RedPoint Ventures Might Have Just Bought Itself A $40 Million Headache

Caterina FakePinWheel founder Caterina Fake

Photo: Joi

This morning brought confirmation of news Business Insider startup reporter Alyson Shontell dug up a couple weeks ago: Menlo Park VC firm RedPoint Ventures led a $40 million round in mobile social network, Path, at a $250 million valuation.Here’s what’s odd: RedPoint just invested in a startup that is in many ways very similar to Path: Caterina Fake’s new startup PinWheel.

PinWheel is a mobile app that lets users “pin” notes to places in the physical world. It has social networking components. Path is a mobile social network – with “check-in” functionality at its core.

Does this make PinWheel and Path direct competitors? “Not yet,” says a source close to PinWheel.

Usually, when a venture capital firm wants to invest in a startup that could compete with a startup already in its portfolio, it asks the startup it is already invested for the greenlight.  

We understand that did not happen in this instance.

The best case scenario for RedPoint is that PinWheel and Path become less similar, not more more so.

If the opposite happens, it will probably not be able to continue funding both going forward. Then it might find itself in the position Andreessen Horowitz found itself in last week: unable to fully profit from its early discovery of a great app or a great entrepreneur.

We reached out to RedPoint for this story, but it did not return our calls.

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