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Last year you made $77,000 in revenue. This year, cracked two fifty for the year. Nice. Wow. You have built this really special, unique audience. How do you get your first 1,000 subscribers? Consistency was the key.

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I know that you have very high standards. You're a very detail-oriented person. I do see this work as an art form. I think about every issue that I put out as a piece.

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So actually, let's talk about the content for a second. The risk and uncertainty of the niche you operate. On Instagram, my account has been, like, suppressed.

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Of course, I wanna make a living for myself, but there are many ways to do that that don't involve dancing right on the edge of legality. [laughs] What word you would use to define yourself? I think that I am a creator.

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I think that's a fair word. I think another word that applies to me is activist. Welcome back to the Creator Spotlight podcast.

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Today, we are speaking with Henry Winslow, creator of Tricycle Day, a newsletter about the professionalizing world of psychedelics research, policy, and business.

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This is a special episode of the podcast in that Henry was the first person I interviewed for Creator Spotlight one year ago. At the time, he was precisely one year into working on his own project, and it was thriving.

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It was a great conversation, but I could only publish a slice of it in the newsletter because we did not have the podcast yet.

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So to mark one full year of doing the newsletter and check in on two full years of Henry doing his newsletter, I figured we'd have him on the pod. How's it going? I love that. I mean, it's going great.

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Thank you for having me back. It's nice to see you. Yes. I, I feel like this is a really momentous occasion. A momentous occasion indeed. Yeah. So the first year was, was good. How's the second year been good?

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Has it been a good year for, for Tricycle Day and for you personally? Yeah, it has been a good year for, for me personally a-and for the business. Mm-hmm.

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Um, on the Tricycle Day side, I mentioned this when we spoke the first time, but the first year was really all about growth for me.

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That was the number one priority was building up a sizable audience 'cause I felt like that was, you know, table stakes to be able- Mm... to do anything meaningful.

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Year two was about turning it into a sustainable business. Mm. And the other thing that I mentioned when we first spoke was my big plans to launch an agency.

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So, you know, this first-- the first year, the path to monetization was the traditional media model. Mm.

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I was selling advertising, um, one sponsored placement per issue, which I've continued to do, and that's still the bedrock, uh, of, of the finances. Yeah.

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Um, but then in year two, I launched, uh, a growth marketing agency for businesses in my space. It was basically a way to serve my most loyal sponsors at a higher level.

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Well, and, and Tricycle Day was kind of the case study for this, right? 'Cause I think what you do with the agency is you help them sell ads, um, which is what you did for the first year with Tricycle Day, right?

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Well, it wasn't so much about helping them sell ads. Mm. It was about using Facebook and Instagram ads to, uh, generate leads- Yeah... and, and conversions and sales.

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So, um, you know, a lot of the sponsors who came on to Tricycle Day were in the plant medicine and psychedelic space, and there's challenges around censorship, content moderation when you try to run ads on these platforms.

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Yeah.

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Even if you are doing things in legal jurisdiction or, you know, in, you know, uh, adjacent spaces that are, that are legal, sometimes you run into trouble and, and I figured that out, and I built a team that also had that expertise, and that's what we've been doing with the agency.

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Okay, so there's... Uh, uh, basically everything you just said we'll be unpacking over the next- [laughs]... uh, forty-five minutes or so. Um, I wanna start with the audience, though.

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So in the first year when we spoke, you had around thirty-seven thousand subscribers from that year. Um, you're- Yeah... a little over double that right now.

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Your publicly available numbers say sixty thousand, and I know you'd spent fifty thousand dollars on meta advertising in that first year.

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I'm guessing you didn't spend that much this year because y-you ha- you didn't double the audience size and probably there's more organic growth there. Mm-hmm.

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Um, did you-- But were you continuing to, like, s- put a lot of money into the business in that way this year, or were you kind of able to dial it back and things were running more smoothly? I did dial it back.

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I should have prepared and figured out exact- the exact amount I spent. That's okay. Um, but you're right, it's-- it was less.

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I'm still spending consistently 'cause I think it is a good way to, you know, keep fresh blood coming into the newsletter. Yeah. But yeah, organic started to pick up.

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I've developed a-- I've built an audience on LinkedIn, of all places, um- [laughs] One of the few people- And then the meme strategy... building an audience around psychedelics research policy [laughs] on- Yeah, yeah...

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this useless LinkedIn. [laughs] Yeah, and, uh, and the meme strategy on Instagram is, is working well too. Mm-hmm. Yeah, you've more than doubled your audience there.

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I forget exactly what it was last time, but now it's eighteen thousand. Mm-hmm. I think when we last spoke, it was closer to, like, six thousand or something. Okay. Yeah. Yeah. Yeah, it's grown.

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And the nice thing about, you know, organic and, and doing paid at the same time is you kinda pay your way at the beginning, and then organic picks up naturally, and it can kind of overtake it eventually.

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I haven't gotten there yet- Yeah... but it's beginning to take up a larger share. Where-- So that's twenty-three thousand subscribers around that since we last spoke. Where, wh-where's the split?

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Like, how much have come from ads? How much have come from organic? Within organic, like, where have they come from? Oh, gosh. Um- [laughs]...

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yeah, I don't, I don't know the breakdown, but- I don't think you need to- It's cer- It's certainly well- Yeah... it's well over eighty percent are coming from ads. Oh, wow. Still, yeah. Yeah.

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Which I mean, for you too, I think in...

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I mean, I've learned a lot more about newsletter ads since we last, last spoke, and a lot of people, you included, kind of use this model that, I don't know if Morning Brew was the-- were the people who invented it, but, like, they're certainly who I associate it with, where it's like in five minutes a day, learn everything you need to learn about X, right?

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Which like- Yeah... for Morning Brew, like, there's-- maybe there's a lot of people now trying to copy the Morning Brew model for, like, business-type newsletters.

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Much harder to do that now 'cause people have seen those ads. But I think for- Yeah... somebody like you or anybody who's in like a very, a niche that isn't as saturated, it's like, it's still pretty effective, right?

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Like, what kind of, um, CPA are you able to command? Yeah, I mean, I've kind of fluctuated anywhere between a dollar and a dollar fifty for a subscriber- That's really good... pretty much since the beginning. Yeah.

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Mm-hmm. Um-One thing before we get too deep into all this year two stuff, uh, because anybody listening, maybe they read the feature on you a year ago, uh, maybe they didn't.

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Um, but I wanna talk a little bit about your origin story, and like...

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'Cause people always ask me, you know, when they reply to the welcome email, when they sign up for Creator Spotlight, like, "How do you get your first 1,000 subscribers?" Or something. Yeah.

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And you- your origin story is that before you did this, you had this kind of this-- Not kind of, you had this yoga teacher arc, and you, you had a podcast where you did over 100 episodes, and you- Yeah...

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were touring and teaching classes, and like, you had like... I, I forget. It was 60,000 or 38,000, something like that, uh, Instagram followers for that.

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You had built up an in- an, an email list of 2,000, largely through like, you teach these classes and, you know, you say to people, "Hey, if you wanna know when I'm next doing it, sign up."

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All that aside, like obviously you built that up. Can you remind me, like, how you built-- how you first got the ball rolling with Tricycle Day? Like, what, what was the kickoff that allowed you to go from zero to one?

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Yeah. [swiping sound] Hey, if you're enjoying this episode with Henry, make sure you follow the podcast so you don't miss next week's episode. We release a new Creator interview every Thursday. I appreciate your support.

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Enjoy the rest of the episode. [swiping sound] Well, good memory, first of all. Of course. Uh, when I, when I started, I wrote the first issue to myself. I didn't tell anyone. I didn't tell a soul.

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I just wanted to see how it felt, um, is this a project that I wanna pursue?

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'Cause it-- I knew from doing a podcast in the past and doing a content business, if you will, around yoga, that consistency was the key, and you needed to be able to, like, hang in there for the long haul.

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So I did one test issue and sent it to myself and thought, "Yeah, this is fun. I could do this. Beehive is cool."

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Um, and then I texted a handful of friends, probably like five to 10 people, and s- I knew that they had some interest in psychedelics, but more importantly, they were willing to support me.

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Uh, so they all signed up, and then I wrote the next issue to them. They actually started to share it with other people, so that was the first taste of, you know, the, the referral network effect.

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And, um, I think that got me close to... You know, I had dozens of subscribers at that point, and then the big next bolus of subscribers came from leveraging my, my previous list.

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So I had left this yoga email list go completely dormant over 18 months or so, 'cause I had stepped away from teaching.

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And, um, and I just reached out to them with this long email that was pretty much like a life update.

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I talked about all the things I had been doing, things that had been going on in my personal life, and, um, at the very end, I said, "If you're interested in following along, this is what I'm working on now."

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You know, there's, there's some overlap between yoga, spirituality, and psychedelics. That was my entry point. That was my reason for reaching out. Certainly your, yeah, your perspective, yeah.

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Um, so I got, I don't know, maybe 300 or 400 people from that email. Um, and at that point, I felt like, "Okay, I'm accountable to this audience-" Yeah. "... so I'm sticking with this for sure." How, uh...

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One more question about that. When did you-- How big was it when you started running paid ads? How many subscribers did you have? I think I got up to about 1,000, and then I started- Yeah... running ads.

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'Cause at that point, too, you'd really, you know, validated the content. Which- Mm-hmm... so actually, let's talk about the content for a second. Um, I, I look back at, you know, your last year of, of, of issues.

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Looks exactly the same as most of the first year. Uh- Mm-hmm... which I think is really good. That means, you know, you dialed it in. You haven't had to change anything. Um- Yeah...

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for the listener who hasn't seen it, there's basically two distinct weekly emails. On Wednesdays, there's a five-minute...

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You know, this classic newsletter format, like five-minute This Week in Psychedelics roundup of things happening across research, policy, business in the psychedelics world.

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Um, and then on Sundays, there's the Psychonaut POV, which is an interview series. Um- Mm-hmm... so every, every Sunday and every Wednesday, two, two issues a week for the last year, steady on.

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Has anything changed about the content at all since we last spoke, or has it just been dialed? As far as formatting, no. I, I sh- I shifted it around a little bit in the first year.

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It probably took six or seven months to get to the format that it is now. Mm-hmm. Um, but since then, that has remained consistent. The, the feedback around it has been great. Mm-hmm. People like it.

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They like the brevity. They like the humor. Um, so I haven't changed that. But one thing that has shifted a little bit, which is a little bit harder to see- Mm...

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immediately, is, uh, I began to get a little bit more first-party data around who my readers are. Yeah. Through, through surveys? And so now I- Through polls? How? There's, there's-- First, it was just anecdotal.

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I was kinda like picking up on it. Mm.

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And then I was like, "Okay, let me get proper about this," and I did a survey, which is now part of my welcome flow, and I sent it to my audience a couple times too to get the people who were already on the list.

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And what I know now directionally is about 70% of my readers would identify as psychedelic enthusiasts. Mm. So, you know, consumers, essentially. And then 30% are in the field in some way, shape, or form. They- Yeah.

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About 15% are practitioners, and another 15% are either students on the way to a career in psychedelics or professionals in some other aspect of the ecosystem. Mm-hmm.

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And knowing that kinda helped me think about the balance of content that I include, and I've started to shift a little bit more towards serving the professionals. Mm.

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In the beginning, it was really, you know, I was thinking about myself- Yeah... a, a general consumer who had interests. Well, now, now you're a professional, so [laughs] Yeah, so it's shifted along with me.

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Yeah, exactly. Exactly. Yeah. Um, what, like-- Could you illustrate, like, what that shift actually looks like? Like, is it something about, like, questions you're asking of your interview guests?

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Is it the selection of interview guests? Is it the specific curation in, in the weekly roundups? What, like, how, how do these actually, these changes manifested? Sure. Um, yes, all of those things. Yeah. Um,

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I try to make sure that every issue has something for both of those audience segments. Mm. And I try to make it, you know, relatively, like, uh, proportional to the- Yeah...

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to the split of the audience.But for example, you know, it's about curating the articles and the things that I choose to highlight.

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So, you know, there's been a lot of movement in the past, ah, few months around this new natural medicine program that's rolling out in Colorado.

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And so I've started to include information that might be relevant to people who are considering becoming licensed facilitators- Yeah... or who already are.

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And I might not have done so much in the weeds there before and just covered it from broad strokes, thinking about like, okay, who might go and actually sit for a session- Mm-hmm...

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versus who's gonna deliver the session. Yeah. Um, so the agency, I think...

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I can't remember if you told me this when we last spoke, but I don't believe you ever really did this setting out to make an a- to start an agency. You wanted to do a newsletter.

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You saw this opportunity for a newsletter, and that was something- Mm... that you thought would be fun to do.

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Um, so you started doing that, and then my impression is you created the agency because you needed to make a living doing this. Yeah.

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And that was kind of the most synergistic way to con- to like branch out another revenue stream besides ads, right? That's correct.

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And the other part of my backstory that you did not mention is my first job out of college was in ad agencies. Yes. Yeah. You're- Yeah.... experienced in marketing.

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I was an account manager, and then I was a brand strategist. So, um, you know, I, I walked away from that because there are things about it that frustrated me- Yeah [laughs]... but I also have the skill set, you know?

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So- Yeah... um, it's different now though. It's, I mean, it's a much scrappier agency serving a much more targeted niche, and also I have a different role in it. You know, I'm- Mm-hmm...

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I'm the owner, operator, and I still am involved in the work, but I have a team that's actually- So the team, um, when, when we last spoke a year ago, you were like on the verge.

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You were thinking about hiring a team, and this was something that you were, you were kind of really, I, I don't know if grappling is the right word, but you were kind of grappling with it in that like you'd done these like entrepreneurial projects and side projects and whatever for, for many years, but they were always just like you and like- Yeah...

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you didn't have to externalize any of this. Um, so actually I want to hear about you hiring the team and like how you worked through this and, uh, how big the team is as well. Yeah. E- ever the solopreneur.

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[laughs] Uh, no, I knew intellectually, um, and even beyond that, I knew from some, some level of experience that outsourcing, delegating- Yeah... empowering other people was the way to have a greater impact.

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But I struggled with it because it takes a certain amount of courage and, um, and a certain amount of changing what you know- Mm-hmm... to, to relinquish control.

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Um, so I challenged myself to do that, and I've been very happy with, with the results of doing that. It's a small team. You know, I have two people who are, you know, on it per- like semi-permanently, you know? Yeah.

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Um, they're not W-2 employees. They're, they're contractors, but they're, they're part of the team. And then I have, uh, some, some creatives who we pull in on more a case by case basis for specific projects.

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And the two people that I chose to hire, you know, for those more stable positions are, one is a client success director. Mm. She interfaces with the, with the clients, and she also does a lot of creative work.

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And then the other is a media director. Mm. So he's got the media buying expertise. Nice. Um, how... I, I'm curious. So I wanna, I wanna linger on like the emotional side of this for a bit because- Okay...

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I don't know, just, just the idea of like relinquishing that control and like figuring out like, well, what do I delegate? What can I really afford to delegate?

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And like my, my standards remain high because I, I know that you have very high standards. You're a very detail-oriented person. Um, I don't know.

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I think that's something that I, I think about as I know this, this year I'll probably be looking for some more help with Creator Spotlight, and I think, um, probably some listeners also, you know, uh, maybe are at a stage where they're expanding the team or something to think about.

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So like, yeah, what's like- Yeah... what are the crucial things to get right that like you really thought a lot about when you did this? Yeah. Good question. Um, some of it is definitely intangible.

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It's like just digging deep, doing the soul searching to be like, "Okay, I know what's right for me. Even if it feels scary, I'm gonna do it." That's what courage is. Yeah.

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Um, but there, there are some practical things too. I think one of the things I thought about a lot was incentivizing good work. Hmm.

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Um, so rather than just paying my contractors a steady rate, what I did was brought them in and gave them upside. So they, they share in... They, they get a profit share- Nice... of that aspect of the business.

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And I think that works out nicely because then they're incentivized to do great work because retention is the name of the game in agency, right? Yeah. If clients stay, stay around, then their, their payout goes up.

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Well, that's interesting c- 'cause obviously that's like a classic like, you know, sales organization model or a startup model where you get a stake in a business.

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Um, but then like with kind of the, the creator economy too, right? Like the appeal of being a solopreneur, a creator, whatever you wanna call it, is like it's your thing. It's all yours. The risk is yours.

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The upside is yours. Um, so I think it's interesting to bring some... bring people in and give them that stake too, because like that's your motivation is that all- Yeah... it's all, all the upside is yours.

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Uh, I, I don't know. I think that's smart.

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I've, I haven't talked to so many people who've done that unless they're bringing somebody in like as like a, a real partner in the business, as like a co-founder, labeling them that rather than like a contractor who also has a real stake.

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So- Mm-hmm... this is, yeah, really important. Yeah. And, and to be clear, I don't, I didn't give them equity in the business- Yeah... just profit share on this, um, this monetization- Yeah, yeah... channel, right?

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And that makes it simpler. Like we don't have to do a whole lot of like legal contracts to make that work. Yeah. I just do the P&L every month. I share... I'm very transparent with it, and then I pay them out.

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So let's talk about P&L in that last year you made $77,000 in revenue in your first year through a mix of ad placements, affiliate links, and courses. Um- Yeah... you also were not making a living from Tricycle Day.

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You'd, you'd reinvested every dollar into the business. You were living off your savings. Um, it sounds to me like you- Yeah...

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probably are making a living here now, uh, and a- certainly at least the revenue has greatly increased in that you [laughs] just like you're doing it, you've hired a couple people. Um- Yeah...

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so tell me, yeah, how's, how's the revenue looking, and are you living off of it now?I am living off of it. Congratulations. I'm not living off it as comfortably- [laughs]... as one might like to. Yes.

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But, you know, it's- Let's hear it. [laughs] Yeah. Yeah, but it, it grew significantly from- Yeah... year one. Year one, yeah, I think it ended around seventy-five, seventy-seven, something like that. Yeah.

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This year, cracked two fifty for the year. Um- Nice. Wow. And the margins, you know, are, are steadily improving. Yeah. How much of that is, is from the agency? It's still the majority from ad, ad revenue. Wow. Yeah.

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Yeah. Have you... Uh, so actually I'm curious about your sponsor pricing.

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You don't have to be exact 'cause I know it varies, but, um, as a reference point, you had told me that your first sponsor, um, back in March 2023, two months into the newsletter, this person or this business paid $480 for a feature in two issues.

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Obviously, that's increased thanks to a number of factors now. Yeah. Um, but can you share like, I don't know, a range how much it's grown relative to that since, since two years ago? Yeah.

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I mean, I can share the, the pricing. Oh, sure. I'm open to that. Perfect. Um, it's always been backed into a f- a roughly $50 CPM- Mm... based on opens, so views- Okay... for the, for the ad.

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Um, and so today a single issue is fifteen hundred, and, um, I do discounts if people, uh, buy bulk. Yeah. Um, because I think that the, the campaigns always perform much better if the audience sees it multiple times.

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Mm-hmm. So I wanna incentivize that. Um, they get like 15% off if they do four or, um, it was 30% off for eight issues, but I just recently changed for the new year to get around just selling eight issues. Mm.

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Now it's like there's a monthly recurring option- Oh, wow... where they can commit to three months and get two issues per month. Do you know approximately how many different sponsors you had last year?

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Not just last year, but in total? Yeah. I have had 59 sponsors. Fifty-nine? Wow, that's actually quite a bit. Yeah.

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I was, I was wondering if it would be a little, like a smaller number just because people do keep coming back because I feel like th- uh, one thing, I don't-- you're not, you're...

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in no means are you an influencer, but I was having a conversation with somebody on one of these interviews, actually the episode that came out today as we're recording this, with Lindsay Stanberry.

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Um, and she is a, she comes from like a, an editor background. She was an editor at Refinery29, then Fortune. She never identified as a journalist.

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She was a, an, a wri- a writer and editor, and now she doesn't see herself as a creator. She sees herself as more of this writer, editor, entrepreneur. Um- Mm... but something I hadn't

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vocalized before, she was saying like, "Well, what's the difference between an influencer and a creator?"

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And I was like, "Well, an influencer is just a freelance marketer, and their skill is like their ability to market, but also the audience that they're marketing to," which like that, that, I think that...

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you're not an inf- I wouldn't call you an influencer, but that applies here where like you have built this really special, unique audience of people interested in these, in this particular type of business. Mm.

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So like it, it, it doesn't work for every newsletter, um, because not every newsletter has such a s- highly specialized, specific audience as you, but like

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I would imagine a lot of these people really come back, and you actually, hopefully, probably... I'm asking, do you have like a wait list, um, for, for the clients, uh, because people... A, a wait list for sponsors? Yes.

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I get a lot of, uh, basically all of my sponsors have been inbound. Yeah.

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I did hire an agency to do outbound, uh, last year just 'cause I wanted to experiment with that and see if there was a difference in the quality or, you know- Yeah... how it would play out.

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Um, but yeah, it's, it's- It wasn't really necessary... other than that, it's been a... It, it wasn't really necessary. Um, I'm glad I did it, you know- Yeah...

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'cause we, I did land some sponsors I hadn't been able to get ahold of that were good for my audience. But, um, there's a lot of inbound every week. Mm. So I, I am in the fortunate position of being able to say no.

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That's awesome. How about with the agency? Agency is, like there's a lot more qualification- Yeah... that has to go into whether it's a good fit.

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So I still say no often, um, but not because it's like, "Oh, we can't handle-" Yeah. "... another client." Well, I know on your, on the, so the- it's called Let Go Studio. I was looking at the website. Yeah.

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Um, at the bottom of the page, it's like right be- right by the, uh, you know, Apply to Work With Us button, it's like, "Wait, don't apply unless you are looking to spend at least $5,000 a month with us."

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Like that's kind of- Yeah... the first- Yeah... level of filtration. Yeah. Yeah. Yeah.

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We should talk briefly, 'cause this is related to the agency too, about like the, the risk and uncertainty of the niche you operate, right? Mm-hmm.

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So at the bottom of every newsletter, uh, of every newsletter, you have a disclaimer, which I'll read now.

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Um, "Disclaimer: This newsletter is for educational and informational purposes only and is not intended as a substitute for prohe- professional medical advice.

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The use, possession, and distribution of psychedelic drugs are illegal in most countries and may result in criminal prosecution."

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Um, so obviously in, a- as in any year, especially recently, as, you know, these psychedelics have come more into these legal conversations, um- Mm-hmm...

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laws passing, legalizing them, delegalizing them, going back, et cetera, um, I'm curious if there have been any developments in that realm that have affected either your work in the newsletter or like your, the way you work with clients, because that's a service you offer is like- Yes...

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helping people navigate these kind of like murky waters of like, well, what, how do we present our business on the internet? Yeah. Yeah. Um, well, first, how it's affected me, fortunately not too much.

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There've been a couple of blips. Yeah. One was last year. Uh, no. No, it was this year. It was since we spoke last time. Yeah.

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Um, there was an issue I ran into with Twilio SendGrid, which is the underlying email str- infrastructure- Yeah... provider below Beehiiv. One of the big... Yeah.

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One of the big ones, and, and under many other ESPs as well. Yeah. Um, they, I guess I'd reached a certain size where they started paying attention to what the content of my emails, and- Yeah... they did not like it.

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[laughs] So, uh, fortunately, Beehiiv was, was really cool. I mean, they like sheltered me from a lot of the conversations.

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They, they interfaced with SendGrid quite a bit before I got looped in, but, uh, eventually they said like, "Look, what you're doing is not okay, and we're gonna turn off your emails," and they did.

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Um, but to, to Beehiiv and Tyler's credit- Yeah... Tyler like called on the investors, and basically, like they raised hell with senior leadership at, at SendGrid and got me turned back on. So I only missed one issue.

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That's amazing. For one time I've missed my cadence, but I got right back on the horse. Yeah. Um, so there was that, which was scary- Yeah... to be honest. I mean, that's e- existential for the businessTotally. Yeah.

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Yeah, it was scary. Um, and then the only other thing that's really affected me is there have been a few times where, uh, on Instagram, my account has been, like, suppressed.

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Not fully shut down or anything, but on your professional dashboard, they show you the knocks against you.

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And it's funny 'cause it's mostly driven by algorithms and machines, so, like, their judgment of it isn't really right.

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Like, I had a, I had a post promoting a, a merch drop, like, a T-shirt that just said, like-- it says, "Plants and fungi are my friends," and, uh, they thought I was selling drugs from that. That's insane. Yeah. Yeah.

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The- Um, so- Oh, go ahead. Sorry. So quickly, as an aside, um,

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Zuckerberg just came out with a video yesterday saying that they were kind of changing their whole content moderation policy to emphasize and prioritize free speech.

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So- Get rid of the fact checkers- We'll see how that is- For community notes, yeah. Yeah, exactly. Taking a page out of X's book. Yeah.

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So we'll, we'll see how that affects things, hopefully in, in a positive way for psychedelic education and harm reduction. Um, that's my hope. Yeah. Uh, but to date, I mean, the way that...

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That's been a big part of the service that we offer to our clients, is helping them figure out how you can run ads both effectively and safely and responsibly for, for your account and, and for the people who you're putting the content in front of as well.

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Yeah. Um, so, you know, one of the things that we do is just really try to get people to focus on educating as the first step.

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Um, even if they are selling, like, let's say they have a psychedelic retreat in Jamaica or something where it's, where it's legal to do that. Yeah.

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We wouldn't advise, uh, those clients to run an ad that says, "Come sign up for our retreat." No. I mean, it's-- First of all, it's not an effective marketing strategy because these are not impulse buys.

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It requires a lot of planning. It's usually high ticket. Uh, but also in terms of protecting their, their liability and, like, the status of their account on Meta, we always say, like, "Let's make this educational.

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Is there something that you can offer as a lead magnet-" Mm-hmm. "... sort of a freebie to get them interested, and then you can contact them off platform through your emails or, or what have you?" Nice.

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Um, I-- So what I wanted to ask about was, what I was interrupting you for a second ago, i- is the Instagram, because you've kind of developed that.

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I remember a year ago when I was looking at it, like, you had all these memes on it, um, and it was, it was, it was thriving. Yeah, I think, like I said, it was like six thousand or something.

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But now, when I was just looking, there's like a great cadence where you have the, like, every three or four posts is the, like, this week in psychedelics, um, kinda roundup, and then you've got these memes.

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Um, I don't know. I, I imagine it's not that deep. You just kind of, like, have posted more, and so it's the marginal gains of getting better at, like, what works with your audience on the platform, et cetera. Mm-hmm.

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Um, but, uh, in as much as, like, you've changed anything there, I'm curious, um, uh, what you could, what you could offer our listeners in terms of, like, advice.

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I mean, what I would offer is, yeah, figure out if something is working.

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Um, even if it's not taking you to, you know, a hundred thousand subscribers or followers off the bat, if, if it's getting you in the direction you wanna go, my approach has always been just stay the course. Keep going.

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'Cause it starts to pick up speed, you know? It's not that it just, it progresses linearly. It starts to... The, the hockey stick starts to happen. Hopefully. So yeah, I ha- I have not changed. Yeah.

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I'm doing the same thing that I was doing back then. Um, has your relationship with your audience changed in any way this year?

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Which, context there, I, I think last time I asked you, um, if people were replying to the emails, whatever, and you said sometimes. Mm-hmm. Not so much, though. It's more about the polls.

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Um, not that the relationship with the audience is just about, like, whether or not they reply to your emails, but, um- Yeah... I don't know.

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Has there, have, has-- is there anything notable from the last year where, like, you've opened up these communication cha- you're, like, commenting on Instagram, whatever. Your relationship- Yes...

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with the audience, what is it these days? Yeah. Has that changed? Two, two big things have changed, um, related to, to launches, uh, in the business.

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So one was, uh, I created something called Maria's List, which is a directory of psychedelic practitioners and providers, and that was, you know, kinda based on that first inkling of this divide between the professionals and consumers in my audience.

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I realized that was a network that these people wanted to and needed to meet.

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So I created this platform that allowed the professionals to list their profiles and, and how they support people, whether it's through integration coaching or, you know, ret- retreats or coaching or therapy.

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And, uh, and now when a reader, who is, uh, more on the consumer side, asks me for advice, which normally I would always have to say, "I'm not a doctor. I can't provide medical advice," I say, I say that- Yeah...

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and I say, "Here's what the research shows that's interesting and might be relevant to you. And if you're looking for a provider, go check out Maria's List. These people are all vetted by me." Yeah.

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That's, that, that's nice. I actually wasn't aware you'd, you'd made this Maria's List. Um, so- That's one. Yeah. And the second one is more recent.

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So, um, di- like, digging into that facilitator professional audience, I kept hearing, um, 'cause I started having conversations with them to learn more, and I kept hearing that they had paid a lot of money in tuition and trainings and programs to learn how to sit with clients.

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Hmm. And they probably put in a lot of, you know, maybe they'd been under apprenticeship. They'd spent a lot of time honing that skill, but no one had really helped them on the practice building side.

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So that felt like a really, like, achy problem. And so I launched something called Practice Expansion, which was a six-week container, and I treated it as a beta program.

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I got 10 practitioners in it, and we spent se- uh, six weeks learning the skills of marketing, sales, how to build a practice ethically, and, um, got a great, a bunch of great feedback on that.

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But one of the most helpful, constructive pieces was that was like a fire hose of information. Mm-hmm. It was too compressed.

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And a thing that I didn't expect was one of the best things they got out of it was connecting with one another.

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So that inspired me to expand Practice Expansion, uh, into, out of a cohort-based model into a indefinite community, and that's the big push for year three right now. Oh, okay. Okay.

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Well, let's get back more into that in a second.

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But, um, talking about all this, I'm reminded of-So another thing that we talked about last time, I asked you, like, if you thought you had a responsibility to your audience, um, both, like, specifically you with the work you do, and then also, like, as a creator contributing to the Internet generally.

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Mm-hmm. And you gave this, this really beautiful answer. You, you clearly did care a lot. I, I think you, you, you were, you were emotional answering because it was kind of a heavy question.

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Like, the work you do is really important to you and, like, has this high stakes for you. And I wanna say I, I- Yeah...

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I kept asking people that question whenever I would interview them, uh, because it was, it was just such a good answer you gave, and it blew me away. Um, rarely have I gotten an answer as good as that to that question.

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[laughs] I have... A lot, some people have said, "I don't think about that at all." Like, I, I guess it's to, like, "I guess I don't really have as, um, the responsibility is to myself," whatever.

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Some people have, like, "Yes, I, like, I really wanna make sure I'm delivering great con- great content," et cetera. Um, but yeah, I, I, I admire that about you.

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And everything you were just saying now reminded me of that because it's clearly, like, still at the core of what you do, where, like, there aren't- Yes... really many people doing this work, right?

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Like, in this space, um, who have, like, your marketing prowess. Uh, and, and very clearly, like with, like what you're talking about with Maria's List, like, you're still-- Like, that's the, the core value.

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I, I kind of get the impression that you're still living. Um- Yeah... so kudos to you for that. Yeah, Tricycle Day has always been very mission-driven. Yeah.

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Uh, of course, I wanna make a living for myself, but there are many ways to do that- Mm-hmm... and that don't involve, you know, dancing right on the edge of legality.

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[laughs] You know, I, I don't-- There are a lot of things that I could be doing that I don't because I want to, you know, limit my risk, for sure. But this is a really important thing to me. It helped me tremendously.

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I've seen it help other people.

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And so everything that I do is really about, how do I normalize the conversation around psychedelics so that more people who have the potential to benefit from it might have a greater chance of, of doing that?

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Um, so, you know, focusing on the consumers themselves and educating them is one way, but also empowering the facilitators who are out there on the front lines actually serving the medicine, actually helping people integrate it, that is a way to exponentially increase the ripple effect of what I'm doing, and that's kind of why I've kinda put my focus there this year.

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Yeah. Um, one question I would often ask in a situation like this is, uh, how do you define the word creator?

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Um, but instead of that, I'm curious what word you would use to define yourself, in that usually the people I'm talking to would say creator, journalist, writer, YouTuber, entrepreneur, whatever.

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What's, what's your word? What are you? What do you do? [laughs] Uh, I think that I am a creator. Mm-hmm. I think that's a fair word.

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I think another word that applies to me, given the space that I work in and, and my mission, is activist. Hmm. Yeah. That makes a lot of sense. Yeah. How do you define the word creator?

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Well, I mean, my, my definition is probably not as fine-tuned as yours i-in terms of like- But I, I tune my definition-... by counterpositioning it against influencer... by these answers. [laughs] You know?

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Y- to me, it's, it's somebody who's, who's creating something. Yeah. You know? Um, and I think that's the essence of entrepreneurship as well.

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Um, I really think it-- The reason why I like the word creator as opposed to entrepreneur in this case is that it feels like it puts a little bit more weight on the artistic side of it, and I do see this work as, as an art form.

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I think about every issue that I put out as a piece, and I feel very accomplished, and I feel a sense of ownership and, and accomplishment every time I publish. Yeah. I, I like that. I think my...

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One, one of my favorite definitions that I think you would resonate with, um, is this idea of somebody who contributes to the corpus of the Internet because I, you know, I strictly use it- Mm... in a digital sense. Sure.

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Uh, one I've, one I used for a while was, like, somebody, anybody creating content and distributing it on the Internet for an audience beyond their immediate friends and family. Um, which- Mm...

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I think is probably the most maybe general, you know, you could write that down, really good one.

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But I like more philosophically this, like, idea of contributing to the corpus of the Internet, which you do with such intent and with such care, which is like that, I think, is the type of thing, maybe influenced by, um, by you being my first interview, but that's one of the kind of things I often look for in the people I interview.

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Um, question about the second year. So, you know, I've heard it said, I don't know if somebody said this to me or I read it online somewhere, but that, like, the first year of a job, you're just figuring it out.

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You don't really know what you're doing, and then the second year is when it really gets fun. You start to figure it out, and you're, you're in the groove.

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Um, but, like, looking at your work, you still are, like, really just building on everything from the first year.

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So I'm curious if that applies to you, if the second year has, like, felt so different or more dialed in in any way.

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I think that I got into the groove of the creation of Tricycle Day newsletter in a shorter time, more compressed timeframe than that.

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I think it took me maybe six months, and, you know, we were talking about how the format has not changed since then. Not at all. I think I've pretty much been on that groove, um, since then.

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So I got there pretty quickly, but the way that I've been introducing novelty into my life and the challenge of creating this project is, what do I stack on top of that? So, you know, the newsletter is kind of...

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It's good. Like, I'm, I'm happy with the way it looks. The readers are happy with how it looks. There's a news flow every week to, to f- push through that filter, and I'll continue doing that.

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But now how can I build upon that and, and go out wider? So the agency, that, that's helping plant medicine retreat centers bring more guests in and have life-changing experiences.

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Maria's List, that's helping more people connect one-on-one. The facilitator community practice expansion, this is about getting these facilitators to connect with each other and, and, uh, affect more lives as well.

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So, you know, I think that-that's the game I'm playing right now is where do we go, um, versus how do I fine-tune the, the existing thing?Have there been any mistakes or missteps you think you made?

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But, but not necessarily just with the newsletter, but with building this thing generally. Any mistakes or missteps you made in year two that you didn't make in year one? Hmm. Oh, well, here's one.

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Actually, we didn't talk about this at all. So in first year, the first thing that I did to diversify my revenue outside of, uh, ad placements was launch courses. I had a, like, a basic harm reduction course.

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There was a, a live event, um, about integration modalities, which I then packaged and sold as an evergreen thing.

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And then the third one was a how to grow mushrooms course, which I partnered with a cultivator on, and they had a physical product as well. Um, that was actually the straw that broke the camel's back for Twilio SendGrid.

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And so they said, "A condition of you coming back online is you have to stop promoting those courses, not just in the newsletter, it can't even be on the website." [laughs] So that was a mistake that was costly.

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It could have been way more costly for me, but, um, I, I no longer have those. Yeah. Well, thanks for sharing. Um, I wanna... Okay, let's, let's now talk about the third year.

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You were saying that your, your theme for year three is this, is this community, uh- Yeah... which, uh, it, you know, community is always something I like talking about because it's such a buzzword.

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Brands wanna do it, creators wanna do it, whatever. Um- Mm-hmm... it's something people wanna create when really it's like, uh, uh, that's usually the wrong way to go about it.

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So it sounds like you, though, kind of have this thing. You have people asking for it and wanting to-- wanting there to be a space to, to talk about these things and stuff.

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So tell me what this community is and, like, how you're going about building it. Yeah. So, um, I think a lot of people, it is a buzzword.

250
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Community is a buzzword, and I think people use it interchangeably with audience sometimes. And so I'll, I'll draw a hard line between the two.

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To me, audience is, you know, it's a readership or a viewership that you speak one to many, and they don't really have a way to get, uh, respond to you. And they can respond to you- That's such a good...

252
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Sorry, that's just such a good-- I've never heard, heard it said like that. Community-- People mistake audience for community. I, I, I- Totally, yeah... had to repeat that. Yeah.

253
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And the, the audience might reply to you, and they might have a way to voice feedback, but they're not communicating with each other unless you actively connect them, right?

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Community is-- puts everybody on the same playing field, and everybody can interact. So the, the platform that I ended up going with is, is called Circle.

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It's basically like, you know, a lot of the features of, like, a Facebook Groups kinda thing, but on its own, has its own app. And, um- I've heard the same conversation as Discord too for, like, chatting, right? Yeah.

256
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Yeah. Similar to Discord too, though it's certainly got... Discord's got a certain connotation and feel to it. [laughs] Um, Circle is a little bit more customizable, I'd say. So it, you can white label it better. Um,

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but what I did is say, like, I'm not creating a community for anybody in my audience.

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It's for a specific segment, which is much smaller than the overall readership, um, because I think that a community, and this is just my view, I mean, I'm sure there are many ways to run a community, and I'm certainly no expert, figuring it out as I go, but to me, it's important that the community be oriented around a common goal or outcome that everybody wants.

259
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Um, and that wouldn't be the case if I created a community for everybody who reads Tricycle Day.

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Um, so yeah, that's the start of it, is it's a digital place for people to come together and have these conversations in what feels like a trusted, safe environment where everybody's supporting one another.

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Um, but the community goes beyond the digital as well. There are gonna be... We haven't done this yet. I mean, we just opened the digital doors, uh, this week, but the goal is to have in-person events.

262
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One more kind of pedantic question. Newsletter as a format, what does that mean to you? What is a newsletter? Why do you like the newsletter as a format?

263
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Newsletter can mean a lot of things, um, but Tricycle Day is the, is the classic definition of a newsletter. It covers the news, um, in psychedelics.

264
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And I know a lot of people have very successful businesses and newsletters where they're teaching something. That hasn't really been my orientation around it.

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It's, I'm covering what's happening, and I'm injecting my personality and flavor into it, but it's still, you know... It, it's unfair to say it's objective. It's certainly not objective. Yeah. But it's--

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I'm not telling people how you should interpret this. I'm- You're, you're gathering and presenting... saying this is what happened. Yeah. I'm gathering and presenting.

267
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Um, so to me, I mean, that's the classic newsletter, but I also think that, you know, if you have a newsletter where you are a marketing expert, and you teach peop- people how to do marketing once a week, that's a fair use of the term.

268
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Yeah. No, that's good. Um, last question. Hopes, dreams for year three.

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If, if we're, if we, uh, [chuckles] sit down again one year from now, what are we talking about that was so great about the third year of Tricycle Day? The thriving community, I think, would be the win.

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Um, I have about forty members in there who are founding members, which is great. I'd love to get that into multiple hundred by the end of the year. A thousand would be amazing. Um, but I'll still...

271
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That, that's not a requirement for it to feel like a suc- a success.

272
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Uh, and then the other thing, which I can't remember if I mentioned this when we spoke the first time, but when I created this, you know, I always had the final end goal as an acquisition.

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And I'm not as attached to a timeframe around that, um, as I could be because I'm really happy doing this work, and I think that even in the event of an acquisition, I will stay on and continue to be the voice, at least for a period, uh, of writing the content, and maybe the other things go to other people.

274
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Um, but that could be a really cool outcome as well that happens this year if there's the right fit with someone who's gonna support the mission and, and make it more- Well, wait.

275
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In as much as you wanna talk about it, um, you don't have to. What are kind of-- What could those right fits look like? Is it like, is it a commercial business? Is it more of like a, a news, a media company?

276
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What kind of... I'm sure there's different scenarios, but I, I am, I'm curious to hear- There are different scenarios. I don't think a news company that

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is, is covering general news and then just, like, wants to own this thing that talks about psychedelics would be the right one. I'm thinking more mission aligned.

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Another company that's doing something to embrace and, and lift the adoption of psychedelic medicine, but just doesn't know how to do content and, like, could use me to plug in and just, you know, explode the impact.

279
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That feels like the right sort of fit. That's smart. Yeah.

280
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I mean, I, I'm thinking of somebody I was talking to the other day, Kendall Baker, who runs this newsletter formerly known as The Sports Internet, who he got acquired by Axios and then, um, traded to Yahoo.

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And it's kind of this like that's one maybe under-discussed path for the kind of a creator project, whether, whether it's a newsletter or like a YouTube channel or whatever, where it's like you build this thing and then another company that wants to have a content arm but doesn't necessarily understand it acquires it, um- Yeah...

282
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under, under, underutilized path, I think. Yeah. Or maybe even a company that does have a content arm, but their content has a different spin, a different focus. I think that, that could happen as well. Yeah.

283
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Well, I, I hope you hear some whispers of that in, uh, twenty twenty-five. I keep-- I'm still at the stage of the year where I don't know, don't know what year to say. I almost said twenty twenty-three- [laughs]...

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'cause that's actually when we, when we spoke was December twenty twenty-three [chuckles] the first time. Um- That's right... but that's it. Thank you, thank you for coming on. Uh, you wanna...

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People go read tricycleday.com. That's what it is, right? Yeah, tricycleday.com or @tricycleday on Instagram if you just want the memes and wanna forget about the news. Go check it out.

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This has been the Creative Spotlight Podcast. I will see you next week. Thank you. [outro music]