A Guide to Podcasts

My recommendations for podcasts and my app of choice.

Recently I’ve found that I’m being asked for (or more often I simply offer) my recommendations for podcasts. I consider myself a pod-listening pro, if such a thing exists, and justify this on the basis that my iPhone reports 18.5 hours of usage of Overcast (my podcast app of choice, more below) over the last 10 days, I listen to most podcasts at 1.5x speed, and have an unhealthy anxiety to achieve Inbox Zero with my podcast queue - those last two are likely closely linked.

I fill large parts of my day with podcasts - making a boring commute more interesting or learning about topics of interest through a low interaction but high-bandwidth medium. There’s something for everyone, from serial dramas to comedy talk shows, and I think audio will continue to grow as our computing become increasingly ambient through speakers, watches, and headphones.

For future convenience and potentially wider benefit, here are my top tips for listening and some curated podcast recommendations.

There’s an App for that

I’ve already mentioned Overcast for iOS; it’s been my go-to for podcast listening since 2014 and continues to deliver the best listening experience on mobile. It’s free to download with the ability to remove ads through an annual subscription. Overcast offers two key features that I couldn’t listen without:

  1. Smart Speed cuts out the silences in the audio, snipping dead parts of episodes without distorting the audio.
  2. Voice Boost rebalances the audio levels to ensure the hosts voices are clear and all shows are equalised.

Other good options include the built-in iOS podcast app (free and well integrated) and Castro for iOS (free with an annual subscription for premium features, such as their own version of Overcast’s Smart Speed).

An aside, Castro is by far one of the best designed apps available on iOS. It’s playful, opinionated, and has a unique podcast queuing system.

I don’t use Android regularly but have been told Pocket Casts is a top choice, also available on iOS.

With your app in hand and a few shows downloaded, there’s not much more to it - get listening. However if you’re like me and want to have both quality and quantity then head on over to the playback settings and start to speed up your hosts. Most shows can be listened to comfortably at 1.2x to 1.4x speeds. Once you get used to this, you’ll find some shows can be increased higher still and 2x speed will become your new default. I tend not to exceed this but I know others who have conditioned their listening habits to accept 3x speed.

For some higher production shows, such as serial dramas, increasing the speed can start to ruin the listening experience. Apps like Overcast and Castro allow for per-podcast playback speeds, simplifying the customisation experience.

My final listening tip is to liberally use the Seek Forward controls (I’ve set mine to 30 seconds) to jump through uninteresting sections and, more importantly, skip any ad breaks. Chapter markers are also a very effective tool for this but not supported by all shows.

With iOS 11, Apple allowed podcast producers to create trailers/teasers and bonus episodes as well as bundle a selection of episodes into a Season ensuring you start at the beginning as a new subscriber. This greatly simplifies your ability to jump into an existing show and binge at your leisure.

Show Guide

I currently have approximately 90 shows within Overcast; a mixture of must-listens for every episode, down to shows that frequently have excellent guests but I regularly skip most episodes. Below is a selection of my favourites from across this spectrum.


Some of the smartest thinking on the leading edge of technology, a16z have invested in companies like Airbnb, GitHub, Slack and more. Generally the topics can be summarised by Marc Andreessen’s famous phrase - “software is eating the world”.

Easy to start at any point with a rich back catalogue to explore depending on your interests.

Do By Friday

A three person talk show where topics range from daily use of tech to US politics. Every week the hosts participate in an agreed challenge that’s as random as the topics. One of the funniest shows I listen to.

There’s a number of in-jokes from previous episodes but you’ll pick them up quite easily and can enjoy the show without.

Against the Rules with Michael Lewis

Michael Lewis’s investigative style, pushed into the populous by The Big Short’s movie adaptation, is very well suited to audio form. Against the Rules is a short series covering the judges and rule makers in society.

Works best if you listen to it as an end-to-end series; it certainly seems like Lewis planned it as Season One of many.

Conversations with Tyler

Tyler Cowen brings an strong economist’s perspective to his interviews with some of the brightest minds across industries. A good place to start is his interview with Daniel Kahneman, of Thinking, Fast & Slow fame.

Pick any episode that seems interesting. I don’t download every episode; instead I check the guest and go from there.


Myke Hurley, co-founder of one of the largest independent podcast networks, and CGP Grey, a creator on YouTube, discuss work, working life, and - more recently - stepping away from technology.

Generally references past episodes but a fairly low threshold for in-jokes. Topics do build as the show progresses but each is standalone enough to be enjoyed individually.


One of my all time favourites, Ben Thompson of Stratechery and James Allworth discuss the impact technology is having on business strategy and society. An impressive back catalogue and very nuanced perspectives on topics.

Some common threads referenced throughout, such as Aggregation Theory, but each episode typically tackles or refreshes a single topic.

FinTech Insider by 11:FS

11:FS have taken the idea of content-led financial services consultancy and dragged it into the internet era. Their methods and delivery are similar to that of most modern digital agencies but their impressive insight into Financial Services gives them a unique proposition. Their podcast will keep you up-to-date on developments in the sector as well as some great in-depth interviews with industry leaders.

Jump in and enjoy at any point. This is another show I download based on the topic, rather than listening to every episode.


Telling the story of the invisible forces that shape our behaviour and society, Invisibilia is a well-produced deep dive into modern human nature. It goes to some weird and wonderful places and some episodes have really stuck with me.

Each episode discusses a new topic and there’s very little continuation. Best listened to as a season to enjoy the overarching themes the show analyses. I believe they are currently on Season Five.

The Moment with Brian Koppelman

Brian Koppelman, executive producer of the excellent TV series Billions, interviews a wide range of pioneering creators. His conversational style and openness invites the guests to explore their creative process and parallels outside their industry in great detail.

Some recurring guests, such as Seth Godin, but each episode is generally standalone.


A fictional portrayal of an AI assistant company and the humans behind the scenes powering it. Easy to enjoy and an interesting case study for the quality that’s possible through audio dramas.

A must for listening start to finish. Not a particularly long show, which makes this easier.

Snacks Daily

Robinhood, the US stock trading app, offers a daily newsletter and accompanying podcast that covers off the day’s most interesting market movements and news. Snacks is a good show to listen to above 1.2x and use the Seek Forward controls where necessary to maximise its relevance to you.

Subscribe, listen daily, repeat. The topics are only fresh for 2-3 days maximum.

I’ll try to update this list as I find more shows I recommend to others regularly. If you have any you think I’d enjoy, I’m always interested in expanding my library - reach out below.