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Curse of the Megaround: Expectations and Power

I’ve written before about the curse of the megaround which can happen, for example, when a startup raises $100M at a unicorn valuation and I’ve described before what typically happens next:

If you were paying attention, you probably just noticed that $50M went up in smoke in the process.  Fortunately, in Woodsideno one can hear a venture capitalist scream.

The Math Behind the Problem:  Expectations and Power
In this post on the Silicon Valley hype machine, I argued that unicorns were the product of three trends:

This got me thinking about what really differentiates a $100M IPO from a $100M late-stage private financing.  Benchmark Capital’s Bill Gurley recently did a great post on this precise subject where he points out several major differences:

While I think Bill’s post his excellent, I think he missed two factors that are particularly important from the CEO’s perspective:  expectations and power.  Specifically, what are the go-forward expectations for the stock and what is the power of the people who have them?

In the IPO scenario, there is a short-term expectation of an immediate pop in the stock price, which is conveniently handled by the endemic under-pricing of IPOs.  So, assuming that takes care of itself through the usual process, what are the general expectations of an IPO stock after that, say during the next three years?

I spent some time researching this, looking at several studies and reviewing the capital asset pricing model.  Since I didn’t find any authoritative source (and since many IPOs actually under-perform), I will somewhat arbitrarily suggest that an public-market investor would be happy with a 20 to 25% annual return on an IPO stock purchased a few days after the offering.  I would be.

What does our late-stage private investor want?  Everybody knows that:  the rule of threes.  They want a 3x return over 3 years.  That’s a 44% annual return.   And, in today’s markets, that will often be atop a considerably higher initial valuation.

So the first big difference is about expectations.  Our private buyer expects roughly double the return of our public buyers.

The second big difference is about power:  who, exactly, wants that return?

So other than getting an investor with infinitely more power seeking double the return, in an environment with far less scrutiny over the numbers, in a situation more likely to cause a loss of operational discipline, and the use of structure / preferences that create potentially large gaps between nominal and effective ownership, there’s no real difference between doing a $100M private round and an IPO.

Well, at least the CEO can sometimes sell into the late-stage round.  He or she may well need to.

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