Ah, the Joy of Truculence. He is walking down Rue de la Montagne in Montreal. When the Toronto Maple Leafs play the Canadiens, he always walks the five blocks to the rink. He admires the flaming passion of Habs fans – French blood easily reaching the natural boiling point of his own Irish blood –…

I experimented with custom fonts in Instapaper last year, but my efforts fizzled out. Before iOS 5, rendering custom fonts in a UIWebView on iOS was extremely buggy and slow. And nearly all of my licensing inquiries to font foundries went unanswered, so I couldn’t legally ship any of the fonts I…

For most of the past decade, the Jays have been a good team, occasionally a very good team. Yet they have nothing to show for it. The loaded AL East has suppressed the team’s win totals and prevented them from cracking the postseason. That killer competition also prompted J.P. Ricciardi to overreach…

Photo by Julie Faith The other day I landed on an article titled “A Social Media Addict Tries to Disconnect.” Something about the headline felt familiar, but I couldn’t put my finger on it. I started reading. As the headline suggests, CNN producer Kiran Khalid attempts to disconnect from social…

Are We Experiencing an Information Technology Fin de Siècle? It is a strange and interesting time for information technology. For every example of technology dominating both markets and mindshare – Apple as the most valuable company in the world, Groupon and Zynga accounting for 31% of all IPO money…

After months of buildup and failed launches, Readability’s iOS app is finally here. I downloaded it this morning and started tossing articles in it. So, how does it stack up? While I recognize that there is a cottage industry of “read later” apps on iOS, to me, the gold standard against which all…

“Is that you, Ms. Boody? You really standin’ out there on my door step?” Donald, my most despondent sixth grade student, coos though the closed door. I’m standing next to a bench press held together with duct tape. I imagine Rodney, from the picture I saw in the paper, lifting weights here days…

How Not To Sell Software in 2012 Though most of our stack at Simple is based on open source software, we occasionally try commercial software. Mostly, we don’t end up buying it. A big reason why is the incredibly time-consuming, aggravating sales process that most commercial enterprise (that is,…

There's a lot to like, even love, about being an entrepreneur. There's agency, opportunity, creativity, the singular challenge and potential rewards of doing something different and new. I wouldn't want any other kind of career. That said, there are things I really don't love about the Startup…

I realized that the communication culture and digital life of my age demographic was changing, and I wanted to be a part of it. I owned a red plastic flip phone, dinged up from constant drops, the fake metal veneer peeling off the front. The audio was so bad I had trouble holding long conversations.…

If the days of the week were a TV show, they would’ve been canceled decades ago. They are a tedious bore. Monday is, ugh, Monday. Friday and Saturday are sometimes fun, but there’s too much pressure to have fun. Tuesday is bland as mayonnaise-slathered white bread with a side of Cheerios. Sunday is…

Observer effect: The act of observation changes the object being observed Like most normal people and baseball players, Ichiro Suzuki prefers to do things his own way. Like almost all successful baseball players, and like many (though not most) normal people, he is committed to his employer's…

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Dave Winer is thinking about writing a book. What do people imagine would be in Dave Winer’s first book? It would be interesting to ask around. I will pretend here that DW has asked. I imagine certain kinds of ideas and two kinds of stories. Stories that DW knows from years of conversation are his…