Despite a $3B valuation with a PE firm, Anastasia Soare believes she should have sold her company to a strategic buyer (e.g., a cosmetics conglomerate) when it was valued at $1B. Strategic buyers offer existing infrastructure and operational expertise that PE firms often lack, which she needed for international expansion.

When selling her company, Bobbi Brown didn't contest a 25-year non-compete, assuming she'd be in her 60s and retired. This highlights the unpredictability of long-term career passion and serves as a cautionary tale for founders underestimating their future drive when negotiating exit terms.

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.

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.

Bobbi Brown's successful partnership with Estée Lauder soured when new corporate leadership, unfamiliar with the brand's DNA, began imposing external consultants and hiring key personnel without her input. This illustrates how a change in an acquirer's leadership can trigger a corporate "immune response" that stifles a founder's vision, even with contractual autonomy.

During a merger, prioritize people over process. Technical integration is secondary to building trust between teams. Use simple, cultural activities like joint happy hours and "show-and-tells" about the tech stack to humanize the engineering effort and foster empathetic collaboration early on.

In high-stakes acquisitions, the emotional desire to "win" and achieve kingmaker status often overrides financial discipline. Acquirers, driven by ego, blow past their own price limits, leading to massive overpayment and a high likelihood of the merger failing to create shareholder value.

For celebrities, the most effective path to massive wealth isn't always starting their own company. A more strategic approach is to identify a promising brand and exchange social capital for a significant equity stake, as Roger Federer did with On. This leverages influence without the operational burden of building a business from scratch.