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Latest Posts

How life was different during the early Internet

How life was different during the early Internet

AI for nostalgia’s sakeDear readers,You know those people who cannot bear to throw anything away? Every menu from a tasty meal in an exotic location, every abstract painting created by...

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1 week ago

To All the Folks Who Are About to Be Rich

To All the Folks Who Are About to Be Rich

Because of IPOs, acquisitions, or just doing some damned good businessYou did it. Congrats! All your hard work and lucky stars and ancestors’ sacrifices have led you to this day:...

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1 month ago

The Art and Excellence of Sales

The Art and Excellence of Sales

7 Lessons from former Meta Chief Revenue Officer David Fischerhttps://medium.com/media/b3d0489edf784520cfcc5c5389db7ac0/hrefThe man, the legend: David FischerDavid Fischer ran revenue at Meta for over a decade.Not a region, not a vertical, but...

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1 month ago

I am an idiot

I am an idiot

Notes on idiocy, in the age of something smarter.i.The title says it all: I am an idiot.It used to be hard to say this. It used to be hard to...

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2 months ago

How to Spot a World-Class Designer

How to Spot a World-Class Designer

7 lessons from designer, inventor and angel investor Soleio on what separate excellent from mediocrehttps://medium.com/media/1a91c961e9524457a44cc0acf555bed3/hrefThe Craft Beneath the CraftSoleio Cuervo has one of the sharpest eyes in design.He’s hired and...

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3 months ago

What Excellent Growth Teams See That Others Miss

What Excellent Growth Teams See That Others Miss

Watch now | A conversation with Brian Hale, Chief Growth Officer at Doordashhttps://medium.com/media/b05271f8cda4dd89b11f93b0d7960c44/href“Seeing” excellenceYour hand can never draw better than your eye can discern.They say that mallard ducks can see...

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4 months ago

Playing Authentic Games

Playing Authentic Games

Intentions for 2026Happy January!I love the start of the year, the collective closing of one chapter and the opening of the next. Some people go through the holiday season with...

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6 months ago

The Lost Art of Crying

The Lost Art of Crying

How to build and dismantle a kingdom of icei.You may not believe this, but if you pull me apart and unpeel me layer by layer, you will discover that I...

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8 months ago

Unsent Letter #25

Unsent Letter #25

To the arrogant young, newcomerAt the time when our paths crossed, all I could see in the fog and smoke of my life was your arrogance.It irked the hell out...

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10 months ago

You’re definitely going to be a manager now

You’re definitely going to be a manager now

Book launch! + Predictions for the manager in the era of AIDear Readers,Today, the revised edition of The Making of a Manager drops! (Note: the revised version is paperback with...

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10 months ago

The Making of a Founder

The Making of a Founder

On conviction and the hero’s journeyWhen you rewind back to the starting point, be honest: you thought it would be easy enough.You conjured an image of yourself making — nay...

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10 months ago

Unsent Letter #11

Unsent Letter #11

To the maestro who passed me byWhen I first met you, I tried to stand taller. Look bigger.You were quiet as a breeze, your manner good-natured, your visage a buddha...

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1 year ago

When AI Has Better Taste Than You

When AI Has Better Taste Than You

How machines conquered our skills, infiltrated our aesthetics, and left us with one final advantageWittgenstein once wrote that when the eye sees something beautiful, the hand wants to draw it.This...

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1 year ago

Unsent letter #47

Unsent letter #47

To the corporate jobber with a faraway gazeThis is a paid subscribers post. I’m experimenting with sharing more personal writing with this smaller group, like little diary entries that feel...

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1 year ago

The Thing You Are Expert at Will Be Your Career Downfall

The Thing You Are Expert at Will Be Your Career Downfall

AI will disrupt some of us more than others.i.Last year, I wrote 189,214 words.Not because a boss demanded it, or a paycheck dangled at the finish line. I wrote these...

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1 year ago

Conversational Interfaces: the Good, the Ugly & the Billion-Dollar Opportunity

Conversational Interfaces: the Good, the Ugly & the Billion-Dollar Opportunity

The five biggest problems with today’s conversational chatbot designi.ChatGPT launched from OpenAI on November 30, 2022, and in two short months, broke consumer app records like a bull in a...

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1 year ago

The AI Quality Coup

The AI Quality Coup

What exactly is “great” work now?What is quality work nowadays, in the era of AI? Traditional definitions are being upended, and it’s up to us to find the new precipice.This...

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1 year ago

The Death of Product Development as We Know it

The Death of Product Development as We Know it

Goodbye three-legged stool, 2-pizza teams, and “managers”Much has been written about what AI’s magical powers can enable — whether engineering, design or documentation. But I believe something just as interesting...

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1 year ago

Our Souls Need Proof of Work

Our Souls Need Proof of Work

On wanting and comfort in the era of AIDear Readers: I’m starting a series exploring AI and how it might change us — the way we work and learn and...

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1 year ago

The Valuable Employee Paradox

The Valuable Employee Paradox

The good, bad and ugly of hierachyThe Valuable Employee ParadoxHere’s a seeming paradox:Every great manager I know tells me that the reports they find most valuable are the ones who...

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1 year ago