Dan Benjamin’s recent announcement that both John Siracusa and Marco Arment would draw their run on 5by5 to a close during the month of December gave me the final push I needed to finally publish this blog. After having spent just over two years listening to these truly brilliant co-hosts discuss everything from TiVO to toasters and Journey and The App Store to artis-anal coffee methods and Fox News, what better way to open my new blog, just as Steven Sommer did, than with a hat-tip to the men responsible for prompting me to take this step? So as the Twittersphere bemoans the passing of these two excellent podcasts as their co-hosts move on to better things, I would like to thank not just John Siracusa and Marco Arment but also Dan Benjamin, not only for providing me with hundreds of hours of first-class entertainment throughout the past two years, but for all the lessons they have taught me as well. I certainly regret the passing of these two excellent shows, but I wish both Marco and John the best in their future endeavors; and I have faith in Dan Benjamin, that he will continue to produce the best podcasts on the internet.

Roughly two years ago I went on a search for an archive of Jonathan Goldstein’s CBC radio program Wiretap. This search led me to dig through NPR’s program archive, scour torrent trackers for a private collection, and, eventually, search Apple’s podcast directory, where I finally succeeded in my endeavor. With the culmination of Wiretap’s first season though, I gradually fell out of step and presently abandoned the world of podcasts for quite some time. A few months later, I happened across 5by5’s newest fledgling podcast, Hypercritical. Hosted by Dan Benjamin and John Siracusa, the pair hooked me on the first episode with an impressively in-depth discussion regarding the state of the television industry and solutions for time-shifting your viewing including the much-hated TiVo solution, a topic which used disruption as a segue to a discussion of the music industry and the reasons Apple revolutionized that space with the advent of the iTunes Store. Continuing the trend in Backup Vortex, John and Dan spent nearly an hour and a half discussing computer backups in the now-famous second episode of Hypercritcal; with this episode, I began my walk down the path of podcasting geekery.

In addition to providing a gentle push in the direction of podcasting, Hypercritical’s second episode also piqued my interest enough to explore other 5by5 podcasts, including the infant Back to Work which aired its first episode just three days before Backup Vortex hit the stream. After slightly more than twenty minutes of introductions and nervous conversation, Merlin Mann checked me into the wall with his explanation of procrastination:

Merlin: Procrastination is an effect, not a cause — in my opinion.

Dan: What’s the cause?

Merlin: What’s the cause of procrastination?

Dan: Yeah.

Merlin: Really?

Dan: Yeah.

Merlin: This is the hippiest thing I’ll say on here today: it’s when you temporarily forget who you are or who you want to be; it’s when you forget what you’re supposed to be paying attention to and when you lose confidence about what your options are for doing something about it.

Over the next year I continued to listen to both Hypercritical and Back to Work, as well as a number of the other 5by5 programs. Specifically, I came across Build & Analyze, The Big Web Show, The Daily Edition, The Dev Show, and On The Internet, all of which I subscribed to. I also tried — numerous times — to get into The Talk Show, Dan Benjamin’s first 5by5 podcast and the show that started it all, though with little success for the first year or so; however, I soon came around and subscribed to that podcast too. At the height of my podcasting consumption around this time, I subscribed to eight podcasts and listened to more than ten hours of program each day in an effort to not only stay current on the latest releases of each podcast, but also so that I could work my way through the back catalog of previously-aired episodes.

Up to this point my focus has remained solely focused on 5by5 programs, leaving out all other podcasts. The reason for this is, unfortunately, quite simple: back then I subscribed exclusively to 5by5 podcasts not due to any prejudice against other podcast producers, but for the simple reason that even among the best podcasts, few could hold a candle to the quality present in any one of the episodes released in a 5by5 feed. Certainly not for lack of trying, but simply because Dan Benjamin is just that good at what he does. Dan actually talked about his impressive setup in an episode of After Dark — a special podcast recorded “after Dan and his co-hosts hit ‘STOP’ and their official shows are over. Behind the scenes, casual, unedited, and uncensored." — entitled Pamphlet. I strongly recommend listening to this episode if you wish to know the best way to go about podcasting. For more podcasting recommendations regarding the best hardware and software to use, Dan posted an article on his personal blog, Hivelogic, entitled Podcasting Equipment Guide 2011 midway through last year. Both the episode of After Dark and his blog past are excellent resources for the beginning and the seasoned podcaster alike.

As time has passed some of the podcasts that initially attracted me to 5by5 have retired for one reason or another. The Daily Edition, for example, as well as The Dev Show and On The Internet all came to a rather abrupt end. Other programs such as The Talk Show and Let’s Make Mistakes, on the other hand, have moved to the Mule Radio Syndicate, where they continue to broadcast today. As one door closed another opened though, as shows such as Amplified, The B&B Podcast, The Critical Path, In Beta, and Systematic have all made a home at 5by5 Productions, as numerous other podcasts have as well.

All in all, Dan Benjamin has been remarkably successful in this space — a pioneer in the field of podcasting. Given the level of success his network has experienced since opening its doors in 2009, one might conjecture as to why he has succeeded so spectacularly when others have either experienced much more moderate success or outright failed.


The most striking aspect of the 5by5 podcast lineup lies in the quality of each episode. Not simply the quality of the audio though, but also the quality every co-host brings to each podcast, neatly packaged and expertly compressed into an easily-manageable MP3 file. Unlike NPR, where the sound of the hosts’ mouths opening and closing is, quite unfortunately, audible in nearly every program, Dan has struck the delicate balance between manageable file sizes and — quite literally — grossly high-quality recordings as in the case of NPR. When a host speaks, his or her voice rings through loud and clear; during the occasional pause, on the other hand, regardless of how loud the recording is played at, absolutely nothing — not even white noise — plays through the speaker. Exceptional quality does not stop at audio fidelity and manageable file sizes though, but extends also into the content of each and every broadcast episode. Often I find myself wondering how Dan found a given co-host and how he convinced that prominent internet figure to sit down and record a podcast every week, the result of which is at least an hour of excellent insight into any number of different industries and markets. Take, for example, The Critical Path hosted by Horace Dediu of Asymco.com: a podcast focusing largely on disruption theory, Horace studies Apple as a benchmark to which other companies can be compared to in order to better understand the causes of success and failure in today’s mobile computing market. Slightly more than a year after the first episode of The Critical Path aired midway through 2011, Horace has sorted through, arranged, and condensed the first year’s worth of podcast content into a book: The Critical Path: The First Year. Also among 5by5’s impressive list of hosts, Marco Arment, creator of Instapaper, editor of The Magazine, and writer at Marco.org, hosts Build & Analyze, a popular podcast intermittently discussing the business of building, marketing, and selling an app through Apple’s App Store between offering parenting advice and continuing the never-ending coffee discussion. Other prominent bloggers such as Jim Dalrymple of The Loop, Gina Trapani previously of Lifehacker, and Merlin Mann of 43 Folders, Roderick on the Line, and You Look Nice Today all call 5by5 home. 5by5 produces some of the best podcasts available to date, conveying the words of insightful internet superheroes at high-fidelity in one small file. These and other similar programs have placed Dan Benjamin forever on the map of podcast fans everywhere, and have also given rise to a number of memes throughout the years since he began broadcasting full-time in 2009.

As Dan Benjamin’s success in the podcasting industry grew — explosively so with the advent of Back to Work and Hypercritical — other podcast producers began to take notice of both his business and the manner in which he conducted that business. This growth in popularity and attention marked the beginning of a steady increase in the number of podcasts on the 5by5 network, which would end in the addition of more than ten podcasts to the already impressive list of shows and result in an accordingly large surge in the popularity of the network. As I said, the growing popularity of the 5by5 network also attracted attention from other podcast producers. This led to an almost exponential increase in the quality of non-5by5 podcasts over the next few years. Although this growth in quality could be the result of natural progression over time, empirical evidence suggests that Dan Benjamin greatly influenced and possibly even set into motion this transition as others strove to emulate his success. We can draw parallels between this occurrence and the release of the first iPhone back in 2007 which revolutionized the mobile phone industry, causing the incumbents to scramble to respond or, most notably in the case of Samsung, simply copy the latest and greatest device in order to survive.

In addition to setting into motion an industry-wide broadcast quality renaissance, Dan Benjamin’s growing popularity also led to the adoption of his business model by other fledgling podcast networks. Just as many websites adopted John Gruber’s practice of posting links to news stories along with relevant commentary once that model was proven fanatically successful, podcast produces such as Mike Monteiro of The Mule Radio Syndicate and Myke Hurley of 70 Decibels have adopted Dan Benjamin’s proven business model of a single network producing numerous primarily technology-related programs, with each program featuring one or more hosts along with the occasional guest, supported by on-air ad readings. Rather than crediting Dan Benjamin with causing another evolution in the podcasting industry this happenstance could be argued, like the evolution of overall podcast quality in the past three years, as simply result of the logical progression in this industry as a function of time. This same theory was argued in the Apple v. Samsung copyright suit when Samsung attempted to defend blatantly copying Apple’s designs, saying that Apple’s patents should be nullified as both the form factor and interface designs were a result of the natural progression of mobile devices over time, not the result of a designer’s ingenuity. The jury ruled against Samsung, signifying that regardless of whether or not natural progression is a valid defensive argument in the case, the fact of the matter was that Apple created an ingenious design, and Samsung copied it. Yet another parallel can be drawn between Dan Benjamin’s podcast network and the world of Apple, as Dan Benjamin was the first successful network to adopt such a business model, and now others are beginning to follow in his footsteps.

As an aside I would like to make it clear that my intent in comparing podcast producers and Mike Monteiro in particular to Samsung is not to disparage their work or cast the fruit of their labors in any sort of negative light; rather, I simply find it interesting that so many parallels can be drawn between the podcasting industry and those that Dan Benjamin discuss with his co-hosts on their podcasts, and feel that the readers of this article may also find these similarities of interest.

Beginning in the early days of 5by5 and on through the relatively slow years leading up to the release of Back to Work and Hypercritical and the frenzy that ensued, we have examined the history behind 5by5 Productions, allowing us to contemplate the causality of success and failure, to use a line from The Critical Path’s description, in this industry. To liken 5by5 to Apple, both companies began modestly: Dan with The Talk Show, and Apple with the Macintosh. Both companies sustained a respectable rate of development for quite some time until each experienced explosive growth, sending both to the forefront of their respective industries. Just like Apple, 5by5 continues to impress year after year; and just like Apple, Dan shows no signs of stopping any time soon.