The fundamental risk profile shifts dramatically between venture stages. Early-stage investors bet against business failure, an idiosyncratic risk unique to each company. Late-stage investors are primarily betting on public market multiples and macro sentiment holding up—a systematic risk affecting all late-stage assets simultaneously.
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Contrary to the 'get in early' mantra, the certainty of a 3-5x return on a category-defining company like Databricks can be a more attractive investment than a high-risk seed deal. The time and risk-adjusted returns for late-stage winners are often superior.
Unlike Private Equity or public markets, venture is maximally forgiving of high entry valuations. The potential for exponential growth (high variance) means a breakout success can still generate massive returns, even if the initial price was wrong, explaining the industry's tolerance for seemingly irrational valuations.
The most dangerous venture stage is the "breakout" middle ground ($500M-$2B valuations). This segment is flooded with capital, leading firms to write large checks into companies that may not have durable product-market fit. This creates a high risk of capital loss, as companies are capitalized as if they are already proven winners.
A large, multi-stage VC firm's growth fund serves as a risk mitigation tool. The ability to concentrate capital into late-stage winners covers losses from a higher volume of early-stage mistakes, allowing the firm to be more "promiscuous" and take more shots at Series A.
A common mistake in venture capital is investing too early based on founder pedigree or gut feel, which is akin to 'shooting in the dark'. A more disciplined private equity approach waits for companies to establish repeatable, business-driven key performance metrics before committing capital, reducing portfolio variance.
A Series A company's valuation isn't based on current financials. Instead, it reflects the purchase of an 'out-of-the-money call option'—a bet that the company could become immensely valuable. The goal is for this option to eventually expire 'in the money,' generating venture returns.
The ideal period for venture investment—after a company is known but before its success becomes obvious—has compressed drastically. VCs are now forced to choose between investing in acute uncertainty or paying massive, near-public valuations.
With trillion-dollar IPOs likely, the old model where early VCs win by having later-stage VCs "mark up" their deals is obsolete. The new math dictates that significant ownership in a category winner is immensely valuable at any stage, fundamentally changing investment strategy for the entire industry.
Traditional valuation doesn't apply to early-stage startups. A VC investment is functionally an out-of-the-money call option. VCs pay a premium for a small percentage, betting that the company's future value will grow so massively that their option expires 'in the money.' This model explains high valuations for pre-revenue companies with huge potential.
True alpha in venture capital is found at the extremes. It's either in being a "market maker" at the earliest stages by shaping a raw idea, or by writing massive, late-stage checks where few can compete. The competitive, crowded middle-stages offer less opportunity for outsized returns.
