Square’s IPO prospectus shows just how much the company needs a full-time CEO


So let’s get this straight.

Square, Inc., has raised $ 590 million in private funding rounds – or about $ 100 million a year – to support it as it racked up an aggregate loss of $ 500 million in that time. It wants to raise at least $ 275 more in an IPO this year, the worst year for tech IPOs since 2009 and one that is growing finickier as the year wears on. 

Square’s dongle and its 2.75-percent transaction fee brought digital payments to many small merchants, but it also brought in copycats from better-funded rivals like Intuit, PayPal and Amazon. A high-profile deal with Starbucks turned into a big bust that led to $ 56 million in losses. Yet when that deal ends next year, Square warns, it could cause revenue to “decrease meaningfully in the future.” And fraud – actually, a single fraudster – somehow bilked the company out of $ 6 million this year.

That’s okay. Running a growing business is hard, especially when there are signs that the global economy you want to expand into is entering a frightening-looking slowdown. A CEO facing an unfriendly IPO market, a slowing economy, a rising tide of competition and a few recent, embarrassing snafus simply doubles down, works twice as hard. Right? What a CEO doesn’t do in such a time is take a second job at another, even more challenged company…

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