The first conversation with a target CEO shouldn't focus on the deal. Instead, focus on their personal story to uncover their core motivation—money, legacy, or team success. This "why" provides the key to framing the acquisition in a way that resonates with them and dictates the entire negotiation strategy.

Canva avoids a delegated M&A team. The COO personally sponsors acquisitions, focusing on the acquired founder's motivations and cultural fit—often assessed over a drink. This deeply personal approach ensures the founder's vision aligns with Canva's distribution power, leading to successful integrations and high founder retention.

Large companies rarely make cold acquisition offers. The typical path is a gradual process starting with a partnership or a small investment. This allows the acquirer to conduct due diligence from the inside, understand the startup's value, and build relationships before escalating to a full buyout.

Leonard Lauder proposed buying Bobbi Brown's company during their very first meeting, viewing her as a modern version of his mother and feeling a strong strategic alignment. This shows that when the fit is undeniable, M&A can move with the speed of a personal relationship, bypassing months of formal courtship.

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.

Enterprise leaders aren't motivated by solving small, specific problems. Founders succeed by "vision casting"—selling a future state or opportunity that gives the buyer a competitive edge ("alpha"). This excites them enough to champion a deal internally.

Lemlist's M&A thesis focuses on acquiring companies like Clapp, which had a superior product built by just seven people but lacked market reach. They believe Clapp is a '$20M ARR product' trapped at $2M ARR, creating an opportunity to plug strong tech into their own powerful distribution engine for rapid growth.

Before an LOI, share your high-level vision, then have the target's founders pitch back their own 6- and 12-month post-acquisition roadmap. This pre-commitment exercise reveals true alignment and integration potential far more effectively than traditional diligence, creating a joint vision early on.

The acquisition of Clapp wasn't driven by market analysis but by the Lemlist team becoming passionate users first. The CEO fell in love with the product, leading to company-wide adoption. This bottom-up conviction in the product's quality was the starting point for the M&A conversation.