2018 List: Podcasts

Like a lot of people, I’ve listened to a lot of podcasts this year.

It’s too distracting for me to listen to them while I’m working, but I’m lucky enough to live in a central area of a very walkable city so there are plenty of excuses for me to listen to the spoken word whilst in the space between. 

Subway commute, walking commute, or scenic route, plus going to the gym, airports or train stations.

Last week someone said to me they’d love to see inside other people’s Netflix history as it would tell them so much about that person.

Perhaps podcasts are even more personal, and telling.

As you can probably deduce from this list, my listening themes this year have revolved around entrepreneurship, dealing with transitions, and understanding the self.

I’ve struggled with fiction podcasts (definitely still prefer books, and the paper kind at that), although I’d like to dive into these more in 2019

In no particular order here are my favourite podcast episodes I’ve listened to this year – and one that I skipped.

Note: some of these were published earlier than 2018. I just listened to them this year. Does it make them lesser episodes? Nope, that’s just recency bias talking.

1. Seth Godin: Freelancers

I could have added several of the Akimbo episodes to this list. It’s one of the very few podcasts I set my watch by – I’m onto it every Wednesday morning.

I’m choosing this episode as it touches on several wider aspects of the way we work and build careers in today’s rapidly changing world. It also lays to rest some of the confusion that comes from the vast waves of information out there about the importance of hustling, entrepreneurship and being a founder. Freelancing is different to being a founder (and also different to bootstrapping and consulting), and blurring that distinction can cause all sorts of mistakes and misery. This podcast helps make these differences clear, and fortifies the fledging freelancer.


2. Startup: Alex Blumberg & Jerry Colonna

This one is from back in 2016 and resurfaced via some press interviews the Gimlet founders did earlier this year.

Coaching company Reboot run a company 360 with Gimlet and then spend some time with the founders.

Of course, ‘Startup’ is a show that intends to entertain and so (particularly via the joy of editing and storytelling) this episode can feel a little like a highlights reel or even a charicature of a coaching session. 

But suspend your cynicism (you should!), and it’s a pretty visceral dive into being exposed to other people’s feedback, and recognising your own blindspots, weaknesses and deeper vulnerabilities.

And whilst Jerry has the odd party piece he brings out, you can’t doubt how good he is at what he does. 


3. Derren Brown with Joe Rogan

Whilst this one definitely won’t come out on top of Joe’s own most-listened list (try beating out Elon Musk on that front), I really enjoyed its journey through magic, hypnosis, art, psychology and celebrity.

Derren Brown isn’t too well known here in the US (hence him appearing on this show and others to promote a new Netflix show), but I sense he may become more prominent as his blend of stagecraft, debunking myths, and tapping into the human psyche aligns with other bigger trends taking off.

Also this is an interesting one to listen to from the viewpoint of understanding both human’s potential and their suggestibility, rather than purely as an interview between two TV personalities and entertainers.


4. Naval Ravikant on The Knowledge Project

Lots has been written about this podcast by others, so I’ll keep it short and say only that it’s the only podcast episode I’ve listened to 3 times in its entirety. The breadth of this conversation includes mastering the monkey mind, to the importance of books, macro economics, and understanding core human values.

It’s probably best summed up by collating some of the summaries and insights:


5. Stoic Meditations

This is a rather lovely series of daily 2 minute podcasts recorded by professor Massimo Pigliucci here in New York. I’ve found them good value on their own, but they’re even better when accompanied by books by the authors featured.

A few other Stoicism podcasts have launched in the past 12 months, but this is still my favourite because of its succinct and aligned nature.


6. How I Built This

This is included for a different reason to the rest. I stopped listening to this midway through the year. I found the format and depth level a little frustrating. Each episode I was left wanting more, and feeling a sense of ‘ok, so what…?’. Sometimes it even exacerbated those difficult, frustrating feelings of worthiness, opacity, exclusivity. Sure, there was talk of the hurdles that were overcome but it always felt a little varnished, viewed with rose-tinted spectacles.

HIBT is one of the 20 most downloaded podcasts around so it’s clearly resonating strongly for a lot of people.

For me, I just found it better to skip it, and I’m happy I did. 

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