2026 Edition · Owner's Guide Series · Volume 2
What rollover is, how it's valued, and how to think about your “second bite of the apple” when you keep practicing. Written for owners in active buyer conversations or negotiating an LOI.
23 pages of institutional-grade analysis of rollover equity mechanics, valuation, terms, and negotiation. Every section works through the same anchor case — a $23M dermatology group deal — so the math connects.
Mechanics, typical percentages (20–40%), where your shares sit in the platform structure, and the tax-deferral advantage.
What alignment, capital efficiency, and retention mean for what's negotiable — and what isn't.
The issuance-price question. Being issued at 12x vs. 8x means $2.3M less at exit on the same $4.6M rollover.
Illustrative math on 0.5x, 1x, 2x, and 3x platform outcomes. What the median actually looks like vs. the pitch deck.
Pari passu vs. common behind preferred, drag-along and tag-along, vesting, leaver, and information rights.
Questions to ask about fund vintage, platform leverage, and prior exits. Reference calls with prior rollover holders.
Platform, add-on, recapitalization, and sponsor-to-sponsor scenarios. Each has different economics and different leverage.
A ranked list of the negotiation battles that move the most value, plus tested language for framing each ask.
New to the Owner's Guide Series? Volume 1, The Middle-Market Healthcare Practice Owner's Valuation Guide, covers how buyers get to your headline price. Volume 2 (this guide) covers what happens to the rollover portion of that price. Both stand alone.
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