My Internet Friends and their Podcasts

by Ben Carter

Last night, I asked a buddy of mine at the Legal Aid Society’s Brush, Bottle, and Barrel event1, “What podcasts are you listening to?” At this point2, Erin discovered she urgently needed to go get a drink.

So, I told my friend I’d send him some recommendations. I accidentally turned it into a blogpost:

Dear […],


Now, onto a more pressing matter: podcasts.

Like I said last night, I listen to many of the podcasts offered on the mighty 5by5 network. Dan Benjamin, the shows’ co-host has invested his time and money into building audio tools and the web infrastructure to create great-sounding podcasts from Skype calls with his co-hosts located in Philly (John Gruber), San Francisco (Merlin Mann), Boston (John Siracusa), Somewhere Outside of New York that’s not Brooklyn (Marco Arment), and Canada (Jim Dalrymple). The website is All of the stuff the guys talk about on that week’s show are captured in hyperlinks on the site.

I discovered 5by5 because Merlin Mann started podcasting there with Dan on a show called Back to Work last year. It wasn’t long, though, before I branched out and found these other great shows. Dan appears on all of them and I find myself sort of continually amazed by what a good radio personality he is. He does a great job and all the shows are deeply entertaining in no small part because of Dan’s ability to draw out the best of his co-hosts’ personalities. Here’s a brief summary of the shows so you can know where to start:

Back to Work: Dan and Merlin will spend the first 15 minutes starting the show and talking about children and what Merlin ate that day. Then, they will discuss some aspect of how to know whether you’re spending your time and energy on the right shit. Like I said, I started listening to 5by5 for this show. Merlin Mann is basically my favorite web personality (more on his other stuff in a bit).

The Talk Show: John Gruber writes Daring Fireball, which is one of the best Apple sites out there. This is going to be your general-purpose Apple news show. John’s personality and perspective on things is great. You’ll see what I mean. They will occasionally talk baseball or football. Last year, they watched all the Bond flicks and talked about them at the end of each show. By the time I discovered 5by5, John and Dan had already recorded like thirty previous episodes. Even though the news was old, I still went back and listened to them, just because Dan and John are so fun to listen to.

Hypercritical: John Siracusa is known for his exhaustive reviews of new iterations of Mac OSX at ArsTechnica. He is not satisfied with anything. Erin calls him “that complainer guy”. His targets range from TiVO, to video game controllers, to toasters. This podcast can get fairly technical when Dan and John start talking programming languages, memory management, etc. But, I still find a glimpse into the computer programmer’s world sort of jaw-droppingly interesting.

Build and Analyze: Marco Arment was one of the two co-founders of Tumblr. He quit and started Instapaper. He’s like 28. This is a show ostensibly for iOS developers and you get a sense of what it’s like to build an app for the iPhone, the decisions that go into making it and maintaining it, and dealing with Apple’s decisions that affect independent software developers. Also discussed: coffee, running a small business, and minivans.

The Ihnatko Almanac: Chicago Sun-Times’ technology writer, Andy Ihnatko, spends thirty tight minutes3 with Dan each week. Interesting dude. Earnest.

Amplified: This is 5by5’s newest show. Jim Dalrymple ( and Dan talk Apple and guitars. Jim has the best laugh of any human I’ve ever heard. Not for people sensitive to Canada jokes.

There are a couple of other 5by5 shows I listen to that are no co-hosted by Dan Benjamin. (By the way, all of these people are great to follow on Twitter, if you are a Twitterer. Their handles are all available on Additionally, there is a separate show, After Dark, which is exclusively Dan and his co-hosts after the show is over. Good times.)

Geek Friday: Faith is as charming as Jason is creepy. It’s a great combo.

Mac Power Users: In terms of practical advice on getting the most out of your Mac, this is the podcast that you must listen to. David Sparks and Katie Floyd are both attorneys by day and spend 90 minutes or so walking you through one particular application or process each week. They also have smart people on in their “Workflows” episodes to explain (specifically) how they use their Macs (or iOS devices) to get shit done.

If all of this is not enough for you, there’s The Critical Path with Asymco writer, Horace Dedieu. This is the podcast I listen to when I run out of everything else, not because it’s not good but because it’s just drinking from the firehose with Horace: Dan rarely interrupts Horace, so it’s just one long, intense stream of analysis of Apple’s performance as a company from an intense dude. But, Horace is great to listen to for an understanding of what drives Apple’s current dominance. He is a student of Clay Christensen who pioneered the idea of disruptive theory in businesses and Horace applies it persuasively to Apple and the tech sector.

5by5 is so good, even the couple of ad spots Dan does during each show are useful. I use a number of the services that advertise with 5by5 exclusively because I discovered them on 5by5, including Squarespace, Smile Software’s Text Expander and PDFpen Pro, Agile Bit’s One Password, Harvest (time-tracking), Wufoo (online form-builder), and Mail Chimp.

There are two other podcasts I think you should check out, both involving my Internet Friend, Merlin Mann:

Roderick on the Line: Merlin calls John Roderick who is the lead singer of The Long Winters each week. John has walked from Amsterdam to Istanbul and is just one of the most interesting people I’ve ever encountered. This podcast is really kind of an archeology of both Merlin and John’s minds and pasts.

You Look Nice Today: Three funny guys being funny together. Now you are starting to get a sense of why Erin walks away when I start talking about podcasts…

Until about two weeks ago, I used the built-in music player on my iPhone to listen to podcasts. Since then, I've been using an app, Downcast, to download and stream my podcasts. There are other "pod catchers" out there (like Instacast), but I think Downcast is the best. Incidentally, 5by5 is lauching an app that will allow you to listen live to any of the shows currently being recorded. Look for that in the next week or so in the iTunes app store. 

Good seeing you last night. Hope these podcasts help keep you entertained as you traverse our great Commonwealth. Keep up the good work.


UPDATE: Also, I podcast my awesome minister's sermons each week. If you're interested in hearing about social justice for the 21st Century, subscribe on iTunes. Here's Douglass Boulevard Christian Church's website

  1. What? You didn’t go? Shame on you. Well, you can still donate to Louisville’s Legal Aid Society. ↩

  2. (and at every point at which I mention podcasting) ↩

  3. As opposed to Siracusa and Merlin Mann’s willingness to go ninety minutes each week. (Not complaining.) ↩