The article tackles a common dilemma faced by employees at successful startups: whether to cash in on paper gains during a tender offer or hold onto their shares for potential future growth. The author shares personal experience from his time at GitHub, emphasizing the weight of this decision. He argues that selling a portion of equity can be a smart move, especially when the potential payout is life-altering. Startup success often hinges on luck and timing, and the reality is that many companies, despite initial promise, can falter. The author warns against the delusion that often accompanies startup culture, where employees believe that their company will continue to thrive indefinitely. He cites the example of Zenefits, which was once considered unstoppable but faced serious setbacks shortly after he interviewed there. This highlights the unpredictable nature of the startup world. The advice is straightforward: don't gamble with your financial future when you already have a substantial win in hand. Selling a portion of equity doesn’t mean you’re giving up; it’s a strategic move to secure some financial stability. He also addresses the psychological burden of making perfect financial decisions, encouraging readers to accept that not every choice needs to be optimized for maximum gain. The pressure to achieve perfect outcomes can lead to paralysis or stress. The author reminds readers that even those who seem wealthy on paper can face financial struggles, often tied to debts or family responsibilities. Ultimately, he stresses the importance of liquidity and the need to balance long-term ambitions with present realities.