🍄 From psychedelics-induced ego death to a 37k-subs newsletter

A few things have changed since last week's issue. We're taking a new approach to the Spotlight. While we're still writing about beehiiv creators, we'll also cover LinkedInfluencers, TikTokers, streamers, even Substackers — creators working across all platforms and media.

It takes immense determination and sacrifice to break through in the creator economy; we want to share a more diverse range of stories from that journey. There's as much, if not more, to learn from creators working outside your niche or in different media as from creators similar to you.

I hope you enjoy this and all upcoming issues, but I have one request: please share your feedback. If you have any thoughts at all about our new look, format, and direction, please reply to this email. It'll go straight to me. Do not hold back.

— Francis Zierer, Editor

On January 19, 2023, Henry Winslow sent the first issue of his psychedelics newsletter, Tricycle Day.

One year later, this newsletter, with its simple pitch, "Subscribe to Tricycle Day and get smarter about psychedelics in under 10 minutes a week. 🫠" is sent twice weekly to 37,000 subscribers and counting. When we spoke, the previous month's issues had a 53% open rate and a 6.7% click rate — strong by any standard.

Why are we writing about Tricycle Day? Three main reasons:

• 📈 Henry's bootstrapped growth is both inspiring and repeatable.

• 🔎 It's a masterclass in niching down to build an audience.

• 🍏 The brand's simplicity, strength, and consistency.

Tricycle Day brought in about $77,000 in revenue in 2023 through ad placements, affiliate links, and courses. Henry invested every single cent back into the business — mostly on advertising, as it happens.

The newsletter's Sunday editions feature brief interviews with category experts — past issues have included journalists, founders, venture capitalists, lawyers, and even an episcopal priest. Wednesday editions round up psychedelic research, policy, and business news items.

Henry's success is the story of a person with the right skills and passions (he studied science history at Harvard before building a career in healthcare marketing) at the right time. It's difficult to imagine a newsletter like this launching a decade ago; as venture capitalists and the tireless founders they fund tout the benefits of microdosing and medical researchers publish more and more reports on the various substances' therapeutic benefits, psychedelics are closer to normalization in mainstream culture than ever before.

We recently spent an hour speaking with Henry. Read an excerpt of the interview below, or read it in full on our website.

Have more questions for Henry? He's offered to do an AMA in the comments of this post on Monday, January 29, from 3PM–5PM ET. Add a comment in the meantime and he'll answer it then!

Don’t have time to read the interview? Here are a few quick lessons from Tricycle Day, applicable across niches and platforms.

1. Identify a clear niche, and making decisions around brand and content becomes simpler. Henry was looking for a media product covering psychedelics in an way “normal” people could relate to and draw intellectual value from. Every decision, like what stories to cover and how to define the brand voice, followed logically. He was his niche, which helps, but what matters is that you have a specific person in mind. Ask yourself, "Would this resonate with them?"
   

2. Success as a creator relies, above all else, on commitment and consistency. Henry wrote 93 issues in his first year. He also put $50,000-plus into Meta ads. You can build an audience without paid ads, but you can't build an audience without a consistent output. Consistent output is the keystone of any creator’s growth strategy.
   

3. An email list is more durable than a social media following. This is core to Tricycle Day's pitch to advertisers, and it's one of Henry's main learnings from his stretch as a yoga creator. Most creators don't work in a niche with the inherent legal implications of psychedelics and the platform ban risk that comes with it, but still — you own your email list. You don't own your Instagram followers; you can't just copy them to a new account.
   

4. Going all-in as a creator can drive growth, but stepping back is also okay. Henry quit his full-time job in 2015 and became a yoga creator, then returned to that job in 2020 for stability in the pandemic. He left again and started Tricycle Day in 2023. Take opportunities as they present themselves, but please take care of yourself.

Read the full interview for more context.

The genesis of Tricycle Day

More than half a decade before he started Tricycle Day, Henry quit his day job at a healthcare marketing agency to follow his dreams in the yoga world.

Among other exploits in the yoga world, Henry built an Instagram following of over 38,000, an email list of 2,000, two yoga apps (he sold both), and even ran a podcast for 108 episodes. This first foray into what was becoming the creator economy was foundational for Tricycle Day.

There’s a concept in yoga (and a few religions) called samadhi, which Henry told us is “the ultimate destination of the yoga practice.” Think of it as ego death. Regardless, shortly before the pandemic, a friend of Henry’s told him she’d found a shortcut to samadhi.

The following interview has been edited for length and clarity.

Creator Spotlight: How do we get from your experiencing ego death to starting a very contemporary newsletter about psychedelics?

Henry Winslow: It wasn't until the beginning of 2023 I came around to the idea of Tricycle Day, and it's similar to the story about why I started a podcast.

I had become a big reader of newsletters over the previous few years. I was reading The Hustle and Morning Brew, then Milk Road. I listened to My First Million. The exits were appealing, but I was also very drawn by the understanding that email is a medium in which people are truly digesting information. Email doesn't just have to be about marketing. And I thought I could do that for psychedelics.

I love writing and have a marketing and branding background, so I knew I could bring a unique brand to it. beehiiv is awesome for that because, compared to Substack, which is very formulaic and templated, I could infuse my brand into it. So I chose beehiiv and got started. 

I wrote the first newsletter issue to one subscriber — myself — to prove I could do it. Then I texted 10 friends and got them to subscribe, so 10 people got the second issue.

Eventually, I sent out an update to my yoga email list. It was a full update on what I'd been doing in my life, and I ended it by saying, “look, if you want to subscribe, click here.” That brought me a few hundred subscribers. Now, I had an audience that I felt committed to, whose trust I was accountable to.

CS: Your branding has been consistent since your first issue. It's clearly designed for an audience following the normalization of psychedelics. What was the thinking behind the brand when you first started?

HW: I found that everyone in the space was speaking at basically two ends of a spectrum, both alienating the possibility of a mainstream audience. On one end, you had this very dense content requiring medical literacy or legal jargon. On the other end of the spectrum, it was people talking about 5D consciousness; it was spiritual, also alienating in a totally different way. 

My hypothesis was that we're at this precipice where psychedelics are very quickly entering the mainstream, which means the market of interested people is growing, particularly at the center of the bell curve. But that center-curve, "normal" person, was being completely ignored. So, I'm going to write in a way that is unintimidating and light. In some ways, the way I write is polarizing because people see psychedelics as sacred medicines, and I use a little bit of snark. I use humor. I use memes. I use emojis. That was an intentional decision from the beginning because I wanted to go after that new group of people.

CS: What were the main growth levers you used to grow from a few hundred to 37,000+ subscribers?

HW: Meta ads have been my main driver. I had around 1,000 subscribers when I started advertising. I figured, why keep writing into the ether if I can afford to scale? Doing so not only allowed me to reach more people (obviously); it also gave me a larger “n” to experiment with formatting and content to gain valuable feedback. And it also accelerated my path to an audience size that was attractive to sponsors.

I let Meta decide where to serve my ads, but there's a healthy mix of IG and FB. I've scaled the spend up and down at different periods, but right now, I'm spending about $5k per month. I plan to do it indefinitely and ideally, I'll increase the budget as I can afford to, while maintaining profitability.

I learned to run Meta ads with a previous endeavor in e-commerce. That business didn't survive but I spent something like $50k on ads in 3 months to make $150k in sales. Margins were razor-thin when you factored in CoGS [cost of goods sold]. It was a great learning experience.

Attending in-person events within the psychedelic sector has been a big part of Tricycle Day’s growth and success, too. It’s brought me new subscribers, sponsors, interview guests, and last but not least, new experiences that have fundamentally shifted my psychology.

I’ve also used beehiiv’s Boosts — I deposited $2,500 into my account, which beehiiv matched during a promotion for a total of $5,000, and I’m still burning through that.

CS: Let's talk more about monetization. Are you making your living off of Tricycle Day at this point? And, especially since you're running Meta ads, what are you investing in the project financially?

HW: High level, I'm not making a living off of it, because every dollar that comes into the business, I've reinvested into it. I'm in a fortunate position where I had savings to live off of, but those savings are coming to an end soon, which is part of why I'm exploring alternate routes of monetization for the business and getting ready to kick off building a team. The newsletter is making pretty good money, and I'm happy with the top line last year. 

The newsletter grossed around $77,000 in 2023. Obviously, in the beginning, it wasn't easy to monetize. So that number is more loaded onto the back half of this year. The first sponsor ran on March 29. I was about two months in, which is early. They paid $480 for two issues.

I'm happy with my first-year numbers, but running those ads is also expensive. I wanted to speed up the growth, but I'm starting to back off the spend a bit and get to a place where it's more sustainable.

CS: This is a sponsor-supported newsletter, but you also offer a couple of paid courses to your audience, and you mentioned that you're preparing to build a team.

HW: Sponsorships have always been the number one monetization source for Tricycle Day, and number two has been affiliate links, which I put into “Cyclist’s Picks.” In the beginning, there were a few times when I was ramping up with sponsorships, and I didn't have a sponsor for every issue, so I would fill that inventory and make it look like an ad — but it was just an affiliate offer. That's a bit of advice for newsletters just getting started; you can always do that. You can apply for and get approved for most affiliate programs out there immediately. 

After sponsorships and affiliate links, I added digital products sold directly to my readers. So, for the first time, I was not just monetizing my audience's attention but trying to sell directly to them.

CS: One of the main draws of participating in the creator economy is the freedom and potentially high upside. Still, it has risks that you don't necessarily deal with in a corporate job. How do you think about the sacrifices you have to make as a creator versus as an employee?

HW: It is very much a sacrifice to do what we do in this space. Those creators who produce meta work about creating always sell a vision of pure freedom. And that may be true, but there are genuine trade-offs. 

When you work for a company, you generally only have to do one thing, and you know you'll get the same amount of money in your bank account twice a month. That can take a great deal of emotional weight off your shoulders.

It's also an option to do both things at once; theoretically, I could run Tricycle Day while working 40 hours per week for somebody else. But I find it difficult to give my best to multiple projects at once, and that's something that I've hedged a lot in the past. So that's another trade-off. It might sound like a best-of-both-worlds scenario, but you're inevitably making too many compromises.

CS: You started Tricycle Day because it was a product you wanted as a consumer — now it’s read by thousands of people twice a week. You’ve touched on the health and legal implications inherent to this space. What do you think about your responsibility to your audience?

HW: I absolutely believe that I have a responsibility to my audience. Tricycle Day has always been a very mission-driven idea and business. Yes, it's a for-profit company. No, I have not taken any profit off of it yet, but it is a for-profit company. Profit or not, I consider it my form of advocacy. The fact that psychedelic therapy is not available or that you have to jump through all sorts of hoops to get access to that care is not acceptable. 

I believe that by publishing this newsletter and doing it in a way that reaches a broader swath of the general population, making it more accessible to the average consumer, I can positively affect public sentiment. 

That's the responsibility that I'm holding myself to. More broadly, I would say if you're a creator and have an audience, I think it is your responsibility to dig deep and figure out what matters to you and use your platform for a cause. It doesn't necessarily need to be everything you do, but I think you should stand up for things you believe in.

CS: You’ve just hit your first anniversary. What's your dream for the next year of Tricycle Day?

HW: I have all kinds of dreams! I'm launching a marketing agency on the back end of the newsletter. I just announced it in a recent issue to create some external accountability. People appreciate the work that we've done in terms of building a brand in the psychedelic space. It's a case study, a proof of concept everyone can see. I'm very pleased with the response that I got to that announcement. Many people, from individual coaches to therapists, non-profits, and even some full-on businesses in the space, want to work with this agency that they know nothing about other than that it's from the people behind Tricycle Day. 

I'm excited, but I need to build a team to do that. I've done a lot of entrepreneurship and side hustles, but I've never assembled a team or led a company like this. It's always been a one-man show. This is the next stage of my growth as an entrepreneur, and it's exciting, but at the same time, it's something I'm grappling with.

I'd always thought about Tricycle Day as just myself and the readers. I've begun looking at it in a new way — building a team is exciting because the business can serve more people in new ways, and others can share in its success and ownership.

CS: One of the harsh realities of running, as you said, a one-man show in the creator economy is that it takes a great deal to be consistent. Why do you keep going, and what would it take for you to turn back to the corporate world? What toll has this taken on you besides burning through your savings?

HW: Well, I'm glad you asked the previous question before this one — I even got a little emotional in answering. Knowing that the work really matters is a big part of what drives me to keep going. As far as the toll that it's taken, beyond anything financial, it's been an emotional challenge. I have a 15-month-old son; he was born not too long before the launch of the newsletter. So that adds additional pressure to do a good job, to make this a success, and to provide for my family. It's not just me and my wife. It's me, my wife, and my son. 

I love the pressure, in a way. There are two sides of the same coin. It's a yin and yang situation. The pressure, in some cases, is really needed — it forces you into an uncomfortable position, which is where all the growth happens.

Editor’s note: Henry works in particularly complex space, and we’d like to share the disclaimer he places at the bottom of every issue of his newsletter:

Have more questions for Henry? He's offered to do an AMA in the comments of this post on Monday, January 29, from 3PM–5PM ET. Add a comment in the meantime and he'll answer it then!

One tactical, actionable takeaway — it worked for Henry; you could apply it to your newsletter today.

Henry has an easy suggestion for newsletter creators trying to attract advertisers for the first time:

If you find the right affiliate program and integrate it well into your newsletter layout, right where you'd want to place a genuine sponsored ad, it'll be easier for ad buyers to see how their ad units fit into your product. As Henry pointed out, this is also an excellent stopgap if you already have advertisers, but only for some issues.

Content we've been thinking about this week.

• Substack has been in the hot seat for months now after initially refusing to take a stance against Nazi content on the platform. They've removed a few offenders, but multiple prominent creators have already jumped ship.

• Kyle Chayka's Filterworld: How Algorithms Flattened Culture came out last week. Read an excerpt. It’s a savvy analysis on what it means to create and consume content online right now.

• A panel of creators dissected creator Ryan Trahan's storytelling style on Patreon CEO Jack Conte's great video series Digital Spaghetti. As always with this series, there’s as much to learn about storytelling from the video’s production itself as there is from subject’s work.

Thank you for reading! As we fine-tune the new Creator Spotlight over the coming weeks, our highest priority is to better serve our audience (that’s you). Let me know what "better" means to you: reply to this email with your thoughts or just click an option on the polls below.

I want to know what you think of the design, the sections, how we’re using images, what other types of content you’d like to see from us…don’t hold back!

All the best,

— Francis Zierer, Editor

P.S. Have more questions for Henry? He's offered to do an AMA in the comments of this post on Monday, January 29, from 3PM–5PM ET. Add a comment in the meantime and he'll answer it then!