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Square: The Mega-Disrupter Everyone Wants to Be In, Even the Investors Who Keep Passing | PandoDaily


Stashed in: Square, @bhorowitz, @a16z

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We talked to Ben Horowitz about this at last month’s PandoMonthly too — as Andreessen Horowitz has been calling Square the one that got away for many months. “We passed on Square in the first round, which was a $40 million round, which seems at least in retrospect a bit of a mistake,” he said. “The big mistake we made on that was we went for lack-of-weakness over strength.” As Horowitz explained earlier that evening, most insanely great entrepreneurs have a big weakness, and the firm prides itself on investing in the strength, not saying no to the weakness. But Square was an exception to their rule– one both Marc Andreessen and Horowitz say they regret, but haven’t rectified with an investment as the price has continually gone up.

It wasn't just him that passed on that round. Almost everyone did, except Gideon Yu, from what I can recall.

Gideon passed on Kerosene. :-)

Wait, now that I think about it a16z did too!

The difference between Square and Kerosene is that Square got one person to say yes to investing in it?

That and they do something useful and profitable.

I wish I could understand Horowitz's statement "…went for lack-of-weakness over strength," but try as I might his logic is eluding me.

Does he mean Square didn't have the expected 'big weakness' somewhere, that it was 'too strong'? Or that they perceived a weakness at the time, and let it (against their usual instincts) cause them to discount the strength?

Quote:

As Horowitz explained earlier that evening, most insanely great entrepreneurs have a big weakness, and the firm prides itself on investing in the strength, not saying no to the weakness. But Square was an exception to their rule -- one both Marc Andreessen and Horowitz say they regret, but haven’t rectified with an investment as the price has continually gone up.

The implication is that even though they thought Square could be a strong business, they let the perceived big weakness of the entrepreneur (@jack) override that believe that Square could be strong.

Whatever weakness Jack might have had, seems to not have affected Square's ability to succeed, and Ben Horowitz learned a valuable lesson:

Invest to win, not not-to-lose.

#winning

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