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.

In a competitive M&A process where the target is reluctant, a marginal price increase may not work. A winning strategy can be to 'overpay' significantly. This makes the offer financially indefensible for the board to reject and immediately ends the bidding process, guaranteeing the acquisition.

When M&A negotiations stall, the root cause is often sentimental, not financial. Uncovering a seller's personal attachment (e.g., hunting rights, a favorite truck, community sponsorships) allows for creative, non-monetary solutions that have high emotional value for the seller but low cost for the buyer, getting the deal across the finish line.

The most lucrative exit for a startup is often not an IPO, but an M&A deal within an oligopolistic industry. When 3-4 major players exist, they can be forced into an irrational bidding war driven by the fear of a competitor acquiring the asset, leading to outcomes that are even better than going public.

The Warner Bros. bidding war reveals that massive M&A deals are often driven by human emotion. Personal factors—like a CEO's desire to keep his job, a rival's lingering resentment from a past lost deal, or a buyer's thirst for power—can influence outcomes as much as financial models.

To maintain pricing discipline, Fairfax has a strict M&A rule: it never participates in auctions or bidding wars. Once an offer is made, it's final. This strategy prevents them from overpaying and ensures they only acquire companies at prices that offer attractive future returns.

In auctions with uncertain value (like oil leases or even NFL draft picks), the winner is not a random bidder but the one with the most optimistic valuation. This often means the winner has significantly overestimated the item's true worth and is therefore 'cursed' by their victory.

Recent acquisitions, like the bids for Avidel and Cedara, have involved rare, publicly competitive bidding wars. This shift indicates a more heated and aggressive M&A environment where acquirers are willing to fight openly for strategic assets, a departure from typical private negotiations.

When Kevin attempted to buy the company he built, his partner inflated the valuation. The partner knew Kevin was emotionally invested and understood the business's true potential, using that knowledge as leverage to demand an overpayment, a common tactic in internal buyouts.