Journalism and Essays

Journalism has only ever been a sideline for me, but a very long-term & consistent one; I wrote a weekly column for TechCrunch for a decade, along with sporadic feature-length pieces elsewhere for 15 years now.

2005 - onwards: Magazine feature writer


2010 - 2020: TechCrunch columnist


May 2020: Magic Leap's $2.6 billion bait and switch.
Explaining the mystery of Magic Leap's rise and fall: what "The Beast" and "The Cheesehead" were ... and why we didn't get them.

Apr 2020: GrubHub's pandemic initiatives are predatory and exploitative.
In which I do the math to show that GrubHub / Seamless are hurting the restaurants they pretend to be trying to support. Days later, San Francisco cracked down on food delivery services.

Mar 2020: Test and trace with Apple and Google.
In which I call for Apple and Google to collaborate on privacy-preserving Bluetooth-based contact-tracing, twelve days before they announced they were doing exactly that.

Feb 2020: What happens if a pandemic hits?
In which I deliberately bury the lede, a declaration that a pandemic is coming -- one of the earliest such in any publication. I was definitely too optimistic about how Western governments would respond though.

Nov 2019: The post-exponential era of AI and Moore's Law.
In which I point out that if current trends continue, we aren't going to see many further AI breakthroughs, because the ones we are seeing are based on unsustainable, hyper-accelerating computing power.

Feb 2019: The infrastructural humiliation of America.
In which I note that American infrastructure is a pathetic shambles and a national embarrassment.

Dec 2018: JIRA is an antipattern.
A very controversial and widely read piece among software engineers, in which I argue that the widely used JIRA issue-tracking platform should not be used for project planning, and propose an alternative.

Oct 2018: At what point do we admit that geoengineering is an option?
In which I argue that we do nobody any favors by pretending the option of artificially cooling the planet (as a response to global warming) does not exist, when it manifestly does.

May 2018: The crypto alternative.
In which I imagine the various futures that cryptocurrency enthusiasts' dreams might lead to, and find all but two of them severely wanting.

May 2018: Personal privacy vs. public security.
In which I explain how privacy as we know it is different from privacy at scale, and that the latter is, in fact, a crucial aspect of public security.

Apr 2018: Where have all the pilots gone?
An attempt to answer that question, and a meditation on dreams of flight.

Nov 2017: In praise of Tesla's bankruptcy.
In which I point out that even if Tesla-the-business goes bankrupt, the mission of Tesla-the-company is still likely to succeed, and people should not conflate those two Teslas.

Oct 2017: After the end of the startup era.
Another controversial and widely read piece, in which I argue the startup era is ending because the next suite of emerging technologies is far more suited to large, capital-intensive companies.

Sep 2017: Technology, complexity, anxiety, catastrophe.
A depiction of how our new ubiquitous interconnectivity is not always good for our souls, written in the second person present tense.

Aug 2017: Seven things I have learned about writing software.
The distillation of some insights from one of my other jobs, CTO of a software consultancy.

Jun 2017: Facebook is broken.
In which I argue that Facebook is deeply and fundamentally broken because its focus on maximizing engagement leads to destructive second-order effects.

May 2017: Blockchains are the new Linux, not the new Internet.
In which I argue that the then-current cryptocurrency boom is using entirely the wrong metaphor and narrative, and propose a superior one.

Jul 2016: Westphalexit.
In which I point out that the fundamental way in which our world is partitioned is arbitrary and often senseless, and we shouldn't expect it to continue forever.

Mar 2016: This war on math is still bullshit.
In which I argue, yet again, that law enforcement's continual attempts to compromise end-to-end encryption are ignorant, counterproductive, and often in bad faith.

Jan 2016: Why Bitcoin Matters.
An attempt to explain why magical Internet money beloved by sociopathic libertarians is, in fact, both crucially important and good for the world.

Oct 2015: I Do Not Want Your Stupid App.
In which I channel Dr. Seuss to express what I still believe is a nearly universal form of frustration.

Feb 2015: Beware The Pretty People.
In which I lament how tech has become a finishing school for the American upper classes, who take on the trappings of subversiveness while remaining fundamentally conformist.

Jan 2015: This Industry Is Still Completely Ridiculous.
In which I continue to celebrate the tech industry's Dadaist, subversive weirdness.

Oct 2014: You Too May Be A Victim Of Developaralysis.
In which I try to be funny about a very real problem that software developers everywhere face; the continual profusion of, well, everything.

Jun 2014: Dear Clients, Please Stop: Ten Ways Founders Sabotage Themselves.
In which I try to prevent startup founders from making the same old boring mistakes I have seen too many times, in the hopes they will make new and interesting ones.

Mar 2014: Enter The Blockchain: How Bitcoin Can Turn The Cloud Inside Out.
In which I realize the decentralizing power of blockchain technology, and try to express how genuinely revolutionary it might become.

Mar 2014: This Industry Is Completely Ridiculous. Let's Hope It Stays That Way.
In which I celebrate the tech industry's Dadaist, subversive weirdness, and express hope for its continuation.

Jan 2014: Such DFW. Very Orwell. So Doge. Wow.
In which I discuss language on the Internet, and David Foster Wallace, and how both language and the nature of trust online is changing. An especially prescient piece, if I do say so myself.

Dec 2013: It's A Wonderful Life, For A Few Of Us.
In which I point out that while Bay Area techies may be living in a new Belle Epoque, more and more of the rest of the world is joining the precariat, and this tension will turn into a backlash against tech.

Jun 2013: After Your Job Is Gone.
In which I express concern about automation taking jobs, and call for a universal basic income, long before Andrew Yang.

Aug 2011: Welcome To The Panopticon.
In which I argue that facial recognition and other forms of offline tracking are inevitable, making online privacy crucially important, as eventually it may be the only form of privacy we have.

Jun 2011: This Is Where The Magic Happens.
Reportage in which I travel to Mombasa, Kenya, to report on the miracle of the physical Internet -- the fiber-optic landing site connecting East Africa to the Internet.

May 2011: Make.Money.Slow: The Bitcoin Experiment.
In which I write about Bitcoin for the first time, and am skeptical but also optimistic.

May 2011: Why The New Guy Can't Code.
In which I lament, for the first of many times, the many ways in which the tech industry's interview processes are broken, and propose alternatives.

2009 - 2011: Columnist at Maisonneuve magazine


2009 - 2011: contributor


2008 - 2011: "World Fast Forward" at The Walrus


2007 - 2009: Occasional contributor to The Guardian's books blog.


2004 - present: Occasional essayist