In 2020, as the markets exploded in volatility, I got into day trading. Made a little cash.
In 2021, as bitcoin was on a tear, I leveraged up. Made a lot of cash.
While this is true, it hides the facts of the day to day. Riding the rollercoaster of the markets had my heart beating at every move and my hand shaking every time I took my phone out of my pocket - and this was all day every day.
It took several failed side hustles for me to understand what’s most important to me. In my search for supplemental sources of income, I learned that the stress was simply not worth it.
Now, the number one criterion I look for in a cash generating activity is that it lets me sleep well at night.
A quick favor: forward this to someone who’d like to sleep better at night.
The macro view
The headlines are unavoidable. Layoffs left, right and center. Companies across the spectrum are reducing their staff by the thousands - all in the name of AI.
Call me a skeptic, but AI is just a convenient story. The reality is that companies have been cutting staff whenever possible for decades. This is business as usual.
Jobs growth is slowing down - fewer jobs for more people.
☑️ Cut your reliance on your job.
🌱 Start by replacing 1% of your recurring bills with assets that bring cashflow
The Federal Reserve chart shows a clear slowdown in job growth in the last 5 years.
Inflation has been and will remain above the 2% mark - has your salary kept pace?
☑️ Take control of your income.
⚓️ Anchor at least one income stream to something you control.
The Federal Reserve chart shows consistent inflation above and even significantly above 2%. Keep in mind this is headline inflation. Real inflation is even higher.
Without AI investments, most estimates put GDP growth at or near 0%.
☑️ Assume your capital gains are near 0%.
💵 Underwrite on cashflow to start. Appreciation-only will not work.The national debt will keep increasing.
☑️ Expect tax increases
🏛️ Weight tax-advantaged strategies: life insurance, return of capital and long-term hold.
A nearly 25% increase in national debt in 5 years.
The message is clear: your paycheck is anything but guaranteed.
I use Claude to stay ahead
Specifically, I use it to help me model my portfolio in real time. Whether I’m adjusting assumptions, projecting my cash flow into the future or stress-testing what happens when the market moves, income stacking becomes a game I run on my laptop.
AI is the biggest opportunity for employees to build outside their day to day. And no, I am not advocating you build a SaaS company or an AI agency. Just build.
My models start out too complex for me to understand them. I then gradually modify them, one input at a time, until I can predict what each input does to my output. That’s how AI builds conviction and ultimately a peaceful night.
A financial planner gives me his opinion, my work with an LLM sharpens mine.