Navan's post-IPO stock drop, despite strong revenue, is a troubling sign for the venture ecosystem. It highlights that even a multi-billion-dollar outcome can be considered a 'bummer' and may not generate sufficient returns for large, late-stage funds, resetting expectations for what constitutes a truly successful exit in the current market.

The traditional IPO exit is being replaced by a perpetual secondary market for elite private companies. This new paradigm provides liquidity for investors and employees without the high costs and regulatory burdens of going public. This shift fundamentally alters the venture capital lifecycle, enabling longer private holding periods.

The default VC practice of distributing shares after an IPO lockup can leave massive gains on the table. Missing a multi-billion dollar run-up suggests a more nuanced, case-by-case discussion with LPs is needed, as holding can be the difference between a 5x and a 15x fund.

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.

Success in late-stage venture resembles trading more than traditional investing—it's about buying and selling on momentum. However, this "new public market" has a critical flaw: while liquidity exists on the way up, it vanishes on the downside, making it impossible to execute a true trading strategy when a correction occurs.

The standard VC practice of distributing shares to LPs immediately after a lockup expires can be a multi-billion dollar error. The case of selling Reddit at a $9B valuation, only to see it rise much higher, highlights that VCs may need to evolve into holding public positions longer, challenging the traditional model.

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.

The venture capital paradigm has inverted. Historically, private companies traded at an "illiquidity discount" to their public counterparts. Now, for elite companies, there is an "access premium" where investors pay more for private shares due to scarcity and hype. This makes staying private longer more attractive.

Contrary to the traditional focus on institutional investors, allocating a significant portion of an IPO to retail investors creates a loyal shareholder base. This "retail following" can result in higher valuation multiples and sustained brand advocacy, turning customers into long-term owners and a strategic asset.