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.

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.

By completing extensive strategy work and securing board approval upfront, Milliken entered the final bidding stage as the "most certain bidder." This allowed them to close quickly and confidently, winning the deal despite not offering the highest price because the seller valued the assurance of a close.

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.

The first question in any fundraising or M&A discussion is always, 'What was your last round price?' An inflated number creates psychological friction and can halt negotiations before they begin. Founders should optimize for a valuation that allows for a clear up-round, not just the highest price today.

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.

When negotiating a price increase, if the customer accepts immediately without pushback, it’s a strong signal you've significantly underpriced your product. Buildots' founder prepared for a negotiation over a 4x price increase, but the client agreed instantly, revealing the product's true value.

Starter Story's founder used ChatGPT to determine his ideal acquisition price before HubSpot's offer. This helped him negotiate authentically to a number he had pre-committed to, free from the emotional pressures and influence of the deal itself.

Even well-intentioned sellers are motivated to close a deal and may present information in the most favorable light. This is often a human behavioral bias, not malicious lying. Acquirers must actively challenge and validate seller statements by testing assumptions and seeking external information.