In a non-control deal, an investor cannot fire management. Therefore, the primary diligence focus must shift from the business itself to the founder's character and the potential for a strong partnership, as this relationship is the ultimate determinant of success.

Veteran dealmaker Andy Cohen argues against a "win-at-all-costs" mentality in M&A. True success, particularly in tech deals where talent is key, comes from ensuring the acquired team feels the outcome is fair and their future is promising. If one side feels they lost, the integrated entity will fail.

Alex Bouaziz's core M&A principle, learned from his father, is to optimize for long-term satisfaction over short-term leverage. Even when holding the upper hand in negotiations, he structures deals to be fair for both sides. The goal is for both the acquirer and the acquired founder to look back in five years and feel the deal was a great outcome, ensuring better integration and alignment.

When a business partner agreed to a deal and then came back the next morning demanding more, Ken Langone conceded. However, he also immediately stated, "I will never do business with you again." This strategy upholds the current deal's integrity while protecting future dealings from bad-faith actors.

A major carve-out risk is the 'captive client'—the seller's remaining business that relies on the carved-out entity. Post-deal, this powerful client may demand significant fee reductions, destroying the target's valuation. Buyers must negotiate directly with these internal client stakeholders early on to lock in future commercial terms and avoid a last-minute deal collapse.

When Joe Coulombe sold Trader Joe's, he used a one-page contract with non-negotiable terms, including complete autonomy and a commitment to not merge with Aldi. This ensured the buyer was acquiring the unique culture and strategy, not just the assets, preserving what made the company successful.

OpenAI previously had highly restrictive exit agreements that could claw back an employee's vested equity if they refused to sign a non-disparagement clause. This practice highlights how companies can use financial leverage to silence former employees, a tactic that became particularly significant during the CEO ousting controversy.

An acquisition target with a valuation that seems 'too good to be true' is a major red flag. The low price often conceals deep-seated issues, such as warring co-founders or founders secretly planning to compete post-acquisition. Diligence on people and their motivations is more critical than just analyzing the financials in these cases.

A deal failed because the acquirer rigidly insisted the target switch from Macs to PCs for compliance reasons, without exploring creative solutions. This highlights how a lack of flexible problem-solving on operational details can escalate into a deal-killing issue, masking deeper cultural misalignments.