5by5: An In-Depth Review

I’m a longtime listener of the podcasts on the 5by5 network. They are an essential part of the soundtrack of my week. I thought it might be helpful to review the network and its shows to help new listeners navigate the various offerings.


5by5 describes itself as “an internet broadcasting network.” Founded and operated by Dan Benjamin, it is a collection of podcasts mostly focused on technology and design. For most of the main shows there is a decidedly Apple centric focus, though other topics are certainly considered.

The lineup is anchored around 4 main shows — Build & Analyze, Back to Work, The Talk Show, and Hypercritical. These shows are recorded live on a weekly schedule, then published towards the end of the recording day.

Additionally, there are 13 other active shows including: The Big Web Show](http://5by5.tv/bigwebshow), [The Cocktail Napkin](http://5by5.tv/tcn), [Content Talks](http://5by5.tv/contenttalks), [The Critical Path, Founders Talk, Geek Friday](http://5by5.tv/geekfriday), [The Incomparable!](http://5by5.tv/incomparable), [The Inhatko Almanac, Let’s Make Mistakes, Latest in Paleo, Mac Power Users The Pipeline, The Web Ahead. [* Shows typically recorded live]

While a few shows are available with video, most are audio only. Most are recorded by Dan from his office in Austin, TX.

As of writing (12/12/2011), there are approximately 689 hours of audio spread across 667 episodes, about a month of content if listened to end-to-end. The shows are syndicated via RSS and iTunes feeds.

I listen to prerecorded shows using an iOS app, Simplecasts, that I wrote specifically for enjoying 5by5 content. I also wrote a Mac app, FiveLive, for listening to the live shows while I work.


There are two types of shows on 5by5. The first are co-hosted by Dan. In these, Dan typically kicks things off with a bit of music and an introduction. Then he lets the host set out the agenda for the show. What follows is typically the main host talking around 80% of the episode, with Dan interjecting with questions, opinions and clarifications as needed. The second type are shows simply syndicated via the 5by5 website, these vary in topic and style.

Every show has a couple of sponsors that are mentioned briefly at the beginning and then given a 1-2 minute promotion during the show.

Specific Shows

All the shows I’ve ever listened to on 5by5 are well produced and high quality. However, I’m now going to walk through some of the shows in depth. I’m going to focus on the ones that I listen to on a regular basis, since I can provide the best characterizations for them. If I don’t touch on a particular show it isn’t a reflection on its quality, just my interests.

Following my thoughts and description of each show, I’ll list a few of my favorite episodes to give you a flavor of the show.


Co-hosted by John Siracusa and Dan Benjamin. John has the unique talent of being able to relentlessly deconstruct almost anything and explain exactly how it could be improved. He shines this laser light of critique on topics ranging from toasters to the Steve Jobs biography.

The thing I enjoy most about Hypercritical is the precision and organization that each episode possesses. In each episode there is a clear point to be made. This point is then made in a concise and compelling manner. Furthermore, this show really benefits from the variety of topics it touches on. Rather than being focused in one particular area, each week is almost entirely unique.

Recommended episodes to sample:

The Incomparable!

Hosted by Jason Snell. This show existed outside of the 5by5 network for a long time before being recently added to the lineup. Jason curates a discussion with a variety of guests on diverse but decidedly geeky topics. Typically they are talking about TV shows, movies, games, or comics. The best part of this show for me is the variety of guests that appear. The show feels like a group of old friends getting together at a bar, each vying and almost competing to get their views across. The Star Wars discussions are incredible.

Recommended episodes to sample:

The Talk Show

Co-hosted by John Gruber and Dan Benjamin. John is the author of Daring Fireball, a news and opinion site focused heavily on Apple and related industries. The show itself is probably best described as a “Director’s Commentary” for Daring Fireball.

The show has a familiar, conversational feel. On a typical show John will expand on his thoughts regarding the topics of note in the week’s technology news. The show typically doesn’t have a particular theme or topic, but jumps from one point to another as the conversation leads. The Talk Show provides extra depth to the opinions voiced by John on Daring Fireball.

Recommended episodes to sample:

Build & Analyze

Co-hosted by Marco Arment and Dan Benjamin. Build & Analyze is theoretically about development. In reality it is a much more similar to The Talk Show, in that it is a “Directors Commentary” covering and expanding on the articles and links found on Marco’s blog.

In the earlier episodes it had a more focused, topical style, but it has evolved into something more general. Marco is a sharp, opinionated, and well spoken engineer who can lend a more technical slant on technology news. I’ve found this show and The Talk Show to complement each other in this regard.

A recurring topic on this show is coffee and its preparation. I discovered a love of coffee from listening to the affection and care Marco uses when discussing coffee. If you don’t run out and get a conical burr grinder and Aeropress after a few shows, then there is something wrong with you.

Recommended episodes to sample:

Back to Work

Co-hosted by Merlin Mann and Dan Benjamin. Back to Work is a harder show to summarize than most of the others. The show is ostensibly about productivity and work, however, I think that narrow of a description would do the content a disservice. The show is really about how to discover what it is you want to do, define and understand that, and demolish the barriers (perceived or otherwise) that are keeping you from accomplishing it.

Back to Work is a weekly reminder that you really can, and should, be happy in what you do. Rather than providing self-help platitudes, Merlin is honest about how tough productivity and satisfaction are. This is probably one of the only ‘timeless’ shows. I’ve re-listened to many episodes, each time getting something new from the hearing.

I’ve heard that the style of the show, and Dan and Merlin’s banter, can be a bit tough for some new listeners to get used to. There a couple of running ‘bits’ and references that make perfect sense to a longtime listener but might come across as rather oblique at first listen. This challenge disappears once you get used to the rhythm of the show. Hang in there, it’s worth it. Sometimes the best things in life take a bit of effort and focus. If you want a podcast that just rakes along the surface, all you’ll end up with is leaves. Back to Work is more like digging with a shovel — hard work but resulting in real gems.

Recommended episodes to sample:

The Critical Path

Co-hosted by Horace Dediu and Dan Benjamin. More than any other show, The Critical Path requires a strong cup of coffee before listening. Horace takes the listener into the deepest and most specific aspects of Apple and related companies, focusing on the business aspects of their successes and failures. This is the only show that I can’t listen to while I work, since it takes a lot of focus to follow the nuance and detail of his arguments.

I come away from every episode with a much deeper understanding of just what goes into the business of being a modern technology company.

Recommended episodes to sample:

The Pipeline

Hosted by Dan Benjamin. This is a more traditional interview-style show. Dan interviews and explores the work of a different guest each episode. The guests range in industry and speciality but most are in some way related to the technology world. These interviews often provide great insight into the lives of people I’ve heard of but only know in a one-dimensional way.

Recommended episodes to sample:

Mac Power Users

Hosted by David Sparks and Katie Floyd. This show, like The Incomparable!, started off outside of the 5by5 network and was recently brought into the fold. The show is generally about how you can be more productive and effective using your Mac. Each episode typically focuses on a particular aspect of use and then drills deeply into how you can be more efficient and effective in that area.

Periodically they have workflow shows, where they interview a notable guest on how they go about their daily work. These are my favorites. It is fascinating to hear the tricks and tools used by some of the leaders in tech.

Recommended episodes to sample:


As you can probably tell from the preceding few thousand words, I highly recommend 5by5 to anyone with time in their week to listen to a podcast. Listen to them during your commute, walking the dog, or while you work. Find the time to listen and I’m confident you’ll enjoy the result.

If you can, I’d recommend trying out listening live too. Get in the IRC room and say hi. I’m DavidSmith in the chatroom; you’ll almost always see me around. Live listening gives the shows a much more personal and fun feel.

Postscript, My experience

I’m, what could accurately be described as, a big fan. In preparing for this article I counted up how many hours I’ve spent listening to the various shows and I came up with a rather shocking 433 hours or about 18 days straight.

My history with the network started a couple of years ago when my then-favorite podcast, Rails Envy with Jason Seifer, joined the fledgling 5by5 network. That was my first introduction to Dan Benjamin and his unique style of podcasting. It reminded me more of classic talk radio than what I was accustomed to with typical ‘tech’ podcasts.

I wasn’t, however, a consistent listener until July, 2010. That was when the Talk Show was launched on 5by5. I have the generally rare ability to listen to a podcast while working without it adversely affecting my efficiency. If anything, I found that listening to the shows while I worked helped me work better. It mitigated the isolation that is often felt when working from home. My water cooler became listening to the shows and interacting in the chatroom.

Ever since, I’ve listened to 5by5 shows every week. They are such a fixture of my day-to-day life that I wrote an iOS app for listening when I’m out and a Mac app for listening to the live shows while I work.


While listening to 5by5 shows you may hear a few terms you aren’t immediately familiar with. I defined them for your reference.

  • Showbot: A website and IRC bot created by Jeremy Mack. It is used to collect suggestions for show titles provided by The Nerds during live recording.
  • After Dark: The portion of the show recorded directly following the main recording. This is released in a ‘secret’ feed not directly visible on the main 5by5 page. They are listed separately in iTunes to avoid the explicit tag. It is unedited and uncensored.
  • Show Notes: A collection of links relating to the current episode. This is provided in the RSS feed for the show, as well as on the episode page.
  • The Chatroom: An IRC chatroom (#5by5 on free node), where listeners can discus the show and interact with the hosts while it is being recorded live.
  • The Jackals: The term of endearment given to the more negative members of the IRC chatroom used during live shows.
  • The Nerds: The term of endearment given to the more positive members of the IRC chatroom used during live shows.
David Smith