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The Makings of a VC

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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:


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?


Written by sheeltyle

February 28, 2016 at 5:46 pm

Skybox – TR’s 50 Most Innovative Companies for 2012!

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A hearty congratulations to Skybox, a cutting edge, atypical Silicon Valley company for being recognized by MIT’s Technology Review as a Top 50 Innovative Company in 2012.  And congratulations to co-founder and current Chief Product Officer Dan Berkenstock, one of the most high energy and thoughtful founders I’ve had the privilege of working with, on being named a Top Innovator under 35 by the same publication.  I joined Skybox in 2010 as a “consultant” right after Bessemer led Skybox’s Series B, working 45-50 hours a week as one of two non-engineers in our small team of less than 20.  And now, the team is 50+ people (with many rocket scientists!) and ready to disrupt a stodgy industry.

Skybox is a company building low cost satellites that provide timely high resolution imagery and video.  Imagine being able to see the protests of the Arab Spring in high resolution video, get timely imagery of the damage done by Hurricane Katrina so FEMA can more effectively act, plan construction sites without ever making a visit, or monitor and defend your national borders with video or imagery feeds.  It’s pretty amazing stuff, and use cases go on and on.  It’s a company built on transparency with the belief that critical information should be available in high quality and low cost to many government agencies and the masses.

CEO Tom Ingersoll (a remarkable, almost paradoxical combination of an aerospace executive and entrepreneur), Dan, and the rest of the founding and broader team are going head on in an industry defined by its staidness.  And they’re attacking it with the zeal, mobility, and leanness of a Silicon Valley team.

The sky is the limit…except in this case.

Written by sheeltyle

February 26, 2012 at 9:56 am