Staying Grounded as a Psychedelic Entrepreneur: A Deep Dive with Tricycle Day founder Henry Winslow
Making psychedelic education accessible and enjoyable
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Henry Winslow managed to essentially own an emoji over the course of a year. When we see 🫠, we think of Tricycle Day! Although we have been working with him since day one and had him join our first two conferences as a panellist, we finally got to talk here to the psychedelic entrepreneur who knows how to stay balanced while accelerating business growth.
We spoke to Henry about the inspiration behind Tricycle Day, which stemmed from his transformative experiences with psychedelics and yoga. Initially a yoga teacher and healthcare marketer, he sought to make psychedelic education accessible and enjoyable, steering clear of the overly technical language often found in the field. We also touch on the importance of protecting unscheduled time to maintain creativity and focus and his exciting new launches.
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Staying Grounded as a Psychedelic Entrepreneur: A Deep Dive with Tricycle Day Founder Henry Winslow
Can you share the story behind Tricycle Day and how it all came together?
I found my way into psychedelics through my yoga practice, which I first started in 2010. Initially, I approached yoga as a way to maintain my physical health, but I immediately discovered the practice was working at a deeper level. As I laid there in savasana at the end of my first class, for once I felt I could simply exist. That was a huge relief for a type-A person like me.
As I dove deeper into yoga, I began studying its philosophical side. One of the foundational texts, the Yoga Sutras of Patanjali, lays out an eightfold path, where asana—the physical postures—is just one component. The final stages—dharana, dhyana, and samadhi—represent a journey through progressively deeper stages of meditation, culminating in a spontaneous realization of oneness with the universe. I was captivated by the concept of a non-dual state of consciousness, but I figured direct experience was out of reach for me—at least in this lifetime.
However, in 2019 a friend and fellow yoga teacher introduced me to the idea of a psychedelic experience as a shortcut to samadhi. A week later, I found myself stepping into my first psychedelic ceremony—with Bufo alvarius or 5-MeO-DMT, no less. That experience was irreversibly transformative for me. It shattered my perception of reality and connected me to a sense of unconditional love and acceptance I’d never felt before.
Even though I didn’t have language around “integration” back then, I intuitively knew it would take time to process what had just happened. It wasn't until January 2023 that I launched Tricycle Day, inspired by a gap I noticed in the psychedelic media landscape. I wanted to create content that was accessible and relatable to everyday people, avoiding the overly technical or esoteric language often found in the field. Most importantly, I thought psychedelic education could be light and—dare I say—fun.
What was your profession before Tricycle Day, and what inspired you to start your own venture?
Before Tricycle Day, I was a yoga teacher and worked in healthcare marketing. I studied pre-med in college, influenced by my parents, who were both doctors. However, I became disillusioned with the medical profession after learning about the challenges physicians face, particularly regarding the business side of healthcare.
Right out of college, I got into healthcare marketing, where I worked as a brand strategist for pharmaceutical clients. While there are valid criticisms of the pharma industry, I found that many individuals within it genuinely wanted to help. Ultimately, though, I felt a strong pull to create a more direct and meaningful impact in the world. That led me to embrace entrepreneurship and focus on teaching yoga, a practice that profoundly changed my life.
How have psychedelics influenced your entrepreneurial journey and the balance between life and work? How do you reflect on that early experience, which seemed to propel you forward with such momentum?
I didn’t try psychedelics until I was 28, several years after I’d ventured into starting businesses. But since then, it’s fair to say psychedelics have played a meaningful role in shaping how I show up and operate as an entrepreneur. For anyone who starts or owns their own business, the lines between personal life and work can easily blur. Sometimes that can even lead to a loss of identity outside of one's “brand.”
Working with psychedelics, alongside practices like meditation and yoga, has helped me maintain a sense of perspective. They allow me to observe my thoughts and emotions from a distance, so I don’t forget the nature of my true Self. It goes beyond my identity as an entrepreneur—or as a body or mind, for that matter. It’s something immutable and infinite, and it’s the same inside you as it is in me. Returning to this perspective helps me manage the challenges of entrepreneurship while staying grounded and connected to what matters.
The branding of Tricycle Day is fun, vibrant, yet grounded and very distinct - I would even say it is already iconic! Could you tell us a bit about the backstory of your branding?
Thank you! Branding is an area where I have some professional experience, from my days in corporate marketing. First, I should say my definition of “brand” extends far beyond design aesthetics. I like to think of it as the space your company or product occupies in the mind of your customer. Or put another way, how would someone else talk about your project when you’re not there?
When creating Tricycle Day, I saw an opportunity to present the psychedelic experience in a fun and accessible way, rather than the overly serious, sacred, or medicalized approaches we usually see. So I leaned into that levity in every aspect of the brand.
The choice of orange as the brand colour reflects vitality and creativity. Fun fact: it’s also the colour associated with the second chakra, Svadhisthana, in yoga philosophy, which resonates with creative expression. One of my yoga teachers used to say Svadhisthana is your inner toddler!
As for the icon, I wanted something playful that still signalled psychedelics. I initially used Midjourney to generate rough concepts. From there, I collaborated with a designer to refine the logo and build out the branding guidelines that show up in all our newsletters and assets today.
What is your vision for the future of Tricycle Day and the psychedelic community?
In many ways, my mission and vision for Tricycle Day are the same as the day I started the newsletter. I’m still trying to make psychedelic education accessible and entertaining for anyone so that more people who might benefit from these medicines have the chance to do so.
That said, there have been a few surprises along the way that have influenced where I’ve put my time and energy. For example, I initially assumed my primary audience would be everyday enthusiasts, or “consumers” as they say. As it turns out, my most engaged segment is made up of industry professionals, even if they are fewer in absolute numbers. So I’ve started to include more content and opportunities that speak directly to the facilitators, coaches, and therapists who read Tricycle Day.
This is a good example of where the buzzword, “mission-driven,” starts to mean something. I have a big, audacious vision for a world where psychedelics are destigmatized, and people are able to use them for healing, personal growth, and spiritual connection without shame or legal consequences. I’m more guided by that ideal than any particular business model or content strategy. Since the mission is centred, I have the flexibility to experiment with different means to the same end.
You branched out to other avenues with the creation of a list of professionals that help navigate psychedelic journeys as well as starting your own marketing agency. I am sure the audience would love to learn more about this!
Exactly. Building on my point above, I’ve realized that helping psychedelic practitioners reach more clients, guests, or patients is a cheat code to compounding Tricycle Day’s impact on society. There’s a limit on how many people I can directly influence with the newsletter. At the end of the day, it’s content.
But if I can leverage the goodwill and trust I’ve built with my audience, along with the marketing skills I’ve acquired over the years, to connect people in need with psychedelic-assisted therapists, coaches, facilitators, and retreats, the potential for impact scales exponentially. There’s a ripple effect that’s hard to even comprehend.
A few of the ways my team and I have executed this realization are Maria’s List, our directory of psychedelic professionals, and Let Go Studio, our growth marketing agency for psychedelic and plant medicine businesses.
Most recently, we’ve launched a new program for psychedelic facilitators of all types who want to attract more clients and increase their impact. It’s called Practice Expansion, and we’re enrolling our first beta cohort right now. It’s a really interesting concept that blends marketing and sales training with a collective mastermind, where everyone shares and learns from one another. I honestly can’t wait to see the transformations that come out of this program.
Last but not least, can you give us one tip for entrepreneurs to stay creative and focused on their journey other than mentioned above?
Between all your tasks and to-do lists, never slip on protecting your empty space. Especially if you do creative work, unscheduled time is not a luxury. It’s essential.
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