Month: December 2014

Dec 31 2014

Books About US Presidents

I was sitting at a Return Path board dinner around a year ago. We were at Frasca having a wonderful dinner when the discussion turned to American history. I sat and mostly listened as Matt Blumberg, Jeff Epstein, and Greg Sands had a vigorous discussion about several US presidents. Within about fifteen minutes, I realized that I knew almost nothing about American history. Sure, I took a class in junior high school (in Texas public schools, you do Texas history in 7th grade, American history in 8th grade, and World History in 9th grade), but I really didn’t remember much.

I got into Lincoln some in 2014 and Amy and I watched the HBO John Adams series while we were in Bora Bora. Each reminded me how little I actually knew about American history, especially the story of American presidents.

During the Return Path dinner, Matt mentioned that he’d been reading at least presidential biography each year. He’d made it through Woodrow Wilson (I couldn’t even tell you the number president Wilson was without the help of the Google.) I asked him to send me the book list, which he did, and then I promptly forgot about. Recently, I asked him to send it again as I’m now starting to march through biographies of Jefferson and Franklin (yes, I know Franklin wasn’t a president but he’s on my biography to read list anyway.)

Matt’s list is below. I’m looking for more great bios – given how I read I expect I’ll do more than one on each president. So if you read something particularly interesting or from a different perspective, toss it in the comments. And, if you have good ones from Harding forward (yes – I used Wikipedia to figure out who was after Wilson), put them in the comments also.

– Imperfect Presidents (Jim Cullen)
– Presidential Ancedotes (Paul Boller)
– A Pocket History of the United States (Allan Nevins)
– Selling the World Ablaze Washington, Adams, Jefferson and the American Revolution (John Ferling)
– Alexander Hamilton (Forest McDonald)
– The First American – The Life and Times of Benjamin Franklin (H.W Brands)
– Benjamin Franklin – The Autobiography (Benjamin Franklin)
– Patriarch (Richard Norton Smith)
– George Washington (Robert F. Jones)
– John Adams (David McCullough)
– The Portable Thomas Jefferson (Thomas Jefferson)
– Amercian Sphinx – The Character of Thomas Jefferson (Joseph Ellis)
– Rot, Riot and Rebellion: Mr. Jefferson’s Struggle to Save the University That Changed America (Rex Bowman)
– Jefferson’s Great Gamble (Charles Cerami)
– Burr: A Novel (Gore Vidal)
– Undaunted Courage (Stephen E Ambrosse)
– James Madison – The American President Series (Gary Willis)
– James Monroe – The Quest for National Idenitity (Harry Ammon)
– John Quincy Adams (Robert Remini)
– John Marshall – Definer of a Nation (Jean Edward Smith)
– The Great Triumvirate (Merrill Peterson)
– The Missouri Compromise and the Afermath (Robert Pierce Forbes)
– American Lion: Andrew Jackson in the White House (Jon Meacham)
– Martin Van Buren (Joel H. Sibley)
– Old Tippecanoe William Henry Harrison and his Time (Freeman Cleaves)
– John Tyler (Gary May)
– Polk – The Man Who Transformed the Presidency and America (Walter K. Borneman)
– Zachary Taylor – The American Presidents Series (John S. Eisenhower)
– Millard Fillmore: Biography of a Presidnet (Robert J. Rayback)
– Frankin Pierce: A Biography (Roy Nichils)
– James Buchanan (Philip S. Klein)
– Lincoln: A Novel (Gore Vidal)
– Mr Lincoln’s T-Mails (Tom Wheeler)
– Team of Rivals: The Political Genius of Abraham Lincoln (Dorris Goodwin)
– Lincoln (David Herbert Donald)
– Battle Cry of Freedom: The Civil War Era (James M. McPherson)
– Manhunt: The 12 Day Chase for Lincoln’s Killer (James Swanson)
– Jefferson Davis, Confederate President (Herman Hattaway)
– Bloody Crimes (James Swanson)
– Abraham Lincoln: Vampire Hunter (Seth Grahme Smith)
– The Avenger Takes His Place: Andrew Johnson and the 45 Days That Changed the Nation (Howard Means)
– Andrew Johnson: The American President Series (Annette Gordon Reed)
– A Short History of Reconstruction (Eric Foner)
– Assasination! The Brick Chronicle of Attempts on the Lives of Twelve US Presidents (Brendan Powell Smith)
– Grant (William S. McFeely)
– Personal Memoirs of U.S. Grant Volume 1 (Ulysses S. Grant)
– Personal Memoirs of U.S. Grant Volume 2 (Ulysses S. Grant)
– When General Grant Expelled the Jews (Jonathan S. Sarna)
– 1876 (Gore Vidal)
– Rutherford B. Hayes: Warrior and President (Ari Hoogenboom)
– Garfield: A Biography (Allan Peskin)
– Chester A. Arthur: A Quarter-Century of Machine Politics (George Frederick Howe)
– An Honest President: The Life and Presidencies of Grover Cleveland (H.P. Jeffers)
– The Presidency of Benjamin Harrison (Homer Socolofsky)
– The Biography of Benjamin Harrison: The American President Series (Charles W. Calhoun)
– Grover Clevland (Henry F. Crapp)
– Continental Liar from the State of Maine (James G. Blaine)
– The Unknown Architects of Civil Rights: Thaddeus Stevens, Ulysses S. Grant, and Charles Sumner (Barry Goldenberg)
– Age of Betrayal: The Triumph of Money In America (Jack Beatty)
– William McKinley and His America (H. Wayne Morgan)
– The Rise of Theodore Roosevelt (Edmund Morris)
– Theodore Rex (Edmund Morris)
– Colonel Roosevelt (Edmund Morris)
– The River of Doubt: Theodore Roosevelt’s Darkest Journey (Candice Millard)
– The Bully Pulpit: Theodore Roosevelt, William Howard Taft, and the Golden Age of Journalism (Dorris Kearns Goodwin)
– The William Howard Taft Presidencty (Lewis Gould)
– The Three Roosevelts: Patrician Leaders Who Transformed American (James MacGregor Burns)
– That Man: An Insiders Portrait of Frankin D. Roosevelt (Robert H. Jackson)
– Woodrow Wilson (John A Thompson)
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Dec 31 2014

Fundamental Software Problems That Haven’t Been Solved Yet

I hate doing “reflections on the last year” type of stuff so I was delighted to read Fred Wilson’s post this morning titled What Just Happened? It’s his reflection on what happened in our tech world in 2014 and it’s a great summary. Go read it – this post will still be here when you return.

Since I don’t really celebrate Christmas, I end up playing around with software a lot over the holidays. This year my friends at FullContact and Mattermark got the brunt of me using their software, finding bugs, making suggestions, and playing around with competitive stuff. I hope they know that I wasn’t trying to ruin their holidays – I just couldn’t help myself.

I’ve been shifting to almost exclusively reading (a) science fiction and (b) biographies. It’s an interesting mix that, when combined with some of the investments I’m deep in, have started me thinking about the next 30 years of the innovation curve. Every day, when doing something on the computer, I think “this is way too fucking hard” or “why isn’t the data immediately available”, or “why am I having to tell the software to do this”, or “man this is ridiculous how hard it is to make this work.”

But then I read William Hertling’s upcoming book The Turing Exception, remember that The Singularity (first coined in 1958 by John von Neumann, not more recently by Ray Kurzweil, who has made it a very popular idea) is going to happen in 30 years. The AIs that I’m friends with don’t even have names or identities yet, but I expect some of them will within the next few years.

We have a long list of fundamental software problems that haven’t been solved. Identity is completely fucked, as is reputation. Data doesn’t move nicely between things and what we refer to as “big data” is actually going to be viewed as “microscopic data”, or better yet “sub-atomic data” by the time we get to the singularity. My machines all have different interfaces and don’t know how to talk to each other very well. We still haven’t solved the “store all your digital photos and share them without replicating them” problem. Voice recognition and language translation? Privacy and security – don’t even get me started.

Two of our Foundry Group themes – Glue and Protocol – have companies that are working on a wide range of what I’d call fundamental software problems. When I toss in a few of our HCI-themes investments, I realize that there’s a theme that might be missing, which is companies that are solving the next wave of fundamental software problems. These aren’t the ones readily identified today, but the ones that we anticipate will appear alongside the real emergence of the AIs.

It’s pretty easy to get stuck in the now. I don’t make predictions and try not to have a one year view, so it’s useful to read what Fred thinks since I can use him as my proxy AI for the -1/+1 year window. I recognize that I’ve got to pay attention to the now, but my curiosity right now is all about a longer arc. I don’t know whether it’s five, ten, 20, 30, or more years, but I’m spending intellectual energy using these time apertures.

History is really helpful in understanding this time frame. Ben Franklin, John Adams, and George Washington in the late 1700s. Ada Lovelace and Charles Babbage in the mid 1800s. John Rockefeller in the early 1900s. The word software didn’t even exist.

We’ve got some doozies coming in the next 50 years. It’s going to be fun.

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Dec 30 2014

Foundry Group Traditions: Gnip Exit Gift

Foundry Group has now been around for over seven years and I’ve been working with my partners for 14 years. We’ve started to develop some traditions.

One of my favorites is exit gifts. When a company has an exit that generates a return for us, we give a gift to the partner who served on the board. These gifts are generally tuned to what the partner loves such as musical stuff for Ryan and Jason, bike stuff for Seth, and art for me.  They are modest, but very thoughtful and something the partner wouldn’t have just gone out and done for himself. They are often self referential, such as the Makerbot sculpture of me created by an artist and printed on a Makerbot after Stratasys acquired MakerBot.

A few weeks ago Seth, Jason, and Ryan corralled me in our small conference room. Whenever they do this, I’m never sure if it’s going to be a happy thing or an intervention. Ryan was holding the following 2′ x 3′ framed print.

Tweets from @bfeld during the time we were investors in Gnip

To get a better sense of this masterpiece, let’s zoom in on the G and the N.

Find a tweet online and RT it for a bonus point.

This is a list of every tweet I made at @bfeld from the day of our investment in Gnip to the day that Twitter acquired Gnip. This first one is from 2/29/08.

@bfeld tweets from day 1 of the gnip investment

The last batch is from 4/14.

@bfeld tweets when Gnip was acquired by Twitter

Ryan told me that Gnip was used to generate the tweet list for the poster. And Postertext was used to print it. Thanks guys – this one made me smile a huge smile. I love this tradition.

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Dec 29 2014

Identify Leaders By Giving People Assignments

As the Boulder Startup Community evolved, I started to become inundated with people who wanted to get involved. Some of these were locals while others where people looking to move to Boulder, or who had recently moved here. Some where people known to me while others were new relationships. As the momentum, size, impact, and reach of the Boulder Startup Community grew, I found myself overwhelmed by the amount of requests I was getting to get together, meet, explore ways to work together, and just generally share food and drink in the quest for figuring out ways to work together.

A while ago I came up with an approach where I could separate leaders from doers from everyone else. I’ve been applying this approach to the Boulder Startup Community, and a number of other things I’m involved in, since then and offer it to you as a simple, yet elegant way to triage an overwhelming amount of inbound requests to figure out who is really going to make shit happen.

The trick: I identify leaders by giving people assignments.

Here’s how it works. I’m going to use a really simple example. Recognize that the range of inbound is all over the place, from a wide range of people, with very different degrees of experience. The initial interactions can be complex and my assignments vary dramatically, but with a goal of intersecting (a) what the person is asking for and (b) a result that will be interesting to me in some way.

So, for a simple case (and assignment), assume that I get an email like the following:

“Brad, I’m new to Boulder and very excited about getting involved in the Startup Community. I moved here from New York and have a deep background in devops, being an entrepreneur, and various meditation techniques. I’d love to get together for a cup of coffee to see how I can get involved in things going on in Boulder. My resume is attached.”

I quickly respond with an assignment. It will be something that will take the person less than 30 minutes to do and require no specific knowledge on their part. For example, my response might be:

“Welcome to Boulder. Unfortunately I don’t have time for coffee in the next few weeks, but I’d be happy to get you plugged in to some of the local entrepreneurs who might be relevant to you. Can you look through our portfolio and tell me who you’d like to get introduced to?”

I never hear back from 50% of the people. I kid you not. It doesn’t matter whether it’s email or someone coming up to me at a public event. I give them a simple assignment, with an easy way to focus what I’m going to do for them so it’s more useful from their frame of reference, and then I never hear back from them again.

This is a very good thing. It reduces my workload of this kind of stuff immediately by half and filtered out people who weren’t going to follow through.

25% (half of the remaining 50%) send me an email something like:

“I took a look at your website and am very interested in VictorOps and Techstars. My last company used pagers for tech support and I really want to do something better than that and VictorOps looks interesting. I’ve got a lot of experience mentoring entrepreneurs, so I’d like to figure out if I can become part of Techstars.”

I categorize this person as a doer. They responded directly to the assignment. I respond by making some introductions with context – usually double opt-in, but not always depending on the level of relevance. Quickly, the person becomes plugged into a few other nodes in the Startup Community and their journey has begun.

The last 25% is amazing. They blow my mind. Their response is something like:

“Brad, thanks for pushing me to be more precise. I realized I didn’t need you to make the intro for me, so I’ve gotten together with Todd Vernon at VictorOps, Nicole Glaros at Techstars, and Ari Newman at Bullet Time Ventures. It looks like there might be a nice fit with Todd’s company and we are exploring a way to work together. Nicole explained to me that there was a very long waiting list of mentors for the next program so the most effective thing I could do is find one of the older Techstars companies and help them out. I’m already talking to the guys from Sphero (which I know you are on the board of) since I have a lot of gaming experience. And, given my previous network management company experience, Ari hooked me up with the Distill Network guys. I hope you don’t mind if I write periodically and follow up with what I’m up to. By the way, I tried out FullContact for Gmail per your blog post and so far it’s working great.”

This person is a leader. They simply went out and did shit. They made it happen. They followed up. They did things that had a potential positive impact on my world. They didn’t ask me for more, but offered up plenty, which makes me want to do more for them.

Remember, these are simple examples. I categorize the responses three ways:

  1. 50% of the people vanish
  2. 25% of the people do the assignment
  3. 25% of the people make shit happen well beyond what the assignment was

The folks who capture my attention and energy going forward are the ones in category 3. The leaders.

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Dec 28 2014

The Endless Struggle That Boulder Has With Itself

I’ve now lived in Boulder for 19 years. It was an amazing place when I moved here and has evolved into an even more stupendous place over the past 19 years, notwithstanding the irrational and self-limiting struggle that the Boulder City Council seems to have with change.

Over the past decade, the Boulder Startup Community has had significant success and impact on the culture and dynamics of the city. I wrote about some of the history and impact in my book Startup Communities and the Boulder Thesis that I came up with has now been used as a template for creating startup communities all over the world.

Since being inclusive of anyone who wants to engage in the startup community” is the third principle of the Boulder Thesis, I get sad when I see phrases like the following in articles in the NY Times about Boulder such as:

“The locals say they don’t like the tech folks pouring into town to work at places like Google. They’re insular. They’re driving up housing prices. And they fear those newcomers are more like invaders than people trying to fit into their new community.”

Earlier this year, Macon Cowles, a member of our city council asserted that Boulder’s startup economy brought a lot of very highly paid white men to the city, and they were pricing out families and others. He then followed up with the statement “I don’t think that’s what people want.” If you know the Boulder Startup Community, you know that it’s actually bringing diversity to what is historically a very ethnically white town. A group of Boulder Startup Community leaders, including Nicole Glaros, Rajat Bhargava, and my partner Jason Mendelson wrote an OpEd titled A necessary education on Boulder’s startup community where they challenged Macon Cowles’ perspective.

“We are women and men. We are parents. We are veterans of the military. We are ultra marathoners. We are musicians and artists. We are foodies. We are sportspeople and environmentalists. We are philanthropists. We are educators. We are graduating students with entry-level jobs gaining valuable experience. We are techie nerds. We are clean energy inventors. We are natural food creators. We are of all races and ethnicities. We are young. We are old. We are straight. We are LBGTQ. We come from every religious background. We are the cross-section of our entire community. We are risk takers who have decided to create our own jobs and jobs for others.”

Cowles eventually apologized but couldn’t help but include a link to an article about Google’s diversity record in his tweet.

I fear Cowles doesn’t realize that the National Center for Women & Information Technology, led by long time Boulderite Lucy Sanders, is on the front edge of the tech / diversity issue. I’ve been immersed in the gender side of the diversity issue as chair of NCWIT since 2006 and Google is a strong, positive participant in this. Ethnic diversity in tech, especially in the US, is a big struggle, but it’s a big struggle in Boulder as well, since the population here is over 90% white.

Boulder ethnicity per US Census

I wish the NY Times article titled A Google Gentrification Fight That Doesn’t Involve San Francisco had a broader, and more than one-sided perspective. It stood out in stark contrast to several other articles I read this morning, including From startup to $7 billion, Zayo encourages ideas, entrepreneurs and Nancy Phillips followed her passion to go ViaWest. These Denver Post articles do a great job of highlighting the positive impact Dan Caruso and his team at Zayo and Nancy Phillips and her team at Viawest have had on the Boulder (and Denver) Startup Communities. And, as a bonus, Nancy has been an incredible leader and advocate for NCWIT.

At this point, the Boulder Startup Community is deeply woven into the fabric of Boulder. There is an incredible positive feedback loop between everything going on here. For those who have so quickly forgotten the global financial crisis of 2008 – 2010, one of the main reasons Boulder was so minimally impacted was the strength of the startup community – not just for employment, but for discretionary spending as well.

But ultimately this isn’t really about economics. Or innovation. Or ethnicity. Or gender.

It’s about change. And evolution. The Boulder of 2015 is not the Boulder of 1970. It’s also not the Boulder of 1995. It’s the Boulder of 2015. And we need to keep being inclusive and working together to keep it great, and make it better.

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Dec 27 2014

Asimov’s I, Robot and Hertling’s The Turing Exception

William Hertling is one of my top five favorite contemporary sci-fi writers. Last night, I finished the beta (pre-copyedited) version of his newest book, The Turing Exception. It’s not out yet, so you can bide you time by reading his three previous books, which will be a quadrilogy when The Turing Exception ships. The books are:

  1. Avogadro Corp: The Singularity Is Closer Than It Appears
  2. A.I. Apocalypse
  3. The Last Firewall

William has fun naming his characters – I appear as a minor character early in The Last Firewall – and he doesn’t disappoint with clever easter eggs throughout The Turing Exception, which takes place in the mid-2040s.

I read Asimov’s classic I, Robot in Bora Bora as part of my sci-fi regimen. The book bears no resemblance to the mediocre Will Smith movie of the same name. Written in 1950, Asimov’s main character, Susan Calvin, has just turned 75 after being born in 1982 which puts his projection into the future ending around 2057, a little later than Hertling’s, but in the same general arena.

As I read The Turing Exception, I kept flashing back to bits and pieces of I, Robot. It’s incredible to see where Asimov’s arc went, based in the technology of the 1950s. Hertling has got almost 65 more years of science, technology, innovation, and human creativity on his side, so he gets a lot more that feels right, but it’s still a 30 year projection into the future.

The challenges between the human race and computers (whether machines powered by positronic brains or just pure AIs) are similar, although Asimov’s machines are ruled by his three laws of robotics while Hertling’s AIs behaviors are governed by a complex reputational system. And yes, each of these constructs break, evolve, or are difficult to predict indefinitely.

While reading I, Robot I often felt like I was in a campy, fun, Vonnegut like world until I realized how absolutely amazing it was for Asimov to come up with this stuff in 1950. Near the middle, I lost my detached view of things, where I was observing myself reading and thinking about I, Robot and Asimov, and ended up totally immersed in the second half. After I finished, I went back and reread the intro and the first story and imagined how excited I must have been when I first discovered I, Robot, probably around the age of 10.

While reading The Turing Exception, I just got more and more anxious. The political backdrop is a delicious caricature of our current state of the planet. Hertling spends little time on character background since this is book four and just launches into it. He covers a few years at the beginning very quickly to set up the main action, which, if you’ve read this far, I expect you’ll infer is a massive life and death conflict between humans and AIs. Well – some humans, and some AIs – which define the nature of the conflict that impacts all humans and AIs. Yes, lots of EMPs, nuclear weapons, and nanobots are used in the very short conflict.

Asimov painted a controlled and calm view of the future of the 2040s, on where humans were still solidly in control, even when there is conflict. Hertling deals with reality more harshly since he understands recursion and extrapolates where AIs can quickly go. This got me to thinking about another set of AIs I’ve spent time with recently, which are Dan Simmons AIs from the Hyperion series. Simmons AIs are hanging out in the 2800s so, unlike Hertling’s, which are (mostly) confined to earth, Simmons have traversed the galaxy and actually become the void that binds. I expect that Hertling’s AIs will close the gap a little faster, but the trajectory is similar.

I, Robot reminded me that as brilliant as some are, we have no fucking idea where things are heading. Some of Asimov’s long arcs landed in the general neighborhood, but much of it missed. Hertling’s arcs aren’t as long and we’ll have no idea how accurate they were until we get to 2045. Regardless, each book provides incredible food for thought about how humanity is evolving alongside our potentially future computer overlords.

William – well done on #4! And Cat totally rules, but you knew that.

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Dec 26 2014

The Great Boxing Day Data Cleanse of 2014

I just spent around an hour shrinking my Facebook friends list from 1,500+ to 535. I ignored another 2,000 friend requests. I made my entire Facebook feed from the beginning of time private, which eliminated 33,000+ followers (dear Facebook followers – you really meant to follow me on Twitter, that’s where all the public fun is.) I turned off all my email notifications.

Hint – if you want to do stuff like this, use the iOS app instead of the web app – it’s so, so, so much faster. Last night I tried to do this on the Facebook web app in front of the TV. It was a total fail – every few unfriends caused the page to refresh and I had to start scrolling all over again. This morning I was pleasantly surprised with how much better / cleaner / faster it was with the iOS app.

I cleared out all my outstanding LinkedIn friend requests. I’m much more promiscuous there and will accept anyone who either I recognize, writes me a personal note, or seems interesting. I turned off all my email notifications and re-inserted LinkedIn in my Daily browser folder.

I spent some time fixing up all the friend requests in Goodreads. I don’t care who follows me, but I got rid of the folks I follow who I don’t know and focused that list a lot better to see if the feed would be useful going forward.

I just deleted everything off my iPhone that I never use and put the infrequently used stuff in various folders. That took things from eight screens to two. Charm King – how the fuck did you end up on my iPhone?

It will continue. Feedly – clean up feeds and add ones from companies in our portfolio that I haven’t been following. Consolidate all photos and music in one place and make sure they are accessible from all computers. And whatever else I run into.

There’s something very satisfying about the winter cleaning that I seem to do every year.

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Dec 26 2014

Mentors 9/18: Clearly Separate Opinion From Fact

I’m in the home stretch of my next book co-authored with Sean Wise, titled Startup Opportunities: Know When To Quit Your Day Job, so I thought I’d procrastinate a little this morning and write another Techstars Mentor Manifesto blog post.

This one is about the ninth element, Clearly Separate Opinion From Fact.

We live in a world of assertions. Many of us, including me, often have a fuzzy line between opinions and facts. We interpret facts to fit our opinions, but then make our opinions broader than the underlying data. Opinions are formed from a single fact, rather than a set of several, or a lot of facts, to form a clearly substantiated opinion.

Entrepreneurs, investors, and anyone who plays a mentorship role often asserts an opinion as fact. I know that I fall into this trap regularly, both on the asserting and receiving end. I often catch others doing it and, when I challenge them based on my own data, they quickly revert to a position that they are expressing an opinion. But, in these cases, if I hadn’t challenged them, everyone else hearing the statement would view it as fact.

Now, opinions are extremely important. But they are different than facts. This is especially important for a first-time entrepreneur to realize. It’s equally important for a mentor to realize.

When you are expressing an opinion, it’s useful to frame it as such. When you are stating a fact, make sure your mentee knows it’s a fact.

In addition to separating opinions from fact, you should separate data from facts. While data is factual, the conclusion from the data is often an opinion. It’s easy to assert the data as a fact but this isn’t helpful and is often detrimental, since it’ll be incorporated into the mentee’s mind as a fact that they will start to extrapolate off of it as a fact.

As humans we get trapped in the fact / opinion / data matrix all the time. As a mentor, be careful and err on the side of being clear about what you are stating. Your goal is to help your mentee, not to be recognized as the smartest person in the room.

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Dec 25 2014

Bora Bora Biographies

I read over 40 books in my month off the grid in Bora Bora recently. I’ve had many requests to blog about my reading list but rather than do one big long post I thought I’d break it up into several “longish” different posts over time. If all you are interested in is my reading list, my Goodreads Brad Feld account has everything I’ve read in reverse chronological order.

This post is about biographies. I’ve always loved to read biography and expect that my 2015 reading diet will include a lot more biography and history than normal as it has caught my interest lately. I’m including company biographies in this post. I didn’t read many, but had a little Google obsession on this trip which you’ll see in a moment.

The order is in the order I read them (even though the Goodreads list is in reverse-chron order).

Boy on Ice: The Life and Death of Derek Boogaard: I finished this just before we took off. I’m not much of a hockey fan – my childhood team was the Dallas Blackhawks – but I was entranced by this book. I learned a lot about how hockey works, much of it distressing to me. The enforcer role was one I didn’t really understand and Boogaard’s story is a powerfully tragic one. The book is well-written and moves quickly, while painting a powerful picture of how hockey can really damage people.

How Google Works: Eric Schmidt (Google chairman, prior CEO), Jonathan Rosenberg (long time Google exec) wrote the trendy book of the year about Google. I knew many of the approaches and anecdotes of the book – and how Google works – from the many other things I’ve read about Google over the years. But having it in one place, organized conceptually, was worth taking another pass through it all.

Memos from the Chairman: I had high hopes for Ace Greenberg’s compendium of memos from his time as chairman of Bear Stearns, which coincided with massive growth and success for the company. While there was some cuteness in here along with a few things to reflect on, I was disappointed in how dull the majority of the book was. Maybe it was awesome in 1996 when it came out, but it felt slow and dated in 2015.

Einstein: His Life and Universe: Einstein is one of my heroic figures and Walter Isaacson  just nails it. If you are an Einstein fan or just want to really learn the full story, this is the book for you.

The Innovators: How a Group of Inventors, Hackers, Geniuses, and Geeks Created the Digital Revolution: If I hadn’t read the Einstein book, I probably wouldn’t have read The Innovators, but Isaacson had pleased me so much that I devoured this one also. This is Isaacson’s 2014 tome an a follow-up to his Steve Jobs book. It was good, but not epic.

Two Miserable Presidents: Everything Your Schoolbooks Didn’t Tell You About the Civil War: I originally saw this at my partner Ryan McIntyre’s house a few months ago when we were over for dinner. I Kindled it and dove in. I loved it – super easy to consume and a very playful way to learn, or relearn, some history. I’m planning at least one serious Lincoln biography in 2015 so this was a good way to get a taste of it.

The Virgin Way: Everything I Know About Leadership: Everyone knows that Richard Branson is cool, and iconoclast, a massive risk taker, and amazing successful. But he’s also extremely introspective and articulate. I’ve never met him or been to Necker Island, but plenty of my colleagues have. When I started reading this one, I felt like I was doing something obligatory to read the autobiography of one of our contemporary business legends, but I really enjoyed it and by the end was glad Branson had put the energy into writing this.

In the Plex: How Google Thinks, Works, and Shapes Our Lives: As with Walter Isaacson, I eventually get around to reading all of Steven Levy’s books (I read his epic Hackers: Heroes of the Computer Revolution in 1984 as a freshman at MIT and it has stayed with me ever since.) His Google book was awesome – much better than How Google Works. I learned a ton I didn’t know, especially about history that had either been ignored, glossed over, or repurposed. If you have any interest, relationship with, or curiosity about Google, this is the book for you.

Ada’s Algorithm: How Lord Byron’s Daughter Ada Lovelace Launched the Digital Age: I’ve read lots of articles on Ada Lovelace, but I’ve never read a comprehensive biography. The story was fascinating, especially when pondering what life much have been like in Victorian-era England and how much of any uphill cultural battle Ada Lovelace had. While we’ve got lots of challenges around gender still in our society, we’ve definitely made read progress in the last 150 years. This linkages to Lord Byron, Lady Byron, and Charles Babbage were fascinating and, in many ways, disheartening. Ada Lovelace was clearly a genius – I can’t even begin to imagine the amazing stuff she could have done if she was born in 1990 instead of 1815.

As a bonus, Amy and I have been watching the HBO Series John Adams and I’ve decided to start tackling biographies of American presidents and other American heroes of mine, like Ben Franklin. Look for some of this in 2015.

Happy reading.

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Dec 24 2014

My Recently Erratic World of the Gmail Spam Filter

Let’s start with a brief history of my investment-led fight against the perils of spam and my never-ending love of SMTP.

We were investors in Postini and my partner Ryan sat on the board. It transformed my life – with one minor change of an MX record some time in 2002 all the spam in my inbox disappeared. Well – it disappeared before it got to my inbox. Or even my server. The awesomeness of Postini was that it was the first cloud-based email anti-spam solution. And it was a beautiful thing that Google acquired in 2007 for $625m.

One of the benefits of our investment in Postini is a life-long friendship with Scott Petry. Scott is the co-founder of Authentic8, which we are also investors in. Scott also sits on the board of Return Path, which is run by another life-long friend Matt Blumberg.

Scott worked at Google for three years after the transaction for Dave Girouard (who used to run all of enterprise for Google and now is CEO of Upstart and on the board of Yesware with me) integrating Postini into all of Gmail’s infrastructure. We continued to use Postini as our spam filter (in front of Gmail) until Google transitioned all of Postini into the Google apps service.

You get the picture. There’s a nice thread through all of this SMTP, email deliverability, and anti-spam stuff in my world, both in investment and relationships. So I generally don’t think much about spam since in the past it just disappeared, or well, never appeared in the first place.

When I came home from my one month sabbatical in Bora Bora, I archived all the 3200+ emails in my inbox. If you missed my vacation reminder during that time, it said:

I’m on sabbatical and completely off the grid until 12/8/14.

I will not be reading this email. When I return, I’m archiving everything and starting with an empty inbox.

If this is urgent and needs to be dealt with by someone before 12/8, please send it to my assistant Mary (mary@foundrygroup.com). She’ll make sure it gets to the right person.

If you want me to see it, please send it again after 12/8.

On Thursday, 12/4, Amy decided to scan through her email so I went to the business center at the St. Regis in Bora Bora with her and did the same. I simply started at the top and “read / archived” each of the around 3,300 emails (using the “[” shortcut). I’m a fast reader so I skimmed the emails I cared about. Mostly I just played a video game with the [ key.I might have had a tropical drink while I was doing this.

I didn’t respond to anything and just ran this drill again early Monday morning to finish up. I then turned off my vacation reminder, had Inbox Zero, and got started again.

Yesterday, I had a weird feeling that I’d missed something that I heard about in another email thread. I was procrastinating from working on the final edits to my new book Startup Opportunities (yes – I’m doing that some more right now, but I’ve got a nice empty day in front of me) so I randomly checked my Spam folder in Gmail. I never, never, never do this so I was suprised when on the first page I saw a legitimate email. I opened it, clicked on Not Spam, and scrolled to the next page, where I saw another one. And another one.

I had 5,500 messages in my spam folder since I got back on 12/8. I went through all off them – it only took about 10 minutes. I found 39 legitimate emails. Not notifications, not email newsletters – but real emails sent to me by people I often get emails from. Here’s a screenshot of the legit ones.

Valid emails in gmail spam folder

I did my dutiful work and hit “Not Spam” on all of them. I was perplexed and talked to my friends at Return Path who gave me some feedback.

This morning, I had 433 messages in my Spam folder. This time, they all looked like they should.

Screen Shot 2014-12-24 at 7.36.51 AM

I’m hoping that this was only a temporary glitch in the matrix. However, I’ll be checking my Gmail spam folder on a daily basis for a while. Boo.

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