What Waypoint Is
Waypoint is a community and program for founder-operators navigating the full weight of a business exit.
We don't run your deal. We help you see clearly through it. The decisions you're facing, the weight you're carrying, and the life you're stepping into on the other side.
Whether you're three years from a potential sale or three years past one, Waypoint is one room. The founder who exited last year has something the founder still deciding needs to hear. The diversity of experience in the room is the point.
All sessions are virtual. The barrier to entry is the quality of the person, not proximity to a conference room.
See the full map of the exit journey.
Monthly Sessions
Every month, a small group of founders gathers for a 90-minute facilitated session. Deep dives, themed conversations, honest exchanges. Conversations with people who actually understand what you're carrying.
A Private Community
A private online space to connect with other members. Weekly discussion prompts. Shared resources. A place to ask the questions you can’t ask anyone else in your life. Confidential and exclusively for founders.
Direct Access
Waypoint is not a faceless membership. I personally facilitate sessions, I'm active in the community, and I'm available when you need a conversation that can't wait for the next meeting.
Who This Is For
Waypoint is for founder-operators of privately held businesses who are:
- Thinking seriously about an exit within the next several years
- Actively in the process of selling, transitioning, or restructuring ownership
- Recently exited and navigating the aftermath, the identity shift, the empty calendar, the questions nobody warned you about
- Months or years post-exit and still searching for clarity, purpose, and genuine peer connection
Whether you're still weighing the decision, deep in the process, or years on the other side, the journey is the same. It's bigger than anyone told you it would be. And that's what we're here for.
Waypoint is built for founders. The room belongs to the people who built the thing.
by Jonathan Sherrill & Andy Harris
The Extraordinary Exit is the guide to exiting your business on your terms. From deal strategy and valuation to negotiation and closing, it puts decades of real-world exit experience in your hands. It’s also one of the few books in the space honest enough to address what happens to the founder personally, not just financially. Waypoint takes that personal dimension deeper. If the book opened your eyes to what’s ahead, Waypoint gives you a room full of people and a process to walk through it.
“A masterclass in how to exit a business the right way — strategically, profitably, and with purpose. This book belongs on every entrepreneur’s shelf.”— Adam Coffey, CEO, Board Member, 4x Best-Selling Author
“I have seen firsthand how Andy and his team have helped multiple CEOs orchestrate Extraordinary Exits. Andy and Jonathan’s expertise and dedication shine through in this book.”— Wayne Cooper, Executive Chairman, Chief Executive Group
★★★★★
“This book completely reframed how I think about exiting a business. Andy Harris and Jonathan Sherrill share powerful insights that transform a complex, high-stakes process into a clear path to financial freedom and growth. Every entrepreneur serious about their future will benefit from their expertise.”— Verne Harnish, Founder, Entrepreneurs’ Organization (EO) and Scaling Up
Masterminds help you build.
Waypoint helps you land.
Not ready to apply yet? Take the Exit Readiness Assessment.
WAYPOINT
Clarity and direction for founders in transition.
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