[00:00:21] Henry Winslow: Today, my guest is Henry Winslow, who is the founder of Tricycle Day, a free twice a week newsletter covering the top stories in psychedelic research, policy, and business that's actually fun to read.

[00:00:30] Henry Winslow: Hey Raad, thank you so much for having me on. What's up friends, listeners. 

[00:00:35] Raad Seraj: Yeah, thanks for, thanks for coming, Henry. I'm a big fan of your newsletter. We sort of connected through another friend last year and honestly, I love the newsletter and so many others as well.. Being a creator in this day and age involves so much more than just creating content. You don't really have to be an entrepreneur. And so, and the road to the entrepreneur is always a zigzaggy, right? It's not it's not, it's not straightforward. It's not linear. There's so many challenges and opportunities.

[00:01:03] Raad Seraj: So I'm really excited to dive into all that with you as well as psychedelics and so on. Where I do want to start, though, is this place this thing that you, or rather how you talked about your journey, how your journey started a couple of years ago, and in your own words, you said that you had walked away from Harvard and became a nomadic yoga teacher.

[00:01:26] Raad Seraj: And it's, it's a, it was a thankless journey in the sense that It's not rotting the capitalistic system, but it has been transformative for you. So give me a little, you know, a flashback of how that came to be. You went to Harvard, but you quit and you said, I'm going to become a nomadic UF teacher instead.

[00:01:45] Henry Winslow: Yeah, well, I should clarify. I didn't walk away from Harvard per se. I finished my schooling. And what I meant by that, I guess, is that I walked away from the traditional Harvard path, if you will. Because, you know, in in a school like that, you can imagine there are a lot of folks who have been very type a kind of linearly.

[00:02:05] Henry Winslow: Progressed you know, focused on taking the next step, always succeeding, earning that next achievement throughout life. And after Harvard, you know, the next logical step is get you know, respectable high paying job for me. You know, most of my friends were going into investment banking or management consulting.

[00:02:23] Henry Winslow: Those were kind of the popular paths, not a lot of entrepreneurship. Interestingly enough. Though there was definitely some but for me, I went into advertising and specifically advertising in the medical and pharmaceutical and healthcare space. So that was my first job out of college. And when I got into it you know, I was like, I felt accomplished.

[00:02:45] Henry Winslow: I felt proud of myself for landing that kind of job. However. For the first time in my life, I kind of reflected on the fact that, Hey, there's no obvious next step here. Yes, you can work your way up the corporate ladder, but it dawned on me that I'm here for a long time. And when you're, everything is only like four year chapters, it's very easy to just put your head down, grind through it and work your way to the next step, but when I was stuck in a situation where.

[00:03:11] Henry Winslow: This could be the next, you know, many decades of my life. Suddenly the standards changed. So for me at that point, I was like, I don't know if I can do this. I had sort of a quarter life existential crisis. You might call it that. And that's when I started exploring entrepreneurship. Along the way, I had also picked up a very important practice to me, which is my yoga practice.

[00:03:33] Henry Winslow: You know, a lot of my friends were kind of like joking that I'd become obsessed with it. A lot of transformation physically, mentally, personality wise. So that became, you know, the, the first 

[00:03:44] Raad Seraj: Henry, just give me one second. Sorry. Yeah, I'm going to, I realized, okay, actually, nevermind. Are you seeing a little bit of buzziness on the, on your side.

[00:03:54] Raad Seraj: No, 

[00:03:57] Henry Winslow: I'm not. 

[00:03:57] Raad Seraj: Okay. All right. Might've been momentary. Okay. I apologize. I just want to make sure that everything was okay. 

[00:04:03] Henry Winslow: Okay. Yeah. Keep going. So yeah, yeah. So the, the path of entrepreneurship that really called to me, there were many other false starts and distractions, but was going full time into teaching yoga.

[00:04:17] Henry Winslow: And. To your point before, that's not the most obvious way to make money. So clearly, you know, my motivation to do that wasn't like, Hey, this is a get rich quick scheme or even get rich slow scheme. It was, Hey, this is a way that I can create impact in the world that is meaningful to me because it it's allowing me to share what has been impactful in my own life with others.

[00:04:44] Henry Winslow: So that's how I got off of the Harvard path into yoga and alternative medicine. 

[00:04:50] Raad Seraj: It's interesting. What do you, you know, a number of guests of mine who've gone to elite schools like Harvard and Cambridge and so on have mentioned, have alluded to this thing about. You know, elite schools cultivating type A personalities.

[00:05:04] Raad Seraj: Yeah. I wonder what that means or what that has meant to you. And, you know, in the world of entrepreneurship and like founders and billionaires, you often hear about people who had to quit elite schools first, actually go build something, which is kind of ironic, right? You think you go to these schools to actually cultivate entrepreneurship, but then it feels like, Nope, screw this.

[00:05:24] Raad Seraj: I'm actually going to go build something else. What do you think? What do you think is happening there? 

[00:05:29] Henry Winslow: Well, I think that elite schools maybe cultivate type A personalities, but even more so than that, they attract type A personality. So these are, you know, personality traits, behavioral patterns mental frameworks that have already long since been cultivated, probably through influence of.

[00:05:48] Henry Winslow: Parents and other mentors and childhood. But yeah, it is very interesting that you see a lot of the success. Obviously there's, you know survivorship by the bias here. Cause there are many people who drop out of Harvard and don't, you know, Facebook, but those anomalies are pretty striking for sure.

[00:06:06] Henry Winslow: Yeah, I mean, I think it goes back to what I was saying before. It's like, you get into this habit of like, You must succeed. And if you must succeed, then that's not really conducive to entrepreneurship. Entrepreneurship is just the path of like repeated failures and lessons built upon them. 

[00:06:25] Raad Seraj: It's interesting.

[00:06:25] Raad Seraj: You also, from that perspective, I find MBA is really irritating because like, Oh, I, I have not had the sunk cost of like 140, 000. I have to believe I'm great. And I'm awesome. So that resonates, but I kind of feel like it's maybe something like that. I obviously haven't gone to an elite school, so I don't know, but like my, my siblings have that's, that's super interesting.

[00:06:47] Raad Seraj: Why, what do you think? Your penchant for yoga, you picked that up during this time. What, what do you think yoga brought to your life and why were you gravitating towards it and why take it so seriously? 

[00:06:58] Henry Winslow: Yeah. So I had been an athlete growing up, usually like a sink, like a individual sport athlete. I was a big into track and field, cross country swimming.

[00:07:07] Henry Winslow: And my main sport growing up was diving springboard diving. So I actually walked onto the springboard diving team at Harvard and it was a big part of my experience there. Not just because of the physical demands of it, which I think carry a lot of mental benefit and you learn a lot from that and the camaraderie of being on a team.

[00:07:27] Henry Winslow: But also, you know, there's just an aspect of discipline that I found extremely important and beneficial on all ventures in life. So when I got out of college and I no longer had a structured. You know, path for doing physical exercise. I was looking for something that could capture my attention. And one of my friends who had been a diver with me, he brought me to my first yoga class and I immediately fell in love with it.

[00:07:53] Henry Winslow: I didn't have, I didn't realize it at the time. Because I think yoga works at a level that often, you know, it goes beneath the superficial, you know conscious mind. But I felt really good afterward. Yes, it was fun. Yes. I got to work on tricks. You know, I was always sort of like an acrobatic person in nature and I wanted to like do handstands and all of that.

[00:08:13] Henry Winslow: But at the end of class, just like being there and Shavasana and feeling like nothing has to be done. You finally have a break. You just get to exist. That was incredibly healing for me. And An addictive in a way. I'm not ashamed to admit that it did sort of become an addiction. So I developed you know, a very serious, consistent practice.

[00:08:35] Henry Winslow: I would practice every single day. It got to the point that, you know, with a, with a corporate job, the only way I could guarantee I'd got my yoga practice in was that I showed up for 6am class every day. Holy 

[00:08:48] Raad Seraj: shit. 6am. I've tried that, but no, it's not works for me. But kudos to you. And I, you know, I.

[00:08:54] Raad Seraj: Again, comparing your statement about places like Harvard and which sort of attracts type A personalities. I'm not going to say it's a bad thing, but I do feel sometimes that the validation that one gets from a practice and not just like with going to yoga, but I practice to your point, which is inward looking, right?

[00:09:13] Raad Seraj: Disciplined, inward looking practice versus what feels like sometimes like, you know, you're driven, but you're driven by some sort of programming from either society, parents. Some sort of validation. You think that you're going to feel a certain way when you get to the destination, it's quite, quite right.

[00:09:31] Raad Seraj: Quite the contrast, right? And society will reward you. We'll recognize you. We'll see you finally, if you go to Harvard and so on. I think it's, it's a very different value system. I'm not saying one's better than the other. I think it's a very different value system. 

[00:09:44] Henry Winslow: Yeah. And if you've, you know, been immersed in one, then you can imagine like stepping over into the other can be refreshing.

[00:09:50] Henry Winslow: Just the contrast. 

[00:09:51] Raad Seraj: Huh. Did it, did that practice validated decision to not take the Harvard path or post Harvard 

[00:09:58] Henry Winslow: path? You're saying after I went for it and was a yoga teacher? Not immediately, you know, I mean, I felt great about the work that I was doing and that part was energizing every day, teaching a class and having people You know, I said before, it's like, thankless in some senses, but another way is it's incredibly thanked.

[00:10:21] Henry Winslow: You finish your class and your students are incredibly grateful. And then, you know, it's the highlight of their day and they express that. So that was very rewarding. And, you know, I stayed with it. So obviously I, you know, I made the calculus and decided I was doing the right thing. 

[00:10:38] Raad Seraj: How did you become nomadic?

[00:10:42] Henry Winslow: So that was kind of a combination of one, like lifestyle design and to financial necessity. So lifestyle design wise, like. Look, if I can use my career, my job to expose myself to different parts of the world and travel, which are things that I value I didn't have a lot of travel growing up so, you know, to expand my horizons was something that I always wanted to do, then that's great.

[00:11:08] Henry Winslow: And then the financial piece was. You know, as it turns out as a yoga teacher, it's really difficult to make a living if you're just teaching regular classes at studios in the city that you live in, particularly a high cost of living city, like New York, where I lived. So the way that we ended up making it work, and when I say we, I mean, my wife and I is we would go on these international workshop tours.

[00:11:30] Henry Winslow: So we, you know, basically like either Airbnb or apartment or not have an apartment for a period. And then go off for three or four months and just balance between studio to studio in different countries, usually in Europe. And we'd either be resident teachers there for a week or two teaching on the regular schedule, or more often we would do special events and you, you can make more money doing it that way because you would do this like revenue share agreement.

[00:11:57] Henry Winslow: Usually it was like 30 in favor of the teachers. That's 

[00:12:02] Raad Seraj: fantastic. In your travels, what are the highlights? Where, where have 

[00:12:06] Henry Winslow: you been? My favorite, and this actually falls outside of the description. I was just giving you around the workshop tours, but we also did retreats. So that was something that we designed up our own and, and, and like, you know, put up a sales page and invited people to come to my favorite was Bali Ubud.

[00:12:25] Henry Winslow: It's kind of like a yoga capital of the world. At this point, like even more so than places in India, which is kind of crazy. Right. But we had an amazing time there. Do 

[00:12:35] Raad Seraj: you see any sort of back when you saw when you're doing this, are you seeing any similarities or how things have evolved while you talk about psychedelic retreats per se or retreats nowadays?

[00:12:46] Henry Winslow: Yeah. So I've actually never been to a psychedelic retreat. All of my psychedelic experiences have been. In small groups or individual. So I can't compare with direct experience, but it's definitely interesting to see that, you know, there's a parallel for sure. Observing from the outside. Yeah.

[00:13:06] Raad Seraj: Interesting. We're going to touch more on this later on, but I want to pivot a little bit to, you know, how you grew up and your sort of formative years. I often think that entrepreneurs have always a interesting. set in setting of their younger years of formative years, right? Because for good and bad, we are informed by our surrounding people that we grew up when you're young siblings, parents.

[00:13:30] Raad Seraj: You know, family and friends and so on. I'm wondering what your set and setting was when you were much younger, right, how was your family? Tell me a little bit about your siblings, your family and so on. 

[00:13:43] Henry Winslow: Yeah, I love this question, Raad. And the reason why is because I actually have a lot more clarity around this now at age, what am I?

[00:13:51] Henry Winslow: 34. Then I did even like at 29 and I actually attribute that to some of my psychedelic experiences, which. You'll probably want to ask about later too. But the thing that's really interesting about this question is that, you know, yes, as a child, our set and setting are extremely formative, but also as a child, we have no basis of comparison, so everything feels normalized to everyone, no matter what your circumstances are.

[00:14:18] Henry Winslow: So I think that psychedelics have been really helpful for me and like stepping back and zooming out and looking at what happened from a more objective point of view. And so. You know, with that perspective, what I can say about my childhood is, yes, I had a lot of privilege for which I am grateful.

[00:14:36] Henry Winslow: And there were also some very serious challenges that I did not fully appreciate as a child mostly around. Mental health struggles and challenges that were in my immediate vicinity in my siblings and my parents. And there's a connection there. Certainly there's like intergenerational transfer happening, which I'm extremely conscious of now as a new parent, because I want to end that cycle.

[00:15:00] Henry Winslow: But I, I say all that, I guess, because it certainly set the stage for me. My interest in yoga, yoga has incredible benefits for mental health which are well documented and also psychedelics. There's this renewed interest around psychedelics, not just as tools for cognitive and spiritual exploration, but also as therapeutic tools for mental health.

[00:15:19] Henry Winslow: And I think that's part of why I'm, I'm so gravitated toward them. In my childhood, there were very serious mental health breaks. Among my mom to be specific and, and siblings so much so that I remember there was one moment where, you know, as a, as a child, like, it's really important that you see that your parents are presenting a united front.

[00:15:47] Henry Winslow: This is something I'm learning as a new parent. Like if you break that trust, then like the child feels very disoriented, not. Not safe and that happened for me because my mom was struggling and you know, she had basically like a tantrum is the wrong word, but just, she went wild and my dad had to break that United front and say to me and to My brother, he was like, I might have to pick you guys up and, and leave.

[00:16:14] Henry Winslow: And so that was really scary. I also remember a moment where he took me to my mom and said like, Hey, you need to tell Henry that you still love him. And this obviously trickled into my own, my siblings you know, their, their mental health and their, the way that they went through life, there were several suicide threats.

[00:16:36] Henry Winslow: A couple earnest attempts and, and some of my siblings, I mean, I'm not going to go into specifics, are still struggling with that to this day. So psychedelics and their importance in mental health have a lot of personal significance to me. I really 

[00:16:53] Raad Seraj: appreciate you sharing this, Henry, and trusting us with this.

[00:16:57] Raad Seraj: I think it's, you know, there's a saying that the future is fixed. It's the past that's unpredictable. And I find with psychedelics, you can revisit your story. And each time, as you do your own healing work, the past feels different. You know, whether you feel detached or it feels less threatening or it feels you can look at it where more with more objectivity to your point or compassion.

[00:17:21] Raad Seraj: So I think it's really powerful because you start with parents, you know, family is the core wound in a lot of ways, right. Then to be able to look at your parents and go like, They're also people. 

[00:17:31] Henry Winslow: Yes. They're parents. Not only are they also people, but they're also children. That was a big unlock for me.

[00:17:38] Henry Winslow: When you mentioned compassion, it made me think of that realizing that my mom and you know, I love my mom and she loves me. But there were definitely some mistakes in the way that she treated. You know, my siblings not so much me, honestly, as more of the daughters. But I see now, I understand that that's because she's replaying something that happened from her mother to her.

[00:18:00] Henry Winslow: And, you know, as a parent now, I realized like, I'm doing this for the first time. Like I'm learning, I'm basically a quote unquote, child of, of being a parent, you know, like I'm new to this and every parent does it for the first time. 

[00:18:13] Raad Seraj: Which speaks a lot to my experience. Maybe I'm the eldest and perhaps the guinea pig and experiment for my parents, but yeah, you brought up your grandmother and you shared with me a story, which I, on, in.

[00:18:28] Raad Seraj: You know, on one hand, really beautiful, but tragic, but also really revealing. And I, I remember it. I was really, I'm wondering if you could recount the story and what it taught you, is that you talked about your mom collecting antique dolls. And she had, after your grandmother had passed away, your mom filled your grandmother's house with those antique dolls.

[00:18:48] Raad Seraj: And at some point it was just full of, Yeah. Mom collected them. Yeah. What, looking back, and I don't know if you talked to your mom about this or not, but what do you think that revealed? What, what, what was your mom doing? 

[00:19:01] Henry Winslow: I think that my mom was getting to act out a childhood that she was denied.

[00:19:07] Henry Winslow: Essentially I have talked to my mom about it. Not like full on, like therapy one on one, but like, right. It's, I mean, this is a big part of her life. She's members. She's a member of multiple antique doll collecting clubs. She hosts these little luncheons at her house with these little old ladies who collect dolls.

[00:19:24] Henry Winslow: But yeah, I mean, it's, it's. I mean, from an outside point of view, most people would say that the collection is out of hand. Like, yes, she filled up my, her, her own mother's house, which she inherited after my grandmother passed away. She filled it up. She made it a life sized dollhouse. So obviously she's still working through that, you know, and it just goes to show that, you know, some of these things you just, you learn to live with for your entire life, I think the impacts that are impressed upon you as a child.

[00:19:54] Henry Winslow: I could see 

[00:19:54] Raad Seraj: that. On the other hand, I also wonder, like, you know, this is where sort of life imitates art, right? Because I think here, expression, collection, collecting these things that you feel really called to, you know it's like collecting stamps. I used to, I'm a big nerd, I used to collect stamps.

[00:20:11] Raad Seraj: Or back in the day when airlines would issue physical tickets, paper tickets that were like, you know, that looked like checkbooks. I had like stacks and stacks of them because we didn't get to travel much. And for me, every trip that we did that we could afford with my family was a very special thing.

[00:20:26] Raad Seraj: And, you know, of course now it's everything electronic, but like, you know, my point being that there's comfort in sort of these things, these actions, but to your point, you know, at what point does it become something else? 

[00:20:37] Henry Winslow: Instead of you holding on to them, they're holding on to you, it seems. Right. 

[00:20:43] Raad Seraj: Right.

[00:20:44] Raad Seraj: Is there is there some form of grieving or reconciliation now? I guess what I'm asking, what is the state of that house now? The 

[00:20:53] Henry Winslow: dollhouse? It's well, actually it's, it's better. It's better now. There's been some downsizing. I think that there's been a lot of reluctance around that, but it's been, you know, a joint effort from my dad and my.

[00:21:09] Henry Winslow: Sister who was actually living in that house for a little while. She came back and moved into that house to take a job in Richmond, Virginia, where I grew up. But she moved out. So. We'll see if that's progress. It's reoccupied by dolls. It remains to be seen. The story continues. How has 

[00:21:29] Raad Seraj: your relationship with your family, dad, mom, your siblings, because, you know, if, if we are to center, let's say your mom's lived experience at that time, and each of your relationship.

[00:21:42] Raad Seraj: With her, how do you think bringing the medicine and the practice into the fold? How do you think that's evolved over time? And where is it now? How much do you attribute that to practice your own role, being a parent and so on? 

[00:21:59] Henry Winslow: Sorry. Can you just rephrase that question? There was a lot in there. I want to make sure I'm answering it correctly.

[00:22:03] Henry Winslow: Yeah. So, I 

[00:22:04] Raad Seraj: mean, I'm, I'm just thinking, how does your relationship with your family evolved over time is what I'm saying, I 

[00:22:08] Henry Winslow: guess. You know, I think. That my it's based on this idea of like understanding where they're coming from more that I've developed a bit more compassion for my parents and rather than seeing them as arbiters of truth, seeing them as just people who are doing their very best.

[00:22:29] Henry Winslow: And are very much not necessarily defined, but shaped by their own experiences. You know, learning about my mom and her relationship to her mom definitely colored, you know, my relationship with my own mom because it helped me understand. Why she acted the way that she did. Also learning about my, my dad's childhood helps, you know, he, his dad was not in the picture, so that I think that really taught him or encouraged him to be different.

[00:23:00] Henry Winslow: You know, he wanted to, instead of replaying the same patterns that he had been exposed to, he said, I'm going to, I'm going to break the, the, the cycle, right? I'm going to do things differently. So I'm going to be a really present father. I'm going to stick around no matter what happens. You know, divorce is not an option.

[00:23:17] Henry Winslow: I feel the same way. It's like you make that commitment. That's for life. And. I respect that. I respect that a lot. 

[00:23:25] Raad Seraj: Okay, Henry, we're back after a 20 minute technical disruption. That is super annoying. But hopefully it doesn't disrupt our conversation flow too much. Where we were is that I had asked with your experience with medicine and your journey so far, how has your relationship with the rest of your family?

[00:23:43] Raad Seraj: Yeah. 

[00:23:49] Henry Winslow: I think that of all the medicines that I've worked with, certainly psilocybin is the one that has changed the way that I've reflected. And engage with relationships in my family. And we can talk about that and the differences between the medicines later if you like, but I think the, the material impact is that I've developed more compassion for where people come from and everybody likes to hear that.

[00:24:15] Henry Winslow: To believe that they are empathic and empathetic. But you know, everything is relative, right? And if you can notice your own change, your own evolution and empathy, it kind of puts in perspective where you were before, which was for me, admittedly more self centered. Just not necessarily in like an egotistical way, I guess, but like, just, this is my experience.

[00:24:36] Henry Winslow: I'm at the center of my own universe and everybody is interacting with me. Whereas now I recognize that. My parents, my siblings have all had unique experiences that very much shape the way that they show up in the world. And so I was talking earlier about my mom and her relationship with her own mother and how that played out in her doll collecting and the way that she's you know, become a mother to my, my sisters.

[00:25:03] Henry Winslow: You know, I, I could say the same thing about the way that I've reflected on my dad's upbringing. You know, he, When he grew up, his dad was not in the picture. He was raised by a single mom. And so for him, you know, I, I feel that. He took the opposite approach, which is instead of to relive his, or like re engage in a childhood that he never got to have, he said, I'm going to interrupt this pattern.

[00:25:24] Henry Winslow: I'm going to be very different. I'm going to commit to being around and I'm going to be the dad to my kids that I didn't have. So I liked that response. You know, I respect that. I, I admire that about him. But if I'm being totally honest with you, you know, I think the, like, The beautiful, like, expected answer to this is like, Oh, yeah, I healed all my relationships with my family.

[00:25:48] Henry Winslow: And that's not the case for me. It gave me more awareness, but really, like, the thing that I realized was important to me as a result of some of these medicine experiences that reflected on my childhood was I get a chance to do this however I want. I'm stepping into a different chapter of adulthood where now I have my own nuclear family.

[00:26:08] Henry Winslow: I've got a wife, I have a son at that time on the way, but now, you know, he's 17 months old. And look, this is the most important thing now. And my relationships to my siblings and parents are important, but they're not as important. I've made that decision. They are not as important as the relationships I have within my nuclear unit.

[00:26:27] Henry Winslow: Hmm. 

[00:26:29] Raad Seraj: Interesting. And I want to talk about that perspective as well, but let me flip that previous question and say, how are your, let's say, family members experiencing you like the Henry that has evolved and become the person today. What are, what do you think they're noticing? If you're truly channel that empathic sense that you talk about, put yourself in your dad's shoes and your sibling shoes and what are they saying?

[00:26:55] Raad Seraj: Who are the, who do you think Henry is now versus the Henry they grew up 

[00:26:58] Henry Winslow: with? I think that. My dad is incredibly supportive of everything that I've done. Even when I've taken swings that did not seem advantageous, like walking away from, you know, a good corporate job and being a yoga teacher. He thought that was awesome.

[00:27:18] Henry Winslow: And in fact, I inspired him to develop a yoga practice of his own, which changed his life. So that's been great. I think my mom is a little bit more scarcity mindset oriented and it has had some fears around, you know, riskier decisions I've made, but ultimately very much loves me and supports what I do.

[00:27:37] Henry Winslow: And my siblings, I think, you know, I'm the youngest of 5. And I've always been the baby there's like, you know, they're all relatively close in age, like two years gap between each one. And then there was a five year gap before me. So I didn't have the typical sibling experience where you're like, you know, fighting and all of this, like, yes, of course there were, there were fights, but I was kind of like the nurtured baby that was kind of like different.

[00:28:03] Henry Winslow: So I think they kind of look at me as. And like, this is funny. He does weird stuff. Now he's off doing psychedelics, but they'd certainly, I don't think they judge it. I think they just say, you know, Henry's being Henry. 

[00:28:17] Raad Seraj: What would he tell us? Like, it does. You talk to your family about it. Like, what do they know about psychedelics either directly or indirectly 

[00:28:23] Henry Winslow: through you?

[00:28:24] Henry Winslow: I haven't talked to my siblings a ton about it. But I have talked to my dad because actually the first. Like my first impression ever even encountering or hearing about psychedelics was that my mom let it slip to me when I was in like middle school or something. She's like, your dad's the one who sampled the magic mushrooms and so I knew that he would not have a problem with it.

[00:28:45] Henry Winslow: And, you know, he, he also went to Harvard. And he was there, he graduated in 1970. So he was there like not long after. The, the crap, like the scene yeah, like he actually was in school at the time when there was a whole semester where the student body just like boycotted class because of the Vietnam war.

[00:29:05] Henry Winslow: And he wasn't like super politically active, but he was like, yeah, cool. We could just get to smoke weed and like go to museums all day. He thinks it's cool. And you know, he sends me. Tips and scoops for the newsletter. Usually I've already seen them, but I just think it's fun that he's engaged and like supports Tricycle Day.

[00:29:20] Raad Seraj: That's fantastic. Yeah, I mean, I think like Harvard at that time with Richard Schultes doing his work as well. Although he did his work, I think a few, a decade or two earlier than that. But yeah, what a, what a fascinating place. And of course, now you see Harvard Law coming into the psychedelic scene and things like that again.

[00:29:37] Raad Seraj: That whole practice coming back again. It's interesting. Yeah, there's like a partnership with Berkeley. Right, right. Let's talk about psychedelics for a second. And you know, your newsletters about that. We talked about our journeys and experiences, but the two medicines that use frequently site or in terms of a meaningful experience, you talk about Bufo various of MDMT.

[00:29:58] Raad Seraj: And then MDMA both are very meaningful. And I've recently experienced MDMA in a, in a therapeutic context, not just recreational, which is super powerful. It was my wife and a number of other couples together, which is beautiful. But I'm, I'm, I'm curious, citing those two medicines in particular, why was it most meaningful to you and how do you see them differently?

[00:30:23] Henry Winslow: They're very different in some very stark ways, but also I find that they have some similarities also say that I think psilocybin has been incredibly powerful and important for me, but focusing on the two that you brought up, so Bufo or 5 MeO DMT. Also, another disclaimer I'll say before I get into it is at the time I was, you know, Bufo was not as popular as it is now, and I also did not have all the information that I have now.

[00:30:49] Henry Winslow: So now I would definitely not recommend using Bufo just because of the concerns around overharvesting of the toads. And also there's a lot of danger now with with like Mexican cartels, like stepping in. The space, so it's really easy to, you know, procure synthetic five email DMT. And I've, I've had both and they both produce a reliably spiritual, you know, game changing experience.

[00:31:12] Henry Winslow: So you know, I, I would go with synthetic at this point. However, my first time was with organic toad derived Bufo alvares five email DMT. And it was, it was the experience for me. I think we were talking before we recorded at one point and it was like, for that experience, there was a before and there was like, it was a pivotal experience for me and understanding who I am, what reality is and what it means to experience being human for me, the reason that it even came into my life was.

[00:31:50] Henry Winslow: As I mentioned before, I was very deep in my yoga practice and in yoga, they teach the system There's an eightfold path and the final step in the eightfold path of yoga. There actually is an end state of yoga. It's called yoga, and it's also called Samadhi. And Samadhi is described in the Yoga Sutras and many other Vedic texts as an experience of dissolution of the illusion of duality.

[00:32:19] Henry Winslow: So no longer is there you know, this, this mask of it's you and everything else. There is just one and that's like, you know, people talk about that with psychedelics and, and they use the phrase ego death which I think is kind of a scary term. Not that we should run away from fear necessarily, but that puts it in sort of almost like a negative light when, for me, that experience of dissolution into oneness was nothing but pure beauty, love, like the most unconditional, welcoming feeling I've ever experienced in my So much so that As it came on and, you know, while my mind was still working and still could produce you know, concepts and, and words in the English language.

[00:33:02] Henry Winslow: The last thought that I remember speaking to myself with the voice of my mind was nothing else matters. You made it. This is the point of existing. This is why you were born. And yeah, that's why it changed me. You know, like after that, I realized like this, there's a reason to exist and it's to feel this feeling, which is love.

[00:33:23] Henry Winslow: I believe that. 

[00:33:25] Raad Seraj: That's beautiful. In what ways do you feel that experience manifested after in your life and still to 

[00:33:33] Henry Winslow: this day? It's really difficult to come back to that completely immersive feeling without help. And by help, I mean some sort of External substance or potentially a practice. I mean, I think you can get to a similar experience using your breath.

[00:33:49] Henry Winslow: I love breath work for that. But really I think the practical takeaway from it is like, look, you can remember that you had that experience and that provides a level of comfort, confidence, context that just allows all of the challenges and like bumps in the life to feel okay. Like. They don't matter as much and it brings a level of playfulness and enjoy into life by removing the weight off of your shoulders.

[00:34:22] Raad Seraj: I think that's really beautiful advice and very practical perspective because you know, like Thich Nhat Hanh has this idea of like micro meditations right throughout the day when you're brushing your teeth take a take a moment when you're drinking some water take a moment right every moment can be that moment of reflection and like as human beings particularly this time i find like there's we have to on one hand balance either great aspirations ambitions along with fear that the world is crumbling, falling apart, completely unraveling.

[00:34:58] Raad Seraj: And also remember that we're just human beings having a human experience. And then we have to find joy among all the violence and everything else that's happening in the world. Right? Right. And I think your perspective is really pointed in that sense that we can find moments of elevation or sort of transcendence or Samadhi, as you said in, in that.

[00:35:17] Raad Seraj: So I think that's really beautiful. Thanks for sharing that. What about MDMA? Of course, but you know, I 

[00:35:25] Henry Winslow: have a lot less experience with MDMA. I don't know if you want me to say this on the podcast, but my, my experience with MDMA, chemically pure MDMA, and what I would consider to be a more intentional container was, was through you, thank you so much for sharing that with me.

[00:35:41] Henry Winslow: Yeah, we, you know, we were at like a social gathering and after party at an industry event, and you offered it to me and I said, yeah, sure. And I kind of expected it just to be like, you know, a mood enhancer for a party situation. Like make them make the music feel a little bit more vibrant and feel it in my body a bit more.

[00:35:58] Henry Winslow: And while that was the case, the real. Benefit of the medicine and and the experience that I'll take with me came after that we had a relatively early night. I think, you know, I was back at my Airbnb by 1130 and. I expected that to be, you know, my wind down time, but that's when I just tuned in in a way that I did not expect.

[00:36:21] Henry Winslow: I just felt very viscerally connected to my body at first. And then, you know, the attention and awareness went into my heart and I could feel my heart just warming. It felt super cozy, warm, fuzzy, and just like a really pleasant way. And then that, that feeling of being connected to my heart changed my thoughts.

[00:36:40] Henry Winslow: And that's the important part. I started to feel a sense of gratitude and like my immediate impulse was to think about all the people in my life who I was grateful for, and I pulled out my phone and I started writing all these like thank you notes, fortunately, I had the wherewithal not to fire them off or compose them in the text at that moment.

[00:37:00] Henry Winslow: But I just saved them for myself. Some of them I shared later. Some, I did not And I had, you know a few hours there to reflect on like what I wanted to take with me from this, like, you know, sort of a pre integration. And I realized that my, my ideas around my business were limited by a sense of needing to hold onto control.

[00:37:25] Henry Winslow: This may feel like a big jump, but for me, it really started from, Feeling other people's wants, desires, hopes, aspirations, and recognizing that building a team for a business, which is something I had never really done before is not about, you know, convincing people to do something for you or leveraging people's skills for your interests.

[00:37:50] Henry Winslow: Yes, that can happen, but. You're also doing something for them. People want to be a part of something. People want to contribute to something that's bigger than themselves. That was a big unlock for me with, with tricycle day and a big part of what allowed me to take the next step for the business, which is building out an agency, you know, it was like a media company that started just as a newsletter, you know, monetized through sponsorships.

[00:38:14] Henry Winslow: But now we have this like service business underneath it, and I've got a small team that's helping me do it. So I don't think that would have happened without MDMA. That's 

[00:38:23] Raad Seraj: beautiful. And I really appreciate the sort of attribution there. You know, this is really like sort of a fantastic perspective. Again, very practical, whether you're, you know, it's for your family or building a business.

[00:38:36] Raad Seraj: And we're going to talk a little bit about that in a second. But, you know, sort of understanding that whatever you do in life, it's really about aligning values. Right. Aligning a vision and hopefully the vision is, you know, is inferred from your value set. And, and I, I, I really resonate with that because At any one time, there's a billion things you can build.

[00:39:01] Raad Seraj: There's a billion things, a billion people you can follow. If you're gonna follow your heart, recognizing that you can't, like, nobody's really self made. I'd actually don't, I've sort of rejected that idea wholeheartedly, Ram. Because Whether you have mentors, whether it's family, whether it's friends, whether it's like bosses, whatever, you know, you need help.

[00:39:22] Raad Seraj: Everybody needs a guiding hand. Everybody needs some sort of advice, right? You know, trusting the fact that you're going to have to sell a vision, not, tell us the wrong word, but you know what I mean? Like, people want to have to opt in into your vision. Conviction is really important in that sense, right?

[00:39:42] Raad Seraj: Why should people work with you? Nevermind for you, but why should we work with you? Right. It's certainly the reason why I wanted to work with you. And I, you know, big fan newsletters grade by also knowing, having the privilege of knowing the person behind that's currently wants me to, you know, be a bigger fan and 

[00:39:58] Henry Winslow: support.

[00:40:00] Henry Winslow: Yeah, yeah. I mean, I guess this is something that I have not intentionally manufactured, which is, I think a good thing. It's just, I'm letting it happen naturally. And in some senses, You know, I'm not even always aware of what's motivating me until some time has passed and I look back and in hindsight and with reflection, you kind of understand what pulled you along a certain path.

[00:40:27] Henry Winslow: But for me, you know, the choice to do something in psychedelics, it feels like. I am contributing something of real import and significance and meaning in the world. You know, you know, this as well as I do entrepreneurship offers potentially a lot of upside, but there's also a lot that you compromise that you sacrifice to start a business.

[00:40:51] Henry Winslow: Like it's a lot easier to just make a steady living, working a job and getting a paycheck. And you can make a Good money doing that. Like I was making good money when I worked at healthcare advertising firms. So to step away, whether it was to go be a yoga teacher or now to do tricycle day and kind of educate the masses around the possibilities of psychedelics is a choice where I'm.

[00:41:18] Henry Winslow: Putting away the possibility of, you know, immediate gratification and in the form of a paycheck in terms of like feeding my heart and soul by doing something that I think can actually help people in a really significant, meaningful way. So that's, what's motivating me. I think it's like, it's not hard to convince people that that's why I'm doing it because why else would you like, there's so many easier ways to make money.

[00:41:43] Raad Seraj: I totally agree with you. And, and, you know, I, I've done a lot of things and I've become increasingly convinced that entrepreneurship. It's really the only way perhaps to change the world. And now I'm going to add, I think the word entrepreneurship, being a founder has been hijacked by a certain idea of what that looks like, right?

[00:42:08] Raad Seraj: Tech CEOs and billionaires and so on. Lifestyle 

[00:42:12] Henry Winslow: entrepreneurs associated with startup, like, yeah, yeah. 

[00:42:15] Raad Seraj: But for me, entrepreneurship is really about having a true sense of agency, right? So, yeah. You know, to your point, why would you want to be a founder entrepreneur? Why would you put to yourself Daily day moment by moment sort of in the paralyzing doubt that comes with entrepreneurship, right?

[00:42:33] Raad Seraj: I'm gonna feed my family. I'm gonna feed myself I'm gonna pay my bills and that's you know, it's like every day is a different roller coaster, right? Yeah, but I think the the beauty of that the upside Even without the payout at the end That's necessarily is to say that at least i'm doing i'm acting with agency Heart and soul.

[00:42:52] Raad Seraj: I'm doing what I believe in. And that's a great practice for anywhere. Like, even if you're an activist, it's like saying I'm doing this and I know what drives me. I know what I'm doing. 

[00:43:03] Henry Winslow: Yeah. Or an artist for that matter. 

[00:43:05] Raad Seraj: Absolutely. Absolutely. And I think with startups, it's funny, right? Like all startup founders, again, whatever that startup might be, start out as artists because you're wrestling with ambiguity, all art and expression is wrestling ambiguity and giving, giving form to abstract ideas or thoughts.

[00:43:24] Raad Seraj: You eventually become a scientist because that's where replication and sort of like scale comes into being, but you start as an artist. That's 

[00:43:31] Henry Winslow: a great point. That's true. You got to start from nothing and you have no data to make your decisions off in the beginning. Later, it becomes systematized. You add your S.

[00:43:40] Henry Winslow: O. P. S. you replicate. Maybe you hire people to, you know, to execute the systems in the beginning. You just got to make it up. Exactly. Isn't it? 

[00:43:50] Raad Seraj: Exactly, exactly. When it, I mean, when you see it working, of course, but the thing is like, we don't have a feedback. We were like, just drive yourself nuts, right? Speaking about 0 to 1, so taking that step you've gone instead 0 to 37, 000 at last count.

[00:44:04] Raad Seraj: You know, you just passed your first year anniversary, which is like insane to me. Congratulations. Like, I mean, what a, what a pleasure it's been for me, at least personally. When I met you, you were like, 19, 000 subscribers, I think, and you're 37 at last count, as from what I've read. Yeah. 38 now. Not 38 now.

[00:44:22] Raad Seraj: Fuck. It's like last week that I read this. Tell me a little bit about, you know, when you started, why start another newsletter? There were a few, and I'm not saying that you shouldn't do it, but like, obviously that's the question. Like, what are you bringing to the table that's going to be different? Why did you have conviction in this?

[00:44:43] Raad Seraj: One. And then, you know, how is it going? Is it, you know, did you imagine coming this far? What work, what, what were the challenges 

[00:44:52] Henry Winslow: and so on? Okay. So first why the newsletter? Well I had been. A reader of newsletters. And I was like kind of naturally taking an audit of the space just by, by virtue of being a consumer myself.

[00:45:08] Henry Winslow: And from my point of view, obviously I had not seen everything, but from what I could see, it seemed that there was a big missing piece in the media landscape around psychedelics, from what I could tell, it seemed that there was. There were materials that spoke to people who are very much immersed in the space, knew the language, whether that's legal, medical, what have you so kind of like high level requires a lot of literacy to, to get.

[00:45:35] Henry Winslow: There was that. And then on the total other end of the spectrum, we had You know, alternative news sources that are speaking more to the neo spiritual crowd. Five D consciousness, you know, that kind of almost like pseudoscience language. And to me, it seemed that, you know, if you imagine a bell curve of the people who could be interested in this content, there's a big section in the middle that is The biggest, and it's also growing because now psychedelics are going mainstream and they were being underserved.

[00:46:07] Henry Winslow: They weren't being spoken to. So I wanted to write to them and my insight there was like, look, they don't have all of the knowledge. It's more of like a basic level of understanding. Maybe, you know, it's not saying they're not smart people, but they just don't know what's going on in psychedelics.

[00:46:22] Henry Winslow: And. Also, they could be alienated by this, like, kind of woo woo talk. So I'm going to write from a voice that's easy to understand, fun to understand, fun to follow, and even injects a little bit of humor, which I can understand for some people is polarizing because these are sacred substances. They're not really heavy topics, but that was an intentional decision, which I knew would.

[00:46:45] Henry Winslow: You know, to my point earlier, kind of might alienate some, but it's going to speak to a group that does not have a new source currently, and it seems to have taken hold, you know it's grown very quickly, you know, in just over a year, you know, we've gotten to 38, 000 active subscribers, you know, and a highly engaged audience too.

[00:47:04] Henry Winslow: I think that's super important to, because it shows more than just, you know, a list of emails that you're collecting that people are actually reading And responding, engaging, clicking through to links all good indicators that people value, you know, the, the information that I'm putting out there.

[00:47:21] Henry Winslow: How do you 

[00:47:21] Raad Seraj: gauge engagement? You just mentioned. So of course, clicking through and opening your newsletters and stuff like how in your mind let's just say, talk about industry standards or segment standards best practices and so on. How do you gauge your engagement? 

[00:47:36] Henry Winslow: Yeah. Open rate click through rate are like the standard metrics.

[00:47:41] Henry Winslow: I use, I, I watch those constantly. Right now the average trailing four weeks open rate is 53 plus percent, which I think is really great. That's fantastic. Yeah. Like industry agnostic. I think, you know, a benchmark is like 20%. So that's obviously including, you know, You know, promotional emails from brands that are selling a product.

[00:48:02] Henry Winslow: So I understand I'm in a position where my product is the, is the email itself. So it should be higher. And then click through rate is like, you know, around six to 7 percent at any given time. So I'm happy with those, but there are some other like less tangibles. Like I get there's a poll feedback form at the bottom of every newsletter where I just ask people to rate that issue and they can choose, like, it's a scale of one to three basically.

[00:48:28] Henry Winslow: And I look at those they can just put in the rating or they can fill in like a dialogue box and, and. Provide more commentary. So I read all of those and often respond to some of them. I love to see what resonates with people. People also reply directly to the emails and start a conversation. I think a lot of people don't realize there's like a human being on the other side, so they don't know they can do that.

[00:48:49] Henry Winslow: So I encourage that. I think it's awesome when people reply to the email. And then the last one is how people engage with like the kind of lighter stuff on Instagram. I know I'd put out a good meme if it gets a lot of shares, if I, cause Instagram tells you every time somebody shares it to their story, it's always people for sharing when they do.

[00:49:07] Henry Winslow: How do you, 

[00:49:07] Raad Seraj: how do you design a good 

[00:49:08] Henry Winslow: name? Yeah. I mean, that's all. So earlier you were talking about like the art of business. That's one thing that's impossible to systematize, which is fun. You know, it creates, it keeps things. Interesting and playful. For me, there are a few different ways I come up with it.

[00:49:24] Henry Winslow: You know, one is just as I'm writing the newsletter or like taking in the news, the sources that, that feed into the newsletter. I'm like, okay, how, what, is there a meme out there that applies to this, that I can riff on? That's one way. Another is following other meme content creators and totally different niches and see if I can take their thing and apply it to psychedelics.

[00:49:46] Henry Winslow: Yeah, I mean, those are probably the two main inputs of how I come across it. The thing about memes is like, you're not supposed to be totally original. It's how do you respond to what's already, you know, popular in the zeitgeist. 

[00:49:57] Raad Seraj: The remixing the meme and having a new interpretation is the whole point, right?

[00:50:03] Henry Winslow: That's the whole point. Yeah, exactly. 

[00:50:04] Raad Seraj: Hopefully having a hilarious interpretation. That is also kind of true. I totally agree with you, your point about the sort of chasm that exists between. Extreme pain and peak performance and the peak performance bin. I put like not only biohackers, but like Superwoo culty bordering on superstition kind of like content not judging But yes, maybe judging but you know putting them but there's a giant chasm in the middle, which is like people who A want to find more reliable information, maybe find a safe way to experience the medicine.

[00:50:38] Raad Seraj: But also like, I kind of feel there's a huge opportunity in talking about how do you integrate these in your day to day life? I do feel that you have to come to baseline and heal your core wounds. And that's an ever growing process. Yeah. But there's also like, how do I use it to become a better partner, a better founder, a better friend, a better, you know, husband or whatever.

[00:50:58] Raad Seraj: Yeah. I think that's really important, right? One, one thing, where do you want tricycle day to go? Like, what does, let's say, a tricycle day in 2024, 2025 look like? What's the next evolution? 

[00:51:09] Henry Winslow: Yeah, so first year for me was all about growth because I recognize that if I didn't have an audience, then, you know, I couldn't do anything with it.

[00:51:18] Henry Winslow: Like, I'd be writing into the ether. So I really prioritize that. I put a lot of my own savings into growth as well. And in 2024, I feel like I have a nice. Healthy foundation in terms of an audience. So I've scaled back a bit on, on just like hammering the growth. Also because I need to make a living out of it.

[00:51:38] Henry Winslow: So I've started, I paid myself for the first time this year in January. Congratulations. Bicycle day, which is awesome. So I just want to keep going kind of continue doing what I'm doing as far as the like newsletter side. And then I'm also going hard into this agency to see how I can you know, serve our sponsors and advertising partners even better.

[00:52:01] Henry Winslow: Amazing. 

[00:52:02] Raad Seraj: I'm so excited to see this next chapter. It's been an absolute privilege to follow you so far. Last question, as we sort of bring this podcast to sort of this logical conclusion, for lack of a better word, is What advice do you have for one, young parents, young dads, you know, a lot of people who started families and recently a couple of years you know, you know, with the perspective that you've shared so far about not having, not doing sort of this intergenerational transference of trauma and hardships and difficult ideas or thoughts.

[00:52:35] Raad Seraj: Sorry. And then second thing, what advice do you have for founders? People who want to start the entrepreneurship journey, want to create something, want to build something. 

[00:52:46] Henry Winslow: Yeah. Okay. So the parent one, first, I just want to acknowledge that. I think it's almost like a little bit silly for me to be giving advice because I'm so green myself.

[00:52:56] Henry Winslow: However, you know, everybody's opinion is valid, right? Let's call it 

[00:52:59] Raad Seraj: perspective. Advice is, I think it's, yeah, let's call it perspective. 

[00:53:03] Henry Winslow: I would say. You know, because everyone has different, unique, personally formed values, the most important thing to do stepping into parenthood is to reflect and become very intentional about the way that you show up for your kid, because it's very easy otherwise to just slide into habit.

[00:53:25] Henry Winslow: Especially when you're so challenged on things like sleep. You just want it, like you want to avoid friction and you want to just like do whatever is natural, but I believe in the grand scheme, that is not the appropriate path to take. And that. You have a very limited window when children are just so, so impressionable.

[00:53:46] Henry Winslow: You know, they're talk about psychedelics, neuroplasticity, children's brains are so plastic that everything you do influence. So I would just be very, very mindful of that and establish habits, behaviors, model behavior that you would like to see them approach and recognize as normal. And then on the founder side you know, I guess I would say prioritize distribution.

[00:54:15] Henry Winslow: That would be, that would be my, my advice. It's a lot easier to sell something, whether that's a product, service, whatever, if you have an audience that already knows, likes, and trusts you. So you got to play the patient, like play the long game, be patient. And it takes work to do that, but you can do it with no money even because of discoverability engines like social media platforms, like you could build an audience there.

[00:54:42] Henry Winslow: And then once you've developed sort of a subject matter expertise or authority in some niche, like it's a lot easier to launch a business off of that than out of nowhere from zero. 

[00:54:55] Raad Seraj: Great advice. As somebody who is not great at building distribution yet, I take that to heart. And I think that's really good advice.

[00:55:03] Raad Seraj: Henry, this has been a fantastic conversation. I just want to thank you again for being vulnerable, for for opening up and sharing all your perspectives and learnings. I think it's, you know, again, as, as somebody who is a fan of the newsletter and watched you as a friend build this thing, it's such a pleasure.

[00:55:20] Raad Seraj: You know, I, I feel like I'm working with an artist looking at, you know, watching an artist build something new and special. So I 

[00:55:26] Henry Winslow: appreciate that. Thank you so much, Raad. I really appreciated this conversation and the intention and care that you brought to it. For the listeners out there, you should know, like, this isn't just like an off the cuff thing.

[00:55:39] Henry Winslow: We spoke beforehand. He had a whole idea around how we could frame the arc of the story. Not, you know, putting words in my mouth or anything like that, but he wants this show to be valuable in a way that is different from other shows out there, and I really appreciate that. That's the artist in you.

[00:55:54] Henry Winslow: You're, you're creating something different here. Thank you. Thanks so much, Henry. 

[00:55:57] Raad Seraj: I really appreciate you. And yeah, to bigger and better things. 

[00:56:03] Henry Winslow: Absolutely. We'll keep going right on.