Writing My Own Ticket As A 1-Man Insurance Co.
TML Portfolio Update + 3 New Trades
Welcome to the ROI Club.
Imagine running a business where you collect steady premiums like an insurance company, without the need for employees, office space, or complex infrastructure. That’s exactly what selling options feels like to me—a highly portable, capital-light business that lets me earn money from anywhere in the world.
For premium members - in today’s update I share a video covering the portfolio of assets I own and the insurance contracts (put options) I’ve sold. These contracts are yielding me approximately 23% on my portfolio value without my having to contributed any further cash - truly a capital light business indeed.
Announcement: Attending The Rule Investing Symposium
I’m excited to share that I’ll be attending Uncle Rick Rule’s (TM) Investing Symposium in Boca Raton, Florida—a must-attend event for anyone IMHO.
If you’re interested in attending, whether in person or from the comfort of your home via live stream, I highly recommend it. From my previous attendance I discovered/invested in the likes of GROY, UROY, WPM.
Use my affiliate link here: it’s an event you don’t want to miss.
And if you’ll be there in person, let me know!
I’d love to connect, exchange ideas, and hear about your journey.
Now, back to running a 1-man Insurance Co.
Selling put options is like insuring someone else’s portfolio: I get paid to take on the risk of buying stocks in the event their prices drop below certain strike prices.
So then, obviously, I choose very carefully the stocks I underwrite.
Why would anyone pay me for this?
Institutional capital and large hedge funds often pay for this insurance as they need their portfolios to remain above certain thresholds due to their way they operate; institutions often need to make payouts and some hedge funds often use an ungodly amount of leverage and therefore can’t afford their books to drop in value and trigger margin calls.
Selling put options is my way of being the insurance company rather than the insured.
Using Options to Fund My Lifestyle.
One of the things I love about selling options is how it aligns perfectly with my lifestyle. Whenever I have a lot of travel coming up - this year it looks like I’ve got 4 big overseas trips in the calendar - I often use this strategy to cover my expenses.
Tickets, accommodation, meals, and even a few indulgences along the way can all be funded by the premiums I earn. When done successfully, it’s like turning the markets into a personal ATM, but it’s NOT for beginners and one must have a disciplined approach.
For my premium subscribers, I dive deeper into how I structure these trades, the criteria I use to select stocks, and the risks you need to manage.
The premiums I collect upfront are mine to keep and if the stock doesn’t hit my target, I simply move on to the next trade. If it does, I buy the stock at a discount and can even sell options on that same stock if I choose.
Want to learn more?
Consider becoming a premium member. I’ll walk you through the exact trades I make and give you exclusive access to:
The ROI Club: Dedicated to the art of Return On Investment
My investment research and analysis.
The Maverick Life: How I Generate Location-Independent Income so you can live:
Where you want
When you want
With whom you want
Doing what you want
Become A Premium Member Of The ROI Club Today.




