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A predictable pattern in IPO investing is a stock price decline following the 90 to 180-day lock-up period. This occurs when insiders (employees, founders) are finally allowed to sell their shares, flooding the market with supply and often causing the price to crater.

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In the 1980s, companies like Apple went public early as a fundraising necessity, allowing public investors to capture most of the growth. Today, robust private markets mean companies stay private longer, making IPOs primarily a liquidity event for insiders and VCs, with less upside left for the public.

For highly-capitalized companies like SpaceX and OpenAI, bankers are designing new IPO structures. Instead of standard 90-180 day lockup periods, they're planning staggered share releases over a longer timeframe to manage immense selling pressure from a large base of private shareholders and prevent post-IPO stock volatility.

The paper wealth generated on IPO day is a misleading metric due to lockup periods and market volatility. A more accurate mental model for an investor's actual return is the company's market capitalization 18 months after the public offering. This timeframe provides a truer 'locked in value' after initial hype and selling pressure subsides.

The first-day surge in an IPO's stock price represents value transferred from the company to institutional investors who bought at a deliberately underpriced offering price. Retail investors who buy after this 'pop' are often left purchasing inflated shares while insiders cash out on the manufactured frenzy.

Gurley argues that investment banks intentionally underprice IPOs to create artificial demand and a day-one "pop." This allows their institutional clients to profit by selling into the retail-driven frenzy, leaving average investors buying at inflated prices.

For trillion-dollar private companies like SpaceX going public, the traditional 90-180 day lockup period is inadequate. The massive volume of insider shares hitting the market at once could crash the stock. Investment bankers are now designing staggered lockup releases to manage this unprecedented liquidity event.

For many large companies today, an IPO's primary purpose has shifted from raising growth capital—which is readily available in private markets—to creating liquidity for early investors and employees. The public offering acts as a valuation marker and an exit opportunity, not a funding necessity.

Employees with equity in a company going public must proactively calculate their potential tax liability before their lock-up period ends. It is also critical to develop a plan to diversify away from having the majority of their net worth tied up in a single, volatile stock.

Zayo's IPO, while successful, led to a talent drain. Key entrepreneurial employees gained significant liquidity, cashed out, and left to pursue new ventures, making it harder for the company to maintain its aggressive pace.

Contrary to popular belief, an IPO should not be viewed as a liquidity event. Instead, its primary value is in marketing and branding. It signals to the market, customers, and potential employees that the company is stable and "here to stay." The actual liquidity is often constrained by lockups and regulations.