Welcome to Owners Outpost
Where Trailblazing Business Owners Go to Prepare for Life’s Next Adventure
Craft a Transition Strategy that
Makes Sense for You and Your Business
Congratulations, You! You’ve not only built a successful business; you’ve created 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.

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.

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.

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.
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.
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.
Choose Your Own Adventure
Stay Curious
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
Owner Freedom
Business Value

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?
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.
Testimonials
Intrigued?
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
Get in Touch with Us
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