question. Let’s run through them:

Johnny Harris: I don’t think anyone is pushing the boundaries on what can be accomplished on YouTube more than Johnny Harris. He got his start at Vox Media but later struck off on his own, and his videos just have an incredible combination of research, editing, animation, and storytelling. He gets me to watch 20-minute videos on topics I’d normally care nothing about. One of my favorite videos of his is called “How I Took a Picture of a Galaxy.”  

Pitch Meeting: Many people are probably familiar with the Honest Trailers YouTube channel, but I think Pitch Meeting is so much better. It just does such a good job of deconstructing the absurdity of movie plots, even when those movies are otherwise good.

Drew Gooden: What I love about Drew Gooden is how he demonstrates what can be done with a guy just sitting at his computer and talking into a webcam. I probably laugh at his videos more often than I would while watching your average TV sitcom.

americanbaron: What if you took Woody Allen and crossed him with Wes Anderson, and then limited him to making 60-second videos?  Great starter video: “Am I there?”

u m a m i: I don’t think I could even begin to describe his animated videos, but I promise you’ve never seen anything like them. Great starter video: “The Cycle of Life.”   

Captain Disillusion: Like Johnny Harris, this dude is just upending everything we thought about what it means to be a YouTuber. He’s basically taking Hollywood-level expertise in special effects and applying them to a platform that’s otherwise known for low-budget videos. Great starter video: “Flight of the Navigator | VFXcool”

Kaptainkristian: Unfortunately he doesn’t post that often, but this guy’s video essays are just top notch. Great starter video: “The Invisible Horror of The Shining”

Against the Rules with Michael Lewis: I might be cheating since Lewis was already a celebrity writer long before he launched this podcast, but I’m including it because it wasn’t produced by a major media company.

The Filmcast: This my go-to movie podcast. There’s nothing particularly innovative about the format — it’s just three guys discussing movies and TV shows — but the chemistry between them is pitch perfect. 

Who? Weekly: You know when you’re in the grocery store and you see a tabloid magazine with “celebrities” on the front, but you have no idea who the hell they are? Well the two hosts of this show know exactly who these people are and they’re able to explain the ongoing drama that gets covered in tabloids and gossip blogs. It’s hilarious. 

She’s a Beast: This newsletter has done so much to change my perspective on health and fitness, particularly my own. For the better part of 10 years, I tried every form of aerobic exercise and dieting to reverse the weight gain. I trained for 10ks, half marathons, and triathlons, and I ate salads for months at a time. Nothing worked. Then in April 2021 I adopted a new mindset: If I couldn’t lose the weight, then I would convert as much of it as I could into muscle. I got serious about weight training, and since then I’ve increased the amount of weight I can lift by over 40%. Check out this essay by Casey Johnston, the woman who writes She’s a Beast: “I Didn’t Start Weight Lifting Because I Wanted to Be Strong.”

Dirt: Dirt is an entertainment newsletter, but you won’t find reviews of Succession or Marvel movies in it. When it’s at its best, it’s unearthing YouTube, Instagram, TikTok, and Twitter accounts you’ve never heard of and reviewing them with the same critical eye that mainstream columnists give to Hollywood film and television. Great starter article: “Dirt: 80s news screens”

Journalists should have no qualms about getting paid

From Alexandra Klinnik

I would like to know what you think about the rise of the ghostwriting on LinkedIn ? Is it a good option for journalists in need of money ?

I’m guessing that you’re referring to this Business Insider article: “The rise of LinkedIn ghostwriters, who can earn up to $700 an hour helping execs build personal brands and become influencers.”

If you listen to an interview with anyone who started their freelance writing career pre-internet, you get the sense that it was an attainable goal to do good journalism and also get paid well. I remember hearing, for instance, about a writer who was contracted by The Atlantic to be paid six figures for writing four pieces a year. 

Was that a reasonable career path for most writers back then? I have no idea. But I doubt that The Atlantic is handing out many six figure freelance contracts today, at least for anyone other than top-tier writers with already-existing brands.

I think the freelancers who make good money today take on two kinds of jobs:

1. Work they’re proud of

2. Work that pays well

The work they’re proud of appears in mainstream internet outlets but only pays a few hundred dollars a pop. The work that pays well falls under the nebulous category known as “content marketing.” It’s paid for out of brands’ marketing budgets and appears in the form of company blog posts, ghost-written CEO op-eds, and social media content.

Honestly, I don’t think writers should have any qualms about creating this kind of content. It allows them to leverage their skills in a way that subsidizes the work that they actually love doing, and as they build up their personal brands, they can slowly transition toward better-paying journalism jobs that both pay well AND make them proud.

That’s how I ended up working on this newsletter full-time. For about six years, I took on content marketing clients while producing my own content during my free time, and by early 2020 I felt like I had enough momentum to make the jump into a career as a full-time creator. I haven’t looked back since, and today I don’t hesitate for a second when turning down (high paying) content marketing gigs. 

Quick hits

Amazon is making a $11 billion bet on streaming live sports. [Insider] This will result in a lot of Amazon Prime signups, but I doubt it'll be very profitable. Sports broadcasting rights are just so inflated because of the economics of the cable bundle, where non-sports watchers unwillingly subsidize cable channels like ESPN.

The company formerly known as Gawker Media is once again profitable. There was a long and winding road that got the company to this point, including multiple acquisitions and lots of conflict with its newsrooms. [Adweek]

I love the media environment we're currently in and am super excited about the growth of the Creator Economy, but I must admit that it would be cool to travel back in time to work for glossy magazines during their golden age. [NYT]

"The Guardian’s main focus in the coming months is to shift more of its newsletter portfolio from being automated or curated newsletters with a brief summary of the news, to more dedicated, in-depth newsletters featuring original reporting and analysis." [Press Gazette]

ICYMI: How Josh Spector monetizes his 25,000 newsletter subscribers

Through a mixture of consulting, advertising, and paid subscriptions.

There’s another way you can support this newsletter

I get it, not everyone is ready to become a paid subscriber. Personally, I’m maxed out on subscriptions and couldn’t justify adding another one even if I wanted to. But you can still support my work by simply recommending this newsletter to others. The more devoted readers I have for this newsletter, the higher the advertising rates I can charge. It really is that simple.

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Thanks in advance!