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.

The $2.5B acquisition of Manus exemplifies a "local maximum" exit. While VCs might push for a higher valuation later, the founders rationally chose to sell. This decision optimizes their personal, undiversified financial outcome by de-risking against future competition and market shifts.

Serial acquirer Lifco improves post-acquisition performance by having sellers retain an ownership stake in their business. This goes beyond typical earn-outs, keeping the founder's expertise and incentives aligned with the parent company for long-term growth, rather than just hitting short-term targets.

While first-time founders often optimize for the highest valuation, experienced entrepreneurs know this is a trap. They deliberately raise at a reasonable price, even if a higher one is available. This preserves strategic flexibility, makes future fundraising less perilous, and keeps options open—which is more valuable than a vanity valuation.

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.

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.

After discovering that buyers of their portfolio companies were achieving 3x returns, TA shifted its strategy. Instead of selling 100%, they now often sell partial stakes. This provides liquidity to LPs and de-risks the investment while allowing TA to capture significant upside from the company's continued compounding growth.

Marshall Haas sold a controlling stake in his company but retained significant equity. His goal was not just a cash payout, but to create a structure that provided ongoing cash flow, a continued advisory role, and a way to avoid the boredom and financial anxiety that often follows a complete, all-or-nothing exit.

Two founders rejected a $20M acquisition offer they felt was too low. After successfully pivoting their business during the pandemic, they returned to the same buyer and received a doubled offer of $40M with better terms. This shows how patience and focusing on business performance can dramatically improve an exit outcome.