Ultra-late-stage companies like Ramp and Stripe represent a new category: "private as public." They could be public but choose not to be. Investors should expect returns similar to mid-cap public stocks (e.g., 30-40% YoY), not the 2-3x multiples of traditional venture rounds. The asset class is different, so the return profile must be too.

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.

Some companies execute a 3-5 year plan and then revert to average returns. Others 'win by winning'—their success creates new opportunities and network effects, turning them into decade-long compounders that investors often sell too early.

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 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.

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.

Financial models struggle to project sustained high growth rates (>30% YoY). Analysts naturally revert to the mean, causing them to undervalue companies that defy this and maintain high growth for years, creating an opportunity for investors who spot this persistence.