Sell-Side M&A Advisory

Sell-Side M&A Advisory

“Founders spend years building something valuable. The exit is the one moment where all of that work either gets properly rewarded or left on the table. I take that responsibility seriously.”
— John Montague

Selling a business is one of the most consequential decisions a founder or ownership group will ever make. The process is intense, the stakes are high, and the legal complexity can determine whether value is captured or lost. John Montague brings over 15 years of experience representing technology company founders, private equity portfolio companies, and closely held businesses through sell-side M&A transactions. As a Visiting Professor of Entrepreneurial Law at the University of Florida College of Business, John understands the founder’s perspective — the emotional weight of an exit and the practical realities of maximizing value while managing risk.

John’s sell-side practice draws on his extensive background in venture capital and growth-stage financing. Many of his sell-side clients are companies he has advised since their earliest funding rounds — giving him deep institutional knowledge of the business, its cap table, investor rights, and governance structures. This continuity is invaluable when structuring a sale, because the terms of prior financing rounds (liquidation preferences, participation rights, anti-dilution provisions) directly shape how sale proceeds are distributed among stakeholders.

Based in Fernandina Beach and Coral Gables (Miami), Florida, John Montague represents sellers in asset sales, stock sales, mergers, and acqui-hire transactions, working closely with investment bankers, accountants, and management teams to drive successful outcomes.

What I Handle

Pre-Sale Preparation and Company Readiness. The best sell-side outcomes start well before a buyer appears. I work with sellers to prepare for diligence — cleaning up corporate records, resolving outstanding IP assignment issues, tidying up equity and option documentation, and addressing any regulatory or compliance gaps that could create friction during the sale process. For technology companies, this often means ensuring that all intellectual property is properly assigned to the company, that open source usage is documented, and that key employee and contractor agreements include appropriate IP assignment and non-compete provisions.

Deal Structure and Tax Planning Coordination. Whether a transaction is structured as an asset sale, stock sale, or merger has profound tax and liability implications for the seller. I work alongside the seller’s tax advisors to evaluate structural alternatives, analyze the impact of Section 338(h)(10) elections, installment sale treatment under IRC Section 453, and the allocation of purchase price among asset classes under IRC Section 1060. For sellers with complex cap tables — common in venture-backed companies — I ensure that the waterfall distribution of proceeds aligns with the governing documents and investor rights.

Negotiating Definitive Agreements from the Seller’s Perspective. Sell-side representation requires a fundamentally different orientation than buy-side work. I negotiate purchase agreements with a focus on limiting the seller’s post-closing exposure — narrowing representations and warranties, capping indemnification obligations, shortening survival periods, and structuring escrow and holdback provisions that are fair but protect the seller from excessive risk retention. Every concession at the negotiating table has a dollar value, and my job is to make sure sellers understand the trade-offs.

Management of the Disclosure Process. The disclosure schedules to a purchase agreement are where many deals get contentious. I manage the seller’s disclosure process methodically, ensuring that exceptions to representations and warranties are properly documented without inadvertently creating new liabilities or providing the buyer with ammunition to renegotiate the purchase price. Disciplined disclosure management is one of the most underappreciated aspects of sell-side M&A work.

Closing Mechanics and Post-Closing Obligations. I handle all closing mechanics including funds flow coordination, third-party consents, regulatory filings, and the execution and delivery of ancillary documents such as employment agreements, consulting arrangements, non-compete agreements, and transition services agreements. Post-closing, I advise sellers on earnout compliance, escrow claim defense, and working capital dispute resolution.

Understanding the Sell-Side Legal Framework

Sellers in M&A transactions face a distinct set of legal obligations and considerations. Under Delaware law — which governs many technology companies even when they operate elsewhere — the board of directors owes fiduciary duties to stockholders in connection with a sale of the company. The landmark Revlon, Inc. v. MacAndrews & Forbes Holdings, Inc. decision established that when a board decides to sell the company, its primary obligation shifts to maximizing value for stockholders. This “Revlon duty” has been refined through subsequent decisions including In re Toys “R” Us Shareholder Litigation and applies with particular force in competitive auction processes.

For Florida-organized entities, the Florida Business Corporation Act (Chapter 607) and the Florida Revised LLC Act (Chapter 605) set forth the procedural requirements for approving mergers, asset sales, and dissolutions. These include board approval thresholds, stockholder or member voting requirements, and appraisal rights for dissenting shareholders in certain transactions. Compliance with these statutory requirements is essential to ensure the enforceability of the transaction and to minimize the risk of post-closing challenges.

Tax planning is a critical component of sell-side advisory. The distinction between capital gains treatment and ordinary income treatment on sale proceeds can result in tax rate differentials of 15% or more for individual sellers. Qualified Small Business Stock (QSBS) exclusions under IRC Section 1202 — which can exclude up to $10 million or 10 times the adjusted basis in gain from federal taxation — require careful advance planning and documentation. John Montague, Esq. works with sellers’ tax advisors to ensure that QSBS eligibility is preserved and maximized wherever possible.

John’s Tip

Frequently Asked Questions

When is the right time to sell my technology company?
There’s no universal answer, but the strongest sell-side outcomes typically happen when the business is growing, the market for your product or service is hot, and you have optionality — meaning you don’t need to sell. Selling from a position of strength gives you leverage in negotiations. John Montague often advises founders to begin thinking about exit readiness well before they’re ready to sell, so that when the right opportunity arises, they can move quickly and confidently.

What is the typical fee structure for sell-side M&A legal representation?
Legal fees for sell-side M&A work are typically billed on an hourly basis, though some attorneys offer hybrid arrangements with a reduced hourly rate and a success fee at closing. The total cost depends on deal complexity, the number of bidders, regulatory requirements, and the extent of post-closing obligations. For most middle-market technology transactions, legal fees represent a small fraction of the overall transaction value.

How do I protect myself from post-closing liability as a seller?
Post-closing liability management starts in the purchase agreement. Key protections include caps on indemnification obligations (typically 10-15% of the purchase price for general representations), time-limited survival periods for representations and warranties, basket and deductible mechanisms, and the use of representation and warranty insurance (RWI) to shift risk to a third-party insurer. John Montague negotiates these provisions aggressively on behalf of sellers to minimize residual exposure after closing.

What happens to my employees in a sale transaction?
Employee treatment depends on the deal structure. In a stock purchase or merger, employees generally remain employed by the surviving entity, though their compensation and benefits may change. In an asset purchase, the buyer typically offers employment to key employees but is not legally required to retain all staff. Issues like change-of-control provisions in employment agreements, acceleration of equity vesting, and retention bonuses are negotiated as part of the transaction.