Dealmakers Podcast

Legal Due Diligence and Deal Structuring When Buying a Business

Jonathan Jay speaks with M&A lawyer John Andrews about getting deals over the line, controlling legal risk, using heads of terms properly, and structuring acquisitions with fewer surprises.

Listen to the Episode

Episode 158  |  Runtime: 27:50  |  Audio Episode

Listen to the Episode

Hear Jonathan Jay and M&A lawyer John Andrews discuss legal due diligence, heads of terms, personal guarantees, asset purchases, share purchases, warranties, indemnities, deferred consideration, and earn-outs.

Episode 158
Runtime 27:50
Topic Legal due diligence
Format Expert interview

Key Takeaways

Three practical legal lessons for buyers who want to reduce acquisition risk without slowing a deal to a standstill.

Heads of Terms Prevent Late Stage Friction

Clear heads of terms can settle major points early, including personal guarantees, payment structure, and the commercial expectations that often derail deals later.

Due Diligence Should Target Real Deal Risk

Strong legal due diligence checks ownership, accounts, tax, contracts, employees, pay compliance, property terms, and hidden liabilities before completion.

Structure Shapes Risk and Negotiating Power

Asset purchases, share purchases, deferred consideration, retentions, and earn-outs each shift risk differently, so the structure must match the buyer's leverage and the seller's motivation.

Episode Breakdown

In this episode, Jonathan Jay interviews M&A lawyer John Andrews about the legal side of buying a business and why some transactions become harder than they need to be. John explains that the lawyer's role should be to make the deal as smooth, clear, and commercially practical as possible, not to turn the agreement into an academic exercise.

The conversation covers the legal risks that appear between heads of terms and completion, including personal guarantees, financial due diligence, tax issues, employment liabilities, property problems, lease terms, warranties, indemnities, and the difference between buying shares and buying assets. John also explains why heads of terms are often underrated and how early clarity can stop avoidable disputes from emerging later in the process.

Jonathan and John then move into deal structures, including cash up front, deferred consideration, retentions, earn-outs, consultancy periods for sellers, and how buyers can protect themselves when the numbers change after due diligence. The result is a direct legal playbook for acquisition entrepreneurs who want speed, protection, and commercial control when buying a business.

Best For

  • Buyers preparing to move from heads of terms to completion.
  • Acquisition entrepreneurs comparing asset purchases and share purchases.
  • Dealmakers negotiating warranties, indemnities, and retentions.
  • Buyers who want to avoid personal guarantees in acquisition deals.
  • Operators structuring deferred consideration or earn-outs with stronger protection.

Questions Answered In This Episode

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