Owners Outpost
Frequently Asked Questions
Still wondering if Owners Outpost is your next step?
You wouldn’t be the first to hesitate before charting new territory. And that makes sense!
Business owners like you ask smart questions before committing to something this personal and future-shaping. We’ve gathered the most common ones we hear, from how the groups work, to who leads them, to what kind of support you’ll find along the way.
If your question isn’t here, don’t hold back. Reach out. We’re here to help you explore whether an Outpost mastermind fits the adventure ahead.
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What is Owners Outpost, and who is it for?
Owners Outpost is a virtual community of mastermind groups for trailblazing business owners preparing for their next chapter, whether that’s selling the business, transitioning leadership, or launching a new venture. It’s designed for owners who want to grow business value, secure financial freedom, and build a legacy-focused exit strategy.
How is the mastermind structured?
- Small group setting: Each group includes up to 10 business owners, led by an experienced Guide.
- Pre-work for deeper conversations: A short video or worksheet (10–30 minutes) introduces a relevant topic and reflection questions. Optional, but powerful and preferred.
- Biweekly virtual sessions: Discussions tap into the collective experience of the group. Members challenge, support, and inspire each other—guided by the facilitator.
What happens after I join?
After applying, you’ll receive:
- A strategy session with your Guide
- A personal tour of the Outpost platform and tools
- A chance to review group member profiles to prevent any overlap with competitors, customers, or vendors
- A warm welcome from your Guide and group at your first session
What commitment is required and how long does it take to see results?
Plan to attend biweekly virtual sessions and set aside 20 minutes to prepare for each session. The more consistently you work on your business, the more results you’ll see. Many members report tangible progress, both in business value and personal clarity, within a few months.
What additional benefits do members receive?
In addition to mastermind discussions, members receive:
- Access to a library of curated resources
- A private, always-on online community
- Monthly virtual Owner Meetups with transition experts
- Tools to track readiness in owner freedom, business value, and life after the business
How does this help me prepare for a business exit?
Owners Outpost focuses on building exit readiness: maximizing business value, designing a business others can run, and preparing for your personal transition.
Mastermind members learn from each other’s wins and setbacks, and help you stay on track with this once-in-a-lifetime transition.
What happens if I miss a session?
Some groups choose to record sessions, with recordings stored privately and available only to members of that group. Your Guide can let you know what your group prefers.
Is there a trial period or satisfaction guarantee?
Membership is billed monthly, and you can cancel anytime. While it often takes six months to build trust and see significant results, we don’t believe in forcing anyone to stay.
How is this different from other exit planning programs or peer groups?
Most exit planning programs are one-to-one with an advisor. Those are great for the final stages. Owners Outpost mastermind groups are for business owners with a 1–3 year runway, focused on increasing business value and letting go.
Unlike Vistage or EO, our peer groups are fully virtual and meet twice monthly. The focus is 100% on transition and sellability, with flexible, high-impact extras sprinkled in. The others are typically all-day, in-person events.