Monday, April 09, 2012

Chris Sacca Interview with Kevin Rose

It's taken me forever and a day to do this post on it, but I came across a while back a terribly compelling (at least for those people interested in business building) blog post containing an embedded video interview with investor Chris Sacca, head of the Truckee, CA based venture fund Lowercase Capital.

I first heard of Sacca from a March 2010 Businessweek piece "And Google Begat..." (which I noted in this blog post) on investing by Google alums and have since come across a number of interesting things noted and linked to by Sacca on his Twitter feed (Twitter a company I've written about quite a bit and also a Lowercase Capital investment).

The recent interview, though, particularly stood out as it's an hour-long conversation between Sacca and Kevin Rose (who founded Digg and hosts for another of his companies, Revision3, an ongoing interview series with business leaders). I found the interview as part of a post titled "How to get started as a business leader" for the blog Six Pixels of Separation from digital marketing agency Twist Image. There's a short introduction by Twist Image President Mitch Joel and my take-aways (which may differ from what someone else gleams) from the actual Rose-Sacca interview are as follows...


Sacca went to the School of Foreign Service at Georgetown and then started down the road of graduate school. However, rather than completing grad school at the time, he received the school loan checks and used the money to start a business with the intention of aggregating class action lawsuit information. The business didn’t do much, but the story probably serves as an early indicator of his entrepreneurial bent. He then began day trading online and during this heyday period went to being up $12M, but then found himself down $4M in the market crash around 2000. With this roller coaster ride in his background, he proceeded to get his law degree and came to Silicon Valley.

While having a day job as a lawyer, Sacca did lots of outside of work business hustling and attended all the networking events and worked hard to build a network. He was at the law firm for 13 months before getting laid off and then created a company that didn’t do a heck of a lot, but having that company helped him land a job at Spedera and from there got hired into Google.

Sacca was brought into Google to buy data centers for server housing and negotiated with local officials on the space Google was looking to take. This role was part of the core engineering function at the company and exposed him to some of the brilliant people working there. He then became Head of Special Projects and worked on initiatives such as free WIFI for Mountain View and the $4.7B bid by Google for wireless spectrum. Sacca came to Google too late to get insanely wealthy, but did do well enough to pay off his day trading debt and return to even by Feb 2005. He then saw Google becoming more territorial and a harder place to get into new areas so left the company in 2007.

Twitter investment

He then started writing small angel investor checks to startups with Photobucket his first investment and Twitter his second. This initial investment in Twitter was done with founder Evan Williams while Sacca still at Google and his relationships there run deep and include other key leaders Jack Dorsey and Dick Costello. While out on his own after Google, Sacca started accumulating additional stake in Twitter (speculated, but not confirmed to now be around 10% of the company). This obviously makes the guy look brilliant in hindsight, but the important thing is the reasons Sacca notes for believing in Twitter as a business. Along with his firm belief in the brilliance of Evan Williams is the appreciation of how things there monetize with ads able to be sold based on actual math and ad conversion rates rather than conjecture of what the ad buy is worth. Additional value offerings noted were the component of mobile that Twitter provides and ability to work within Social Networks and promoted tweets / promoted trends.

Other investments

At some point, Sacca put together his Lowercase Capital LLC fund and other investments have included FanBridge (which he found from sending out a tweet asking about entrepreneurs working late on a Friday night), Instragram (quite in the news today), turntable and Kickstarter. He notes doing less startup investing now due to the high valuations and focuses on companies and areas where he can be helpful. It’s also noted that VC investing not an exact science and there being a number of now successful companies that he could have invested in, but didn’t due to a lack of familiarity with the space in which they operated. Also brought up in the interview is how VCs make their money when they reinvest in companies already involved with.


Sacca describes himself as someone who grew up tenacious and determined, but along with that notes the import of building yourself through being helpful to others. To this point, he brings up that you often don't know where you're going to be able to contribute the most until you get in there doing things. The phrase used by Sacca was “create value before you ask for value back” and at this point, his interviewer, Kevin Rose, related his own story of wanting into Square so producing a demo video of how the product works and Sacca told of Ryan Graves, current GM at Uber who hustled and demonstrated helpfulness to get himself into foursquare.

In terms of people he looks to work with, these ideas of contribution and hustling definitely come up as valued traits. Additionally, Sacca extols the idea of people who have had crappy jobs they had to grind at as well as those who are rounded enough that they have things outside of work. This last point being about working with people that he wants to spend time around as well as invest with.

Overall, it was a terribly interesting interview with someone who seems to have combined together the elements of skill/intelligence, hard work and good fortune. I say good fortune because the concept of "in the right place at the right time" often part of many success stories... but, Sacca's story from the interview shows effort getting him to the places where good decisions and solid work would pay off. In short, you gotta make your own luck.