Clarity and direction for founders in transition.
The deal manufactures the gap.
The Room Nobody Built
You built a company. People depended on it.
Customers, employees, families. It carried your name and it meant something. Now you're approaching the sale, or you've already been through it.
If you're still running the business, you're carrying this alone. The weight of the decision, the questions about timing and who to trust, what it's going to do to you and the people closest to you. If you've already sold, you know what the deal team didn't warn you about.
Either way, you're the only one asking what happens to the person who built the thing. What your days look like when the calendar is suddenly empty, what it feels like to introduce yourself at a dinner party when you're no longer "the CEO of," what happens to your marriage when the person your spouse married, the one who was always busy, always needed, always building, is suddenly home with nothing to do.
The Exit Planning Institute's owner-readiness research found 75% of owners experience "profound regret" within a year of the sale. Not because the deal was bad. Because the entire industry is built to get you through the deal, not to prepare you for what the deal does to you.
What Waypoint Is
The personal side of the exit, mapped by a founder who's been through it.
Waypoint is the work I built after selling. The book I co-wrote with Andy Harris. The Exit Map that charts all six phases of a sale and the sandbars inside them. The assessment that shows you where you stand. The talks I give to CEO groups and advisor audiences. And a small private advisory practice for founders heading into a sale.
None of it runs your deal. Your sell-side advisor does that. This is the other half, the decisions you're facing, the weight you're carrying, and the life on the other side of the sale. See the full map of the exit.
The Exit Map
Six phases, every sandbar, every question you're left holding. The full passage of selling a privately held business, mapped from the founder's seat.
The Talk
The six phases and what the deal does to the founder, for CEO groups, advisor institutions, and conferences. Built from the inside, told straight.
Private Advisory
I work with a few founders at a time, each one scaling toward a sale that's one to three years out. The engagement runs through the close and ends there. Small by design.
The Talk
For your stage, your members, your clients.
I speak to the people founders already trust: peer groups, advisor firms, the conferences where owners actually show up. The talk walks the six phases and the part the deal team isn't built to address, told through my own sale and the stories in the book.
Owners come up afterward every time, because the personal side of the exit is the conversation they haven't been able to have anywhere else.
The five dimensions anchor all of it: Clarity. Identity. Relationships. Emotional Readiness. Practical Navigation. Every talk and every advisory engagement runs on the same map.
Who This Is For
Founder-operators of privately held businesses.
Waypoint is for founders who are:
- Scaling a business with a sale somewhere in the next few years
- Actively in the process of selling, transitioning, or restructuring ownership
- Recently exited and dealing with the aftermath, the identity shift, the empty calendar
- Months or years past the close and still searching for clarity and purpose
Whether you're still weighing the decision, deep in the process, or years on the other side, the experience is the same. It's bigger than anyone told you it would be.
Waypoint is built for founders. If you built the thing, this was built for you.
After the Close
The phase the whole map has been pointing at.
Phase 6 is where the deal team isn't built to go and the calendar quietly empties. The Tuesday morning when you have nowhere to be and the wire long since cleared. The dinner-party question that doesn't have a clean answer anymore. The marriage adjusting to a version of you it hasn't met.
Wealth advisors handle the tactical side. Coaches return to operator work that isn't yours anymore. I lived the whole map, not just this stretch. The year after closing is the part you cross alone, and the advisory work gets you ready for it before the wire clears.
The Extraordinary Exit
The book.
By Andy Harris and Jonathan Sherrill.
The Extraordinary Exit is a guide to exiting your business on your terms. Deal strategy, valuation, negotiation, closing. Also one of the few books in this space honest enough to address what the deal does to the person making it.
The book opens the question. Everything here, the map, the assessment, the advisory work, carries it further.
Press Coverage
Featured Interview
Jonathan was interviewed by Authority Magazine on "Five Things You Need to Know if You Want to Build, Scale, and Eventually Sell Your Business."
Authority Magazine Read on Medium →Founder Endorsements
"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 insights that turn a complex, high-stakes process into a clear path to financial freedom and growth."
Verne Harnish, Founder, Entrepreneurs' Organization (EO) and Scaling UpWork With Me
Bring your group the talk, or bring me your exit.
Invite me to speak to your group, or talk with me about private advisory if you've got a sale ahead of you. Both start with an email. I read every one and answer personally.
Email me directly at jonathan@waypointfounders.com