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.

Michael Dubin didn't conduct market research; he found his business opportunity in his personal annoyance with the high cost and inconvenient process of buying razors from a locked case. This shows that powerful business ideas often hide in plain sight as everyday frustrations.

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.

Instead of constantly chasing new leads, businesses can find immense growth by deepening existing relationships. A tech company ignored a referral partner for two years, but two follow-up meetings later generated $11.2 million, demonstrating the untapped potential within current networks.

Instead of a formal M&A process, Unilever's initial contact was an executive visiting The Laundress's retail store and questioning staff. This unprofessional start was a red flag, foreshadowing the chaotic post-acquisition integration and lack of process that followed.

Michael Dubin spent 8 years doing improv comedy purely for fun, with no thought of its business application. This seemingly unrelated skill became the cornerstone of Dollar Shave Club's viral marketing, proving that personal passions can unexpectedly become powerful professional assets.

Assessing cultural fit can't be done in a formal, time-crunched diligence process. Snowflake approaches M&A like dating, building relationships with companies over time. This long-term engagement allows for genuine discovery of values and operational style, de-risking the 'cultural diligence' aspect of a potential acquisition.