Lend Me Your Ears: A Guide to Selecting Podcasts

Management theorist Peter Drucker wrote many tips on how executives should obtain knowledge. Here’s one tip from his book The Effective Executive:

“The first thing to know is whether you are a reader or a listener. Far too few people even know that there are readers and listeners and that people are rarely both. Even fewer know which of the two they themselves are.”

President Kennedy was a reader, President Johnson a listener. Drucker contends the passage of administrations was fraught with problems since the aides who managed the transition — trained to convey information in written form — didn’t get through to the listening-oriented Johnson.

Consider your coworkers. It’s probably good to know which type they are. If you convey to someone multiple times “I emailed you” or “I told you,” perhaps it’s time to flip the method. You’ll likely have to conform to what works best for them.

But what works best for you in gathering knowledge? How should you choose what to read or listen to? Listeners are at a disadvantage.

Readers can skim first, although skimming can be a double-edged sword: the fire hose of material can cause us to skim too much for understanding. However, skimming gets a bad rap because it’s actually fundamental to selecting books properly: you have the blessing even of Mortimer J. Adler, creator of the University of Chicago’s great books program, to skim. Skimming is the second level of the reading hierarchy in his How to Read a Book: “Inspectional Reading.” Without skimming first, you could spend unprofitable hours or days on a book not suitable to your goals.

If you are a listener, or just someone stuck in traffic and looking for a lifehack, how should you choose your material? The easiest bite-sized is the “podcast.” This neologism of obvious roots is just under a decade old and still an emergent form. Podcasts come in audio and video flavors, repurposed and original material. I’m defining podcasts as any material custom-made for the medium, or material easily transferred. A podcast typically means something episodic, but often the best content isn’t lurking in episodic form.

For these listening activities you need to dedicate time, daily or weekly, to make it worthwhile. My post is intended to emphasize technology-related podcasts, audio snacks in the car or on the treadmill which, if listened to regularly and intently, can advance a career.

Still, it’s an almost endless buffet. Where to start?

Some podcasts have transcripts where skimming can be applied. But you can miss a lot: “Double down on something good and you might become great at it” is a good aphorism from Jason Calcanis’ This Week in Startups with Jason Shellen as a guest. There were some also unexpectedly good observations about the NSA surveillance story in the same podcast. A transcript wasn’t available, but I think had I glanced at it I would have passed on listening. Sometimes the delivery is important to the content’s impact. How quickly does someone reply? With what intensity in their voice?

Tags are the next logical filter. But they are more expressive of what the content is than critical of it. Even so they’re too broad; every proper noun gets tagged. In some future browser it would be nice to crowdsource upvotes and downvotes to overcome the gaming of the algorithm.

The media brand publishing the podcast should be a good indication of quality, but often the podcast is an afterthought. The New York Times runs afoul of this most notably, and even the New Yorker’s podcasts don’t bring much more to the table than the articles they’re associated with.

Despite this, I think there are some useful categories that can help listeners to optimize their podcast experience.


When a new media format comes along, the first thing producers do is bring nearly the exact production from another media to the new one. Few performers of any type can make a switch because new mediums demand new formats. These formats also make different demands on their audience. In Marshall McCluan’s famous formulation from Understanding Media, media exist on a spectrum of hot to cool.  “Hot” media includes film, which accentuates one sensory aspect. “Cool” medias demand greater user engagement but is not as intense (such as a comic book). Podcasts, whether audio or visual, are usually very cool media. The longer and more engaging the podcast, the more cool it is.

Unfortunately many podcasts are stuck taking the production values and cadence of other media. They bring the “heat” of this media to podcasts with ill effects. They can bring the overproduction of television or the shortness of radio.

The too short to be useful category has one sample illustrious member: the Harvard Business Review. Their IdeaCast has to be counted among the least effective brand extensions. Many real estate and other “small business tip” podcasts share this flaw. Compare Aaron Levie of Box here versus any other podcast appearance of his. Most podcasts with the word “Tip” or “Minute” in them can be avoided because they’re simply not memorable enough. There are very few Paul Harveys out there whose marriage of aphorism and euphonious tone can merit short audio blurbs. It is hard enough to do in radio, and it’s best done there as seasoning on otherwise dry news recitation.

Television-style overproduction plagues a large number of video game podcasts – it is unfortunately the hallmark of some entire podcasting brands. A major flag that overproduction lurks is the presence of an extended or flashy video intro. These dizzying quantums of energy from the Adobe Creative Suite are meant ultimately to appeal to advertisers. They want to believe their brand will not be sullied by any hacked-together production values. The waste of time is not large. As on TV, often these are 30 seconds or less, but it is invariably a flag for the rest of the values of the show. Anything more than an opening song introduction is asking for trouble, and the sizzle can drown out the steak.


A mixed bag. TED podcasts are problematic in the camera angles, length, and exclusion of questioning. The camera is notoriously unsure of whether to cut to a PowerPoint behind the speaker or stay on the speaker. Audio quality can be mixed either in production value itself or in the speed the presenter has to divulge their thoughts. Good editing can cure the former, and Youtube playback at accelerated speed cures the latter. Still it’s rare for the medium’s food to be that processed and come out tasty.

Relatedly, podcasts of classes suffer from the same technical fates. Humanities lectures can still be engaging, such as James Vernon’s Modern British History or Ben Franklin and the World of the Enlightenment from Stanford. Many universities rushed to the web in a reprise of the publish-or-perish of the tenure track life with mixed results scattered over iTunes U. Natural science courses should be taken in the MOOC form polished by Coursera, EdX, and Udacity. Hitting a “content not licensed for online distribution” is a big buzzkill in many science podcasts.


Listening to Spencer Ante on George Doriot or Adam Lashinsky on the organizational culture of Apple is a good use of time (Knowledge@Wharton or Stanford’s ETL). A better use of time is to read the books themselves, or listen to the audiobooks. When a subject matter expert is on a book tour, the material is usually a selection of material straight from the book. Good writers think about various ways to express something and try to find the best expression of their ideas in the book itself. When interviewed, the interviewer is often only bringing a superficial understanding of the book’s general topic. The author on tour is left to reformulate words already chosen. You could listen to the audiobook in three or four hours or skip to read the chapters you’re most interested in in the same hour you’d spend on a podcast. I would have been more interested in hearing Lashinksy on Walter Isaacson’s bio or vice versa than on their own works. A reconsideration of their books a few years after publication would be very satisfying. Why not ask Ken Auletta now instead of 1991‘s Three Blind Mice (about TV Networks) instead of the still fresh Googled?


A variant of the journalist on book tour problem. Here the complexity of the expression of the idea is often not suitable for the format.  The topics can be effectively closed in and of themselves, and the historian is in the position of trying to draw parallels to some contemporary issue. This can work well when interviewer, interviewee, and audience are all knowledgeable about both the historic episode and the contemporary issue, howeverthe risk of sputtering out otherwise is high, and you wind up in Newshour territory.  Doris Kearns Goodwin has many great observations about Lincoln’s Cabinet or the life of Franklin Roosevelt.  But the anecdotes are predictable: Got a problem with your Generals? Lincoln had those too!

The tech industry’s relative newness and rates of change make historical citations rare and harder to pull off.  Apple is certainly very aware of the risks and rewards of licensing versus exclusively vertically integrating around an operating system — this “lesson” of history is probably less clear than those citing it make it out to be, simply becausetoo many things have changed.

Some special exceptions exist.  For example, a techie who listens to even a two minute podcast from NP about the history of The Great A&P will probably exceed his or her need to learn about the perils of expansion from a different industry, regardless of actually reading the book. (Thirty minute podcast from WNYC here.)

A huge treasure, for the relaxed, but still penetrating approach he took, was Brian Lamb’s Booknotes.  It is a matchless trove of fifteen years of in-depth interviews. The entire archive is available online and allows for a good gut check.  “What happens to your career if your prediction fails?” was his first question for James Glassman’s 1999 work Dow 36,000.


The apotheosis of this category is also the eponymous.  Tim Ferris and Kevin Rose’s the Random Show is twenty one episodes strong as of this writing and is a bricolage of the quantified-dude lifestyle.  Hit or miss, the literally random construction allows for large dollops of personality and charisma. The outcome for the listener falls on what he or she think of the personality, rather than the material. Pando Daily’s WITN is another example. The podcast might open with, and be punctuated by, coverage of infants’ clothing being changed, and how the weather was in different visits to New York City. Some viewers might like that, others not. If an episode is both “random” and produced over skype, it’s going to be very hard to get an informative and not sarcastic podcast out of it. In gaming and tech you’ll sometimes get very engaging characters and these shows are akin to eavesdropping on a conversation at a coffee shop. Most coffee shop conversations would benefit from an editor.

One litmus to apply: has the “random” format kept going for a long time? Rock Paper Shotgun has been doing something well for almostfive years of podcasting. There is probably a worthy ghost in the machine there (for very hard core & indie gamers.)


An air of not just self-confidence but breezy truculence marks many entrepreneurial careers. That can make for engaging shows — he earlier in their career, the better. The ideal period is after the entrepreneur has experienced both pain and pleasure, some success but not too much. Before that, you will get simultaneously grandiose and defensive visions with few applicable life lessons. Phrases like “disrupt the industry” to “dent the universe” will be used with shamelessly and with numbing frequency.  Listening to Drew Houston wonder whether a large check from a VC can be cashed is honest, not smug, but certainly best to hear when first told. Subsequent iterations can become more practiced, and the speakers themselves are doing less self-discovery. David Sacks’ podcasts before and after the sale of Yammer are both good; the one before feels more earnest. So too Kevin Systrom before the sale to Facebook: who knew if it would be the next Digg or presage other billion dollar social media buyouts?  Once a company is sold to a larger company while the earnout is still in place, the visions of an entrepreneur as divisional manager are warped and tongues are tied

An exception to this is when the billions have had some time to settle in and larger philosophical reflections can be had.  Acting as the statesman instead of the revolutionary can bring good perspective to an audience. Tom Siebel gave a great example of this in 2009. Many of this genre will be found as guest speakers in academic settings, such as Robert Schiller’s Financial Markets Course at Yale which has featured among others Steven Schwarzman and Carl Icahn (same year: 2008; whole course available here.)


Properly organized and often best if in the same room, this is where the full potential of the medium can flower.  The guests are knowledgeable and assume their audience will be.  They know the topics in advance but not what others will say.  They likely know each other and you’re dipping into a stream of an ongoing conversation. This is the ideal recipe. Ingredients matter. Sarah Lacy and Jason Calacanis’ together in any situation work themselves into a torrent of honesty, gossip, predictions and reflections that is hard to miss.  The differential between her work there and the sarcastic-ironic cauldron of WITN is hard to miss. Kara Swisher or Michael Arrington are also at the top of their game when improvising or on the spot. While the familiarity can sometimes descend into a festival of backscratching or journalist minutiae, even those byways keep the stream running. That’s why the News Roundtables of This Week in Startups is a must-listen.


These are nearly always a pass. Mid-level managers at large organizations get to become CEOs partially because they stay on a tightly scripted message. And tightly scripted effectively by committee.  The question and answer sessions are duds. One Facebook manager, after waxing poetic about the culture of “move fast and break things,” was asked what exactly had moved fast and changed in the last few years at Facebook. Facebook Home was the answer – alas before it was really proven broken. Any company exec whose employer has “General” in its name (except for General Assembly, come to think of it) can profitably be avoided.


Entrepreneurs looking for funding should listen to nothing else. A good selection process is already in place – venture capitalists without much interesting to say will tend to keep their mouths shut and he good ones can differentiate themselves through demonstrating thought leadership about the industries they cover. Most VCs who will in fact be the “smart money” and provide extra value will have done a podcast or two. They will often be guest lecturers at classes in the bay area, and usually are very reflective and insightful, willing to share the data that lead to their decisions. From “super-angel” to top tier fund, they are also forthright about the funding process and what they themselves are looking for. The interviewers often have a gravitational pull to ask what is happening with Google, Apple, Facebook and Twitter, but when they let loose like Chris Sacca it is very informative. Also importantly you get a sneak preview for how the cadence of a meeting might go in ways you don’t from reading their blogs.


The best podcast is like an eavesdropped conversation – you’re listening to a conversation emerge and in the best of cases, inform the speakers themselves.  Productions that accentuate this by minimizing production values for its own sake and let the dialog happen are the best sign.  Find your own filters. If the podcast doesn’t engage you almost immediately you’re not obligated to keep paying attention.  Better to hit “Stop” and go on to the next one instead of letting your attention drift.

What are your favorite podcasts?  Let us know in the comments!