The Pop Star with No Aura

A snapshot of two decades of the digital music revolution

In the middle of last year, we let our intern Michelle take over the Sonos for the afternoon. One of the songs she played, a piano ballad, full of falsetto and earnest pining, immediately jumped out:

I need somebody to heal
Somebody to know
Somebody to have
Somebody to hold
It's easy to say
But it's never the same
I guess I kinda liked the way you numbed all the pain

If you’ve listened to commercial radio at all in the past year, you would know the song I’m referring to - Lewis Capaldi’s Someone You Loved.

Sidebar: I get my commercial radio fix by catching Ubers a lot. Smooth FM seems to be the favourite of the Melbourne Uber driving community.

Capaldi’s on the pop spectrum somewhere between James Blunt and Adele, which means Spotify’s algo would be unlikely to push him to me.

YouTube’s algo on the other hand… had other ideas. I love unearthing epic live versions of songs recorded by audience members, which is probably why YouTube sent me to Capaldi’s cover of ‘Don’t Look Back In Anger’.

And there began my Lewis Capaldi rabbit hole. It turns out he’s almost the perfect encapsulation of where the music industry finds itself in 2020.

Sidebar: My first career was in music, I think of A&R for artists as VC for startups, and I’m fascinated by the discovery and supercharging of new talent in all industries.

But back to Capaldi:

His manager discovered him via Soundcloud, through an iPhone recorded demo:

The bit I enjoy the least about [being a manager] is sitting, trawling through SoundCloud and YouTube for seven hours a day, but that’s what I did. I would open – no joke – about 500 SoundCloud tabs at a time, listening to 10 seconds of each artist to get a read on it.

About four and a half months into that search, I was in my mum’s house, and I stumbled across a recording of Lewis on SoundCloud singing into his iPhone in his bedroom.

Immediately I thought: ‘This is amazing, I’m in.’

Sidebar: My first big career break came from launching a blog for EMI with a Soundcloud account for new artists to send their music straight to the A&R team. Wired Magazine wrote about it here. SoundCloud has had its ups and downs, but it deserves credit as one of the purest creative communities the internet has ever seen.

Capaldi initially broke in Germany, and not the UK:

After the switch to streaming five years or so ago, at first the UK took a while to find a way to properly break artists again. In Europe, the barriers to entry at radio were much lower; the gap between streaming and radio was smaller than the UK. At the UK [networks] it was like, ‘You need crazy streaming numbers and your socials need to be on fire [before we playlist you].’ We felt it was a helpful entry point to have Germany lead that.

Note the phrase: “your socials need to be on fire” as a prerequisite to success, and not the result of it. Also note the continued necessity of radio to break a song.

Capaldi’s breakout track Bruises, released independently in March 2017, led him to being named one of Vevo’s ‘Artists To Watch’ that year. Then, without having released a full-length album, Capaldi became the first artist ever to sell out a UK arena tour.

iPhone recording ↠ Soundcloud upload ↠ serendipitous Soundcloud discovery ↠ independently released single ↠ Vevo artist to watch ↠ German radio ↠ hot socials… that’s the formula now!

Sidebar: For another amazing recent example, see Tones & I. From busking in Byron Bay on NYE to Jimmy Fallon and 20M views on a saxophone cover of her song in less than a year.

Perhaps the most interesting thing about Capaldi though is his personality. In contrast to the music, he is funny, disarmingly honest, unvarnished and completely… normal.

Here he is getting his celebrity mates to sing along to Bruises.

Here he is befuddling a Swedish interviewer with stories about toilets and referring to himself the Scottish Beyonce:

And here he is ridiculing himself on a trip back to his hometown:

It is hard to think of a pop-star precedent. But rather than being an anomaly, I think we’ll see more of this. The era of the manufactured, inaccessible artist is gone.

No more Spice Girls at one end of the spectrum. No more Nick Cave at the other.

We’re in a TikTok/Snapchat artist/Billie Eilish world now, where your favourite artist in your Instagram stories, everything is seen, and nothing much is left to the imagination.

Quick Links:

This video of people singing together on a subway platform after a Robyn concert made me so nostalgic for New York. The fact there are multiple YouTube clips of this event says something else about the way music works in 2020 too.

It is amazing to see the cultural resonance of Don’t Look Back in Anger growing over time. 25 years on, and its meaning to people is at an all-time high, perhaps now eclipsing Wonderwall as Oasis’ defining song.

And to end, my most played amateur live music YouTube clip ever. I can even singalong to Frank’s crowd chatter now… WE LOVE YOU FRAAAANK!

Actually, before I go, YouTube Bon Iver is veritable gold mine:

My favourite live recording:

My favourite studio recording:

A magical version of Beth/Rest:

Perfection in an echoing Paris stairwell.

And Woods.

Time is a Good Critic

Or, why does so much stuff just fade away?

It's interesting to look back at the best of the decade lists from 2010 and see how much stuff has faded away ... Time is a good critic.

I have been thinking over the New Year break about this through the lens of a question: where should I focus more of my attention?

If most of the content we consume every day, quickly fades away, then why consume it at all?

In his newsletter this week, EF co-founder Matthew Clifford concluded that the answer was to focus time on reading history, and not popular “ideas books”.

I also decided to try to select the best books I read in the last ten years. This was a sobering exercise. It underlines how few books - particularly non-fiction - stand up well a few years on. Almost no popular “ideas” books do; the list is dominated by history. 

Nassim Taleb’s assessment of Obama’s year-end book list comes to a similar conclusion.

Sidebar: If you want to go down an internet rabbit hole reading about the #Lindy Effect let me guide you: article explaining the original idea in 1964, the Wikipedia page, counter-argument that the #lindy effect doesn’t exist, and a Farnam Street article explaining how to use the #lindy effect to choose what to read.

To pull in another related idea from Chuck Klosterman:

In Western culture, virtually everything is understood through the process of storytelling, often to the detriment of reality. When we recount history, we tend to use the life experience of one person — the “journey” of a particular “hero,” in the lingo of the mythologist Joseph Campbell — as a prism for understanding everything else.

So, in summary:

  1. Almost everything we consume daily is going to vanish with time. Twitter, podcasts, YouTube, Instapaper, the news… all empty cognitive calories (including, therefore, this newsletter).

  2. As we try and understand the past, we will grossly oversimplify it, and gravitate towards finding a single defining character to explain it.

  3. The longer content survives, the more likely it is to survive for longer (the #lindy effect).

So where does this leave us?

I think the key point is that most things will evaporate. But some won’t. Some will stay with you. And you can’t always know going in which are going to stay, and which will disappear.

The first CD I was ever given was Counting Crows’ ‘August & Everything After’ in 1993. I still listen to it regularly today. It is still, somehow, after listening to thousands, and thousands of hours of music, and living years and years of life, enduring and meaningful to me.

It’s worth trying to search for the lights that will never go out.

But I think tactically, there’s a few more things to keep in mind:

  1. It’s OK to read less news.

  2. It’s definitely worth reading less Twitter.

  3. It’s OK to miss out on year to year trends, you have plenty of time to catch up, and by the time you do, it will be easier to see in retrospect what was worth your time.

  4. If you start a book, movie, show, essay and it isn’t for you, you don’t need to finish it. Life is too short, and it probably won’t matter any way - it’ll be one of the ones that ultimately disappears.

  5. Books are probably better than essays which are probably better than tweets, or photos on Instagram, or the ‘Just In’ section of the news.

  6. Popular ideas books are probably less likely to stick than history books.

  7. If something old is still being mentioned today, pay attention. You’re probably not making a mistake jumping in to Dylan, or Shakespeare, or Casals, or James Baldwin…

But the great books, the ones you find on a syllabus, the ones people have continued to read, don’t reflect the conventional wisdom of their day. They say things that have the permanent power to disrupt our habits of thought. They were revolutionary in their own time, and they are still revolutionary today. And when I say “revolutionary,” I am deliberately evoking the American Revolution, because it was a result of precisely this kind of independent thinking. Without solitude—the solitude of Adams and Jefferson and Hamilton and Madison and Thomas Paine—there would be no America.

- William Deresiewicz, Solitude & Leadership

The Best of 2019

Songs, albums, essays, movies, TV, apps, podcasts, YouTube clips, and books...

Looking back on my favourite songs, albums, essays, movies, TV, apps, podcasts, YouTube clips, and books of 2019…



The best song of 2019 was James Blake’s Where’s The Catch, featuring Andre 3000’s otherworldly verse:

Harmony, harmony, how many?
How many days of amazing will it be before it phases
And I say I told you so? (Told you so)
Summer bee, summer bee buzzing
Some will be hovering over nothing
All of a sudden, it's falling, it's over though
Come with me, come with me, calming me down
Be chamomile, calamine lotion, camel motion

It’s like listening to the genius of a Coltrane saxophone solo. And it’s that genius that makes his conversation with Rick Rubin recently all the more interesting.

My most played song of 2019 was The 1975’s I Like America and America Likes Me which I listened to for the first time on a sunny afternoon walk from the Presidio to the Tenderloin in San Francisco April.

Nils Frahm’s My Friend The Forest made me cry when I heard it live in December. Though in my defence, Nils was playing when both my sons were born, so his music carries a particular weighted resonance for me.

I also had three playlists on high repeat: David August Radio, oriental deep house, and El Buho’s Tulum Boiler Room set.

My top 100 most played songs of 2019 are here.


I think 2019 was a bad year for albums. Pitchfork’s top 50 albums list is… kinda flat? I mean, Lana Del Rey’s Norman Fucking Rockwell! is the album of the year? Really? 😱

I thought Bon Iver’s new stuff wasn’t as good as his old stuff. Ditto for James Blake.

Maybe I’m just getting old.

In any case, the highlight records for me were The 1975’s A Brief Inquiry Into Online Relationships from 2018, and I Like It When You Sleep, for You Are So Beautiful Yet So Unaware of It’ I had studiously avoided The 1975 for many years, only dipping into them accidentally, and finding them too herky-jerky, too gimmicky. But in full album form, they’re glorious, and I spent hours lost in both records.

East Atlanta Love Letter by 6lack, another 2018 release, was also on high repeat.

And that’s it!

Just three records that I can say I genuinely loved this year, none of which were released in 2019.


Movies & TV

Halfway through Parasite, at about the point where they shave the peach, I thought to myself, this is a charming movie, so light and airy… and then an hour later I left the cinema in a daze, wondering what had just happened to me.

Marriage Story was five stars. I love Noah Baumbach. A Star Is Born was equally good.

You are missing out if you haven’t watched The Price of Everything, American Factory, and Free Solo.

Drive To Survive was my TV series of the year. A mesmerising look into the world of F1.

Succession was 10/10. Chernobyl was 9/10. Fauda was 8/10 (and still worth watching).

And LeBron’s The Shop was truly compelling viewing.



And I feel asleep most nights to some mix of Bill Simmons, Ryen Rusillo, Zach Lowe, Woj, Winging It and All The Smoke talking about the NBA…


YouTube was and is my happy place content-wise… you can dip in for 15 minutes or 150, the algorithms are scarily good, and they get better the more you watch. We are finally in the era of hyper-personalised content.

I think we haven’t come close yet to tapping how good YouTube as algorithm-driven TV will be… and I haven’t even quite wrapped my head around how to explain it. Much like watching House of Highlights clips on Instagram instead of a 2.5 hour NBA game, YouTube is the highlight reel of your favourite movie, with the DVD extras thrown in.

Maybe another way to explain it is just to compile the best clips I watched in the past month into a playlist (I just scanned my watch history to compile it)… this list is likely <5/10 interesting to you, but that’s kind of the point - to me it’s 10/10 interesting: stand-up comedy, single scenes from TVs show and movies, random meme-phemera, bites from around the edge of music, NBA clips, F1 analysis, boxing, a Warren Buffett interview, and a handful of classic SNL clips… perfect.


Patrick Radden Keefe’s Say Nothing was the best book I read this year.

I also loved:

  • Bob Iger’s Ride of a Lifetime

  • Helen Garner Everywhere I Look

  • Malcolm Gladwell Talking To Strangers

And I devoured Catch And Kill, Bad Blood, Super Pumped, and Red Notice.

If I missed something this year you think I’d love, just hit reply to this email :)

Happy New Year.

On Being Self-Authored

Robert Kegan's Theory of Self-Development

I was first introduced to the work of Robert Kegan in this excellent talk by Daniel Gross - ‘How To Win’.

Kegan is best known for his Theory of Self-Development.

Kegan’s work didn’t connect with me at first. But a few months later, my coach introduced it to me in a different context, and I’ve since fallen into it completely. As it’s not widely known, I think it’s worthy of much more attention.

The original research was published in a book called The Evolving Self in 1982. Wikipedia notes that: “due to the density of Kegan's writing and its conceptual complexity, some readers have found it difficult to read,” which is an understatement. If you don’t have 12 hours to read the book, here are two good introductions:

The part of Kegan’s theory I’m most interested in, is where most of the adult population is stuck - at Level 3 - where you move from defining yourself through others, to being self-authored.

What finally made all this click for me was taking the research and turning Kegan’s description of Level 4 into a set of statements that would be true if you had reached the level.

I’ve shared the statement set below. It’s long, but hopefully it’s worth it.

I think for many people, being able to say that all of these were true would bring a great sense of relief.

I have an independent sense of self. 

I have clarity about who I am, what I think, what I want and why.

I am “self-authored”: I choose my own principles, projects, and commitments.I don’t look for external validation to derive my sense of self.

I understand that others choose their own principles, projects, and commitments. They have experiences that are not my experiences. 

I am no longer in relationships that define me; I have relationships. 

I am no longer a stream of transient emotional experiences; I have experiences.

I can take responsibility for my own inner states and emotions.

I am referential to a system that treats people impartially, based on rights, responsibilities, principles, and procedures.

I can prioritise the roles I have. 

I recognise that my responsibility for a particular role has particular limits; and I can enter and exit roles by choice. 

My personal systems honour certain boundaries and distinctions. 

When there is a conflict between important ideologies, institutions, or people, I don’t have a hard time answering the question: what do I want? 

I understand that I am a person, with thoughts, feelings and beliefs that are independent from the standards and expectations of my environment. 

I generate my understanding of the world and am not unduly shaped by the context in which I find myself.

I realise that I am always changing, that who I am is something that I can still negotiate.

I can distinguish the opinions of others from my own opinions to formulate my own “seat of judgment”. 

I have developed an internal sense of direction and the capacity to create and follow my own course.

I do not get my thoughts, beliefs, morals (what I know to be true) from external sources.

I can question expectations and values, take stands, set limits, and solve problems with independent frames of mind.

I take the time to state and explain my beliefs and thoughts.

I don’t do things because I feel guilty or ‘bad’ - I do them because they align with the person I want to be.

I have shifted my energy from worrying about what other people think, to clearly determining what I think.

I don’t spend too much energy trying to avoid hurting other people’s’ feelings.

I am not oblivious to or ignorant of others’ experiences. But I am not flooded by them, and can evaluate whether or not to respond to them, and how best to do so.” 

I’m no longer focused on others’ expectations or societal roles.

What I think, believe, and feel is not dependent on how I think others experience me.

I generate my own understanding of the world and am not unduly shaped by the context in which I find myself.

I operate from the place of “what do I want” versus “what do other people want from me”.

1. I clarify what I want to myself.

2. I clarify what I want to the other person (they can decide if they can give me this or not) and

3. I decide what I’m willing to live with.

Click, Click

1. After reading this Derren Brown profile in the New Yorker, it gave me more appreciation for the art of what he does.

2. Superorganizers is my new favourite newsletter. Nerd alert: it’s about the way people use their productivity tools. Foursquare cofounder Naveen’s interview is a good place to start.

3. Writing processes are becoming increasingly popular to pull apart - see Working, by Robert Caro - but I also loved this one on John McPhee. His profile of Bill Bradley - A Sense of Where You Are is a personal favourite.

4. This is a great framework from Atlassian’s Dom Price for reflecting back on 2019 over the Christmas break: what did you love, what did you loathe, what did you long for, and what did you learn?

5. We have just hired a Chief of Staff at Blackbird (hallelujah!). Here’s my original ode to the role. I think every leader should have one.

On Sunday night, I saw Nils Frahm play Hamer Hall,. Nils is one of my musical heroes and his records were playing when both my sons were born.

I compiled his setlist from Sunday into this Spotify playlist. He’s so good.

Inside Bill's Brain

And my favourite hagiographies.

Seven days ago, we welcomed our second child, Noah, into the world. I’d forgotten so many of the details of newborns - they’d blurred into my fatigue-drenched memory.

But what could be more spectacular than a tiny human with their entire existence in your hands, the endless possibilities of life ahead of them, and for now, just soft sleep on warm afternoons.

In the quiet of these first days, I’ve found time to watch Inside Bill’s Brain on Netflix. I loved it, especially seeing Gates’ efforts to create better third-world sanitation, eradicate polio, and invent alternative forms of nuclear energy. But Rotten Tomatoes only gave it 40%, and I didn’t disagree with Brad Slingerland’s SITAL assessment which described it as “30-40 minutes of breezy questioning of Gates spliced into three hours of miscellaneous Microsoft history”.

Perhaps the divergence for me comes from the fact that biographical documentaries are just about my favourite movie genre. To get these movies made, too often they verge on hagiography, which is a great word that means “a biography that treats its subject with undue reverence.

Without further ado then, here are my all-time favourite hagiographies.

Please reply and tell me if I’ve missed a good one!

If you’re interested, I had a great chat last week with Ted Richards on The Richards Report about Blackbird’s investment decision-making process, why and how I track every minute of my time, and the transformative power of storytelling.

In a now iconic line, Lena Dunham’s character in Girls said: "I think I might be the voice of my generation. Or, at least, a voice of a generation." I think Jia Tolentino can rightfully claim that mantle now. I’m enjoying her book Trick Mirror, which is full of crystalline insight into the internet-powered world we all inhabit:

Throughout the eighties and nineties, people had been gathering on the internet in open forums, drawn, like butterflies, to the puddles and blossoms of other people’s curiosity and expertise.

In the twenty-first century it would sometimes be impossible to differentiate between the pretext for an experience, the record of that experience, and the experience itself.

On the internet, a highly functional person is one who can promise everything to an indefinitely increasing audience at all times.

“His dream must have seemed so close that he could hardly fail to grasp it. He did not know that it was already behind him.” ― The Great Gatsby

Loading more posts…