Most advice treats all owners the same. The reality? There are two different games.
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For the 98% (smaller, tightly owner‑dependent companies), the job and the asset are commingled. Generic “exit planning” advice often creates noise: the math, buyers, and timelines rarely line up.
For the 2% (true middle‑market owners with durable EBITDA and a management team), the game shifts to the boardroom. It’s about capital allocation—protecting value, preserving options, and making decisions across time, cash flow, and wealth.
That’s the conversation in this panel debate with Mike Finger (Exit Oasis), moderated by Graham Stephen and Kyle McCulloch. Mike advocates for pragmatic guidance that helps the 98% make real progress. I argue for a clear line between the two games—and for ownership thinking when you’ve crossed into the 2%.
We dig into:
- How the U.S. company landscape actually breaks down—and why that matters more than slogans
- What’s signal vs. noise for the 98% (cash flow, role/asset separation, transferable systems, realistic debt math)
- What’s signal for the 2% (board governance, valuation lenses, optionality, capital allocation)
- Where demographics, debt costs, and normalized EBITDA distort decision‑making
- Why many “exits” below the middle market don’t pencil—and what to optimize instead
- How to decide whether to design a great job (time + cash flow) or build a true asset—and what each path demands
- Where I think Bitcoin fits as long‑term store of time/value for owners—and where it doesn’t help
Bottom line: Know which game you’re in. Filter the advice accordingly. If you’re in the 98%, focus on cash flow, dependability, and de‑risking. If you’re in the 2%, think like an allocator and run from the boardroom.
Graham Stephen is a former banker and chartered accountant turned entrepreneurial strategist. After witnessing firsthand how the traditional financial system fails owner-operators, he co-founded Bizval to bring clarity, simplicity, and first-principles thinking to the messy world of valuation. His work helps owners understand their true worth—not just on paper, but in cash terms they can act on.
Kyle McCulloch brings a ra...
Chapters
- (00:00:00) - Independence by Design: Business Valuation
- (00:03:41) - The State of SMB Businesses in the US
- (00:04:49) - How to Get More Out of Your Business
- (00:06:15) - In the Elevator With Carl McCulloch
- (00:07:01) - Small Business Owners: The 100 Million Club
- (00:12:47) - Small Business Owners: The 1% Truth
- (00:21:12) - SBA vs MSBA: Ownership Trap
- (00:24:03) - What Would Be the Options to Get Out of the Trap?
- (00:25:24) - Small Business Valuation
- (00:30:13) - Michael Glassman on the Exit Planning Environment
- (00:33:11) - Small Business Exit: Life-Changing
- (00:38:47) - Ryan Munroe on the Independence Flywheel
- (00:44:27) - Reasons to Retire Early vs. Investing in the Business
- (00:49:56) - Small Business: Is it futile for the 97%?
- (00:51:25) - Small Business Owners: How to Change Their Life
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