Brexit and Trump; applied CRISPR and the Gigafactory; the rise of self-driving vehicles, the fall of pollsters; the global saturation of smartphones, the first mass-market VR headsets; the first drone-delivered terror bomb, the first drone drug mule; Signal and the Secure Enclave; Ethereum and the DAO; AI and SpaceX — we can all agree, I hope, that this has been one hell of a year.

This election week also happens the six-year anniversary of my very first TechCrunch column. (I like to imagine that it set the tone, in that a) in retrospect I was 100% correct, b) I got angry hate mail for writing it. Remember when people still cared about BlackBerry? Those crazy days.) I’ve been writing a column every week, rain or shine, ever since. No one is more surprised about this than me.

Most years I mark this anniversary with a where-I-went-wrong piece discussing my predictions of the previous year… but this momentous year, I think it makes more sense to go back further, look at the broader themes I’ve been writing about for six years, and see how they’ve changed, and whether I was right about them:

Technology and Politics

An often cringeworthy subject:

…but I’ll claim some credit for asking, four years ago, “What Happens When Pollsters Are No Better Than Psychics?” Sure seems like we’re getting there now. To quote 538, “In the average state won by Trump, the polls missed by an average of 7.4 percentage points.” That’s a huge polling error — and the American presidential election is just another in a long series of polling failures over the last few years.

It doesn’t help that political journalists, like most journalists, don’t understand anything about technology, and all journalism is tech journalism now, whether we like it or not. Consider Clinton’s emails; Trump’s “secret Russian server”; Wikileaks.

Six years ago, the American security establishment was furious with Wikileaks. Whose avowed target then and now was the so-called Ruling Party and the deep state. Those were the days, eh?

I’ve also speculated about disrupting democracy, voters left behind or fearful of tech, and, most out-there of all, the notion that the entire global system of power division among nation-states may be crumbling. Which sounds a little less crazy now that serious tech figures are talking about Califexit. A lot of this seemed highly speculative and faintly paranoid even to me, at the time! It seems a lot less so now. Grade: B+

Law Enforcement and Online Security

By day I sling code for a living, so while I’m no expert, I’m more comfortable with the subtleties of security and encryption than most — and, sadly, apparently much more so than much of the security establishment, viz. “Intelligence Agencies Keep Getting Dumber” and “Is The FBI Dumb, Evil, Or Just Incompetent?

It has seemed clear to me that government attempts to surveil ordinary people, militarize the police, and seek “golden keys” for encryption have been, not to put too fine a point on it, complete bullshit, and that Edward Snowden deserves not just a pardon but a medal.

Maybe most relevant: I keep arguing that no matter how much centralized services, from Apple to Google to Microsoft, claim you can trust them, you can’t. Governments can and will intervene, and ultimately they’re answerable to them, not you. E2E or GTFO, because, well, just imagine if the below were to have happened. Grade: A-.


I write a lot about corporate surveillance, both deliberate and de facto, and I feel a bit like Cassandra: for years I have been warning, again and again and again, that ubiquitous sensors (ie the Internet of Someone Else’s Things) plus machine learning means that soon enough virtually everything any of us do out in the world will be tracked and monitored.

We need to save online privacy because it’s the only privacy we will have left; we need to give people either guarantees of data anonymization or legal control over their data; we should have root access to the devices we “own” (because otherwise we don’t actually own them); the services we use need to be secure, but we can’t labor under the delusion that Apple can save us from intrusive governments, so eventually they need to be decentralized, too; and the powerful need to be as accountable as the poor. Otherwise only the rich will be able to afford privacy. Am I right? Pretty sure I am. Does that actually matter? Sadly, probably not. Grade: B


I know you’re probably thinking I’m vastly overrating my own analyses. Won’t pretend I’m not biased to do so! But here’s an ongoing outright prediction failure on my part. I keep saying that bad actors will start using drones to wreak untraceable havoc. (I’m clearly biased by having written a novel about just this way back in 2009.) And despite some desultory drone use by Daesh and Mexican cartels, the reality is that I keep being completely wrong. At least so far. Grade: C-


Also: one of my favorite pastimes appears to be complaining about Facebook. Six years ago Fred Wilson argued “Facebook is not an unstoppable juggernaut.” I disagreed. Then I complained (repeatedly) about Facebook Comments and Messaging, lambasted them for never doing anything interesting and being devoid of any real innovation, conceded that they are only vulnerable to a platform shift … but then speculated that, as people realize that machine learning can deduce things about them that they may wish to hide from apparently innocuous Facebook behavior, their popularity may greatly diminish. Was I all wrong? No. Was I particularly prophetic? I was not. Grade: C


I’ve been writing about Bitcoin and its descendants for more than five years, and I’m pleased to say that my first few Bitcoin pieces, in which I conclude it’s a developed-world sideshow but a potential developing-world breakthrough, remain not completely embarrassing.

It wasn’t until I dug into the cryptocurrency’s technical details, though, and began to understand the implications of its distributed-consensus solution, that I became a believer. Which I remain to this day — though I still think we’ll need to wait for Bitcoin 2.0, eg sidechains, before we see real breakthroughs that go beyond true believers.

True, there’s been a lot of strife, sturm, and drang in the cryptocurrency space: but that’s how new tech develops. Between sidechains, the Lightning Network, Ethereum, ZCash, etc., the world of cryptocurrencies is bursting with possibilities. I still believe they are a very big deal — but I concede I can’t actually point to a breakthrough application. Yet. Grade: Incomplete


All that said, though, my chief interest in Bitcoin is that it’s a live example of wildly successful decentralization. A shocking amount of our online activities — which means, in these ultra-wired times, our lives — is mediated and controlled by what Bruce Sterling calls “the Stacks”: Alphabet, Amazon, Apple, Facebook, and Microsoft. The Internet was built to be decentralized and independent; we’re doing it wrong. We can, and should, decentralize our email, our messaging, our social networks.

I’ve even speculated that decentralized reputation economies and a decentralized basic income could supplant (parts of) capitalism as we know it. That’s more pie-in-the-sky, but there are green shoots of decentralization out there. I hope to keep writing about that a lot. Grade: B

Technological Unemployment

I’ve actually been beating the drums for basic income for years now, because since 2011 — at least a little ahead of the curve, I think — I’ve been suggesting that technology is destroying jobs faster than it’s creating them. I wrote piece after piece about this — America Has Hit “Peak Jobs”, Get Ready To Lose Your Job, After Your Job Is Gone, “Jobs, Robots, Capitalism, Inequality, And You“, and —

— well, at best, I was premature, and at worst, I was simply wrong. Technology is not destroying jobs faster than it’s creating them, at least not yet. Now, a lot of people believe that it will, soon enough! Elon Musk, Steve Jurvetson, and Bill Gates, to name a few.

But in the present day, I’ve come up with a more nuanced view: technology will atomize jobs, make workers more fungible and easier to replace — think Uber drivers and other on-demand economy gigs — and software will drive the world into Extremistan, wherein ~20% of us do very well, while the other 80% struggle to get by as part of the Precariat, with no careers and no security.

Whether that or fully automated technological unemployment is the future, though, I believe we will ultimately need to replace the expectation of near-universal full-time employment with a universal basic income. And I think the last five years back me up on this. Grade: B-

Now on to the next six years…