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.
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The 'classic' VC model hunts for unproven talent in niche areas. The now-dominant 'super compounder' model argues the biggest market inefficiency is underestimating the best companies. This justifies investing in obvious winners at any price, believing that outlier returns will cover the high entry cost.
Mega-funds can justify paying "stupid prices" at the seed stage because they aren't underwriting a seed-stage return. Instead, they are buying an option on the next, much larger round where they'll deploy real capital. This allows them to outbid smaller funds who need to generate returns from the initial investment itself.
Deals like Naveen Rao's $1B raise at a $5B pre-money valuation seem to break venture math. However, investors justify this by stipulating that proven founders in hard infrastructure markets compress key risks, making market size, not execution, the primary remaining question.
The memo details how investors rationalize enormous funding rounds for pre-product startups. By focusing on a colossal potential outcome (e.g., a $1 trillion valuation) and assuming even a minuscule probability (e.g., 0.1%), the calculated expected value can justify the investment, compelling participation despite the overwhelming odds of failure.
Top growth investors deliberately allocate more of their diligence effort to understanding and underwriting massive upside scenarios (10x+ returns) rather than concentrating on mitigating potential downside. The power-law nature of venture returns makes this a rational focus for generating exceptional performance.
Contrary to the instinct to sell a big winner, top fund managers often hold onto their best-performing companies. The initial 10x return is a strong signal of a best-in-class product, team, and market, indicating potential for continued exponential growth rather than a peak.
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.
An investor passed on a fund that paid 30-40x revenue for startups, believing quality alone justifies price. Three years later, that fund and its predecessors are underwater. This illustrates that even for great companies, undisciplined entry valuations and the assumption of multiple expansion can lead to poor returns.
The venture capital business requires consistent investment, not sprinting and pausing based on market conditions. A common mistake is for VCs to stop investing during downturns. For companies with 50-100x growth potential, overpaying slightly on entry price is irrelevant, as the key is capturing the outlier returns, not timing the market.
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.
