Successful founders prioritize cash upfront over potentially larger payouts from complex earnouts. Earnouts often underperform because founders lose control of the business's future performance, leading to dissatisfaction despite a higher on-paper valuation.

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.

The firm requires sellers to roll 20-40% of their deal consideration into the acquirer's equity. This is a critical screening tool that goes beyond financial alignment, acting as a 'put your money where your mouth is' test to ensure sellers genuinely believe in the combined company's future vision.

Go beyond standard performance-based earn-outs by structuring payments with 'kickers' that reward sellers for specific de-risking actions. For example, if there's high customer concentration, offer an additional payment for diversifying revenue away from the main client, aligning them with the buyer's risk mitigation goals.

In its acquisition of Bluejay, Mirum employed a creative deal structure combining stock and cash. The stock component ensures Bluejay's shareholders remain invested in the asset's success, while sales milestones de-risk the acquisition for Mirum and allow the selling team to share in future upside, creating a win-win partnership.

Instead of lowballing, Bending Spoons makes a very fair, near-final offer immediately. This tactic builds a reputation for seriousness, similar to Warren Buffett's approach. It avoids lengthy back-and-forth and signals that they are not a buyer that can be "pushed around," creating an efficient and powerful deal-making process.

After skillfully negotiating two offers and nearly doubling the price for SiteAdvisor, Chris Dixon felt he had maximized the deal. However, the acquiring CEO later revealed his board had authorized a price twice as high, a humbling lesson that a seller rarely knows the buyer's true willingness to pay.

Instead of hiding information, Todd Capone's "transparent negotiation" advises telling buyers the four levers they can pull for a better price: contract term, volume, timing of cash, and predictability (signing by a certain date). This builds trust and turns negotiation into a collaborative process.