I met Jesse at a wellness retreat outside of Austin, TX this past spring. He and I were on the same hotel shuttle from the airport and I remember liking him right off the bat. He was an interesting character who was very open, and he seemed more enlightened than most people I knew. Over the course of the trip, we had some great conversations and got paired up to practice yoga together. By the end of it, I felt like I’d found a new great friend.
Jesse has a story I find inspiring on a soulful level. A successful music industry vet, Jesse co-founded Cantora in his early 20s before he decided to leave almost a decade later in order to pursue his true passion of bringing meditation and community to a wider audience.
Leaving his record company took no small amount of guts. He walked away from what many would consider to be an entrepreneur’s dream actualized – a successful record label, and the money and lifestyle that goes along with it.
But that’s part of what makes Jesse’s story so interesting. Why did he walk away when he’d achieved so much? As challenging as it was, Jesse talks about the wisdom of following his heart, and how ultimately trusting his intuition led him to a place where he feels more aligned with himself and his purpose. Jesse now runs two new ventures: Mediclub and The Big Quiet, both of which revolve around meditation and help people become more connected with their self and their communities.
Both businesses are doing well and making a big impact, but it wasn’t always easy getting to this point. Through his experience, Jesse encountered many challenging trials and dark days, yet he’s learned from them and persevered in finding his way.
It’s an inspiring story, and for those seeking rich entrepreneurial and cultural insight that you can only get from the story of someone who has experienced it, here is Jesse Israel’s By the Bootstraps.
You co-founded Cantora when you were still in school and things were going pretty well. Why did you decide to change paths when, from an outsider’s perspective anyway, nothing was wrong business-wise?
It was in my heart. I’d had this incredible nine-year run that I was deeply connected to at another point in my life, but around year eight I started to get this feeling and my intuition was just to move on.
I tried to address it logically; what if I change my role?; what if we go to business partner therapy?; etc. I’m so glad we tried all those things because it was not a logistical thing or a simple change or tweak, it made me realize I was meant to move on to the next thing in my life.
I made a list of pros and cons. Pros: incredible business partners, we were making money, sick office space, etc. So many good things! The cons were just that my heart was not in it. That’s it.
I’d learned meditation in my twenties, and I can point to that as a tool that gave me clarity and taught me how to trust my intuition. With that, I could make the leap. I’ve got to say that as emotional and tough as it was, it was like an amicable divorce, and acting on opening myself up to what was next was so affirming to me.
After that period, the genesis of Mediclub seems very organic.
I left the company, traveled to Africa and dedicated myself to Cyclones, a side project that I’d been working on (Cyclones is a bike club helping students in rural Africa become better students by cutting down their commute time walking by giving them access to bikes.)
It helped me realize that it is one thing to build a community through a shared interest in riding bikes and discovery, but it is a very different thing to have a deeper purpose within that shared community.
I was so moved by the growth of that Cyclones community, but by then I was maybe six months into my process of transitioning out of the Cantora business and it was too cold to ride bikes in New York (December 2014) so I wanted to find something else I could commit myself to.
Using my gifts of bringing people together was always my passion, and, at the time meditation was the most consistent thing in my life, as well as something I was finding myself increasingly passionate about. Also, I was noticing all of these colleagues and friends that I knew from nightlife and music and tech that were starting to learn meditation and practice it but that didn’t have a place to do it together.
We started MediClub in my buddy’s beautifully designed loft in Soho. We told everyone to come over and for 20 minutes, whatever style of meditation you want to do, let’s just do it together and then we’ll have a conversation. Basically, “we can put on a cool Spotify playlist and have some food and a little party that’s centered around meditation and discussion.”
And that really resonated. I realized at that first event how powerful it was to share quiet with people, especially those who are typically very busy. Also, I noticed that people who come together and share meditation as a common thread tend to be deeper in how they communicate, socialize and speak about the self.
After twenty minutes in a safe space, important topics would come up: inner relationships, money, fear and intuition, and career changes. In the past, these were topics I would only talk about with my therapist yet here I was talking about this stuff with my peers - my equals - and there was something so powerful about being heard; hearing people and knowing that other people were going through the same things.
And it grew from there. The Mediclub experience continued to attract people to our community and I heard many people say, “I’ve been looking for something like this, a place where I can really go and open up.”
After five months, it was time to share our value system with the rest of the city, and that’s when The Big Quiet was born. To build the experience we brought in DJs and food, we received support from the brands that our friends were involved with and in turn, we supported them as well. We added some ice breakers and tried to get guests out of their comfort zones a little bit.
As I hear it, it’s almost like there were no struggles. The way you presented the growth of the business to me it’s almost as if it was meant to be. Were there any challenges you faced? Or, anyone that guided you along the way?
This whole process has been full of challenges and fear. I’ve never experienced so much fear. I wasn’t able to commit to this work for so many reasons: who I am; who I am as a “working man” in this world. I’m still processing those challenges. I’ve come to learn that the work I’m doing now sits right at my biggest trigger points and greatest fears.
Taking it back a few years, when I first left my company, I was elated for a few weeks, but then I went into a dark hole of comparison for several months where it felt pretty much impossible to enjoy anything. I was 29 and I was watching all my friends around me at the highest points in their careers. Meanwhile, I had minimal savings and a lifestyle I’d just walked away from.
I had supportive parents but no friends going through that process, so it was very lonely. On top of that, I’d speak about the work that I was (and am) doing as “little group meditations.” I allowed myself to see it from this one lens of, “this is some soft, lame shit to be doing as a grown man…” Basically, I was thinking, “Good for you dude, but how are you going to make a living at this?” There is an entrepreneur in me that wants to build something big and I never thought Mediclub would or could be that.
During that time, I would give a share after every meditation and reveal the fears that I was going through and that gave people the permission to say their fears. I was willing to share my process and I still do. Fear, challenges, and adversity are all critical pieces to my process and what we do in our groups.
Like I said, where Mediclub and The Big Quiet sit right now is on one of my biggest triggers; The Big Quiet has grown to thousands of people! I’m positioning myself talking about meditation in non-denominational ways… that’s something that a lot of people aren’t going to agree with or appreciate, especially compared to what I was doing before which was something they could understand.
So much of my energy has gone into making sure that everybody “likes” it, “likes” me and wants to come back. It’s been draining to try and create that for everyone especially when my biggest fear is to be un-liked.
To be honest, I was at a low point when you saw me at the last Big Quiet in Central park. (Editors’ note, It was this past Summer, I went with my team and loved the experience.) The need to please every person was so strong, I was barely able to show up and host that event. It was a turning point for me. I felt so uninspired and drained but I was able to spend time with (mentor and friend) Jonni who helped me understand why I was experiencing the shutdown and why I wasn’t able to enjoy what should’ve been a positive night.
It’s so important to me to be seen as ‘liked’ and ‘cool’ and operating on this very safe plane. And my biggest learning over the past two months has been to connect with my core and put my faith in the fact that I’m doing it because I believe it’s what I’m meant to do. I need to do what feels right to me and that’s OK whether people like it or not.
That’s powerful stuff.
I’m still going through it, ya know?
In truth, we’re always in the middle of it. I’ve just turned 40 so that may have something to do with it. Also, running a company with 17 people is a challenge, but on the other hand, you can see these things as opportunities. When you do commit to pushing your business in a new direction, it gives you an opportunity to figure out yourself and there is an actualization that happens.
The dark periods or low days are awesome opportunities to learn about the self. The more that I’ve learned to not fight those days and just accept them has made the whole thing more enjoyable.
Tell me more about mentors and Jonni.
My mentor is named Jonni Pollard; I met him through the Vedic meditation community. He’s renowned and is essentially an empowerment coach, a personal consultant for CEOs and political figures and icons, and a very meaningful guy. He’s been studying under masters for twenty years but is also this cool modern guy and he blends these worlds together in a solid way. He had been doing mass meditations in Australia, so when we were going to do it here in the U.S. I got in touch and he started advising me on how to build out Big Quiet.
And after he did that, he started counseling me as an individual. I was going to him with fears and relationship stuff and I found him to be this incredibly meaningful sounding board with refreshing wisdom. I felt fully heard and he helped me make sense of going through things without ever forcing or trying to “fix” me. He has experience with similar work in meditation, creating safe spaces and meaningful conversation. I don’t know if I could’ve done this without him, the universe really allowed for that to happen.
There’s a Jeff Bridges quote I like where he describes intimacy as "the main high in life.” It seems like MediClub and The Big Quiet are really aimed at facilitating that connection. What’s the vision/hope for your businesses moving forward?
Mediclub gatherings are a few hundred people, the first Wednesday of every month. Then, we have our circles program, about 45 people who are trained to facilitate conversations in small group settings in their homes. As you alluded to earlier when we were discussing the Andrew Sullivan piece, people are lonelier as a whole, as a people. Research shows that we are lonelier and more disconnected than ever before; especially those under 35 who are more digitally connected. We are hungrier for a connection of the communal type that we no longer find useful to us, like religion. A large percentage of millennials don’t consider themselves religious but I think they’re mistaking social and digital for that type of connection. I think a lot of the issues that we’re seeing in the world come from that rampant disconnect now present between humans, and now we’re seeing a lot of young people starving for more ways to connect. I love creating solutions to that problem.
Whether it's creating a cheeseburger club for men to connect and bond; a bike club to have adventures and feel alive; or safe spaces for people to share meditation and talk about what is going on in their lives; I love creating solutions in ways that have a big impact.
You never sketched out a business plan. Not to take us off the higher purpose but since this blog is a resource for other entrepreneurs, have you thought about your business model?
The vision is to do what we’re doing here all over the world. Fulfilling that need and hunger that we’re talking about; our circles model could be meeting in lots of cities and, eventually, lots of towns.
That’s the first part of the vision because right now, what we’re really focused on is creating spaces for people to come out and talk about what’s going on in their lives and discover their truth.
The circle groups are the baby steps to people finding connections and I want a global community of empowered people living their truth. It sounds like a cliché but there is a real power in this, and there are lots of people that want that.
Right now, we are an events business. We charge for everything from a circle to a ticket for a Big Quiet event. There is a 4-person team, including me, so that’s how we make it work: the event fee. This thing we created over a year ago is supporting itself (though my lifestyle is very different than when I was running my own label) and there are tons of ways that we can create revenue but those things will become clear to us as we keep kicking ass and coming from the heart.
Our team will talk about goals but I always say at the top of all those documents, ‘this will shift’ and ‘it’s only in pencil’. We create the space for how things will naturally evolve.
As a business owner, that’s so counter-intuitive to what you typically hear.
That’s the magical thing; I spoke to one passion problem I want to find a solution for, but there are a lot of problems that need to be solved that will come from acting from faith and following your gut and your heart. And that’s different from what we’ve been raised on, at least in the West.
Any advice for people starting their own business?
Find a style of meditation that fits and then practice it for ten minutes a day. Having a tool that will allow you stay somewhat grounded, somewhat clear, somewhat less reactive to all the things you have ahead of you will be your first step.
Step two? Get into the habit of listening to, and then acting on your gut. Like a muscle; the more you use your gut, the easier it becomes to make decisions from it and it will become an invaluable compass as you enter into the unknown. It really is our true nature, our ability to connect with something deeper and guide us in the right direction.
The third thing is being O.K. with some people not liking or not responding to what you’re doing. My advice would be to question yourself first, then give yourself fully to what you’re here to do and not listen to others’ insecurities.