Venture Power Law
A handful of outlier outcomes dominate a portfolio's returns, so the middle is irrelevant and every loss is costless on the margin.
The distribution and its consequences
Ryan Petersen passed on Cruise in his Y Combinator batch because the founder's camera rig, bolted to a Honda Civic roof, looked to him, at the time, not legitimate.1 He cites the miss as the clearest evidence for his own rule: a tiny number of outlier outcomes dominate a venture or angel portfolio's returns, which makes the middle of the distribution nearly irrelevant. Petersen describes the shape from roughly two hundred angel investments, the vast majority of which he says did poorly, alongside a couple that returned a thousand times or five hundred times and, in his words, strictly completely dominate everything else.1 From that shape he draws a set of conclusions he applies to his own behavior.
The first is that a modest multiple does not matter. He describes a founder proud of returning three times the money, and notes that if he replaced that outcome with a zero it would have essentially no effect on the fund's return, because the middle of the distribution carries no weight against the tail.1 The second is a psychological rule he states plainly: when he writes an angel check he marks it to zero immediately, assumes it is a loss, and by removing the expectation removes the worry, since the arithmetic says the failures cost nothing on the margin anyway. The third is to chase the unusual company: because only the tail matters, he says the crazier the company, the more he wants in, and that if he does not get it, he is probably missing something, exactly the test the Cruise miss failed.
How Petersen sourced the tail
Petersen describes starting to angel invest inside Y Combinator, exploiting peer access because the other founders did not see him as an investor, which he says let him get the real story.1 His screen was negative rather than positive: he says it was obvious who was terrible, and that eliminating the bottom half already puts an investor ahead. He invested in about thirteen of roughly fifty batchmates and names being an early investor in Parker Conrad's Rippling among the hits, while Cruise got away. The account treats the discipline of avoiding obvious losers, combined with volume, as the practical way an angel gives the power law room to work.
What Petersen says founders should take from it
Petersen turns the principle toward the founder's own choices. He argues that a long grind for a small multiple is a mistake, saying a founder grinding five to ten more years for a 1.5x should not, and that from an investor's perspective a faster smaller return can be preferable because the fund needs the swing, not the modest outcome, and the founder's time is the scarce input.1 He carves out one exception, that a genuine life mission is a different matter where the calculus does not apply.
The principle is closely tied to Petersen's account of VCs as Herd Animals, which he offers as the reason the power law is often left unexploited: the job's incentives push investors toward the consensus deal, which by construction is not the contrarian outlier that returns a fund, an idea he connects to zero-to-one monopoly thinking. He also uses the distribution to reframe failure as a market signal rather than a cost, since on the margin the losses do not move the return.
Where the rule stops transferring
Petersen's own framing carries a caveat. Marking to zero is a discipline available to an angel who can spread roughly two hundred small checks across a diversified book, and it does not transfer cleanly to a concentrated early-stage fund or to a founder who cannot diversify a single company. The same arithmetic has also produced opposite conclusions in other investors, some of whom read it as a reason to stop angel investing entirely rather than to keep spreading checks, which suggests the math underdetermines the behavior a founder or investor should choose.
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References
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Flexport CEO Ryan Petersen on Revenge, Patriotism and the VC Herd
Ryan Petersen · podcast
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