betting on failure

Gene Yoon
ginsudo
Published in
2 min readSep 26, 2009

It’s interesting to watch reaction to the news of Twitter’s financing at a $1 billion valuation. The vast majority of commenters seem appalled (or at least cynically amused) at such a lofty valuation for a company with no meaningful revenues.

The shocked reaction misses an important point: Everyone believes that investments in companies like Twitter are likely to fail, including the investors in Twitter. For the most part, people who invest their money in companies like Twitter are not putting their life savings into a single company; they are investing their portfolio (or an allocation of it) into high-risk, extremely-high-return-potential companies. For that high-risk portfolio, it could be rational to invest in companies with a 90% chance of failure, if there is sufficient return for the other 10%.

Now, there aren’t many actual portfolios that are (intentionally) structured with any allocation to a class of investment with a 90% failure rate. But it would be completely typical if every single non-employee investor in Twitter made their investment from an allocation that has a greater-than -50% failure rate. In other words, most Twitter investors believe that it’s likelier than not that Twitter will fail. (Here, “failure” means that the investment will fail to reach the modeled return, not that the company will completely go out of business.)

It’s easy to say that Twitter will probably fail, but how many critics are confident that there is a less than 10% chance at a 10X return? Investors in Twitter don’t bank on Twitter, they plan that either Twitter or one of the other companies in that allocation of their portfolio will make an outsized return. Many of those investors have been right time and time again about their projected portfolio performance, which means that as a reward they will continue to invest in companies that are likely to fail.

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