Essays
Bored to death.
At some point I got really good at my job. Nobody talks about what happens after that. I was bored to death.
Get out.
We squeezed into two bar seats on Valentine's Day without a reservation. When the bartender handed us menus, I noticed something that changed how I think about business.
Rock bottom.
She threw herself down a mountain at 70mph — the same mountain that nearly ended her career four years ago. She won by four hundredths of a second.
He was only 25.
The winemaker was only 25 when he took over one of California's best wineries. What he said about patience stuck with me for weeks.
One person away.
A sushi speakeasy that seats eight. A hidden door. A chef who changed careers at 40. One person can change everything.
Being a purple squirrel.
Eleven years ago, I watched a sales guy tape together a paper pyramid in a WeWork. What happened next taught me what 'purple squirrels' are — and why you want to be one.
Small by design.
A tiny Champagne bar in Healdsburg seats twelve people and there's always a line. They have no plans to expand. On purpose.
Nobody's even trying.
Everyone says the market is saturated. But when I look around, most people aren't even doing the basics.
One question I've been dodging for years.
Every podcast host asks me 'What's next?' I always dodge the question. Here's the real answer I've been avoiding.
The addiction to relevance.
My wife looked up from her phone in disbelief. 'Have you seen Madonna's Instagram?' The addiction to relevance is everywhere — including in our businesses.
Nobody is coming to save you.
My boss told me to move to San Francisco in two weeks and fire the entire sales team. I'd never even visited the city.
You've changed.
A friend paused his newsletter and podcast after ten years. His reason shook me: it no longer brings him the feeling of 'aliveness.'
The case for anti-scale.
A consultant at a mastermind was doing $1.3M a year and wanted to 'scale.' The room's advice surprised him.
Hustling your way to nowhere.
Back in 2018, I was burning out and had no idea how to get attention for a consulting business. The hustle advice almost ruined me.
We all remember insults.
I found a two-and-a-half-year-old email from someone explaining in four paragraphs why I'm a terrible writer. I never forgot it.