🔴 Newsletter ads + agency = living wage

Two days short of one year ago, I sent my first edition of Creator Spotlight after taking over the editorship. Our guest for that issue was Henry Winslow, creator of a newsletter called Tricycle Day, a bi-weekly covering psychedelics research, policy, and business.

At the time, he was only one year into the project. I asked him if he would sit for a second interview to reflect on the second year. My understanding of what it means to be a creator on the internet has evolved; it was an opportunity to ask new questions about his work.

In this issue:

• 🤔 Subtly adjusting Tricycle Day’s content in year 2 for a shifting audience

• 💹 How Henry grew and diversified his revenue to make a living

• 🤝 Creators have a responsibility to their audiences and broader society

— Francis Zierer, Editor

P.S. Watch our interview with Henry on YouTube or listen to it on any podcast platform.

A successful second year

When I interviewed Henry Winslow one year ago, he reflected on a by-most-accounts successful year. The newsletter he’d started one year previously, Tricycle Day, had over 37,000 subscribers. He’d shipped 106 issues, built an 8,000-strong following on Instagram, and brought it some $77,000 in revenue — all as a solo creator.

Caveat: Henry did not pay himself a single dollar from Tricycle Day’s revenue last year. He lived off his savings, putting every dollar the project earned right back into it, and some of those savings.

When I spoke to Henry, he was spending “about $5k per month” on Meta ads. This is where most of his subscribers came from in both years of the project.

Today, Tricycle Day boasts:

• 18.1k Instagram followers

• 60k Subscribers

• $250k revenue in 2024

• Three (part-time) team members besides Henry

Admirable growth across the board — most importantly, he’s now making a living from the project.

If it ain’t broke, don’t fix it

Last week, I asked newsletter growth expert Matt McGarry how he’d recommend growing a newsletter subscriber list from 0 to 1,000. His first point: “If your newsletter isn’t valuable, people aren’t going to sign up." Henry found content-market fit early in Tricycle Day’s lifetime — two months in, he’d nailed a two-issues-per-week cycle. There’s been no fundamental change since.

Around that same time, Henry hit 1,000 subscribers and started running paid ad campaigns through Meta, representing the bulk of his spending in year one and bringing in the bulk of his subscribers. “Over 80%” of his 23,000+ new subscribers in 2024 came through these same ad campaigns, where costs have “fluctuated anywhere between $1 and $1.50 per subscriber” since he started.”

First-party data (answers to surveys and polls Henry ran last year) and anecdotal notes gave Henry a new understanding of his audience: 70% identify as psychedelics enthusiasts, 15% as practitioners (researchers, guides, lawyers, etc.), and another 15% as students (“on the way to a career in psychedelics or professionals in some other aspect of the ecosystem”). Two years ago, Henry was in no way a professional in this space — now he’s built one of the leading professional media companies in the industry; he is a professional serving professionals, a self-described activist working to professionalize an industry.

From this understanding of his audience, Henry has launched his agency, a professional directory, and a professional community (using Circle) for these professionals that already hosts some 40 members (he dreams of 1,000 by the end of the year).

An agency born of necessity

When we first spoke, Henry was on the verge of launching his agency. “Ever the solopreneur,” he was nervous about bringing more moving parts into his operation, but bet it would make the business sustainable in his second year. That bet made good.

Let Go Studio works with clients in the broader psychedelics industry, including retreats, clinics, and coaches, who generally have an ads budget of “at least $5,000 per month.” Henry and his team provide full-spectrum Meta advertising services: strategy, campaign asset creation, monitoring, and reporting.

Besides Henry, the team is two “semi-permanent” contractors, a client success director and a media director, and a number of case-by-case creators. To incentivize those two contractors, Henry provides a profit share — appropriate for a creator economy business where the creator has near-limitless upside while incurring all the risk; I’d expect to see this model more.

The majority of Henry’s revenue still comes from the ads he sells in Tricycle Day. This was his primary but not only source of revenue in 2023, when he brought in $77k (affiliate programs and low-ticket courses were the other sources). In 2024, he cracked $250k. The more-than-tripled growth is due to three factors:

• Starting 2024 with an established ads program and a sizable audience

• Continued audience growth driving up placement prices

• The addition of a second revenue stream through Henry’s agency

Henry tells me his ad pricing has “always been backed into roughly a $50 CPM [or cost per mille] based on open,” and he does discounts if people buy placements in bulk because “the campaigns always perform much better if the audience sees it multiple times.” A single-issue ad buy currently costs around $1,500; purchasing four triggers a 15% discount. He also offers a monthly recurring package — three months of two issues per month. There have been 59 sponsors over nearly two years of ad sales.

How Henry plans to double down in his third year

I want you to understand precisely what Henry is doing. Yes, functionally, we’ve already laid it out: publishing a bi-weekly newsletter in which he sells ads, growing that audience with Meta ads, and, through his agency, selling ads on behalf of clients in his industry. But all of this is towards a specific end.

I’d be remiss if I didn’t share the disclaimer Henry places at the bottom of every newsletter issue:

Henry did not set out to start an agency, a directory of psychedelics practitioners, or a community of industry professionals. He set out to produce a newsletter he wished existed. As he puts it:

He’s a curator with a specific ideology that presupposes some psychedelics are legitimate medicine and should be treated and regulated as such by governmental bodies; creating a serious media product is his form of activism to this end, as is every project born from the newsletter.

When I first interviewed Henry, I asked him if, especially given the health and legal implications of his industry, he thinks about his responsibility to his audience and society at large. His answer moved me — he became visibly emotional while answering. You can read that answer in full in our previously-published interview, but I want to stress this point: you do have a responsibility to your audience and society at large.

Whether or not you accept that responsibility is another question. The internet, inasmuch as it is a massive quantity of data we access and exchange moment to moment, is made up of what we contribute to it. Every contribution is a choice.

The information you put out there will be read by someone. It may be used as training data for a large language model; parts of it may form the answer to some question some teenager asks of ChatGPT, affecting their understanding of the world, affecting the actions they take out there in the world.

When people speak of creators as the new media — when Elon tweets, “You are the media” — this is what they mean: that shared information shapes individual and group perceptions of reality; that traditional media institutions have less power than ever to do this; that information you publish may shape realities. Do not take this lightly.

Connect with Henry on Twitter or LinkedIn.
Read and subscribe to Tricycle Day, or follow on Instagram.

🎙️ Here’s what you’ll find in this week’s podcast that isn’t in this newsletter:

• 📣 A detailed look at how Henry approaches his ad sales business

• 🍄 The particular challenges of operating a media company in Henry’s niche

• 💵 Henry thinks through a potential acquisition-based exit

Listen on your preferred podcast platform or watch on YouTube.

Don’t mistake an audience for a community

One of Henry’s tentpole projects for his third year is to create a community. I wouldn’t bet on most people pulling this off; I would bet on him.

There can be overlap between audience and community. For example, some YouTube and TikTok accounts support thriving comment-section communities, with regular viewers having conversations across videos over long periods of time. But that’s a flimsy and ephemeral form of community compared to what happens in, say, a Discord, Slack, or Circle setup.

Henry is not building a community for Tricycle Day readers — he’s building a community for a tightly specific segment of people who may read the newsletter: “psychedelic facilitators who want to connect and build the skills to scale their practice and increase their impact.”

Listen to the latest episode of Tasteland, the weekly podcast about media, tech, and business hosted by Spotlight editor Francis Zierer and Dirt Media CEO Daisy Alioto.

• This week, we spoke to Mike Pepi about his just-released book Against Platforms: Surviving Digital Utopia. It’s a book I’d recommend to anyone working in tech, working as a creator, or otherwise using tech platforms in their everyday lives; it’s a book I’m recommending to you.
  
  We spoke about bullying ChatGPT, what exactly a “platform” is, techno-utopianism, free content is free labor, and a belief in pluralism.

And if you want to know more about Henry and Tricycle Day, read my interview with him from one year ago.