Essays
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.
The great social media exodus?
Something interesting is happening online. Some of the biggest creators are quietly leaving their platforms.
Luck is mostly just math.
Luck isn't random. It's math — and the equation is simpler than most people think.
“Someday” is a dangerous lie.
A friend is crushing it by every business metric. His SaaS just crossed a major milestone. He told me he's never been more miserable.
The smartest people often fail the most.
Being clueless might be your greatest business asset. The people who 'know what they're doing' are often the most handicapped.
Willpower is a lie.
Willpower is the most overrated concept in productivity. After years of building my business, I've learned the opposite is true.
Performative BS.
Ashton Hall wakes up at 3:53am and has a 5.5-hour morning routine. I wake up at 7 and start working in my pajamas. Guess whose business is more profitable.