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.

Sales teams focus on out-competing rival products, but the biggest threat is the buyer's preference for their current "good enough" process. Losing to "no decision" is more common than losing to a competitor and requires a different strategy that focuses on the cost of inaction.

Contrary to popular belief, successful entrepreneurs are not reckless risk-takers. They are experts at systematically eliminating risk. They validate demand before building, structure deals to minimize capital outlay (e.g., leasing planes), and enter markets with weak competition. Their goal is to win with the least possible exposure.

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.

Founders who try to perfectly time an exit with market conditions are twice as likely to have second thoughts and report less satisfaction. The most fulfilled founders are those who sell when they are personally ready, regardless of market timing.

When competing against a large incumbent, reframe the comparison away from company vs. company. Instead, frame it as you—the dedicated founder—versus their salaried, indifferent employee. This shifts the focus from resources to personal commitment, turning your small size into an advantage.

Many founders focus on generating personal income, inadvertently creating a job they can't leave or sell. To build a true business asset, you must define an end goal (like a sale) from the beginning and structure operations, processes, and financials accordingly.

A founder's decision to sell was triggered by her first-ever panic attack during a casual conversation about the business's future. This intense physical reaction served as an undeniable gut signal that her ego-driven push for the next funding round was the wrong path, prompting her to explore an exit.

Social media's "highlight reels" create pressure to build massive companies. Instead of chasing vanity metrics, owners should define what success looks like for them personally. A profitable company that affords a great life is often a better goal than a stressful, high-growth venture that doesn't align with your values.