In this installment of the Sell Side Master Class, Ryan and Mike break down deal structure, the terms behind the headline enterprise value and why structure can matter as much as (or more than) price. They walk through the most common components of consideration in IT services M&A: cash at close, earnouts, seller notes, and rollover equity, including where each can create upside and where hidden risk lives. Mike explains why earnouts often get an unfair reputation, what “good” earnout design looks like, and why indexing to revenue is typically safer than profit. They also cover how seller notes work (and why they’re subordinated to bank debt), what rollover equity really means in a PE-backed deal, and the “often missed” lever of working capital, including how sellers can accidentally leave money on the table without the right guidance. Tune in as we talk Deal Structures 101.

DEAL STRUCTURES WE DISCUSS:

Cash at close: The portion of the purchase price you receive when the deal closes. In the episode, this is framed as the most straightforward form of consideration and the “baseline” sellers compare other components against.

Earnout: A contingent payment you can earn after closing if the business hits agreed performance targets. Mike explains that earnouts often work best when they’re indexed higher on the P&L (commonly revenue, sometimes gross margin) and structured with a “lane” or prorated payout range instead of an all-or-nothing cliff. Example from the episode’s concept: if revenue lands within a defined band around the forecast, you receive a proportional earnout payout.

Seller note: Seller financing where the seller effectively becomes a lender to the buyer for part of the purchase price. The transcript describes this as the seller “acting like the bank,” typically with interest, and notes that it is usually subordinated to senior bank debt. Example conceptually: you receive part of the price over time as principal plus interest rather than all at close.

Rollover equity: The seller reinvests a portion of proceeds into the new ownership structure, keeping equity in the business post-transaction. In the episode, this is discussed as the “second bite of the apple,” often seen in PE-backed deals where the seller participates in future upside at a later liquidity event.

Working capital adjustment: A structural mechanism that sets a working capital “target” at close and adjusts the seller’s proceeds up or down depending on whether the company delivers more or less working capital than agreed. The transcript emphasizes this as an often-overlooked lever and discusses that many owners are overcapitalized, meaning working capital can meaningfully impact what the seller takes home if negotiated correctly.

Mixing structures to optimize EV and share risk: The episode repeatedly frames structure as a way to balance risk between buyer and seller and sometimes increase headline enterprise value. Example concept: a buyer may offer a higher total value if some portion is contingent (earnout) or deferred (seller note) versus paying the entire amount in cash at close.

OTHER EPISODES IN THIS SERIES:

Part 1. Knowing When It’s Time to Sell: Listen now >>

Part 2. Get Your House in Order: Listen now >>

Part 3. Valuation Drivers: Listen now >>

Part 4. What is my Take Home? Listen now >>

Part 5. It Takes a Village. Listen now >>

Part 6. The First 30 Days of a Process. Listen now >>

Part 7. Finding the Right Buyer. Listen now >>

Listen to Shoot the Moon on Apple Podcasts or Spotify.

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