Rain clattered against our home windows, a sound that meant one thing: time to play. I was ten when our Monopoly box opened, dice flopped onto the board, and my piece moved by the numbers. While other kids fought over Boardwalk or Park Place, chasing fashion, I targeted the four railroads, the power company, and waterworks. Quiet moneymakers.
You don’t win by showboating—you win by multiplying your cash flow.
And I did that. Game after game. Quadrupled rents collected like clockwork. Utility rent multiplied by a chance throw of the dice, and the more railroads I owned, the pile of cash grew while theirs dwindled. I knew why.
Decades later, not much has changed—except the board is bigger. My electric and gas company is Sempra Energy (SRE). My phone bill? AT&T (T). My auto and house insurer? Hartford (HIG), all rigged to increase my billings when a fire breaks out—by a bolt of lightning catching fire, by an earthquake, or by flash floods … chance throws of the dice.
Which I’m now seriously considering trading with covered calls. And like the kid I was, I’m still charging board rent—only now, I call it stock option premium income. The dice still rolls, but on the chancy adult game of life.
The Hidden Tax You Didn’t Know You Were Paying
As a California homeowner, I’m part of a legally enforced “social contract” — a forced pooling of wildfire risk through soaring insurance premiums. It’s a sort of involuntary socialism: everyone pays more equitably, whether you personally caused a blaze or not.
I live in San Marcos, ZIP 92069, near a fire station, with a hydrant on my property. This year, my home insurance jumped 30% despite zero claims for fifty years and with every discount applied. Hartford dropped my neighbor’s insurance. He found new coverage, but at a doubled premium.
This isn’t just a rate hike, but a pulled-off heist, forced on homeowners—a hidden tax.
Add in my mint 1999 Honda Accord insurance and rising DMV fees, and now my yearly auto and house insurance bills top $2,100. Assume a 10% increase every year in a worst-case stagflation scenario, and their total cost amounts to about $35,000 in ten years.
Monopoly Taught Me How To Turn Rising Utility Bills into Income
Today, I can own shares of the companies gouging me, and by using covered calls (Buy-Writes) in my Roth IRA, I can generate steady income to cover all my utility bills.
Want to turn your billing angst into income? Here’s how:
- Buy stock in the utility and insurance companies you pay bills to.
- Sell covered calls (Buy-Writes) to collect option premiums (in Roth).
- Keep the (Roth tax-free) premium income to pay your bills.
- Manage your risk carefully—know when to hold and when to fold.
- Rinse and repeat regularly for steady cash flow.
If I trade ten options in each of these three stocks, several times a year, I could collect Buy-Write premiums amounting to:
- Sempra’s $220 monthly bill → about $3,900 in option premium income yearly
- T-Mobile’s $120 monthly bill → about $4,000 yearly
- Hartford’s $2,152 insurance bill → about $3,000 in premiums
My bills don’t drain me because I make those utilities pay me, so I can then pay my bills.
If you’re new to options trading and Buy-Writes, contact your broker to discuss the proper strategy and how to effectively manage the already low risk.
“You’ve got to know when to hold ’em, and know when to fold ’em.” (–Kenny Rogers)
A Greedy, Gleeful, Gratifying Game
I admit—I’m justifiably greedy. But not in a vulgar way. I want my insurers and utilities to pay me for decades of rising premiums. I never placed a claim in 50 years, so they pocketed on average about $37,000 of my hard-earned money. I’m grateful to have the means and savvy to turn the game around in my favor, playing it on my terms. Maybe I can repocket that sum in ten years by shrewd option trading.
Another Strategy: Self–Insure If You Can
As a Monopoly fan, I learned as a kid that the only way to win is to assume the risk of ownership. So why keep paying premiums to Hartford and other insurers who take on your property risk for a fat fee, if you fortunately have the capital to self-insure? If you have a sufficient cash surplus to rebuild a total loss of your home, then consider buying only personal liability insurance. Do you, as a senior, drive less than 25 miles a week, carry few passengers, have no pets, few visitors to your home, and no dependents? A no-brainer. Go for it.
The Hidden Tax Rip-Off
The involuntary rise of insurance and utility costs is a kind of forced social pooling for assuming risk—a masked DEI protocol—a hidden tax homeowners pay with little say. But the Monopoly game taught me well: own the utilities, and the game is yours.
By owning utility stock, selling options, and self-insuring where possible, you quit being a renter—and start being a rent-collecting owner. This is a winning strategy for fixed-income seniors against inflation-induced corporate greed.
Take a quick look where your premium goes:
The CEO of Sempra Energy made $23 million in total compensation in 2020. The total compensation for the CEO of Hartford Insurance, Christopher Swift, was $16 million in the 2023 fiscal year, and AT&T CEO John Stankey’s total compensation was $26 million. Now you know what happens to your increased premiums from all that increased fire risk.
The End Game
What the Big Boys always count on is our inertia, our fear, our fatigue, and our sense of futility.
What they didn’t count on was an old Monopoly champion with a hefty Roth IRA, a long memory, and zero tolerance for their thieving financial hubris. They didn’t expect that I’d stop being a passive payee and start eating their lunch. They didn’t figure that a gray-haired retiree would start collecting their cushy profits.
And they sure didn’t want the global website exposé of this loyal, steady customer, weary of all the shady contrivances in their neo-monopolies . . . someone who would tell it like it is, and shout it from the rooftops.
Let the insurers and utilities sweat. They had fifty years to prove their worth and instead proved their insatiable and destructive avarice, as hapless homeowners go uninsured, or have to pay much more.
I paid on time.
I made no claims.
I earned every discount.
I should have had a rate rollback but still got fleeced.
Not anymore.
Now I’ll trade their stock while they legally scramble to justify their soaring premiums to federal and state government audits. I’ll roll the dice— not on hope, but on the probable profitability stats for covered calls. Nearly every time I roll the dice, they’ll pay me fat juicy premiums.
I’ll exploit their stock options to keep increasing my own income stream.
Tax free in a Roth IRA!
You and I can manipulate their stock options.
We can roll the dice on our terms, not theirs.
Now, about this board game card that I just drew:
“Utility error. Collect at will.”
Game on.
THE TRIQUETRA OF LIFE: Wisdom, Wealth, and Wellness 
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