When faced with a life-changing $500M acquisition offer, Ryan Smith's wife provided the clarifying perspective: "if it's going good, just keep it rolling." This, combined with a mentor's advice against selling, empowered him to turn it down and aim for a much larger outcome.

Successful founders prioritize cash upfront over potentially larger payouts from complex earnouts. Earnouts often underperform because founders lose control of the business's future performance, leading to dissatisfaction despite a higher on-paper valuation.

An investor's best career P&L winners are not immediate yeses. They often involve an initial pass by either the investor or the company. This shows that timing and building relationships over multiple rounds can be more crucial than a single early-stage decision, as a 'missed round' isn't a 'missed company'.

After selling her company, Create & Cultivate, to a private equity firm, founder Jacqueline Johnson opportunistically repurchased the business for a lower price. This rare maneuver demonstrates a savvy understanding of market timing and negotiation with institutional buyers.

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.

Taking a small amount of money off the table via a secondary sale de-risks a founder's personal finances. This financial security empowers them to reject large acquisition offers and pursue a long-term, independent vision without the pressure of life-changing personal wealth decisions.

The most lucrative exit for a startup is often not an IPO, but an M&A deal within an oligopolistic industry. When 3-4 major players exist, they can be forced into an irrational bidding war driven by the fear of a competitor acquiring the asset, leading to outcomes that are even better than going public.

An exit that provides a significant financial win but isn't enough to retire on can be a powerful motivator. It acts as a 'proof point' that validates the founder's ability while leaving them hungry for a much larger outcome, making them more driven than founders who are either pre-success or have achieved a life-changing exit.

For years, CNX turned down acquisition offers from firms that only wanted to "milk the existing customer base of maintenance" and halt development. They ultimately sold to Izzy Software because it presented an exciting vision for growing the product, not just harvesting it.