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COMMUNITY membership

entrepreneurship can
be a lonely journey.

But it DOESN’T HAVE TO BE

Welcome to the wayfinders community.

We are a community of insatiably curious, growth-minded entrepreneurs motivated by personal development, business evolution, reaching our highest potential, and co-creating what the author Charles Eisenstein calls “the more beautiful world our hearts know is possible.”

“Around the world, humankind shares a deep and resonant yearning for connection with the cosmos, with spirituality, community and the planet. “

— Richard Wagamese

who are we?

The Wayfinders community is already 100+ members strong, made up of incredible entrepreneurs from North America and beyond.

Spanning a wide range of industries, our 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 an ongoing commitment to personal growth - with trusted companions at our side.

Community Benefits

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

  • A container of support and accountability to help you achieve your most profound goals

  • Opportunities to further your personal development, and to do so in a community context

  • Opportunities to grow and optimize your business, through networking and working with other community members

HOW WE SUPPORT YOU

Member programming

Our programming pillars

  • Growth

    Programming to support personal transformation & alignment to your most authentic self.

  • accountability

    Structures for accountability and support to achieve your biggest goals, and systems to ensure commitment and progress tracking.

  • Connection

    Programming designed to foster and deeper your relationship to other community members.

Our member SUPPORTS & programming

GROWTH

Alignment Labs: Quarterly, two-hour virtual workshops designed to help you deepen your journey toward living an authentic and fulfilling life.

Discovery Dinners: Growth, connection, and inspiration-themed evenings in Toronto, with guest speakers and facilitators.

Wilderness Adventures: Reconnect with your true nature in nature. 1-day adventures in Ontario that embody the same wild and adventurous spirit of our international Adventures around the world.

ACCOUNTABILITY

Annual Visioning Calls: Annual call at the beginning of January to help you cast your vision for the year, with clarity exercises sent in December to help you prepare.

Quarterly Planning Calls: Each quarter, we’ll host a Planning call so you can revisit and refine your annual goals and map out your quarterly actions to support that vision.

Summit Teams: You’ll have the option to join a Summit Team of 5 to 6 Wayfinders, with a monthly call for accountability and support to help you reach your Basecamps & Summits.

CONNECTION

RealTalks: 1-hour calls designed to create a space for open vulnerability and real connection—where members can share openly, and foster deeper relationships.

Threads: Opt-in, 3-person connections every other month. We take care of the groupings and conversation prompts, you take care of the scheduling and deep conversations.

Holiday Gathering: Join us in December for our annual Holiday Gathering, with great food, fun, and lots of laughter and joy!

Our Summit framework

We love mountains and mountaineering, so our accountability and support framework borrows from this world.

We use this framework to provide you the structure you need to hit your biggest goals (Summits) and help you get laser-focused.

SUMMITS: What are your big annual goals? Are you clear on your Summits?

BASECAMPS: What are the Quarterly and Monthly milestones along the way that will help you reach your Summits?

STORMS: What are the challenges you’ll encounter along the way to your Summits and how can you anticipate and prepare for them?

OXYGEN: What is the support you will need en route to your basecamps?

SHERPAS: Who are the people you’ll need at your side to help you reach the Summit?

Your Summit Team is an (optional) group of 5 to 6 fellow members with whom you’ll meet monthly for support and accountability to your Summits.

  membership criteria

Our members are established, successful entrepreneurs on a journey to become the best version of themselves.

Membership is for you if you…

  • Are an established entrepreneur (5+ years experience), with a staff of at least 3 FTE

  • Are open-minded, humble and motivated by your own growth

  • Spend more than $20,000 annually on your own growth and development

  • Are a lifelong learner, driven by an insatiable curiosity and desire to know more about yourself and your place in the world

  • VIP/Expedition members (see below): Minimum $2.5M USD in annual company revenue

MEMBERSHIP LEVELS

We offer two membership levels: Basecamp and Expedition/VIP. Both come with access to all programming & additional benefits.

NOTE: Basecamp membership is included with 2025 Adventures & Retreats (this is the last year it will be included. For 2026 and beyond you will need to pay separately if you want to access membership benefits)

BASECAMP MEMBER BENEFITS

Membership comes with access to all community programming, plus:

  • Members get a $1000 discount on all Adventures and Retreats (except Expedition/VIP Adventures)

  • Members get priority invites to all Adventures and Retreats, ahead of alumni and general public (most Experiences sell out a year or more in advance).

    NOTE: VIP members get the first round of invites.

  • Shenanigans are our new, non-facilitated and fun-focused small-group Experiences for members only.

  • Basecamp members have the option to join a curated Summit Team with whom they’ll meet monthly for support and accountability.

VIP/EXPEDITION MEMBER BENEFITS

Membership comes with access to all programming and Basecamp level benefits, plus:

  • VIP members get access to our annual VIP/Expedition-level Adventure (you must be a VIP member to participate)

  • VIP Members get a $1500 CAD discount on all Adventures and Retreats (except Expedition/VIP Adventures)

  • Expedition members can access a free VIP day before our Adventures.

  • Expedition members have the option to join VIP-level summit teams.

  • Expedition members get 50% off all single room upgrades (default rooming on our Experiences is 2/room)

  • Quarterly half-day mastermind sessions with world-class facilitators

YOUR INVESTMENT

BASECAMP MEMBERSHIP

Annual payment: $2000 CAD

Monthly: $200 CAD/month (minimum 12 month commitment)

EXPEDITION/VIP MEMBERSHIP

Annual payment: $7500 CAD

Monthly: $750 CAD/month (minimum 12 month commitment)

Become a wayfinder

Ready to join our amazing community?

If you’ve been invited, or referred by one of our members, click on the link below to start your journey.

If you haven’t been invited or referred, please click here to submit your application.