The Art of the Deal — Why Structure Matters More Than Price in M&A

By Scott Gelbard, Founder — SGI Global Partners / Managing Partner — Peak Ventures

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Everyone focuses on the number. The headline valuation. The multiple of EBITDA. The per-share figure that gets announced in the press release. After 25 years advising businesses through acquisitions, divestitures, and capital transactions across three continents, I've watched that fixation on price cause more failed deals — and more post-close regret — than almost any other factor in the process.

Price matters, of course. But structure? Structure is where deals live or die.

Why Price Is the Wrong Place to Start

When a business owner first walks into an M&A conversation, the instinct is to ask: "What's my company worth?" It's a fair question. But it's the wrong first question. The better question is: "What outcome am I actually trying to achieve?"

Those two questions lead to very different conversations — and very different deals.

I've seen founders accept lower headline valuations and walk away far better off than peers who fought for top dollar. Why? Because the founder who prioritized structure negotiated clean exits with no earnout exposure, no lingering reps-and-warranties liability, and no operational involvement post-close. The founder who won on price got stuck in a multi-year earnout tied to revenue metrics they no longer controlled, with 30% of their proceeds at risk.

Price is a number on paper. Structure is what you actually take home — and how cleanly you get there.

The Four Structural Variables That Matter Most

In my experience, most mid-market M&A transactions come down to four structural variables that dwarf the price discussion in terms of real-world impact.

*Earnout provisions.*

An earnout defers a portion of the purchase price, tying payment to future business performance. For sellers, earnouts feel like free money at signing — and like a tax on everything that goes wrong afterward. If you accept an earnout, understand exactly what metrics govern it, who controls those metrics post-close, and whether the buyer has incentives to suppress them. The best earnouts are short, simple, and tied to metrics you can verify independently.

*Representations and warranties.*

These are the contractual promises you make about the state of your business. If something you represent turns out to be inaccurate — even unintentionally — you may face indemnification claims that claw back proceeds. Reps-and-warranties insurance has become a standard tool to mitigate this exposure, but it adds cost and requires negotiation. Know what you're promising before you sign it.

*Working capital adjustments.*

Most purchase agreements include a mechanism to adjust the final price based on the working capital delivered at closing versus a target. This sounds technical — and it is — but I've seen working capital disputes erode seven-figure deals. Get clarity on the definition of working capital in your specific deal, and make sure your finance team is modeling it accurately before signing.

*Management retention and non-compete terms.*

If a buyer is acquiring your business in part because of your expertise, they'll want you to stay. How long? Under what constraints? With what compensation? These terms shape not just the transition — they shape what your next five years look like. Negotiate them with the same rigor you'd apply to price.

Structure in Cross-Border Deals: An Added Layer of Complexity

International M&A adds structural complexity that domestic transactions don't face. Currency risk, foreign ownership restrictions, regulatory approvals across multiple jurisdictions, tax treaty implications, labor law differences — each of these can reshape a deal that looked straightforward on a term sheet.

I've advised on transactions where currency fluctuations between signing and closing materially changed the effective proceeds for a seller receiving payment in a foreign currency. I've worked through deals where a standard indemnification clause in North America ran into hard limits under European data protection law. I've watched transactions stall — and eventually collapse — because neither side adequately modeled the regulatory timeline in the target country.

In cross-border deals, local counsel in each jurisdiction isn't optional. Neither is a deal team that has actually navigated those markets, not just read about them.

The Advisor's Role: Protecting the Outcome, Not Just Closing the Deal

I'll be direct about something: not all M&A advisors are optimizing for the same thing. Some are optimizing for their success fee, which means their incentive is to close — not necessarily to close well. A good advisor is willing to tell you when a deal isn't right, when terms are dangerous, and when walking away serves your long-term interests better than signing.

That's an uncomfortable conversation to have. It's also the most important one.

The businesses and families I've worked with over 25 years remember the deals that were structured thoughtfully — the exits that actually delivered what was promised, the acquisitions that integrated cleanly, the transactions that didn't generate years of post-close litigation. They don't remember the headline multiples. They remember whether the structure held.

Structure the deal for the outcome you actually want. Get the price right. But get the structure right first.

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About the Author

Scott Gelbard is the Founder of SGI Global Partners Inc., a boutique strategic advisory and family office services firm, and Managing Partner of Peak Ventures, an international business consulting practice. With more than 25 years of experience advising businesses, entrepreneurs, and high-net-worth families across North America, Europe, and Asia, Scott specializes in cross-border transactions, capital strategy, and long-term business advisory. He writes on leadership, international business, and the strategic decisions that define companies and careers.