Innovations & Inspirations

In Silicon Valley, there is a constant debate about whether venture capitalists should have previously been entrepreneurs.  While it can certainly be helpful, history shows us that some of the very best VCs took completely different career paths: Mike Moritz was a journalist, John Doerr was a salesperson at Intel, and Arthur Rock was an army veteran who then did corporate finance.   Some argue that there are actually more failed entrepreneurs-turned-VCs than non-entrepreneur VCs, but in general the asset class is one where failure is so prevalent that the numbers are likely a wash.

Although I haven’t founded a company (beyond the candy store in my 3rd grade desk, or my nonprofit), my time at Skybox Imaging, which was later acquired by Google, taught me a lot as it relates to building a business: selling a product, scaling an organization, and raising money from the other side of the table.  But as a venture capitalist, it gave me something that I’m not sure I could have gotten any other way:

Empathy.

The longer I’ve been in venture capital, the more I admire entrepreneurs.  Everything is against them: incumbents, families, lack of capital, and even the government in some cases.  Those who succeed are truly remarkable, and often lucky.  But nobody gets it right all the time, and even successful businesses go through ups and downs.

Entrepreneurs don’t usually need VCs when things are going well; in fact, sometimes the best thing that we can do is get out of the way.  But when things aren’t going well, that’s when the truly best VCs truly show their character.

When choosing a VC, I recommend that all entrepreneurs ask VCs for references not just from their companies that did well, but from their companies that failed or went through tough times.  It’s where you will find out the VC’s true colors.

Are they scared, or empathic? Do they resort to drastic measures, or are they more measured?  Have they seen ups-and-downs before, or do they believe that everything should always go well?  Do they fire immediately, or are they more deliberate?