This blog is all about words because they matter, they influence, they entertain and when you put them down on a page in a meaningful order, they acquire permanence. Contained here is my writing over the past 10+ years, primarily book reviews over the past ~5 years, and I also have a book review podcast, Talking Nonfiction, available on Apple or Spotify.
Wednesday, April 08, 2015
Interesting business pieces - on Dropbox, Chris Sacca & Ron Conway
The latest issue of Fast Company Magazine had the feature story "Dropbox Versus the World" by J.J. McCorvey on the cloud storage company and the recent Forbes cover story was "How Super Angel Chris Sacca Made Billions, Burned Bridges And Crafted The Best Seed Portfolio Ever" by Alex Konrad.
Sacca is a venture capital who I've a few times posted on writing from and about him and after reading the Forbes profile, I then read two interesting older pieces, both written by Miguel Helft. "A Post-Google Fraternity of Investors" was from the New York Times in 2007 and in part about Sacca and "Ron Conway is a Silicon Valley startup's best friend" was done for Fortune in 2012 on the venture capitalist noted in the Forbes piece as a former mentor of Sacca's.
Sunday, January 25, 2015
Chris Sacca interview done by Jason Calacanis
The interview Calacanis did with Sacca is split up into two parts, which each 60-90 minutes long and the first episode 291 of This Week in Startups and second episode 295. The interviews themselves are definitely worth listening to, and below are the things that stood out to me (not an actual transcription, but what I found most interesting) from episode 291:
Background overview - Sacca started his Lowercase Capital investment company in 2007 and prior to that was an attorney, then worked at a startup, and then Google.
Being helpful - Most of his investments made haven't come from leads through his site or meeting people at conferences, but through his network and relationships that he's built and people he's been helpful to. He notes that there's many different opportunities to be helpful and types of types of people to be helpful to, entrepreneurs, the press, users, service providers, and more.
Startup founders & belief in themselves - Sacca notes how important startup company founders are and how with more and more startups there's many founders that aren't that great, but that truly disruptive founders have a different gene. Examples of this provided include Ev Williams and how Williams views situations without really viewing failure as a possibility for himself, rather he looks and says the world would be cooler if something built and the failure option isn't a part of his math. Another example noted is Elon Musk and how he goes after huge problems and huge opportunities, it's a a fearlessness. Sacca notes how one challenge he faces is if he has to be asking founders how a business can be 100 times bigger as the founder should be doing that on their own. Another leading founder example given is Travis Kalanick of Uber and how he’s both unreasonably fast moving and executes on huge plans. Additionally, Kevin Systrom of Instagram is mentioned as a founder that's bullish and magnetic and someone who you look into his eyes and have no doubt he’s going to succeed.
How now a great time to have a startup - It's covered in the interview how 10 to 15 years ago it was harder to have a startup as bankers controlled much of the access to capital needed to run a business. Now the tools like Amazon Web Services are more in place to empower the new class of entrepreneur.
Sacca background prior to the Valley - Sacca details how starting in sixth grade, he went to the University of Buffalo to do math and then by high school got burned out on it, applied to the top school in the country that had no math, and went to the School of Foreign Service at Georgetown. Then he was living in Spain and Netscape went public and helped rekindle his interest in computers and math. He came back to the U.S., didn't know any venture capitalists, applied to law school, got in, took the student loans and used the money to start a company. His company went nowhere, but he had enough left to start trading, and in 1998 picked good stocks that went on huge runs and turned $10K into $12M in 18 months. Nobody told him to cash out, rather that he a genius, and he was fully leveraged in two stocks, had the market unwind and within a couple weeks was $4M under water in his own name.
Time in the Valley prior to Google - Sacca came out to the valley, got a job at a law firm and was working for them during the day and at night writing business plans. He was still heavily in debt, but didn't want to go bankrupt and have that potentially get in the way of a future career so worked out payment plans and started grinding away to get the debt down. Things were going well, but then he four days prior to Sept 11, 2001 got laid off and had to go out and hustle, attending every networking event he could find. People would pat him on the back and say things will work out and Sacca then rebranded myself, creating for himself a fictional company, the Salinger Group, which did any number of things that he may want to do later. People began hiring him for work and Sacca ended up at a company called Spedera, about which he said he learned more working there at a small company than at Google as he did so much, heard so much, and came away with a generalist knowledge.
Early investing - Sacca covers how he finally made it back to zero, had some money to do angel investing, and his first was Photobucket and second investment was Twitter. That came about because he was an early user of Twitter and Ev Williams called and said "hey, I've got you for $25K" (which Sacca didn't really have, but went in anyways). He notes how he as a non-employee just started showing up at the company and helping as he could, and how people often don't give themselves enough credit for how helpful they can be. Even if not an expert, insight someone has can be valuable. This notion of being helpful that was mentioned earlier in the interview was credited as then leading to him building up a portfolio of investments.
Later investing - He first raised an $8.5M fund that was broad based and went across the startup market. It's noted in the interview how when you’re raising money for a fund, potential investors are evaluating just you, which can be harder then if it’s your company, where they’re evaluating both you and the company. That first fund went well and Sacca then raised a fund to buy Twitter shares from early employees and investors. He covers how he depleted his entire checking account on Twitter shares and had less money than any reasonable angel investor should have, but just believed.
Venture capital industry - Sacca noted how the relationships between investors and founders change depending on the stage. In the first few rounds of investment, people are in it together, but then as things reach Series B investments, there can be a divergence of interests. It's easy for a VC who already has the money to tell a founder to swing for the fences, a million dollars or zero dollars. Basically, people can have different agendas financially in terms of exit strategies.
Twitter as a company - Sacca covered how he got into Twitter because Ev pulled him in and later doubled down on the company. He also spoke of how Twitter has had three CEOs now, feeling that each the right person for that phase of the company, smarter than he, and when he sits down with current leadership he has confidence in the decisions they make. Also covered about Twitter is how it's so simple, but people don’t recognize how powerful its simplicity is and how hard it is to get there. He notes how on his business card it says simple is easy to use, hard to make, and hard to charge for, but complex is hard to use, easy to make, easy to charge for. The beauty of Twitter is all the stuff that’s not there, and that’s not an accident, but years spent letting the simplicity spent for itself. Additionally noted is how Twitter is a commercial platform and place to get things done. Basically a massive commerce engine that helps people take cues from others who they know or care about that give signals about what they should be buying.
Current investing by Sacca - He notes how he's got over a billion dollars under management in funds and is an opportunistic buyer. Covered is how at the time of the interview Sacca had two funds primarily, Lowercase Spur which is larger and writes half million checks to startups and Lowercase Stampede which invests at the intersection of tech and content. Sacca notes that he wrote a whole thesis on it, but the space finally makes sense as traditional VCs were afraid to do content, but there a gap where valuable stuff not getting done. Also covered was how he invests in entertainment and another investment was Kickstarter. In relation to that, Sacca spoke of how when he saw the opportunity, he thought it would make the world a better place, but didn't know if it would make money so put his own cash in and didn't include it in the fund. He additionally talked about how Kickstarter being run for the long haul, like a 20-year horizon where the company founders don’t want to sell, but want to just draw salary and not go public. Sacca talked about how he knew this up front and had to soul search before investing.
The final thing to mention from the interview that I found interesting was Sacca and Calacanis both Howard Stern fans and knowledgeable about the show. More reason in my mind to like the guys and part one of the interview was really interesting and beyond reading this writeup, totally worth viewing/listening to.
Monday, August 18, 2014
Great pieces from and related to events in Ferguson, MO
The most detailed piece I've seen about the shooting death of Michael Brown by police officer Darren Wilson that precipitated everything was "In Ferguson, three minutes — and two lives forever changed" for the Washington Post by Manuel Roig-Franzia, DeNeen L. Brown and Wesley Lowery. The story was published on August 16th so additional details have and will continue to come to light, but it seems a really solid account.
In terms of the police action both that August 9th day and since, two pieces of writing I keep thinking of that weren't about Ferguson and the events there, but seem very much related, were by Jason Fagone and Matt Taibbi. For Mother Jones, Fagone wrote "How a Squad of Ex-Cops Fights Police Abuses" on retired cops working as investigators for a Florida Public Defender's Office and Taibbi authored the book The Divide (which I wrote on a few weeks ago). Taibbi provided an excellent and infuritating look at the application of justice in America and how there's different sets of consequences for breaking laws depending on what group someone a part of.
Two really well done pieces of writing done as a result of police reaction to protestors in Ferguson were both political in nature, and from two people perhaps often on different ends of a political spectrum. For Time Magazine was "Rand Paul: We Must Demilitarize the Police" by the Kentucky Senator and for his own company site, Venture Capital investor and Barack Obama backer Chris Sacca wrote "A few thoughts on race, America, and our President" about what the unfolding situation calls for.
The last thing to note here on something that I've seen posted in relation to Ferguson and which has stuck with me was video of the speech Robert F. Kennedy gave in which he annouced the death of Martin Luther King Jr. I six years ago linked to an audio-only version and the speech more powerful today than ever.
Tuesday, May 14, 2013
Fast Company Writing
Going furthest back, the Feb issue had both an interesting interview piece and really well-written feature story. The interview was by Charlie Rose with Biz Stone and Ev Williams who co-founded Twitter and begins with Stone and Williams making the extremely important point that Twitter not simply about 140-character expression of thought, but also the linking to content of all subjects and length around the web. Also noted in the interview was the blogging site Medium and the feature story from this issue was by Max Chafkin with "The Zen Master of Silicon Valley Chatter" on Kevin Rose. It was a detailed and interesting look at the Digg founder and internet investor who first backed early stage companies on his own and now as part of Google Ventures.
The March issue had "Working Beyond the Cube" by Greg Lindsay on co-working and Fast Company's annual "50 Most Innovative Companies" list.
The April issue had three different feature stories that stood out. Cover story was a lengthy piece by Nicole LaPorte title "The Rebels Saving Hollywood" and then Max Chafkin wrote "Why Kickstarter Won't Sell" on the crowdfunding website (with both features referencing Angel Investor Chris Sacca). Finally, Danielle Sacks contributed the feature "'Fifty Percent Of 'The Tipping Point' Is Wrong' Jonah Berger Shows You Which Half" on the author of Contagious: Why Things Catch On.
Finally, an interesting mention from the May issue was the short pieces "What's Hot in Alaska" on startup companies in the state.
Thursday, May 03, 2012
Business Success Pieces - Evan Williams / Chris Sacca / Paul Saffo / Asana / Jordan Cooper
There's been a few interesting business pieces I've seen lately that all seem connected enough to be pulled into one (hopefully coherently written) blog post...
Starting off with the oldest (by far) was "Ten Rules for Web Startups" from Twitter founder Evan Williams on his blog in Sept 2005. Williams track record is remarkable in that he co-founded both Pyra Labs (parent company that created Blogger) and Twitter. Additionally, he's referenced by venture capitalist Chris Sacca as someone to back in a venture regardless of the idea. The rules as laid out in the blog post from Williams were all interesting, but what really stood out to me was number one... "Be Narrow", with the first few sentences why noted below:
"Focus on the smallest possible problem you could solve that would potentially be useful. Most companies start out trying to do too many things, which makes life difficult and turns you into a me-too. Focusing on a small niche has so many advantages: With much less work, you can be the best at what you do."
With this (and since I so enjoy melding together different iterations of the same theme), it seems high time to bring in something from the excellent Ken Jennings book Maphead. I reviewed the book here and note how in it a collector was quoted saying "if you're going to specialize, specialize as much as possible." It's a tremendously interesting (and logical) concept that applies to map collecting, business creating and I'm sure many other ventures.
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Continuing with this approach of blending and connecting together in this blog post, I saw from the same Chris Sacca Twitter feed that directed me to the Williams piece a link to the recent Wired Magazine story "8 Visionaries on How They Spot the Future" by Joanna Pearlstein. It's written as a wisdom compilation story and below are the people and their insights that struck me the most (or at least insights as I took them):
Paul Saffo (Technology Forecaster) - looks for things that seem out of place as an indicator of events to come. Yea, that's a bit nebulous of a statement, but he describes the idea well is his short missive.
Chris Sacca (aforementioned Venture Capital guy) - you don't need to be a seer (prophet - soothsayer - diviner - augur - clairvoyant) to spot (and potentially invest in) the companies that could be poised for success. Barriers to entry are low enough in many technology realms that evaluation decisions can be made based on the actual product or service experience (or at least an early stage iteration of it). Tied to this idea is how many ways there (Twitter as probably the largest) to discern customer experience (as I wrote about featured in an Oct 2009 Businessweek) with a company and it's offering.
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With yet another "hopefully not a stretch" connection for the purpose of this blog post... rule number ten from Williams of "Be Balanced" reminded me of something else from Sacca in the same interview that he spoke of backing Williams regardless of the business idea. Point as I recall it was the import of working with people that he wants to spend time around as well as invest with.
This idea seems very much in evidence with two other pieces I've seen recently. Peter Delevett wrote "Facebook co-founder Dustin Moskovitz brings new startup Asana into the marketplace" on the company started with a former colleague from Facebook, Justin Rosenstein and I also saw "In Pursuit of 'Brain Doppelgangers'" from the blog of an entrepreneur, Jordan Cooper.
I'm not familiar with Cooper at all, but his description of the power in being with like-minded people made sense and I was pretty amazed to see the title right after reading the excellent GQ piece "The Cooler Me" (haven't yet seen it posted online) by Eric Puchner about... yep, doppelgangers.
Monday, April 09, 2012
Chris Sacca Interview with Kevin Rose
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...
Background
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.
Principles
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.
Monday, March 08, 2010
BusinessWeek Career/Business Pieces - Mar 15 issue

The first story that struck me as interesting was "What I Learned from My Dad"... a commentary by Peter Buffett following the much larger profile of his uber-investor father, Warren Buffett. The piece is actually excerpted from his forthcoming book "Life Is What You Make It: Find Your Own Path to Fulfillment" and tells the interesting tale of how the younger Buffett was staked with a roughly $90K inheritance at age 21... and used the money to fund making a go of it in the music field he loved.
Immediately following that in this BW issue was "And Google Begat..." about the Angel investing (no, not these kind of Angels) done by current and former Googlers. Pretty interesting stuff about the "next generation" impact Google wealth is having by helping fund tech startups such as Twitter, Tesla Motors and a host of smaller unknown (but, probably not always) ventures. The story was also noteworthy to me with mention of Truckee, CA based ex-Google guy Chris Sacca (his blog here). Granted, the town is what I noticed, but it was cool to read how Sacca came across one of his investments after posting a message on his Twitter account one Friday night asking if any startups were working late.
Finally, from this issue I liked "The Road to Reinvention" about career changes following personal setbacks. Specifically the one that got me (out of three vignettes) was that about Todd Morris... a 30 something tech sales guy who had an interest in a product category (security and surveillance gadgets), didn't see anyone dominating the field and up and created a now successful company, BrickHouse Security) in that space. Gotta be something to that idea of building a business around something you think valuable, but not already out there.
Three stories... one theme. Two guesses... that's right, building a career/investing in a business around something that interests you. Solid.