Bill Gurley, part of the Amazon IPO team, recalls Jeff Bezos being an anomaly. He insisted on a high price, caring more about long-term value than a celebratory first-day pop. Bezos was unconcerned that the stock might trade down initially, a mindset contrary to today's IPO norms.

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.

Venture capitalist Bruce Booth explains that bankers, lawyers, audit firms, and VCs all have strong financial incentives for a company to go public. This creates systemic pressure that may not align with the company's best long-term interests.

By offering only a small fraction of its shares ($75B out of a trillion-dollar valuation), SpaceX is creating a supply-demand imbalance. This classic IPO strategy forces index funds and institutional investors to buy into a potential price bubble, risking significant losses when more shares eventually hit the market.

When a high-profile IPO like SpaceX reserves a large portion (30%) for retail investors, it may not be about democratization. This can be a strategic move to offload shares at an inflated price to emotionally invested fans rather than price-sensitive institutional analysts.

Contrary to the popular VC idea that IPO pops are 'free money' left on the table, they actually serve as a crucial risk premium for public market investors. Down-rounds like Navan's prove that buyers need the upside from successful IPOs to compensate for the very real risk of losing money on others.

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.

Public market investors feel compelled to buy into major AI IPOs, even if they doubt a company's fundamentals. The strategy is driven by market dynamics: the expectation of a 'pop' from massive retail investor demand forces funds to participate to avoid underperforming their benchmarks.

Gurley suggests that conducting IPOs "on-chain" via tokenization could create a fairer market. This method, already used in crypto, allows for true price discovery by automatically matching supply and demand, eliminating the manual price-setting that benefits Wall Street insiders.