Welcome to Owners Outpost

Where Trailblazing Business Owners Go to Prepare for Life’s Next Adventure

Craft Your Business Transition Strategy

Congratulations, You! You’ve not only built a successful business; you’ve crafted a thriving community, a testament to your leadership and impact. You’ve been the architect of dreams, witnessing ideas blossom into tangible realities that matter in this world. You’ve put people to work, watched families grow, and reveled in the ripple effect of your endeavors. Yet, amidst these triumphs, a sobering truth lingers – nothing lasts forever.

success icon

The First Step

You’ve observed colleagues, once on parallel journeys, not having the privilege to script their own exit stories. Now, standing at the precipice of your own next chapter, you’re determined to defy the statistics.

upwork icon

The Strategic Journey

For 50% of business owners, an unplanned exit is a harsh reality. But it doesn’t have to be yours.
Instead, embark on a strategic journey, ensuring that your legacy endures and your exit is a tale of triumph, not chance.

pattern lock

A Seamless Exit

Welcome to a path of readiness – where you can exit your life’s work with the same care and consideration you’ve always given to your business. Where you know exactly how your business exit will seamlessly support the next stage of your life’s story (and your business’s story.)

Will You Be Ready?

At Owners Outpost, we believe readiness matters most. Readiness is the quality that best maximizes value, reduces risk, preserves legacy, ensures financial security, considers stakeholders, and facilitates a seamless personal and lifestyle transition.

Built on the pillars of Owner Freedom, Business Value, Next Adventure, & Personal Growth, Owners Outpost is a premium and affordable Virtual Mastermind Group to learn, grow, and create your exit readiness.

Each Mastermind is a group of up to 10 adventurous business owners like you, led by an Owners Outpost Guide that facilitates bi-weekly, virtual discussions on proven strategies to get you – and your business – ready for the Next Adventure.

But that’s not it. Also, inside the Owners Outpost:

  • Resources that target critical areas of improvement
  • Best practices from other business owners
  • Stories from owners who are near, in, or have been through their transition
  • Celebrating (and commiserating – we all need to vent sometimes!)
  • Monthly workshops to engage with other owners on relevant topics
  • Learn from experts who support owners through this stage of business life
  • Regular, short self-assessments to gauge your progress towards readiness.

For Only $1,000/Month!

($1,500 includes one seat for the owner and one for the next-gen leader) 

Our Process – Guiding You to Readiness

Inside the Owners Outpost, you’ll have access to a treasure trove of resources, including best practices, shared stories from fellow owners, engaging workshops, insightful self-assessments, and a supportive community.
Guides Icon Yellow

Choose Your Own Adventure

Your freedom takes precedence over any rigid system – Owners Outpost is not a pathway to follow but a versatile toolbox tailored to your unique journey.
Waypoint Icon Yellow

Stay Curious

Embracing a mindset of continuous learning is paramount for business owners preparing to exit, as it ensures you remain adaptable, receptive to new insights, and ready to learn in the uncharted territory of leaving your businesses behind.
BizIndependence Icon_<br />

Don’t Go It Alone

Your fellow travelers and your guide will provide immeasurable guidance and support through the challenges and triumphs of this transformative journey.

Campfire Gatherings

During our Campfire Gatherings, we talk about:

Owner Freedom

The process of moving you out of daily operations, covering aspects such as personnel management, streamlined processes, problem-solving frameworks, and performance measurement.

Business Value

Understand the 8 critical characteristics that definitively impact the value of a business, encompassing factors like growth potential, cash flow dynamics, and strategic considerations like monopoly pricing.

Next Adventure

Navigating the post-exit landscape by exploring the possibilities of what comes next, guiding you through the transition from your current endeavors to the untapped potential of your next adventure.

Personal Growth

The person who got you here isn’t the person who will get your business ready for transition. Grow into the person who will carry you into your next adventure.


Who Are the Members of Owners Outpost?

At Owners Outpost, our Mastermind program services businesses that employ between 10-50 people from a variety of industries.

Our members are Visionary Boomers. They founded their businesses at least 20 years ago, and they’re frustrated that the younger generation isn’t prepared for ownership. Oftentimes, their next-gen leaders also participate in groups designed specifically for them.

If you’re a freedom fighter, an adventurer, a pioneer, or a seeker, you’re in good company.

We attract those who value authenticity, vision, and the thrill of pushing past limitations.

As a non-conformist, you understand the power of collaboration and recognize the benefits of not shouldering every responsibility alone.

You may have even found yourself…

  • Engaging in conversations with your spouse, partner, CPA, or fellow entrepreneurs about what it might be like – or what it will take – for you to exit the business
  • Doing exit-strategy research via articles, podcasts, and books
  • Enrolling in courses, webinars, and seminars on the topic
  • Interviewing financial advisors, exploring equity payout possibilities, obtaining a valuation for your company, or testing the waters with business brokers and M&A advisors.

If these attributes and actions resonate with you, it’s a clear sign that you’re ready and eager to start your Owners Outpost adventure.

Who Is Owners Outpost?

Founder Kelly Cousineau is your Exit Strategy Guide, ready to guide Boomer Business Owners through the possibilities of life’s next adventure.

Growing up in a family of self-employed individuals, Kelly has always been immersed in the world of business. Over two decades, she provided strategic planning and business process improvement consulting to corporate executives.

Certified as a Professional Value Builder System Advisor, Gallup Strengths Champion, Professional Leadership Coach, and Emotional Intelligence Assessor, she brings a wealth of knowledge to empower you on your exit readiness journey.

Kelly’s adventurous spirit extends beyond business—like navigating treacherous trails on ATVs and cross-state drives with her husband—making her uniquely qualified to lead you through the guideposts of readiness and onto your next adventure.



I was sharing what I’m working on with another business owner. He asked, “where did you learn that?” I told him about our mastermind. “It’s like a MBA in a crash course.”


One member’s gratitude for another: “Thank you for sharing that suggestion about (…). I’m going to work on that.”


Boomer owner’s observation of a next gen leader’s progress: “Last year, your response to everything was ‘I can’t because…’ Now you are controlling everything!”


At the beginning of the year, I saw my business as my baby. Now I see it as an asset.

– boomer owner


I think more CPAS, Attorneys, and other advisors need to know about this. Nobody else is offering this.

– next gen owner


It was good to hear what another business owner is looking for from a business like mine. That helps me a lot. – boomer owner


We just had a key employee quit. We are so much more prepared for this now than we were last year.

– father/daughter boomer/incoming


Don’t wait to experience the transformation that comes with being ready for life’s next adventure.

Join Owners Outpost today, and you’ll be on our next call, on your way to ensuring you are well-prepared for the journey ahead.

Do you have a few more questions before you join?

Adventure Awaits. Take the First Step Today.

If you’re the type that likes to try before you buy, register for an upcoming conversation or roundtable.

Let’s Get Started

Start your journey to your next adventure with Owners Outpost!

Get in Touch with Us

Contact Form

"*" indicates required fields

Skip to content