A board's duty to maximize shareholder value is an expected value calculation. A $100B offer with a 75% chance of closing is valued at $75B, making an $80B offer with 100% certainty more attractive. Boards weigh financing and regulatory risks heavily against the headline price.

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.

An exit isn't just about founders and investors. It requires balancing the needs of at least seven groups: investors, the founder (as employee, creator, and supervisor), their family, the team, customers, and vendors. Satisfying one group often means making sacrifices with another.

When pursuing a distressed company, understand the investors' intrinsic motivations. They often prioritize avoiding a public failure and protecting their reputation with LPs over recouping sunk capital. Frame the deal as a success story for them, not a fire sale.

Many M&A teams focus solely on closing the deal, a critical execution task. The best acquirers succeed by designing a parallel process where integration planning and value creation strategies are developed simultaneously with due diligence, ensuring post-close success.

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.

Brex's acquisition, despite being a lower valuation than its previous round, is a heroic success. The negative feelings associated with a "hubristic financing" round are fleeting compared to the massive value created, proving the ultimate outcome outweighs temporary valuation optics.

When a startup's valuation is less than capital raised, later investors with liquidation preferences can block exits. The solution is often a negotiation to give a slice of the proceeds to employees and early investors, incentivizing everyone to find a graceful exit rather than letting the company die.

To generate returns on a $10B acquisition, a PE firm needs a $25B exit, which often means an IPO. They must underwrite this IPO at a discount to public comps, despite having paid a 30% premium to acquire the company, creating a significant initial value gap to overcome from day one.