Wayfinders COMMUNITY memberShip

Entrepreneurship can be a lonely journey.

Let’s make it a shared one.

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Welcome to the Wayfinders community.

We are a community of insatiably curious entrepreneurs called to explore how our work can align with the world’s emerging evolution, or as writer and philosopher Charles Eisenstein puts it,
“the more beautiful world our hearts know is possible”.

The Wayfinders Community

The Wayfinders community is already 90+ members strong, made up of incredible entrepreneurs and amazing humans from the Toronto area and all over North America.

Our members are based all over North America (and a handful outside of N.A.), with the majority in and around Toronto. Spanning a wide range of industries, their average entrepreneurial tenure is 12 years and the average age of our members is 42, with a roughly 55% male/45% female split.

Our diversity is our strength, but the one thing we all have in common is a desire to embark on a journey, one that Wade Davis refers to in his book The Wayfinders as a ‘journey of discovery, seeking to understand the human experience and our place in the world.’

And we share a desire to undertake that journey with trusted companions at our side.

Community Benefits

We are a community that prioritizes connection, especially in-person connection. The right information can be useful and powerful, and we will have plenty of incredible learning opportunities, but most of us already have access to lots of useful information.

The right connection(s), however, can unlock new perspectives on our biggest challenges; can open doors to new connections and new places; can be a sympathetic ear when we are going through our deepest struggles.

Joining our community offers a variety of benefits, including:

• A sense of deep belonging in a community of welcoming individuals

• An ongoing, collective journey of exploring our place in the world and how our work aligns with it

• Exclusive quarterly summits: half-day learning opportunities where you’ll gain valuable professional insights and make deep and meaningful connections with like-minded individuals. Events are facilitated to provide opportunities for deep exploration, connection and collaboration.

• Quarterly challenges in the supportive company of a community of peers, to provide you with inspiration and accountability to reach your health, work, love and other goals.

• Opportunities to grow and optimize your business, through networking and working with other community members, in an ethical and ‘un-sales-pitchy’ kind of way

About Me (Mike)

I’m the founder and Chief Explorer at Wayfinders, which I founded in 2017 because I saw so many of my fellow entrepreneurs struggling with feelings of isolation. I wanted to create experiences and places for us to have fun, share our struggles openly, and connect on a deep level.

I’ve been an entrepreneur for 27 years. My previous company, Sacred Rides (which I sold in 2019) ran/runs high-end mountain bike trips around the world. During that time, I also had stints as a CBC journalist, the Dean of Social Enterprise at the world-renowned Centre For Social Innovation, entrepreneur-in-residence at Toronto Public Library, and running my own startup boot camps and a social enterprise incubator.

Entrepreneurship is in my blood, and as of late my focus has been on exploring how it can be used in service of the emerging, larger story of our time: the story of, as Charles Eisenstein calls it, ‘Interbeing’.

I live in the west end of Toronto, just down the street from Dufferin Grove park. I ride bikes as much as I can, write about human connection on my Substack channel, and am a multi-instrument musician (my current focus is on learning to play the drums).

The 5 Cs Model of Reconnection

Our model is based on restoring connection in the world, starting with our members and rippling outward.

As I’ve written about in my Restoring Connection series, the root of many of our current crises can be traced back to disconnection. When we are disconnected from self, from others, from our calling, from the natural world, and from a sense of mystery, we feel a profound sense of loss at our core, even if we can’t quite put our finger on what has been lost. This sense of loss, this void at our centre, plays out in various ways: anxiety, unhappiness, violence (literal and metaphorical), addiction, distraction, and more.

If we are to chart a better path forward for our species and our planet, it only will be through restoring connection.

The Wayfinders model of restoring connection is based on the 5Cs:

Connection to Self: Returning to who we are at our core and living life authentically, on our own terms

Connection to Others: Developing rejuvenating connections with others through a sense of deep community

Connection to the Natural World: Restoring intimate connection with the natural world

Connection to Calling: Developing a profound connection to our calling, our reason for being

Connection to Mystery: Remembering that everything is interconnected, and that a thread of exquisite mystery runs throughout all life

Each of these types of connection informs all of our programming at Wayfinders.

The Specifics

This is how our model will deliver deep value and profound positive change to members over the coming year (you’re welcome to participate wherever your energy feels called and your bandwidth allows - nothing is mandatory).

Our programming focuses on 4 Pillars:

1. Wellness and Wellbeing

2. Love and Relationships

3. Inner Work and Inquiry

4. Work and Calling

These pillars inform our get-togethers, summits, challenges and more, and they work hand-in-hand with the 5Cs model outlined above.

• Monthly in-person get-togethers (mostly in Toronto but members in other locations are welcome to participate and/or host in their location)

  • Dinners

  • Urban adventures

  • Outdoor activities (hikes, bike rides, etc.)

• Monthly Connection Calls for all members (1-hour calls to connect and share and have fun)

• Quarterly half-day learning summits with incredible experts, speakers and facilitators

  • Q1: Wellness and Wellbeing

  • Q2: Love and Relationships

  • Q3: Inner Knowledge and Inquiry

  • Q4: Work and Calling

• Quarterly challenges where we benefit from the support and accountability of a group of our peers to develop new positive habits.

  • Meditation challenges

  • Journaling and self-reflection challenges

  • Fitness challenges, and more!

• Book club: Quarterly reading and discussions on books related to the 5Cs mentioned above (1 book/quarter)

• Monthly Duo Dialogues: The opportunity to connect deeply with another member through structured 45-minute calls or in-person get-togethers

• Private Signal channels for members, where we can share, ask for help, and connect

• Rotating coworking spaces: Toronto-based members host occassional coworking days on a rotating basis

• Priority invitations to upcoming international adventures: 1st-round invitations to our events in places like Uganda, Bhutan, Mongolia (2025!) and more

The Investment

There are two investment options for membership in the Wayfinders community. Both options renew until you tell us you want to stop (but we know you’ll want to stay forever):

• Annual payment: $2495 CAD

• Monthly: $249 CAD/month (minimum 12 month commitment)

If you’ve been invited to the community by Mike, or referred by one of our members, click ‘Join the Community’ to sign up (password required)

If you are interested in joining but haven’t been invited or referred, please click here to apply.