Startup equity benefits your boss, not you

So a startup wants to hire you.

They’re probably offering you two major pieces of compensation beyond the typical benefits and mundane startup perks:

Cash money, which is useful for many things.

Equity in the company, which is useful for nothing right now, but could turn into something later.

What they’re not telling you is that the equity isn’t for you.

It’s for them.

In the beginning

Equity is worth less than a 12-pack of toilet paper at the beginning. For equity to take on value that you, as a startup employee, can meaningfully enjoy, someone has to decide they want it.

These “liquidity events” take on two general forms:

An acquisition, where a larger company decides the talent and technology of a startup are worth money.

An IPO, where a startup morphs overnight into a stodgy, corporate, publicly-traded thing.

For certain hot startups, you can go and sell your stock through other means to interested buyers, but the above circumstances handle the majority cases.

Eric Ries, of Lean Startup fame, defines a startup as “a human institution designed to create a new product or service under conditions of extreme uncertainty.”

That was my emphasis. See, you have to remember they’re offering you equity in extreme uncertainty.

Here are just a handful of filters standing between a startup and its liquidity:

  • The startup can hire the right team
  • The startup can keep that team
  • A compelling product is created
  • A scalable business strategy is discovered
  • An audience for the product is successfully persuaded to use it
  • That audience grows to a meaningful number
  • Competitors fail to steal that audience
  • The startup is managed well through multiple stages of growth
  • The technology infrastructure scales well through multiple stages of growth
  • The startup doesn’t run out of money
  • Investors can be persuaded to give the startup more money when needed

I’ve seen estimates for startup failure going as high as 90%.

Whatever the number is, let’s be real: it’s not on your side. You wouldn’t take salary in lottery tickets. But that’s exactly what a startup is offering you when they offer you equity.

Uncertainty abounds

But let’s say it all works out for the startup. Who’s to say it’s going to work out for you?

Equity is typically doled out according to a vesting schedule. You have to stick around for a minimum period just to get the chance to buy it all.

Satisfying the schedule assumes that:

  • Your boss’s management style is healthy and agreeable
  • Your growth trajectory in the organization matches your needs
  • No major life events require you to relocate
  • Your work environment is a safe and healthy space
  • Your passions don’t shift to a different line of work
  • You maintain sufficient health to continue working

And in many cases, you’ve got to have money in the bank in order to purchase your equity when you decide to leave. I don’t have to enumerate all the reasons why that might not be feasible during the 90-day window where the purchase is allowed.

When you layer in the personal uncertainty against that of the business, the odds of a payout grow even slimmer.

But what if I’ve got the golden ticket?

For all the failures, there will be some startups that succeed.

Let’s walk through who wins when that happens:

  1. The founders

  2. The early investors

  3. The later investors

  4. You, maybe

The founders and major investors are going to get the lion’s share of the winnings, here. Together they own the majority of the company.

Even as an early employee, you will get less than one percent of the takings. Depending on how many times the founders went back looking for more money, it might be far less than one percent.

So a startup has to exit big for your lottery ticket to pay you out meaningfully.

That’s its own uncertainty continuum. Maybe you’ll get enormous IPO lucre, the stuff of Google millionaires.

Sometimes the casino pays out.1

But more likely, you’ll have something a lot more modest from your tiny slice of the company.

Then, who’s this for?


This is for the leadership of the startup that’s trying to hire you.

This lets the leaders incentivize you by giving you a share of the company’s successes. Which is an excellent carrot. It can be fun2 to work knowing that less than one percent of the value you help create will be returned to you in the event of success.

It also allows the company to give you less of their precious cash.

But make no mistake: these are their benefits, not yours. Money that only has a small percentage chance of existence isn’t money. It’s a securitized casino game. Which is fine. But treat it like that.

Don’t confuse it for compensation.

Alternatively, create your own exit

You can keep playing the silicon slots. And maybe after enough pulls, the machine will pay out.

But there’s another way out. After a few turns around the Silicon Valley merry-go-round, you’ll develop:

A network of people who know and trust you.

A history of work you’ve accomplished.

Experience that helps you create better stuff and avoid pitfalls others fall right into.

What do you do with that? The part they don’t tell you about is that you’re getting a pretty one-sided deal when you sell a startup your time.

Let’s do some math

Consider this scenario:

$110,000, a reasonably generous startup salary

55 hours a week, a common average workload in Silicon Valley

For 49 weeks a year

That works out to $41 an hour. $43, when you consider the cost of replacing your health insurance3 and a few free lunches a week.

On the other hand, if you leverage your startup experience to freelance and bill just $80 an hour, you get to average 40 hour weeks, take three whole months off per year and still keep that $110,000 income.

You could spend all summer fucking around.

If your skills and network are juicier, you can bill more, get even more time back in your life, or make more money.

The real options

Point is, you don’t need to wait around for someone else to make it rain. If you’ve got the skills to work for a venture-funded startup full-time, you’ll eventually have the option to sell that time more selectively and create your own payday.

Freelancing isn’t for everyone. It’s got uncertainty of its own. But in a realm of uncertain outcomes and abundant venture funding, that’s the one you control most.

  1. But even when it does, there’s often an asterisk attached, like a minimum period before you can sell. But that never goes poorly or anything. 

  2. For certain definitions of “fun.” 

  3. About $300 per month. Thanks, Obamacare! 

Y Combinator and the negative externalities of Hacker News

Hacker News is a crown jewel of Y Combinator, Silicon Valley’s premiere startup accelerator.

Hacker News benefits YC in a few ways:

  • It’s an account system for applying for funding
  • As a news aggregator, it lets Y Combinator get in front of tons of potential founders during each funding cycle to solicit applications
  • It’s a captive audience before which Y Combinator’s portfolio companies may post jobs and attract talent

Hacker News activity also provides context for funding decisions:

The first thing I notice when I look at an application is the username it was submitted under. If it’s one I recognize for making thoughtful comments on Hacker News, I give the application extra attention.

So you’ve got a tool that handles logistics, juices deal flow, and captures talent. How’s Y Combinator doing with all that?

Their portfolio is valued in excess of $30 billion.

Hacker News has been central to that rise: it launched in 2007, bearing witness to every startup launched in the portfolio since. As Y Combinator’s star has risen, user engagement has matched.

It’s hard to imagine one without the other. Hacker News is YC, for the vast majority of people who will interact with YC.

There’s just one problem.

Hacker News is a cesspit

For some, Hacker News is a fantastic place for making friends and getting the word out about a new essay or product.

But get to know someone from a marginalized background who also works in tech. Ask them privately what they think of Hacker News—as I have in preparing this post. Almost always, the response starts with one word:


But it gets worse. One sentiment I often hear echoed:

I wish I could share my male colleagues’ excitement for the page views, but after having two posts on the home page of HN, I only sigh heavily knowing the onslaught of the trolls is incoming.

Another comment sums up how HN feels to outsiders:

They’re terrible to anyone who doesn’t look/act/believe like them.

Hacker News has developed a reputation for toxic sexism and other insensitivity toward folks outside the Silicon Valley in-group of white, upper-class men. But you don’t have to take my word for it. Before we get to Y Combinator’s duties to correct these problems, let’s do some show-and-tell.

I’ve been cataloging some of the nasty, ignorant stuff that sometimes passes for discourse on the site. Here’s a tiny sample.

Now, you might look at these comments and think “welp, that’s just how the internet is.”

But that’s not good enough.

Y Combinator has built thirty billion dollars of value at least in part on the community it has created in Hacker News. YC’s new chief, Sam Altman, asserts: “Sexism in tech is real.

Yes it is, Sam. And you permit it in your own backyard every single week. If we’re going to have a conversation about how tech marginalizes, we need to be honest about our roles.

Y Combinator has a role to play

It’s wrong to profit from marginalization. Y Combinator cannot continue this practice if it hopes to exercise anything approaching leadership on this issue.

I renew my calls to Sam Altman and Y Combinator’s leadership to expound a Code of Conduct for Hacker News. These issues persist, in part, because the organization has yet to draw a line in the cultural sand.

It is the height of hypocrisy to claim that sexism and discrimination are problems while leaving unchecked one of the most obvious sites of infection for those ills in our industry.

I renew my calls to Y Combinator’s partners to be active participants in its community—and champions for its most underrepresented constituencies. I know these partners to be men and women of conscience and principle. For that reason, their silence is all the more deafening.

The debates in this forum are important and most of the more heated arguments seem to favor exclusion. Seeing tech’s finer luminaries step up and argue that yes, our industry’s exclusion problems are real, consistently, would make a big difference.

After providing clear guidance for what kinds of comments are acceptable to its values, YC must fund a means of consistent enforcement when content is posted outside those bounds.

Finally and most importantly: Y Combinator must publicly accept its complicity in building and maintaining a business asset with these negative externalities. Algorithmic adjustments behind the scenes are insufficient. A lone moderator without prestige is insufficient. Opacity of policy is unacceptable.

YC must submit to accountability for improvement. The Hacker News benefits of discussion, fellowship, networking and content distribution should be open and inclusive to all.  And I’m not the only one who thinks so.

To quote Sam Altman:

“We—the tech industry as a whole—need to fix this.  Most importantly, it’s an ethical issue.”

If there’s a problem with marginalization in tech, and industry players are obliged to address it, it follows that the one toxic territory completely under Mr. Altman’s control is most subject to these duties.

So. What’re you waiting for, YC?

Special thanks to @jcoglan for inspiring the title of this post.

Why we fight for tech diversity: the stakes are only everything

“We’re gonna change the world.”

This bit of cheerleading is so overused in startup circles that it’s lost any meaning. It feels like every team, whether they’re selling hotel bookings or the next big social product, has deluded themselves into saying it aloud.

But there’s a reason it keeps being repeated.

Give me an internet and I shall move the earth

The internet is a communications medium that spans the entire planet. Billions of people use it. Because of this, the internet has dramatic influence on culture and commerce.

The rise of the internet has brought entire industries—think newspapers—to the brink of destruction. It has destroyed once-mighty businesses—think Blockbuster.

The destruction is a function of changing how information reaches people. Newspapers were once the most efficient and cost-effective means to sync people’s brains with current events.

Today, the hours necessary to print and distribute a paper lag behind the seconds necessary to receive and review a few tweets. The costs of printing are astronomical compared to moving a few bits around.

Another example: Amazon’s destruction of retail.

The retail game used to serve two purposes: purchase decisions and purchase fulfillment. You entered a store a to learn about something and if you felt good about it, you bought it.

Amazon provides, for some classes of product, a superior solution for making purchasing decisions. Thoughtful product descriptions and user reviews usually trump whatever employees can give you in the average store.

Because Amazon can address your purchasing decision in your home, it doesn’t have to build millions of retail outlets to serve a worldwide audience. While they lag behind retail in fulfillment speed, their efficiencies in not maintaining stores often allow them to make up for it in their pricing.

The internet is a powerful cudgel. Just ask Borders or Blockbuster.


Communication is only part of why this all works, though.

We had worldwide communication for a few decades. What’s different now?

We’ve also got software.

You can now build an automaton that will happily serve five customers or five million. Traditional businesses had to hire more and more people to keep pace with their success. Not so in the 21st century.

Consider the Netflix example.

They’ve built a system that heals itself when damaged. Entire chunks of Netflix infrastructure can go offline. Automation will identify the fault and compensate by re-routing to backup systems, without having to summon any human actors.

So you can reach anyone in the world. And, within certain problem domains, you can scale more cheaply than any other business in history.

If the internet is a cudgel, software enchants it with magical powers.

Everybody wants to rule the world

But why the fight for a diverse technical workforce?

You can now reach billions of people.

You can now scale a business to serve, well, all of them. If you’re clever.

What this means is that an unprecedented stack of power exists in the world.

But so far, that power is controlled by a very narrow subset of the human condition.

Google, Facebook and Twitter. Three titans of the internet. Billions of dollars, billions of users. Global impact.

Dominated almost entirely by white men.

Sometimes, when a startup says it’s going to change the world, it ends up being right. I don’t know about you, but if someone’s going to change the world, I’d like them to understand a little about my place in it.

Now, don’t get me wrong. Some of my best friends are white guys. But when only one caste has access to power and global impact, this means that the solutions built might not consider the needs of people who come from other backgrounds.

When only one group can access this prosperity, entire generations in other groups see an ever-widening gap in their income potential and social mobility.

There’s a lot of work left to perfect the human experiment. We’re only going to succeed with lots of help.

But, so far, the class of work with the largest potential for impact is the most exclusive and least diverse.

That’s a goddamn waste of potential.

And it’s why we fight.

The least Twitter could do

Today, as part of a press stunt, Twitter CEO Dick Costolo and CNBC invited Twitter users to ask questions with the hashtag #askcostolo.

A significant chunk of tweets on that tag concerned abuse and harassment on Twitter. This problem disproportionately affects marginalized groups.

Concerns around harassment were not substantively addressed. Twitter seems helpless to stop the madness. Maybe it’s because their team is so overwhelmingly not comprised of the marginalized groups I mentioned.

Policing a global community of Twitter’s scale is tough work. No one knows how to do it yet. But protecting users from abusive content is a software problem.

Here’s a handful of things Twitter could be trying to protect its users. Allow users to optionally:

Block all users whose accounts are less than 30 days old

This is easy—it takes an arrow out of the quiver of serial harassers who use alternate accounts generated as needed.

Block all users whose follow counts are less than whatever threshold users set

Google used the social proof of “back links” to establish credibility and ranking for content over 16 years ago. This is old hat by now. Users should be able to block anyone who can’t convince other people to follow them.

Rings of followers created just to subvert this will have to be detected.

Again, hire a Google engineer. They’ve cracked this one.

Block new users whose @replies include any words the user decides

Users who are on the receiving end of harassment face startlingly unimaginative adversaries. The  same slurs and threats are used over and over. Brand new account with no followers using the n-word? Block!

That’s stupidly easy to express algorithmically.

Block any user who has been blocked by more than N people I’m following

Let’s also share the load. If all your friends block someone there’s a decent chance you’ll want to also.

Auto-blocks are opaque

There should be no feedback when a behavior triggers these measures. The harasser should believe that everything is working as normal.


This is, at best, a box of bandaids. But it arms every user with substantially more tools than they have today to control and enjoy their experience with the platform.

A company that produces a turd of an iPhone app with over 30 dedicated engineers can surely spare a couple souls to work on basic content filtering mechanics.

Savor the magic—then destroy it

Any sufficiently advanced technology is indistinguishable from magic.

This is Arthur C. Clarke’s third law of prediction. It’s one of the most important truths in the human condition.

Consider a reasonably literate resident of the 1500’s. Suppose they fell through time to our present day in 2014.

Let’s further suppose we showed this person a tablet computer. The mere act of illuminating the screen might be mind-blowing on its own.

But then we whip out the camera app, or do some video conferencing, or load up YouTube. Imagine our traveler’s response.

To us, the tablet is fun but nonetheless comprehensible. We understand it as something that fits within our world and expectations.

The traveler, meanwhile, knows nothing of the tablet’s internal workings. No understanding of radio, electricity, optics, or signaling. To say nothing about programming or microprocessors.

The implementation details are so outside the traveler’s grasp, any explanation—from Capital-G-God to extremely thin gnomes—might be viable. It’s magical.

Target lock

The traveler from our thought experiment has certainly gone off the deep end.

Though you and I are unlikely to discover any artifact with the same magical freight to our 2014 brains, magic still persists all around us.

The reason is simple: the brain is a finite container in a world of near-infinite knowledge. You cannot possibly know the implementation details of every single thing that affects your world. We might be quite lucky to understand even a small portion of how our lives work on a deep level.

We walk past technologies, businesses and structures of power all the time, their inner workings concealed from view. Often quite deliberately.

Much of the time, you don’t care. There’s so much competing magic.

Other times, though, the magic snags. Either through delight or envy or rage,  the magic captures your imagination entirely. For me, these moments have always been technological.

Computers of all sorts, internet technologies, software.

For others, the magic might be musical, visual, even commercial.

Whatever it is, it’s a hook in your mind. A register on your sense of curiosity that’s hard to let go of.

If I had a hammer…

Once the snag happens, you’ve got a couple options. You can bask in the glow—or seethe in the face—of the magic forever.

Or you can pull out a hammer and chisel, get to work.

Your mind is a machine optimized for processing patterns. Whatever your magical target, it has patterns of meaning waiting to be consumed. Whether basic laws of physics or the notes in a system of music, all that exists has a pattern that your mind can chew on.

I mentioned physics, so spoiler alert: on the grand scale of human achievement, what I’m describing is an enormous field called science.

Any amount of time spent critically analyzing the subject of your magical obsession will yield scraps of pattern you can glue together later.

More time, more scraps. More scraps, more complete patterns.

Burst the piñata, build a new one

Once you have a few complete patterns in your mind, the equation shifts.

It becomes possible for you to conceal your own implementation details. It becomes possible for you to make magic.

And from magic—from your unique information—comes power.

The world’s knowledge is not something you can fit in your head. But that’s true of everyone else, too. That’s the advantage. So while you can’t know everything, you probably can know anything, with enough persistence.

Your book of spells awaits.

You are already a cyborg

“What is the internet?”

The immediate, obvious answer: it’s a big tangle of computer networks.

Which it is.

But that’s not really the point. It’s like describing a restaurant as a room with chairs in it. Technically true, entirely misses the good bit.

The internet is us

And we are the internet.

The way it worked in the past was you went into a space and a handful of other people did too. Some spaces were about having a conversation. Other spaces were about learning or selling.

Meaningful exchange between people required shared space.

What’s interesting about the internet is its potential to define  a single shared space as anywhere on the planet.

People and machines

When it comes to exchange between humans, the internet is a sort of hyperspace. The energy cost to you to move data across a room is about the same as moving it across the planet.

In this hyperspace, it’s also cheap to construct, test and maintain machines. Software is digital machinery that inhales data, stores it, transforms it, and vends it back.

Since software is so cheap, it’s dominant in hyperspace. There are many more machines than people. But in the end, the machines’ only role is to relay existing data. They’re not reliable or interesting sources of new data1.

For that, we need people. It is the humans who take vacation and baby photos and load them into Facebook. The humans capture thoughts and disgorge them into Twitter. The humans write stories, make movies, record songs and load it all into machines who dutifully distribute them to anyone who asks.

And we can’t get enough of it.

Join the collective

A cyborg is an organism built as a composite of machine parts and biological parts.

The cellphone nearby is your first tentative step toward a cyborg future. This device augments a core human ability to superhuman levels.

A cellphone allows instantaneous transmission or retrieval of almost any data to or from almost any2 place.

Let’s be real: this is fucking magical.

Except it isn’t. It’s entirely mundane. I just assumed the presence of the cellphone in the room with you. I’m almost guaranteed to be right3.

Many sleep beside their phones. Cellphone charging stations are becoming as common as bathrooms in airports.

While the cellphone isn’t something implanted into our bodies, there’s a meaningful human/machine symbiosis in progress.

Irrelevant distinction

So on the one side you have a pile of machinery built to capture and relay any data. On the other side you have an always-on connection between the meat and hyperspace.

Or you don’t have any sides at all.

Just an unprecentedly thorough and accessible collection of humans and their unique data.

Just a vast cybernetic organism.

We’re the internet and the internet is us.

  1. Yet. But @horse_ebooks hints at an interesting blurring of these lines. 

  2. Any place with network access, anyway. 

  3. You may even have it shoved right next to your body. It may even be in your hands right now

A fervent but rational belief

We are one.

That’s The Truth. That’s The Word.

I think a final moral criteria is a good idea to have.

I’m a little concerned there’s a lot of decision making that happens without one. Decisions that may affect millions or more, made based on personal bias, ambition, greed, fear.

Decisions ungoverned by an absolute principle that considers and protects a big picture.

Still, I get why moral systems have fallen out of use and fashion.

I’ve seen a lot of them sold over the years. Complicated stuff, looks like an MLM scheme sometimes. There’s books and services you go to. There’s a lot of blaming and hypocrisy.

Not to menion all the supernatural shit going on. None of that resonates for me.

But we are one? I can get behind that. It’s simple, it’s easy to understand.

It’s a perspective of preservation. Instinctively, intuitively, that seems positive. But I have to be able to justify it outside of any superstitious or emotional realm.

Maybe like this

Humans are information systems. We ingest data. We analyze it. We form pattern matching systems to optimize that work.

Continuously. All of our lives.

The richest possible sources of information we have are other humans. Other information systems matching our level of processing complexity and storage capacity.

Humans are information firehoses. Data pours out of us through sight, sound and smell. It’s a good thing we communicate on so many channels because we’re each bottles filled with entirely unique information.

Sure, there’s redundancy in facts and shared experiences. But every single human being also carries a completely unique point of view.

The things only you’ve seen. The angles only you caught – and the resulting freight of feelings they inspired. You carry a payload of data that is unique across all human history, past and future.

So we get together. Share stories. Exchange our data. Relay ideas, schemes and solutions. Humanity is an information network.

In network theory, Metcalfe’s Law establishes that networks become more valuable the more users adopt them. The more nodes on the network, the more possible connections there are between nodes.

A network of humans

The human network is old and scarred. Data from nodes as old as 6,000 years is still relayed everyday. Tragicaly larger amounts of knowledge have been lost.

While old data echos, new data is being generated and stored continuously. Every human’s cache of unique experiences is growing every second, and there are more humans all the time.

This network is a substrate that promotes creation, exploration and discovery. It has uncovered scientific mystery and produced ongoing technological development.

If you seek a rational justification for an absolute moral principle, as I do, I think there it sits: we are components of a system that is bigger than ourselves.

It is older than us.

It will outlive us.

With each node that we include and preserve, the more opportunities for connection. The more valuable the human network is. The more solutions for problems it may generate. The more beauty through cultural expression we may experience.

We are one

If we agree we are one, we have to demand dignity, respect and kindness for all of the other humans. No matter how different they may seem. What we do to them, we do to ourselves. Every human node contains unique and irreplaceable information and to lose it is to lessen the whole.

If we agree we are one, we preserve and protect everything required for the health of the human network. We consume that which we need to grow, since that serves the network. But we do not consume at the expense of tomorrow’s nodes. They will one day take over the hard work of maintaining the system—we shouldn’t burden them with preventable obstacles or a damaged planet.

If we agree we are one, we insist that depriving any node access to the human network is inhumane. This condemns isolated imprisonment along with government disruption or censorship of telecommunications.

Those are the obvious duties of this conviction. I’m certain there are others. The point is: the network is doing important work. It’s not done yet. It’s up to the humans to protect it—links and nodes alike.

This duty is sacred, if you choose to care that the network survives and thrives after you’re gone. Which seems right.

Now what?

“We are one” is not a unique idea. I’ll have to go digging around the religions and see how other people came at this. Meanwhile, it’s an interesting lens for testing behavior, goals and structures of power.

All the time

I’ve been catching up on Babylon 5. And then:

“No one knows, but I’m afraid all the time…” - Garibaldi, Ceremonies of Light and Dark

It was a line that almost knocked me off my couch.

I could have said it myself.

Of not being enough

What is enough? I have no idea how to quantify it. But I know what it’s supposed to get me.

Enough is the thing that gets you where you want to be. Enough is the thing that opens doors for you. Enough is the thing that makes the people you take seriously return the favor.

Am I talented enough? Smart enough? Wise enough? Attractive enough? Confident enough?

Brave enough?

I never know. And without knowing, it’s easy to fear that the answer is a negative.

Of not being welcome

For much of my childhood, I walked into spaces where the other people I met wished I wasn’t there. I was an outsider.

I was The Other.

I’ve spent decades trying to pretend that it was all okay. But it isn’t. The pain of those experiences lives inside me. It coalesced into a gland that excretes anxiety when I approach social situations.

I’m afraid the people I meet won’t welcome me into their worlds.

I’m afraid I don’t belong anywhere.

I’m afraid it’s all somehow deserved.

Of constantly getting it wrong

All the things I want to be, but am not.

All the things I try to do, but fail at.

All the values I try to uphold, but betray.

All the times where the best I can output is a crude, waxy crayon scribble, barely approaching fidelity to my color photo ambitions.

This highly enriched fuel is fed into the fear reactor, charging it with reality-tested data on all of my shortcomings.

Of falling off, never to return

I grew up broke. I grew up with parents who transmuted hard, physical labor and craft into money so I could eat.

The world I now occupy is strange. I’ve climbed to a place where I can afford to live in a wildly expensive city. Doing work I never expected. Making value not with sweat, but with my mind.

The process of getting here feels like climbing a tree. And sometimes, when I look down, when I see the path that got me here, I feel like I did as a child when I’d climbed too high.

Unsure how to proceed.

Afraid that my reach has exceeded my grasp. Afraid that the system of branches I’ve found myself on is outside of my ability to navigate.

Afraid that I’m not strong enough to hold on.

Afraid that I’ll fall – and that the fall will end my story.

I don’t know how not to be

Sometimes I’d like to turn it off.

Sometimes I’d like to know what it is to be truly, entirely without fear.

But thirty years into my existence, I’ve never succeeded at ending my fear.

The best I can hope is to manage it. To use it as a tool. To interpret my fear as a signal that I’m attempting something interesting.

I feel my fear more than I’m proud of. But I use all my energy to try and ensure that the fear doesn’t get to make the decisions.

The fear sits on the instrument panel. It doesn’t get to drive.

Most of the time.

My lapse

The biggest crime of fear is getting my mind so wrapped up in itself, I forget that that I’m not the only one who is afraid. We’ve all got things that haunt us.

I suspect you guard your fears just as carefully as I do mine.

So we walk around bluffing, pretending everything is okay. We don’t talk about our fears. We don’t talk about what keeps us awake during the hour of the wolf.

We don’t lean against each other, even when that’s what we need more than anything else.

I’m tired of keeping my fear a secret. It’s so much work.

How you doing with yours?

Everything I wish I’d known at 17 about social mobility

Hey. I’ve got some important stuff I want to talk to you about.

It’s presumptuous as hell for me to claim any authority at all here. I haven’t won anything yet.

I’m pretty excited, though, to be in a position at last to pursue my dreams and goals. No knowledge is ever perfect, and if I hoard it much longer it may reach you too late to be useful. Or worse, I might be hit by a bus and then it just ends inside me.

So contained here is everything that I, at the age of 17, wish someone could have told me about winning the game.

Which game?

The game.

The one we’re all playing.

I’m going to define winning as you closing the gap between what you are and what you want to be. You get to define the goalposts. You’ll know it when you’ve got it.

But you may be very worried. Worried that the goalpost you’ve chosen for yourself is a little (or a lot) out of range from your current position.

You may be worried that navigating the path is beyond your abilities.

You may be worried that even if you arrived, you would not belong.

If those anxieties are familiar, then we have things in common. I’m going to open the vault for you on everything I know about addressing those concerns.

Spoiler alert: it’s going to lean heavily on the internet.

If you’re rolling your eyes as though this is obvious, we’re cool: you know everything you need to know. You’re good to go; skip the rest.

But I need to make the case to anyone who was like me at 17 that this perspective is relevant.

Here’s what I’ve got.

Life is risk

To advance from one position on the board to a more favorable one, the player must venture.

Some ventures are straightforward:

Buying a slice of pizza requires a small amount of capital and minimal risk. You need to survive traffic and have four bucks in your pocket. There’s risk but it’s small and if everything goes as well as you hope, you get pizza.

Other ventures carry more risk:

You need to learn a skill in order to compete for a job.  This used to be nearly as risk-free as the pizza example. But in the last 10 years, this deal got broken. “Learn a skill” got defined as “go to college” and then going to college lost a lot of value.

The costs for this sort of venture can vary dramatically. And what happens if the job hunt fails? You’re still on the hook for the education bills.

The more ventures you can undertake, the more spaces you can advance around the game board.

Risk requires resources

Resources determine how many ventures you can safely undertake within any given period.

Since each venture has risk, sane pursuit of them has certain costs. Some costs are immutable: you only have so much time and energy.

Other costs can be mitigated through investment, or infusion of resources.

If the only pizza in walking distance was in a neighborhood that made you feel unsafe, you might not undertake the venture. But if someone came along and offered you a free ride across town to another pizza shop, of course you’d go.

And you’d pick something up for them, if they wanted, too. It’s only fair.

So on this game board, resources equal game moves. The more you’ve got, the further you can go. You can cooperate with others for access to their resources.

Money is not the only resource

A resource is anything that has value. Your resources can be used for your ventures. They can also be used to trade for other resources.

Money is a pretty great resource, don’t get me wrong. It’s accepted almost universally. It is very well quantified. It can be transmitted instantly and electronically. Money’s efficiency makes it very easy to convert into almost any other specific resource.

Another pivotal resource is information. The more information you have, the easier your transactions will be. Persuading your counterpart often requires information. Information protects you when your counterpart is dishonest. Information illuminates opportunity, and often unlocks other resources.

Information, when applied as a skill, is often traded directly for money. Economics apply here: if your skills are uncommon, they may command a higher value. Governments often try to give this resource away through public education and college subsidies.

Companionship is a critical resource that impacts your ability to survive. Everybody needs other people. The people who care about you give of their time and flexibility to share in the joy of companionship. Neglecting your responsibilities to this resource can have devastating consequences.

Imagination can be a transformative resource, but trading in it can be challenging. When combined with sufficient skill, imagination commands substantial value.

Time and energy, or sweat: the work you’re able to do. You’ve got finite time between now and when you fall asleep tonight. You’ve got a finite number of nights. Sweat is scarce and irreplaceable, so it should be traded carefully.

Resourcefulness is your ability to identify and use resources, even when they’re less than obvious.

There are other resources. Even if you don’t have money, you’ve still got other tools to work with to advance your ventures.

Resources are allocated inefficiently


So you want to move across the board. But you feel like your resources are lacking. I understand that.

I was conceived as the bastard son of a 51-year-old philanderer and a 20-year-old girl haunted by addiction. There were not resources, of any kind, in abundance.

I wasn’t there, but as I understand it, prevailing opinion in those days was that my mom should’ve terminated the pregnancy. I hasten to say the world is best when women have first and final authority on decisions regarding their reproductive future.

But for my case, it seems to have worked out that my mother chose to ignore our family’s advice and buy me a ticket to the game. The cost was pregnancy, a brutal delivery, and diverting resources toward me for over two decades.

All starting at age 20.

That’s not an easy deal for anyone at that age, much less someone who is resource-constrained.

My mom would kill me, at this point, if I didn’t mention this: she never took foodstamps, or welfare. She was too proud for that. She preferred to convert her sweat into resources, rather than accepting them as a gift from the government.

And I never starved. There was always food, there was always a safe place to sleep. I don’t know how she pulled it off, because I know it wasn’t easy. But that stuff was always solid. Many things, indeed, were solid.

Other things were less solid.

Domestic violence was a feature of my home for several years. At one point I slept through a robbery: I had grown so used to the sound of commotion, I thought my mom and her then-partner were just fighting again.

My mom had never had the time or resources for college. This limited my access to people who could give me meaningful advice about education decisions.

I had no mentorship on the development of my skills and talents broadly, either. I didn’t know anyone who could help me grow or give me advice on my passion for computing devices.

And sometimes money was just fucked. I was registered to start high school. I was looking forward to seeing all of my friends again.

Suddenly, my family and I were moving across the country, fleeing bills that had stacked too high. Living in a house filled with roaches. Cigarette ash piled anywhere that remotely resembled a bowl.

Eventually we dug out of that one. Eventually I didn’t feel a searing shame when I thought about anyone knowing where I lived.

But all this stuff piled up.

Then I chose a college. A college that cost me over $85,000 in debt. Nine years after I finished, I’ve barely made a hole in this.

By 22, I’d given up on getting anywhere close to my dreams. I didn’t know how to find them. Even if I did find them, it felt like I had started too far behind to do anything meaningful with them. The weight of debt took so many options off the table. The dysfunctions of childhood made me feel like such an irredeemable fuckup.

The transition of someone with dreams to someone with a listless acceptance of whatever was painful.

I felt like a failure. I didn’t know what I had failed at – but when I stopped dreaming, I stopped feeling like me.

Punishing student loan bills demanded I work a job. I did. But my heart wasn’t in it. I was treading water.

But other forces would intercede.

Network effects

The most precious resource of all is your network.

You will hear network used in many slimy ways, often as a verb, especially as applied to business.

But in the great game of competing/cooperating apes that is humanity, network has a specific meaning. Here I describe the series of connections you have to other people willing to trade their resources with you.

The more people connected to your network, the more valuable it is.

If I have garnish and you have meat, big deal. If we’re both also friends with Jordan and she has a loaf of bread, the three of us have a sandwich to split. Neither of us know Danny but Jordan does and he has mustard.


If you’re behind on other resources, you may be behind on the breadth of your network as well. Of all resources, the network returns the highest yields in the long term because it is renewable. Uniquely, a network can potentially provide literally any other resource you need.

You can expand your network by doing things that connect you to more people. But it’s not enough just to meet them. You must invest in them. You have to develop deep relationships.  Life is miserable without companionship.

People trust you based on the personal connection you make with them. The more trust, the more opportunities your network will deliver.

But not all nodes are created equal. Your goals may require cooperation with very specific individuals. How do you find them? How can you build a connection with them?

Well. What if there were a way you could move around the game board instantaneously? This teleporter has limitations: only your mind can go. Your body must stay put.

But so much of what we are is our mind. So this advantage is better than nothing, right?

That teleporter is the internet. With the internet you can reach nearly anyone else on the planet. Instantly.

On the internet you will find other disembodied minds. They’re tweeting each other. They’re murmuring around discussion forums. They’re writing essays to each other.

There are piles of communities according to every interest you can imagine.

So. Connect.

And in doing so, you will find friends who’ve been waiting forever to talk to you. You’ll find new ways of seeing the world. You’ll find recommendations for all the stuff your brain just needs to put inside itself. Everything from classes to take to music to hear to shows to watch.

These minds also want help. They have projects they’re working on. Maybe you can pitch in.

This teleporter allows you to invest yourself in people based on your shared values, rather than your geographic proximity. This is a great way to come up from behind in the network department.

To market, to market

The internet is also a collection of markets.

There are uncountable numbers of places to buy, sell or trade resources. Resources of every stripe, from game currencies to computer components to Beanie Babies.

There are also markets for ideas. Places where your voice can cooperate or compete with others.

The internet has global reach built in as a default parameter. Every single one of us who can connect to it is a potential player in the global economy.

Producing any sort of online content, from funny jokes to awesome cat photos to apps, puts your name into a stream that can flow to anyone. What if it flows exactly past a future friend? A future boss? A future spouse?

You won’t know if you don’t play.

Reputation aside, if you create stuff that’s good enough, markets can make you money. By 19 years old, I was selling my ideas for money in Second Life. I made enough to pay my real-life rent.

But you don’t have to take my word for it.

Dem Broads

Broad City is a refreshing, hilarious, filthy show.

Broad City began as a startlingly funny series on YouTube. Two comedian friends recording tales of being young and broke in New York.

Today Broad City is on Comedy Central. Somewhere out there, a fan base was craving stories only these two could tell. The internet provided an audition that made a whole TV show seem like an obvious choice. The folks with money noticed. The rest is history.

All Mine

Then there was that time a guy from Sweden made a side project that turned into a profitable, global business.

Cycle of progress

Okay, fine. So if we buy that the internet is a valuable tool, how is it leveraged?

It’s going to be different for everyone. Different based on goals and values. Different based on passions.

But in general, the cycle seems to have three stages:


Use the vast data and connections afforded you by the internet to learn new ways of being creative. New tools, new techniques, new communities to share with. The hunt is up to you.


Then you have to try to apply the combination of your passion and your learning. Maybe you participate in photoshop contests. Maybe you build websites. Maybe you make photo collages of cats being funny. Maybe you write essays with sweeping advice.

Hell, maybe you record yourself in front of a camera. Anything that you can create is fair game.

The most important thing to remember: you do not need anyone’s permission to try. You can try whatever you want, whenever you want. It’s in your hands.


Once you’ve tried, you need to tell people. You need their feedback so you can be better. But you also need them to know you exist. Sharing is a discovery strategy.

Your output will let other people understand your values. If they find them resonant, you may find yourself with new friends and opportunities.

But even if, at first, no one cares…


You have to keep learning, trying and sharing. The more times you go through this cycle, the more your talents grow, the more your connections strengthen.

Not every cycle bears fruit. Not every venture pays off.

But I believe that sustained application of effort this way is the most reliable means of developing the skills and network to overcome whatever deficits you feel you were born with.

It’s not cheap, it’s not fast. But the last ten years have taught me its incredible power. I couldn’t be in the position I am without this approach.

While I didn’t have much in the way of resources at the beginning, the internet allowed me to make leapfrog progress at many stages.

Even if it all comes tumbling down and I’m begging in the streets next year, I can’t believe coming this far was possible.

What about college?

As in, should you go?


Schools are a great way to recover from a network deficit. But they cost money and results vary. The better the school you attend, the better your network upgrade.

Schools are also a great way to develop knowledge and skills.

But you have to choose school very early in your path. You may have limited resources. You may not know quite yet what you should do with your talents.

Attending school in that position can leave you with debt so painful, it cancels out any other resource benefits. Choose carefully. Evaluate the resource trade closely. Don’t let inertia carry you into the decision.

No guarantees

All this to say: life is risk.

Nothing is guaranteed.

But what’s essential is understanding the problem space. Understand just how much is under your control, even if it feels like you’re behind.

Understand that the game is winnable. Social mobility has stagnated in the United States. This is not an easy challenge. But you have a tool at your disposal that is unprecedented in human history. You have a means to reach everyone.

Starting from anywhere.

The tl;dr

We live in an information age.

This is a tedious cliche but it’s the foundation of my argument.

The part of you that you think of as you?

That’s information. Everything it sucks in, everything it knows, everything it spews back out: all information. You’re compatible with the teleporter.

As of the 21st century, there are teleporters all over the game board. You can use these to exchange resources and bring them to you in a way that’s unprecedented in human history.

This is it: this is the whole opportunity. Whatever it is you think a path to your success has to look like, throw it out. Those blueprints  were written in a different age.

As of right now, everything is up in the air. Grab a handful of it.

Mobile interaction designer + developer. Unreasonable person. San Francisco—for now.