Friendly Conversation for the Drive

It’s snowing again, which means my normal 40-minute commute will now be closer to an hour. I’m actually a bit excited by the prospect of a long drive; it will give me some time to catch up on my favorite podcasts, most of which come from Dan Benjamin at 5by5.

What Dan has built at 5by5 is important. He’s amassing a collection of incredibly smart people, the people who design and build the things we use on our computing devices every day. Dan is an accomplished developer himself, and has been publishing online since the paleolithic age on Hivelogic. The 5by5 interviews are an audio library of intelligence. Inspirational and honest, Dan has a talent for asking meaningful questions that cause his guests to think. What I love most about the 5by5 shows, especially The Pipeline, is that Dan always asks questions along the same subject line: “How did you get to where you are?” and “How can the guy sitting in a cubicle get to where you are now?”.

The answers to his questions are often hard, but always truthful. There’s a theme of hard work and dedication that goes through all his guests. You don’t get to be a successful developer, designer, producer, writer, or any other profession without hundreds of hours of sweat and tears. You don’t get to be a successful small business owner without the guts to take the necessary calculated risks.

I don’t subscribe to all of the 5by5 shows, but here are my favorites:

  • The Talk Show: John Gruber, from Daring Fireball, and Dan Benjamin talk about technology, Apple, Star Wars, and all kinds of assorted nerdery. Listening to the Talk Show is like sitting at the pub with a couple of good friends over a pint.
  • The Pipeline: The main 5by5 interview show, Dan’s guests are makers, they build what we use. The Pipeline is an inspirational, entrepreneurial show about chasing your dreams, never giving up, and being honest with what your passion is.
  • The Big Web Show: Tagged as “Everything Web That Matters”, Dan co-hosts this show with Jeffery Zeldman, author, speaker, designer, developer, and pioneer of web standards. Dan and Jeffery’s guests range from the unknown trying to get tracktion on a start up to Roger Black.
  • Back to Work: Merlin Mann brings his unique view on work, attention, and real productivity to the newest addition to the 5by5 network. I’ve been a big fan of Merlin’s for a long time, and I’m happy to see him back in the public again after his hiatus to write a book. As of today, there has only been one episode of Back to Work, but I’m excited to see where this show goes.
  • Build and Analyze: Marco Arment, co-founder of Tumblr and developer of the amazingly awesome Instapaper hosts this show about programming, coffee, and doing things the right way. Marco is super intelligent, and equally opinionated, a combination which that for a really great show.


    The 5by5 shows remind me of broadcasting in the 1950s, an idea that I think Dan shares, if the current design of Hivelogic is any indication. One of my favorite parts of each show, strangely, is the advertising. At some point in the show Dan will stop and acknowledge the sponsors, and read a prewritten release. It feels low-tech, and so much more authentic than a gimmicky advertising agency, and far, far more human than a banner ad on a web page. Whenever I hear the ad I imagine a guy in a suit standing at a microphone tossing papers on the wooden floor after each page is read.

My daily drive is easier now because of 5by5, so, thanks.