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.

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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.

Preparing a company for acquisition can lead founders to make short-term decisions that please the acquirer but undermine the brand's core agility, setting it up for failure post-sale. The focus shifts from longevity to a transaction.

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.

Don't wait until you're completely exhausted to sell your company, as buyers will sense your desperation and gain the advantage. The ideal time to exit is when your passion for the market wanes or growth slows, allowing you to negotiate from a position of strength before burnout sets in.

Instead of optimizing for a quick win, founders should be "greedy" and select a problem so compelling they can envision working on it for 10-20 years. This long-term alignment is critical for avoiding the burnout and cynicism that comes from building a business you're not passionate about. The problem itself must be the primary source of motivation.

Many people start companies seeking control over their schedule or finances. Bianca Gates warns this is a fallacy. Entrepreneurship is a 24/7 commitment where you're the "last person on the ship." Unlike a regular job, you can't just give notice and quit, especially after taking on investors.

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.

Building a significant enterprise requires a level of commitment that fundamentally owns your life. It's a constant presence that demands personal sacrifices in family and relationships. Aspiring founders must consciously accept this trade-off, as the biggest fallacy is believing you can have everything without cost.

ZICO's founder learned that the conventional goal of selling a company for "freedom" is a fallacy. True freedom to operate at a high level comes from intense personal discipline in daily routines and energy management, not from a financial windfall.

Despite terrible market timing (a pandemic, one week before a presidential election), Bobbi Brown launched Jones Road Beauty on the specific day her non-compete ended. This decision was driven by the deep personal motivation of regaining her freedom, proving that powerful intrinsic drivers can override conventional business logic.