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So I asked four of the top investors in technology what they thought about this: Fred Wilson from Union Square Ventures, Chris Dixon from Founder Collective, Paul Graham from Y Combinator, and Ben Horowitz from Andreessen Horowitz. I figured that if something new was working, these four — a mix of East and West Coast, early and later stage investors — might have heard about it.

Fred Wilson said:

“We have not been able to quantify it. We haven’t even tried. Although I am sure someone could do it and they might be very successful with it.

 

To us, the ideal founding team is one supremely talented product oriented founder and one, two, or three strong developers, and nothing else. The supremely talented product oriented founder should have been obsessed about a product area/idea for a long period of time and just has to build something to satisfy their passion/curiosity. That’s about it. Joshua Schachter/Delicious, Jack Dorsey/Twitter, Dennis Crowley/Foursquare are the iconic examples of this kind of person in our portfolio.”

Chris Dixon said:

“One of the main activities of good investors is trying to find ‘accurate contrarian theses’ about what make good startups, markets, founders etc. So there is a lot of Moneyball-esque activity. I’ve seen a few attempts to do it quantitatively (I recall an academic paper on it and also some studies done internally at VCs) but I think those are often flawed because the quantitatively measurable things are either obvious (e.g. founders who sold their last company for a boatload of money are more likely to be successful than founders who failed), irrelevant, or suffer from ‘overfitting’ (finding patterns in the past that don’t carry forward in the future).

 

Personally, I think the biggest ‘Moneyball’ opportunities in seed investing are around the processes used. For example, I think the format of spending a few hours getting ‘pitched’ is a deeply flawed process for getting to know whether a first time founder will be successful. You can think of [Y Combinator] as an example of trying a new process. I’m personally constantly experimenting with different ‘getting to know founders’ processes.”

Back then we did it the hard way basically making our own Dropbox API. We had a Windows server running with the Dropbox client installed. You would share a folder with our Dropbox username and our script would auto accept it, and then we ran rsync to sync up the Windows folders with our web servers. Back then getting the Linux client to run was a bit of a pain which is why we went the windows route for that part of the site.