From the desk of Jake Sasseville
14 – 18 minute read
Welcome to Imiloa’s Newsletter.
Most good ideas are simple.
This newsletter is about observing beauty, and giving form to it.
Why?
This is what the word Kaleidoscope means in its Greek origin and we’ve decided to launch Imiloa’s Newsletter in parallel with the Imiloa Kaleidoscope Membership.
🔎 Because, what are educators, retreat leaders and impact-driven entrepreneurs just like you doing, if not observing beauty and seeking to give form to it through your retreats, projects and companies?
We are here to champion people, courage, mindfulness and truth. This is what we’ve been working toward every day since June 1, 2018 – the day Imiloa began.
Three hundred retreat contracts later, thousands of lives touched and transformed, we know for sure that marketing and selling is simply about a way of being. Cultivating that way of being is usually preceded by building the capacity to have conversations that matter.
That’s not a particularly popular thing to share. Most online courses and gurus would have you believe it’s about hacks, strategy, action, courses and ads.
We’re here to tell ya that all those pieces are necessary and they come after you’ve cultivated a way of being in the world.
💡 The more you focus internally, instead of externally, the more you start to realize there’s a light flickering deep inside of you that wants to burn brighter than it already is.
It needs to be nurtured. The reason it’s hard is because you’ve got to deal with what-is. You’ve got to deal with the truth, which is right in front of you, so the past gets put in the past where it belongs. That’s the first step to cultivating a way of being.
We avoid truth and tend to ignore the flickering light because life’s been tough, failures feel like unexploded landmines all around us and we’d rather distract and numb rather than create a future that’s so bright, so enrolling and so courageous that everyone around you gets touched by it.
When you create a future that’s worth living into, your way of being begins to transform as you pursue it.
We understand the challenge. That’s why we created the Imiloa Kaleidoscope Membership. As transformational leaders, retreat hosts and educators, we can only tend to the flicker in community and we can only create a future that’s worthy of the community’s time by cultivating our capacity for having conversations that matter.
We can only build capacity by being engaged.
Clarity through engagement.
Our external focus on results – the marketing, selling, life hacks and all the rest of it is a smoke and mirrors show until you cultivate a way of being.
If you’re focused externally instead of internally, it’s not your fault. This is how our society has evolved. But to transform it is your responsibility.
Dr. Martha Beck and Rowan Mangen, 2025 Imiloa hosts, show us how.
Martha, a Harvard-trained sociologist, best-selling author (22 books) and life coach – including for the past quarter century to Oprah Winfrey – alongside Rowan Mangan, her wife, business partner and expert on creativity, are co-facilitating their “Pure Wild Self” retreat at Imiloa in early 2025.
Sometimes our destiny, as Martha and Ro shared with us, is shaped by the culture that we have access to in our earliest moments of becoming.
We are limited by the expression of our purpose and destiny because of the cultural limitations all around us.
The best way to deal with this? A culture cleanse, they say, which they’ll be doing as part of their retreat at Imiloa.
📖 These concepts are deeply intertwined with Martha’s philosophy, as detailed in her book “The Way of Integrity: Finding the Path to Your True Self.”
Martha and Rowan care deeply about helping others live in alignment with their true selves, free from societal constraints.
The “culture cleanse” at the heart of their retreat is designed to strip away the layers of cultural conditioning that often obscure our inner navigation systems.
The cultural conditioning doesn’t allow us to connect directly to our purposefulness in this life. What are we doing if not living with purpose?
When we commune purposefully and live into our destiny, we’re creating a future so enrolling, so exciting that everyone around us can’t help but be touched by it. This is what we mean by a “way of being.”
If we feel we’re here to impact millions, and we grow up in the West, our only example of how to do that might be to pursue fame, celebrity, building big tech companies and the like.
📺 I tried to do it when I became the youngest host in late night TV history at 21 years old after Jimmy Kimmel Live on ABC. As a kid, studying Oprah and other luminaries, I felt so deeply that my purpose was to serve and impact millions by raising others up around me.
The examples I had were people on television. I thought that was the route to take and I pursued it religiously and unapologetically. You can read about my exploits in my first memoir from 2012, “Slightly Famous.”
Despite worldly success, the shoe never quite fit for me in television. As I wrote in my book, the failures I was experiencing as I pursued success I thought were rights-of-passage. In reality, they were whispers to adjust the course slightly. I can only now see that 17 years later.
🧭 If a ship headed to Europe has a compass that’s adjusted by just a few degrees, it ends up on a different continent entirely.
I had to adjust but I couldn’t figure out how. The idea was right — big impact, millions of lives touched — but the vehicle (a late-night talk show, fame, celebrity) was limited by what the culture gave a kid from Maine.
We create big, purpose-filled futures by putting something at stake, a stake in the ground.
We don’t necessarily know how to achieve it right away. But something must be at stake in order to create a future that’s worth living into.
Most good ideas continue to be simple.
If you’ve had an awakening in your life – a transformation – it means you’re qualified to be able to touch another person’s life.
You may do so imperfectly.
You may need to refine your offering.
You may become a zealot and a preacher before you can really be in service.
You may need to be told by the community that your zealtory doesn’t work for them.
You are qualified and the whisper your life has been speaking to you is real.
It’s not your imagination.
32% of recently signed retreat leaders at Imiloa Institute have hosted 0 retreats and are selling out faster than most seasoned retreat hosts. Many are renewing their contracts before they’ve even hosted their first retreat.
Why is this trending in that way?
The hunger that people are experiencing to gather — and gatherwell — is at an all-time high.
Retreat hosts these days aren’t just limited to spiritual folks who are perceived to have answers for the rest of us.
Retreat hosts these days at Imiloa are physicians, Beverly Hills facialists, wellness professionals working with army veterans, United Nations cohorts, pilates instructors, University professors who support PhD candidates writing their dissertations and so many others.
Retreat leaders are anyone with a community, showing up to serve that community imperfectly, and creating a future that the community collectively wants to live into.
It’s an exciting time in the world of hospitality, wellness, education and transformation.
Ready to talk about hosting your retreat or experience at Imiloa?
Join the Discovery Series Now
or Book Your Shared Vision with Imiloa’s Team
In the recovery program that I am affiliated with, before I had any recovery, solvency or sobriety under my belt, my sponsor suggested I immediately begin taking someone new through the twelve-step process.
“I’m not qualified,” I begged.
“You’ve had one more day in recovery than the person you’re working with. You’re qualified, she insisted.”
I really believe this was one of the pivotal moments that saved my life.
Realizing that I had one more day than the newcomer and therefore that qualified me to serve removed the barriers of “recovery” or “perfection” and instead invited me to simply take action and serve.
Fear is removed when we take action.
Joy is experienced when we take that action for the thrill of the action, not for the results it may produce.
The point was not whether I was qualified to take someone through the steps. The point was that there is a spiritual significance, and spiritual potency, about serving others on the pathway to our own becoming.
This is a story of becoming who you were meant to be.
Your retreat, your big idea, your business or company is just a vehicle for the actualization for you and everyone you touch.
We teach what we most need to learn. Being authentic about this is a breakthrough in your way of being and shapes the conversation that you’ve been unwilling to have up until now.
We know what you’ve done and what you’ve accomplished, but how have you been being?
The most successful retreat leaders don’t have prior experience.
They aren’t rolling in the cash.
They may not even be fully developed experts in the world.
The most successful retreat leaders have cultivated a way of being that is attuned to what their right-fit clients are most needing.
For me, it has nothing to do with experience, access to capital or even a solidified vision.
Before starting Imiloa, I had never attended a retreat.
I’m a college dropout.
My SATs were 880 (combined) and I got rejected from 8 of the 9 colleges I applied to.
Two years before starting Imiloa, I was living in my Grandma’s Basement, penniless, with a credit score of <460.
I started and failed at five businesses and was nearly half a million dollars in debt.
I didn’t have a vast network of teachers who led retreats nor friends with capital willing to invest.
What I had was an idea based on lived experience. And that idea was starting to shape me to become the person I’d have to be in order to create the dream that is Imiloa.
I thought I could help create a home and experience where human beings can awaken their consciousness in service to themselves and the planet.
I thought how cool it would be if the same transformation would be possible for the team that created the experience for our guests.
Less of a business idea and more of an experiment.
I took action for the thrill of action and let life unfold on its own terms.
Imiloa was born.
I cultivated a way of being with people that was curious, open, flexible and pivot-friendly.
I had a house, but not a home. My parents were often away for days or weeks at a time caring for my brother who was sick with cancer at Boston Children’s Hospital. My dad had Parkinson’s and my mom drank a little (too much).
Home wasn’t safe. It wasn’t a place to thrive. But it was a place to get curious about the world around me.
As I discovered more about people and places around me from my tiny town in Maine, I realized transformation was possible. I just had to discover something new about me or the world.
If I could just continue being curious enough to discover, I could transform my life.
As Imiloa formed, I was clear I wasn’t meant to be its figurehead. I was meant to raise others — other teachers, other team members — to be able to contribute to the world.
I spent 25 years figuring this out, trying to be the star of various projects, only to discover I’m meant to be the vessel, the channel for other people’s good, big heart-felt ideas to flow through.
I’m living into my destiny with a sense of clarity and purpose because I’ve gone through my own culture cleanse.
You likely are, or recently did, too.
Clarity through engagement and most good ideas are simple.
Imiloa in 2024 looks nothing like it did in 2018.
Someone’s way of being impacts their ability to earn, market and share about themselves. When you’re tuned into “being” instead of “doing,” you are able to identify what people are needing before they know they need it.
Take action and turn the results over to a higher power of your understanding. God, creator, universe, source, whatever. Rinse, wash and repeat.
Don’t forget: Your way of being is preceded by putting something at stake. Your word creates your world. What is at stake for you and for those you serve?
When something’s at stake and we begin to pursue it, who-we-are in this moment begins to transform. You can feel it.
I want support in putting a stake in the ground.
Take me to join the Imiloa Membership Waitlist!
I envisioned Imiloa as an intercontinental institute where we support retreat hosts unlike ever before so they show up for their guests in ways like they’ve always dreamed.
They are the future of education and that’s a stake in the ground we have at Imiloa.
As such, if we’re serving the future educators of human beings, we must support them beyond what any other venue or company in the world thought was possible. We are still figuring out how to do this. That’s what a stake in the ground is. You don’t know how to accomplish it but you’ll spend your days trying to figure out how.
Who we’re becoming as an organization that pursues this purpose is causing us all to transform. We see our community touched as we pursue it. Lives are being transformed. New possibilities are arising from other organizations that see the need to elevate.
This is a Purpose-Driven Audacious Goal (PDAG) and it’s what we explore in Imiloa’s one-year mastermind, “Wisdom Trust.”
We don’t “live in the results business” yet we drive results that our beyond our imagination (paradox).
“We take action and turn the results over.”
Inauthenticity is solved by telling the truth.
When I started practicing Ashtanga yoga, I attended my first class with my best friend on Maui.
I kept going to every class thereafter because of the authenticity of the teacher.
He was the kind of teacher fat people want to learn from.
Avi Elkayam, a former member of the Israeli military, shared with me after my first class that at nearly 300 pounds, when he discovered Ashtanga Yoga twenty years before, it saved his life. He’s now a small guy, strong and has daily practice.
Fat people want someone that’s been there, or is there now, and is committed to creating a world beyond where they currently are. My Ashtanga practice has continued and it’s because I could see myself in the teacher because of his own commitment to authenticity.
Authenticity isn’t about being or selling something; it’s about leaning in fully to who you are and trusting life. Nature trusts itself. Why shouldn’t we?
We don’t need charlatans or influencers to tell us that life is going to be OK. We need people in the trenches with us that remind us that life is OK right now and it can continue to get better.
Jeremy de Tolly hosts at Imiloa Dec 2-7, 2024.
Jeremy’s approach to teaching authenticity, using one's voice, and facilitating personal and professional growth is deeply rooted in his background as a transformation coach, musician, and vocal liberation teacher.
De Tolly emphasizes the importance of unlocking stuck or shut-down voices to foster heart-centered and empowered interactions with the world.
His teachings focus on overcoming obstacles to self-expression and stepping into the joy and freedom that confident communication brings.
Jeremy teaches: “What appears to be in the way, is the way.”
This philosophy ties directly to the concept of authenticity, suggesting that the journey towards an unblocked and free voice is also a journey towards becoming more authentically oneself.
🎤 His work, including the “Radiant Voices Retreat” at the Imiloa Institute, emphasizes creating a safe, supportive environment where individuals can explore and activate their “powerful, heart-centered radiant voice”.
This focus on authentic being rather than doing, supported by a deep understanding of the voice's connection to personal identity and trauma, enables individuals to connect more deeply with others and themselves, fostering an environment where authentic expression leads to success.
It wasn’t the creation of Imiloa that mattered. It was the decision to try.
That’s the reward of our creative, impact-driven endeavors.
And when you try, who you become as a result of your pursuit is the gold (or, goal).
People think I had this grand vision for what Imiloa would become seven years ago.
The truth is I had a vision that was playing with the idea of a home for transformational work to be done. I liked the idea of welcoming a variety of retreat leaders. I saw the future of education as an experiment and experience.
Try to capture this in brand messaging or marketing?
Or for potential investors?
Forget about it.
It was challenging and took years to articulate.
People want to understand the origin story of Imiloa so that the birth of their own dreams becomes possible.
All many of us want to believe is that our dreams are possible. When we see others living theirs, and they also stand in authenticity and integrity, we can feel lit up at the prospect that it’s possible for us, too.
The origin story of Imiloa, while inspiring and uplifting, isn’t going to convince you to do what is the very hardest thing: the decision to try.
I was recently talking about this idea with my friend Anthony David Adams.
Anthony and I lived together in New York City in 2009 when I was a rabble-rouser in the entertainment business and Anthony was enjoying the sunset of his 20s figuring out ways to get to outer space and coaching tech billionaires. The network of people that he considers friends is dizzying and inspiring.
I recently met Anthony in Costa Rica who’s now nearing his mid-40s with a beard on top of what once was a cleanly shaven face and head.
“In order to be 80 with a long beard, I must start growing it now,” Anthony shared as he got off the plane. This was the first time we’ve seen each other in about a decade.
Anthony was sharing with me over breakfast that he summited a mountain in Corsica, France, recently.
⛰️ He thought the mountain would be easier than it was. He and his friend spent a grueling several days going through peaks and valleys until finally, the day came to summit it.
“It wasn’t summiting it that ultimately gave me the high of climbing the mountain,” Anthony shared.
“It was the morning of the summit and it was the decision to try that made the experience everything it ended up becoming.”
Observing the beauty within and seeking to give form to it.
My invitation to you is this: You’re likely here because you’ve been observing beauty, and you’re earnestly trying or currently giving form to it.
🫶🏽 We’re here to celebrate and support you.
Your way of being starts with a single decision to try.
It starts with a stake in the ground, where something is at stake. It continues with having the courage to take action despite the fear.
When you start to take that action, even if it’s not the right direction, everyone around you will start to be moved. You’ll notice it. It might feel different or exposing. That’s how you’ll know you’re on the right path.
Once the community is moved, you also become touched, and who-you-are begins to transform as you pursue it.
But it starts with a decision to try.
Anthony’s decision to try to summit the mountain in France has touched me, and now hopefully you, all these months later.
It’s not the doing that matters. We’ve tried that already. Look where it’s gotten us.
It’s the way of being that matters.
And when this snapshot of eternity is complete and our time on the planet is in its final moments, we’ll likely only care about a few things.
Among them will be that we made the decision to try.
