Books I Read In 2018

Not gonna lie. All those “Books of 2017” posts made me kinda wishing I kept a list of my own. No way for me to go back and figure out what I read last year (I give away most books once I’ve completed them) so instead will make this a living post, where I add as I finish. If we generously start 2018 on 12/26/2017, here’s what I’ve read so far in reverse-chron order:

10) Bad Stories: What The Hell Just Happened To Our Country – Steve Almond [non-fiction]

All the feels. This book left me nodding my head but did little to mitigate my anxiety about the combination of forces challenging our society today.

9) Better Off Without ‘Em: A Northern Manifesto for Southern Succession – Chuck Thompson [non-fiction]

Yeah, uh, the title says it all. Part bomb-throwing humorist, part OpEd, part nutty screed.

8) Janesville, An American Story – Amy Goldstein [non-fiction]

Ethnographic study of a Wisconsin town in transition that makes you feel what “economic insecurity” feels like outside of its too-broad application in the 2016 election punditry. Beginning with the 2008 closing of an auto assembly plant that was already thousands of jobs smaller than during America’s industrial peak, Janesville is a pop in the mouth and tug on the heart. Here’s the NYTimes review from April 2017.

7) Brotopia – Emily Chang [non-fiction]

A year after Susan Fowler’s blog post we’re now at the point where talented writers like Emily can look at the “tech bro doing wrong” stories from a 10,000 ft level to help frame why we got here and some advice for how we get to a better place. It’s easy to read a book like this, encounter the most grievous examples of sexism, and shrug “that’s awful, but I’d never do that.” It’s more difficult for even well-intended men to know there’s still something (more likely *somethings*) we do that makes tech a less inviting place for women, and to resolve to listen, ask, learn and evolve.

6) Red Sparrow – Jason Matthews [fiction]

A friend recommended this on Twitter and I saw it was soon to be a movie starring Jennifer Lawrence, who I generally like. Unfortunately, I forget that I don’t really love spy novels and the author used the word “sexpionage” non-ironically. So, yeah, maybe don’t read this one.

5) Against the Grain – James C Scott [non-fiction]

So, that whole thing about humans moving from hunter/gather to fixed agrarian society, and how it was awesome? Well James Scott has a bit of a contrarian viewpoint. He makes the argument that populations weren’t necessarily healthier and better off for domesticating themselves around crops. And that rather than these configurations giving rise to the stability of nation-states, that it was kinda the other way around. That nation-state needed agrarian populations to produce food for the kingdom, that this food could only be effectively harvested through use of slaves or indentured classes and that grains weren’t necessarily the *best* crops but rather than best crops for purposes of taxation. Read this if you’re into societal development stuff.

4) Finding Flow – Mihaly Csikszentmihalyi [non-fiction]

You know when people talk about “being in the flow” – the stretches where you feel most alive and creative? When time passes without being aware of it? When you’re locked-in on a task that’s both hard and enjoyable? Mihaly is the grandfather of that concept. In Finding Flow, written 20 years ago, he further explains the concept of flow but also how to more regularly optimize for achieving flow in your everyday life. It’s ~150 pages (about 1/3rd of which are skimmable).

3) A Uterus Is A Feature, Not A Bug – Sarah Lacy [non-fiction]

A “personal” one for me as we’ve known Sarah and her family for a quite a while, but really bonded over becoming parents around the same time earlier this decade. Half-memoir, half-reporting, this was one where I didn’t want to let the year end without reading given my hope that 2017 was a turning point in how we think about gender in technology.

2) Lovecraft Country – Matt Ruff [fiction]

I read very little fiction but when I saw that Jordan Peele optioned this book to turn into a HBO series….! Historical fiction + sci-fi + sociology of American racism I imagine this read is a bit too “pulp and cult” for some but I really enjoyed it.

1) Reset – Ellen Pao [non-fiction]

Bought this one after reading a stunning excerpt in New York magazine. I’d met Ellen a few times previously, but wasn’t until this past year that I’d say we became “friends” as we find our daughters in the same school, and more reasons to collaborate given her return to venture. Ellen used her voice to raise a bunch of systemic issues in our community and it’s hard not to see a straight line between her lawsuit and the #MeToo movement of 2017.

In 2018, Focus on Quality of Decision Over Quality of Outcome

We’d barely made our first venture investment when I tattooed Homebrew’s logo deeply into my right shoulder. What did this moment represent, besides a strong conviction we’d never rebrand? It wasn’t a victory lap, that’s for sure, because it takes many years to prove you’re great as a VC. No, it was memorializing the decision to *start* Homebrew, independent of the eventual quality of outcome. Of course I believe that Satya and I have the potential and capacity to be excellent investors and now approaching our third fund there’s ample evidence that at least we’re not terrible and, hey, we might even be good at this. But that wasn’t what I was capturing when that needle jabbed into my skin, depositing a little black ink each time. What I was capturing – what I was owning and memorializing was that it was a really good decision.


Pale, hairy shoulder described above

There’s a tendency to wait for an outcome and then use that data to pronounce whether the decision itself was a good one or a bad one. Careers, investments, relationships – was it a success? Then it was a good decision, right? Oh it failed? Bad decision.

Not necessarily. Maybe it was the right decision, just a bad outcome. You should make that decision 100x more times, because the probability or magnitude of good outcomes are actually in your favor. In any system with relatively low cost of failure and repeatable game scenarios, it would seem that getting the decision right is actually what matters.

I meet people early in their professional lives who spend too much time calculating the anticipated outcome versus understanding why they were making the decision in the first place. This title versus that title. This salary. That equity grant. And so on and so on. Trying to reverse engineer the right decision using lists of pros and cons, versus an understanding of who they are and who they want to be. My advice to them is usually pretty simple – answer this single question and don’t let fear hold you back from making the right decision. If you build that muscle memory and apply it at each junction, your career will be fine. And you’ll end 2018 in an even better place than you’re starting.

[I use “place” symbolically, but you know, if you’re literally working at a place that you don’t like and think you want to make a better decision, many Homebrew companies are hiring]

Evolutionary Biology: Movies are Slow Humans. YouTube are Fast Guppies.

When Wired claims YouTube is the world’s best film school available, I would agree, but suggest they’re actually thinking too narrowly in their explanation. Writer David Pierce steps us through what he calls “YouTube Film School,” a loosely organized community of content on the platform which unpacks and analyzes the craft. Pierce believes “the best channels are the ones that teach film as an art form, that help you understand why a particular cut or camera move makes you feel the way it does.” And while there is a tremendous amount of YouTube content supplying technical analysis, critique and breakdowns, to focus on these videos alone ignores the most wonderfully disruptive aspect of YouTube: the 100x faster cycles of content creation over traditional media.


Compare the evolutionary cycles of humans versus guppies. Humans evolve v e r y  s l o w l y, while guppies can experience rapid evolution, seeing meaningful change in just several cycles. Let’s stretch this comparison to movies versus YouTube. Innovation in movies travels slowly because of production constraints: expensive, long development time periods, delays before public release. We think about cinematic influence in generational  timeframes – Scorsese was influenced by Citizen Kane and Tarantino was influenced by Scorsese!

Now the guppies – YouTube videos. Any new trend in YouTube content will be discussed, mimicked, iterated, improved and remixed over just days or weeks. It’s much closer to the “view source” era of website creation than it is to film. During my time at the company I was consistently amazed by how quickly formats would spread and, mostly, how willing the creators were to share their tips and techniques.

In some ways you can think about these differences impacting design principles for systems depending on the outcome you want to bias towards. Systems which have evolutionary friction, prevent easy cut/copy/paste, restrict creation to a small group of individuals – these are likely to be more static and predictable but produce a certain type of complex work. On the other hand, if you support remixing, sustain longtail content and foster collaboration, your system will be more chaotic but also evolve faster and more broadly. Professionally I spent my operating years in the latter (Second Life, AdSense, YouTube) and *loved* the creator population we supported.


Should Regulators Force Facebook To Ship a “Start Over” Button For Users?

I don’t really understand most of the calls to “regulate” Facebook. There are some concrete proposals on the table regarding political ads and updating antitrust for the data age, but other punditry is largely consumer advocacy kabuki. For example, blunting the data Facebook can use to target ads or tune newsfeed hurts the user experience, and there’s really no stable way to draw a line around what’s appropriate versus not. These experiences are too fluid. But while I want keep the government out of the product design business, there’s an alternate path which has merit: establish a baseline for the control a person has over their data on these systems.

Today the platforms give their users a single choice: keep your account active or delete your account. Sure, some expose small amounts of ad targeting data and let you manipulate that, but on the whole they provide limited or no control over your ability to “start over.” Want to delete all your tweets? You have to use a third party app. Want to delete all your Facebook posts? Good luck with that. Nope, once you’re in the mousetrap, there’s no way out except account suicide.


BUT is that really fair? Over multiple years, we all change. Things we said in 2011 may or may not represent us today. And these services evolve – did we think we’d be using Facebook as a primary source of news consumption and private messaging back when you were posting baby photos? Did you think they’d also own Instagram, WhatsApp, Oculus and so on when you created accounts on those services? We’re the frogs, slow boiling in the pot of water.

What if every major platform was required to have something between Create Account and Delete Account? One which allows you to keep your user name but selectively delete the data associated with the account? For Facebook, you could have a set of individual toggles to Delete All Friend Connections, Delete All Posts, Delete All Targeting Data. Each of these could be used individually or together to give you a fresh start. Maybe you want to preserve your social graph but wipe your feed? Maybe you want to keep your feed but rebuild your graph.

Or for Twitter: Delete All Likes, Delete All Tweets, Delete All Follows, Delete All Targeting Data.

Or for YouTube: Delete All Uploads, Delete All Subscriptions, Delete All Likes, Delete All Targeting Data.

The technical requirements to develop these features are only complicated in the sense of making sure you’re deleting the data everywhere it’s stored, otherwise every product already support “null” state – it looks very much like a new account. This leads me to believe that the only reason these features don’t exist today are (a) it would be bad for business and (b) actual or perceived lack of consumer demand. Anecdotally, it feels like (b) is changing – more and more people I know wipe their tweets, talk about deleting their histories, and so on. Imagine the ability to stage a “DataBoycott” by clearing your history if you think Facebook is taking liberties with your privacy and such. This is what keeps power in check.

So regulators, you want to help consumers? Don’t prevent tech companies from building the best products they can. Instead require them to consistently provide an escape hatch by giving their users the ability to START OVER without having to fully delete their accounts.

Request For App: Calls I Need To Make

Here’s what I want.

The ability to add a phone number/contact to a list. With one-touch dialing from that list entry.

The ability to set variables at the contact/# level that are either persistent or apply only to this call. For example, time zone or priority, or expected call duration (how long I need for the call).

Default is for the list to be sorted “manually” (probably reverse chron of entry – Last In, First Out) but also apply “smart sort” based upon an amount of time I have to make calls before next meeting, what part of day it is in each contact’s home time zone, and so on.

After making this prioritization decision, I want to be able to press “Play” and have the app automatically call the first number. If it connects, we start talking. If it doesn’t connect, it moves to next number in my list (figure there’s also a “skip” command).

Maybe there’s a feature that texts the person first to say, “Hunter is available to chat, reply Y if you’d like him to call you” or something like that.

Basically it’s a To Do App that’s optimized solely for phone calls.

Does anything like this exist?


2018’s Word of the Year: Coalition

Screen Shot 2017-12-21 at 11.09.01 AM

Type “coalition” into Google Trends and you get a disturbing result. A 12-year decrease in interest. It’s anecdotal but easy to also map this graph to the increase in political and societal tribalism. Moving away from the idea we can work together even if some of our beliefs are in conflict.

Screen Shot 2017-12-21 at 11.06.25 AM

“We might not agree on everything but can we agree to work together on this?” seems like a pretty powerful and potentially effective solution. One that most of us learn informally during childhood. “Politics makes strange bedfellows” is another idiom I recall hearing often when studying governance (turns out its origins are from Shakespeare’s Tempest).

Going into the next year perhaps we can all be a little more open to finding the common ground in our relationships.

What I Think We’re Talking About When We’re Talking About What We Can’t Talk About

It’s no longer worth it to vocalize controversial beliefs. Silicon Valley has become a PC echo chamber. I can’t say what I think without fear of reprisal.

These are not convictions I personally hold but ones which I’ve heard expressed with increasing volume from people I know well and people I don’t know as well, in public spaces and in private conversations. Often these sentiments are voiced by 30 – 50 year old white men (and women) of economic privilege. I say this not to discredit their feelings or observations but because (a) it does seem to be relevant and (b) that’s the group which dominates my own social circles, which means that my POV is constrained by limitations in perspective.

But obviously since you’re reading this, I felt confident enough I had something to say that I’m wading into this conversation. Not to dissect a blog post. Not to provide sufficient evidence that anyone is right or wrong in their assertion. And certainly not to call out any one person in particular. Rather, here’s my grand unified theory as to why this We Don’t Tolerate Unpopular Beliefs Any Longer feeling exists.

Tech is No Longer the Underdog And We Still Haven’t Fully Grokked What Power Means.

The oversimplified historical founding myth of the technology industry was that a critical mass of nerds found themselves in SV and built a beautiful meritocracy, where good ideas and data win the day. And where wealth was almost a bug not a feature – a byproduct of being right, rather than the goal itself. Of course much of this is false but it’s powerful. Fast-forward to modern day and you have an industry amassing tremendous amounts of power and money which hasn’t yet fully come to grips with these circumstances – the responsibility, the gravitas. So we can see ourselves as well-intended underdogs while the reflection in the mirror is no longer as simple. It’s sorta like when people complain that it matters what the President says – that there are no throwaway lines when you have that role.

Information Broadcast Means More People Have Voices and We’re More Often Speaking to People Who Don’t Know Us.

Maybe segments of the population always had strong reactions to controversial ideas but those people (women, non-whites, the poor) didn’t have a microphone. Perhaps nothing has changed other than giving voice to a broader set of the population? This is a good thing by the way and does lead to the increased exposure and examination of racism, classism, misogyny, and so on. Some of those “unpopular ideas” are just plain wrong, lead to real harm for people and work only to preserve an existing power structure (which actually *constrains* innovation versus allowing new ideas, voices and people to rise).

Additionally, broadcast technologies allow us to reach larger groups of people than ever before. People who often don’t know the speaker or who are receiving a snippet, our of context. I’ve had words of mine ‘blow up’ in communities of people who don’t know me – it sucks and doesn’t feel great, but in some ways it’s the tradeoff for using these tools right now. If the tools and our desire to use them constructively continue to evolve, it’ll get better (hopefully).

There’s an Outrage Economy

Because there’s a surplus of content but finite attention, one currency of these broadcast platforms is emotion, and outrage is a strong magnet. “RT With Comment!!!!” SNARK GETS LIKES. Any white male tech worker who fucks up is either a “Google Executive” (when he was really just a middle manager) or a “Tech Bro.” It’s weary, it’s tiresome, it’s unnecessarily broad and it divides people. Try not to participate.

Opinions Are Like Assholes. And Groups of Assholes Are Your Tribe.

Since when do you need to have an opinion or be an expert on everything? Sometimes you need to STFU. But of course one of the best things about the internet is the ability to find a critical mass of people who think the same way you do. So having opinions actually increases the surface area of your ability to be part of a group, to be accepted, to feel secure. These are very basic human needs and emotions. So there’s opinion inflation where it feels better to have one and find your tribe.

You’re Supposed to Be Willing to Take Heat for a Belief. 

Ok, unlike the previous concepts this one isn’t specifically linked to the technology industry but somewhere along the way we wanted there to be zero cost to have an unpopular belief but I’m not sure zero cost is optimal. Maybe a bit of friction is what forces you to consider why people disagree with you? Maybe a bit of friction helps you prioritize what’s worth your time and energy? Maybe there are hills worth dying on and hills that aren’t even worth scaling? Oh wait – hot take: because social spaces have been primarily built for us to react with support (LIKE, FAV, THUMBS UP), we’re now skittish and soft when it comes to DISLIKE, THUMBS DOWN. There, I knew I could find a tech angle.

Now, let me transition to the responsibilities I think we each have as part of the SV community.

Softer Eyes

When someone says something you disagree with or you see a tweet that sounds dumb as fuck, what if you read the whole thing in context? Or assumed the person behind the idea isn’t a terrible racist, SJW, tech bro, whatever but a person. A work in progress. Someone who probably has some redeeming qualities too. Doesn’t mean you need to engage them. Doesn’t mean you need to be their buddy. Doesn’t mean you need to tolerate despicable beliefs, but let’s try to separate limited worldviews or naïveté from truly horrible individuals. [note: I’m a bit of a hypocrite here because ideas such as “not all Trump voters are racists but they didn’t find his racist beliefs or enablers to be disqualifying for their support” personally resonate with me. So yeah, it’s an aspirational responsibility but tough to implement fully.]

You Don’t Have to Fucking Talk About Everything to Everyone

You’re not a fucking expert about everything. Maybe sometimes it’s ok to listen, to read, to evolve and experience versus pontificating. Communication is listening, not speaking. Your desire to share might be rooted in your own desire for attention not always some joyous quest for knowledge or intellectual rigor. “I tweeted something dumb and now people are mad at me.” The problem might not be the second half of the sentence.

We Can Disagree About Many Things and Still Be Friends

Yeah, it’s possible. We don’t have to be ideological perfect matches in order for me to work with you, respect you, or be interested in your ideas.

Do the Work to Understand Why You Might Be Wrong

It’s so healthy to ask someone why they believe what they do – not because you’re looking for a way to attack them to win the argument but because you want to inhabit their eyes for a moment. Present your point of view and ask them where they believe you’re wrong or why they feel differently. Never assume your truth is an unqualified truth.

There. This is what I think we’re talking about when we’re talking about what we can’t talk about.