We Don’t Talk Enough About Money In Silicon Valley. No, Really.

“Look, I’m incredibly thankful for this industry. It made me a millionaire.” The person seated across the table from me went through a series of facial microexpressions as I said this — surprise, disgust, analysis and finally, calm. We don’t really talk about money in Silicon Valley. At least not in public in a personal way with near strangers. We *speculate* about people and wealth a shit-ton – based upon a company’s last fundraise, based upon current stock price, based on the market price of BTC – but we don’t really talk our own situations, challenges, learnings. When a notable exception occurs – Jason Hirschhorn’s post about selling his first company – it really sticks for me as important. Don’t values and community come from sharing experiences and being vulnerable together? I think so but then why am I getting nervous about writing this post? This is a fraught area of privilege, assumption, envy, fragility. I’m told I’m in a position of power even if it doesn’t always feel like it. I know I’ve got some reach for what I write, at least within a narrow community.

Over the past 20 years in San Francisco I went from negative net-worth grad student to Silicon Valley “Middle Class” (the 2%) to running a venture fund that, if we do our job, will ultimately put me in the 1% or better (in California the average annual household income of the 1% is an astounding $1.4m+). Over my career I’ve benefited from being in the right place at the right time, from being born TallWhiteMale and from working hard. 21 year old Hunter would be very happy to hear how 44 year old Hunter ended up, even if 44 year old Hunter is still a bit insecure.

[Deep breath] There are five conversations about money I’ve had with zero to a handful of people in private that I’ve been wanting to write about. [Another deep breath]

1. The Big Money Ball Bounces Semi-Randomly, Or At Least It Can Feel Like It

One of the things that’ll kill you is equating wealth with self-worth and constantly comparing yourself to your peer group. The money ball bounces too randomly around here and because of outsized returns from new ventures, being at the right company in the right role during the right few years can be worth $$$$$. Even though your equity is unlikely to make you rich, there are plenty examples of when it does to extraordinary levels. And it doesn’t always end up in the hands of diverse, hardest working or ethical people. We can – and should – continue working on changing that system, particularly with regards to pay gaps between the genders and between whites and underrepresented populations. But at a personal, human level you can’t let this eat you from the inside. Ensure you are treated fairly – never let an employer take advantage of you, make sure to get guidance on compensation, don’t be afraid to negotiate – but take a zen-like approach and reject envy. There’s always going to be some dumbfuck who lucked into a multimillion dollar payday. Don’t waste your energy on him.

2. Knowing There’s Another $20 In The Bank Never Stops Feeling Good

It would be an exaggeration to claim I’ve personally known poverty, but I have had zero dollars in my checking account and a negative net worth. It feels shitty even if the anxiety experienced was only a fraction of a percent that true struggle brings. It leaves a mark, one that you don’t forget. The easiest way to translate my own emotion is this: when I go to an ATM and take out a few $20 bills, there’s an accompanying endorphin surge tied to knowing there are many other $20 bills there for me if I need it. It’s like a low rent version of that Oprah story where she keeps a million dollars of cash on hand just to know she’ll never be poor again (or something like that).

What’s the takeaway from this parable? Just to realize that people experience – or are searching for – economic security in different ways based upon their own personal histories. And this influences in an emotional, sometimes irrational way, the types of decisions they make. When I hear “just start a company, you have nothing to lose” know it won’t ring as true to the realities many founders come from and what they need to overcome. Which brings me to…

3. Many People Are Supporting More Than Themselves. And Many Self-Made People Had Safety Nets.

I was lucky – my parents saved money for my college before my dad’s job disappeared in  a corporate downsizing. That salary never came back. Having four years of school paid for in full already put me in rarified air especially as I met more and more classmates who were drawing major student loans to make their education possible.

Now, as an adult, I also see people who are supporting their parents, or their siblings, a nephew, and so on. The compensation needs of these folks might be different than a 24 year old who still has some help paying the rent. It’s why we counsel founders to understand the situation of a potential employee when designing a compensation package (in ways that remain legal and appropriate). Because maybe someone needs a little more stability in the short-term to make the transition possible. And you lose out on great talent if you can’t at least have these conversations. Don’t assume everyone can just eat ramen and sleep on vesting options. People will make sacrifices to work at your startup – seed companies don’t (and shouldn’t) pay the same cash comp as a Google – but if you’re “one-size-fits-all” then you’re less likely to build a diverse team.

4. How Do I Give My Daughter A Great Life But Instill Values & Appreciation?

I signed my daughter up for the major airlines frequent flyer programs when she was born. Might as well start earning free tickets right? The other day she received a mailing to participate in a private test drive event for the new Volvo SUV. My five year old apparently has the marketing profile of a 32 year old upper middle class mom!

Caroline (my wife) and I raise our daughter in SF because we want her to have a sense of community. Caroline is especially important here through her day job leading Twitter for Good (Twitter’s philanthropy and volunteerism effort) and a myriad of personal nonprofit activities. We do a lot of things to expose our kid to the idea of service, to generosity, to diversity. But she also eats organic blueberries and has too frequent Amazon deliveries of books, arts & crafts and Lego kits.

San Francisco has real challenges in its growth but I get sad when I hear people talk about how they don’t want to raise a kid here because of the homelessness and inequality. These are what we need to take a hand in solving! We don’t shield our daughter’s eyes from it; we answer her questions about sidewalk tents. But still, she’s been to Hawaii three times already. Did I mention the organic blueberries – $6 for six ounces – what the fuck!

I’m open to suggestions on this one. We’re just trying our best to instill compassion, work ethic and citizenship.

5. At Some Point It’s About Giving It Away

This afternoon a second-time entrepreneur told me he, at founding, gave most of his equity in his current company to a nonprofit he cares about. That it motivates him each day more than if he was just creating an outcome for himself. I LOVE THIS!

It feels like something is changing – people around me are giving more to political causes, putting their name next to causes. At the fringes I’m hearing more people take pride in their philanthropy and exert social pressure to their peers to donate. Am I naively optimistic? Are the next generation of bitcoin millionaires going to look to buy fifth cars and third homes? Or will we have more people like Halle Tecco and the anonymous Pineapple Fund?

Personally, I’ve got a number in my head – if I can bank that amount everything else is going towards philanthropy. Today, as a family, our charitable and political donations are between $15k-$30k annually. That’s down a bit from when I was vesting Google stock quarterly and could donate appreciated shares, but it’s still an ok percentage of our combined annual salaries. The tech sector is in a privileged position – can our generosity match our accomplishments?

[exhales]

Ok, those are the five $ conversations I have in private or have been afraid to have at all. Not sure I used all the right words or framed all the issues correctly. If there’s something I can learn more about or expose myself to a broader point of view, I’m open to feedback. Thanks!

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:

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.

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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.

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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 proposals 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.

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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?

DonAdams

2018’s Word of the Year: Coalition

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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.

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“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.