Essays
Your parents advice is outdated.
His parents spent an entire dinner explaining why he should go back to a 'safe' job. Their advice was 30 years out of date.
I'll draw your dog for $350.
A woman in a tiny shop inside Fishs Eddy in NYC was selling custom dog portraits for $350. She was booked solid. Here's what she understood about business.
The corporate detox no one warned me about.
She wanted a 'behavioral hack' for the corporate-to-solopreneur transition. The real shift is much harder — and more important — than a hack.
Reverse engineering attention in 2025.
I used to think getting attention was about great hooks. After all these years, I've landed on a completely different formula.
The day I 7x'd my prices (and it worked)
I went from $250/hour to $1,800/hour in one year. What happened in between rewired how I think about pricing.
The content nobody likes (but everyone remembers)
A piece I wrote about my panic attack two years ago still generates emails today. Not likes — actual emails from people saying it changed how they work.
The portfolio life experiment.
One friend spent thirty years becoming great at something he hates. Another is on her third wildly different career. The difference is instructive.
Lifestyle inflation kills freedom.
My friend makes $500K a year and still feels trapped. Lifestyle inflation is the silent killer of freedom.
I almost made a terrible mistake last week.
I almost automated the one thing that keeps me connected to my readers. I'm glad I caught myself.
The anti-VC playbook.
When I started, my only goal was to avoid having a boss. Then doubt crept in: am I thinking too small?
An idea nobody wants.
The fastest way to waste time and crush your own confidence? Build something nobody asked for.
My complete $10M journey (all 23 steps)
My business passed $10M in total revenue. Here are all 23 steps of the journey — including the ones I'm not proud of.
Ambition is overrated.
Ambition is the one virtue everyone celebrates. I'm starting to think it might be the most dangerous one.
AI is coming for us (here's my plan)
AI is coming for a lot of jobs. Here's the plan I'm betting my business on.
Creator vs. Operator
He's got a loyal audience, three products, and $350K in revenue. Sounds like a dream — until you hear the rest.