The Big, Slow Company Stereotype

The playbook for “startup disruption” has remained the same for a while: the small startup moves faster than its much larger competitor, hustling out new features, products and markets at a much higher clip. Raw speed and iteration overcomes money and people[1], and the criticism against the big and established firms is that they get […]

The Troublesome Portrayal of Women in Video Games

Video games are notorious for catering to teenage boys. Puzzlingly, it’s an increasingly outdated focus, persisting mostly in the creative direction and subsequent marketing of games, reflected in big budget titles moreso than in general-appeal casual games. The recent controversy over Assassin Creed’s exclusion of female avatars is just the latest of a long-running series […]

The Risk of Failure

Silicon Valley is often derided as a place that non-ironically accepts and celebrates failure. For people who have not bought into this culture, it’s natural to make fun of the notion that people are failing their way to success, and be cynical of the effectiveness of the sheer amount of capital spent. As the vast […]

Developer Ageism and the Escape into Management

Is the software development industry ageist? For some industries, this is not an unreasonable proposition. Professional athletes peak in their late 20s[1]; professional gamers (e.g., e-sport atheletes) peak even earlier, in their early 20s. If you were to apply for the job of the president of the United States, you are legally required to be […]


Misusing Apple Design as a Shortcut to Success

About a month ago, there was some discussion over this provocative Quora post on how design-lead products have not worked out as well as the industry has hoped. That is, despite design’s elevated status the last few years, a number of high-profile apps have not seen assumed marketplace success from their focus on user experience. Subsequently, […]


Hatching Twitter

One of my guilty reading pleasures are tech company biographies. That I’m a part of the industry and can relate to the motivations of founders and early employees is a given; I’ve also followed companies’ chronologies and can remember the news as it happened, tying them back to product announcements and mergers and lawsuits and […]


Cloud Atlas

I’ll admit: I picked up the Cloud Atlas novel mostly because the trailer for the movie adaption of the same name looked pretty interesting, a juxtaposition of what seemed like many different places and time periods and themes. Indeed, the novel is a series of Russian nesting doll stories, set in both the past and […]

Best. Autocomplete. Ever.

During a recent role-playing portion of our interview training session at Square, I was trying to come up with a caricature of an interviewing engineer attempting to impress my counterpart across the table. I ended up embellishing upon my starter project at Google; in retrospect, it was easily one of the most over-engineered pieces of […]


The Hard Thing about Hard Things

There aren’t that many good articles on management in a technology company, and even less good books that go into much detail[1]. Square’s leadership courses reference High Output Management, written by the president of Intel in the 70s, as the classic book on management but also only one of a handful that applies to the […]

Finally got my desk at the BankSimple offices.

The Cleanliness and Messiness of a Computing Workspace

The design magazine available in Flipboard is a bedtime guilty pleasure. There’s something surreal about flipping through the architectural creativity exhibited in many of the living and housing feeds, the condos and homes that are built as showpieces for world-renown architects along with the carefully orchestrated, yet completely unrealistic, living spaces set by interior designers. […]


Down and Out in the Magic Kingdom

Whiffies. A silly name for a foreboding concept. Down and Out in the Magic Kingdom is a book with a few concepts ahead of its time. It takes place in a time when resources are effectively unlimited[1], where it takes no effort to fulfill the basic human needs of shelter and food, and where humans […]


Tech Leads, Managers, and the Hybrid in Between

The software engineer’s career path is pretty straight forward at most companies. Starting at the intern or new grad level, there’s essentially a number of levels to progress through, each adding some amount of responsibility and technical complexity, until the rungs culminate into a position of leadership within a team. That position is either a […]