January 20, 2017

Today, as Donald Trump takes the oath of office, America is diminished.

And yet, I have hope.

After the election, I worried that protest would be meek and partisan. It has been neither. Voices across the political spectrum have risen in dissent. I’ve been particularly heartened to find many thoughtful conservatives who understand exactly what Trump represents, and who will give no inch when none can be given. John Kasich, John McCain, David Frum, Evan McMullin, Mindy Finn, Susan Hennessey, Eliot Cohen, and Rick Wilson have all spoken clearly, and unequivocally, about Trump’s perilous potential. These are Americans with whom, in sunnier times, I might entirely disagree. But such disagreements live within normal political boundaries. Trump operates far outside those boundaries; we must realign in response.

From Eliot Cohen’s savage and sobering Truth in the Age of Trump:

Trump lies because it is in his nature to lie. One suspects that there is nothing inside this man that quivers, however slightly, at an untruth. It is not uncommon for politicians, to a greater extent than most people, to believe what they want to believe, or to change their take on reality depending on what is convenient for them. With Trump, however, this will to believe is pathological: his psyche is so completely besotted by Trump that there is no room for anything, or anybody else.

I hope to one day revisit what I’ve written about Trump and laugh at how hilariously wrong I was. I hope, but I fear that day may never come.

Political Priority Alarms

January 6, 2017

Of all the political issues I might be worried about, why am I so concerned about trust and nuclear weapons?

Given Trump’s terrifying statements about nukes, I think the fear should be obvious. I don’t worry for the children of Seattle; I absolutely do worry for the children of cities across the Middle East. Do I think Trump would actually do something so nightmarish? No, not with high probability… but not with zero probability, either. The truth is, I genuinely have no idea. Does anyone?

Trust strikes me as the far more insidious concern. Trust may have been eroding before Trump, but he willfully accelerated the process. I have no doubt that he will continue to sow distrust in our government and media institutions throughout his tenure. This is a poison that will linger, harming our country long after Trump is gone.

A friend asked me whether these should truly be my top two concerns. After all, we should probably be alarmed by Trump’s autocratic tendencies, his malicious xenophobia, and the apparent conflicts of interest that could lead us to kleptocracy or worse. To all of these I say yes, I’m worried, but I also think we can muddle through this sort of madness. One doesn’t muddle through a nuke, however, and depending on how far one travels, one may never quite return from the dangerous road of distrust.


November 10, 2016 :: musings

The trouble with black swans is that, even when we know we’re looking at them, it’s hard to foresee their consequences.

Trump is undoubtedly unique in the history of the American political experience. To attempt to parse his victory, or to shoehorn our expectations for his presidency, within the confines of politics-as-usual is to fail to see what’s right in front of us. Trump lives far outside the political norm; why should we expect his presidency to live within it? I don’t believe the republic is likely to collapse, but it strikes me as dangerous to assert that everything will be okay.

President-elect Trump arrives at the White House on the winds of alarming political, economic, and racial unrest. There can be no argument that he channeled our lesser instincts — those of the bully, the bigot, the racist, the anti-factual, the petty authoritarian — into an effective political weapon. This is unforgivable, but it doesn’t diminish the validity of at least some of the unrest that led half of America to vote for him. I can understand how the economically downtrodden and culturally sidelined might, in some warped way, have felt like a vote for Trump was the only viable path forward.

There’s so much work to do. We need to understand and address the root causes of the unrest that led us here. Perhaps a Trump presidency will give us the opportunity and impetus we need to get started.

But the KKK? The Nazis? They never left us. Now, emboldened by our President-elect’s words and deeds, they’re coming out of the woodwork. On this count, I think Trump is already a tragedy of unimaginable scale.

Inflection Points

May 27, 2016

It’s been a nutty couple months.

Peter, Nick, and I sold Cloak! It turns out selling a company can keep you plenty busy.

The sale was a surprise ending for us. It’s also an exciting new beginning.

We didn’t need to sell; Cloak was happily profitable, and those profits were growing. We didn’t necessarily think we wanted to sell, either, at least at first.

However, as we began to plot out Cloak’s next eighteen months, we realized we were at an inflection point. Our investments in engineering automation had allowed us to run lean almost to a point of absurdity. But our leanest days were clearly numbered.

It didn’t take long to realize that we couldn’t take the next steps without growing our team. We needed to ship native apps for Android and Windows. We had to move aggressively to better serve our growing list of corporate customers. We wanted to scale our VPN network. We hoped to make our apps behave more gracefully even in the face of less common network failures.

All told, it was clear that Cloak in mid-2017 was going to look quite different than Cloak in early 2016. We assumed we would lead that charge… until a few potential suitors knocked on our door. The question then became: would we lead the charge? Or would we team up with a larger organization to make the next big push?

In StackPath we found an ideal suitor. Their plans nicely complemented and strengthened our own. They had a deep bench of business, sales, and marketing talent that we knew we needed. And it didn’t hurt that StackPath understood the value of what we’d built, and was willing to pay a fair price.

So here we are! I’m a full-time employee of StackPath. I have a boss. We have a mission. It’s the same as the old mission, only bigger. I’m excited to see what we can build.

An Absolutist View of Encryption

March 11, 2016

President Obama spoke at length today about privacy and encryption. He cautioned against an “absolutist view of encryption”, claiming that search warrants can apply to the virtual world just as well as the physical provided we build our technology wisely.

Alas, Obama is fundamentally wrong. Digital encryption has no analogue in the physical world. Doors locked by lost keys can be busted down. Digital doors locked by lost encryption keys can never be re-opened.

What Obama misunderstands is that “encryption absolutism” is not an ideological position. It’s a technical one.