Brian Chesky argues that large, late-stage private companies experience the downsides of public scrutiny without the benefits. There's an "insatiable desire" from outsiders to "get to the truth," creating more speculative pressure than the regulated transparency of being a public company.

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The biggest risk for a late-stage private company is a growth slowdown. This forces a valuation model shift from a high multiple on future growth to a much lower multiple on current cash flow—a painful transition when you can't exit to the public markets.

Similar to the short-lived direct listing wave, the idea of staying private indefinitely will likely only apply to a handful of elite, capital-rich companies like SpaceX. The vast majority of successful startups will still follow the traditional IPO path to provide liquidity and access public markets.

Contrary to the prevailing wisdom of staying private as long as possible, VC Keith Rabois counsels his portfolio companies to pursue an IPO once they hit ~$50 million in predictable revenue. He believes the benefits of being public outweigh the costs much earlier than most founders think.

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.

While many private founders fear going public, David George of a16z claims he's never met a public CEO who regrets it. Key benefits include easier and often cheaper access to capital compared to private markets, increased transparency, and the discipline it instills. The narrative of public market misery is overblown for most successful companies.

The public markets offer a unique advantage over staying private indefinitely: discipline during transitions. Daily stock prices and investor scrutiny force management to confront hard truths and balance growth, profitability, and innovation. As seen with Netflix's pivot to streaming, this pressure is crucial for realigning employee incentives and making tough capital decisions during strategic shifts.

When a founder faces a major acquisition offer, the pivotal question isn't just about valuation, but temperament. A board member should ask, "Are you built to be a public company CEO?" The intense stress and public scrutiny aren't for everyone. Pushing a founder who isn't an "IPO guy" to reject an offer can be a disastrous long-term decision.

The trend of companies staying private longer and raising huge late-stage rounds isn't just about VC exuberance. It's a direct consequence of a series of regulations (like Sarbanes-Oxley) that made going public extremely costly and onerous. As a result, the private capital markets evolved to fill the gap, fundamentally changing venture capital.

The primary risk in private markets isn't necessarily financial loss, but rather informational disadvantage ('opacity') and the inability to pivot quickly ('illiquidity'). In contrast, public markets' main risk is short-term price volatility that can impact performance metrics. This highlights that each market type requires a fundamentally different risk management approach.

By staying private longer, elite companies like SpaceX allow venture and growth funds to capture compounding returns previously reserved for public markets. This extended "growth super cycle" has become the most profitable strategy for late-stage private investors.