The A$$et Origin Story
A tale of index funds, unrealized gains, spreadsheet trauma, and one very stubborn donkey who refused to settle for bad software.
A Broke A$$
A$$et did everything right.
Maxed the 401(k). Bought index funds. Diversified across sectors, market caps, and whatever Vanguard said was sensible that quarter. Dollar-cost averaged like a monk performing a daily ritual. Read the books. Listened to the podcasts. Nodded along to compound interest charts that promised untold riches by 2057.
Did. Everything. Right.
And every month, the same ritual: open the brokerage app, look at the number, close the brokerage app. The number was going up. Slowly. On paper. In the way that a glacier technically "moves" — imperceptible, theoretical, and completely useless if you needed something right now. Like cash flow. Or a reason to believe this whole investing thing wasn't just an elaborate exercise in delayed disappointment.
Portfolio up 8%. Savings yield: 0.02%. Cash generated: zero. Vibes: fiscal existential crisis.
No income. No dividends worth mentioning. Just a number on a screen and a vague promise about "retirement" — a concept that felt roughly as concrete as "the heat death of the universe" but less cheerful.
A$$et was, by every conventional measure, doing fine. Responsible. Disciplined. Diversified. And yet somehow, despite a portfolio that charted upward like a hopeful PowerPoint slide, he felt like what he was: a broke a$$. A hardworking, rule-following, financially responsible broke a$$ with an unrealized gain and nothing in the checking account to show for it but automatic transfers to a brokerage that sent him encouraging emails about "staying the course."
He was staying the course. The course just wasn't paying him.
The Discovery
One Thursday evening — could have been a Tuesday, but Thursdays hit different when you're questioning your entire financial philosophy — A$$et was deep in a corner of the internet where people discuss options trading with the intensity of medieval scholars debating theology. A certain corner of Reddit where theta is king.
And there it was. A post. Nothing flashy. Some guy named ThetaDecayGary42 writing about selling covered calls against stocks he already owned.
"Wait — I can sell options against shares I already own? And people will pay me for that? Actual money? That shows up in my account? That I can spend?"
A$$et went deep. Strikes, expirations, DTE, the Greeks — he liked Theta best, obviously, because Theta was the one that paid you to wait, which was essentially his entire investment philosophy but with a cash register attached. Delta was interesting. Gamma was dramatic. Vega was for people who enjoyed anxiety. But Theta? Theta was a donkey's best friend.
He started writing calls. Conservatively at first — 30-delta, 30-45 DTE, the kind of boring, mechanical, "collect your premium and move along" approach that would never make the front page of anything but would absolutely make his brokerage account balance go up in real, withdrawable, spendable dollars.
And it worked. Income started flowing. Actual cash. Not "unrealized appreciation" or "notional value" or any of the other polite euphemisms Wall Street uses for "money you can look at but not touch." Real premiums. Deposited weekly.
For the first time, his portfolio was paying him to own it.
A$$et had found his thing. Covered calls. Not day trading. Not YOLO puts on meme stocks. Not whatever it is those people with six monitors and a Red Bull IV drip are doing. Just plain, boring, beautiful covered calls — collecting rent on stocks he planned to hold anyway.
The money problem was solved. Which, naturally, meant a new problem was about to walk through the door.
The Spreadsheet Nightmare (And What Came Next)
Five positions. No problem. A$$et opened a Google Sheet, typed in some tickers, noted the strike prices and expirations. Easy. Organized. Very Type A donkey energy.
Ten positions. Fine. Added some columns. Cost basis. Premium collected. DTE countdown. A formula here and there. Maybe a conditional format. Still manageable. Still under control. Still the master of his domain, spreadsheet-wise.
Fifteen positions with active calls, some rolled, some expired, some assigned, income scattered across three months and two tabs that were supposed to reconcile but absolutely did not?
The spreadsheet had become sentient. It was angry. And it was lying to him about his YTD income.
The rolls were the killer. Roll a call and suddenly you need to close one row, open another, track the net credit, update the cost basis, recalculate the income, and somehow remember whether the original trade was against Lot A or Lot B because your accountant is going to ask in April and you're going to stare at this sheet like it's written in Linear B.
He forgot to update it for two weeks. Opened it back up. Three positions had expired. One had been assigned. The income column was showing a number that was either his YTD premium or his ZIP code — honestly, could have been either.
So he did what every reasonable donkey does when a spreadsheet has failed them: he looked for software.
Found one. The main one. The one everybody mentions. Won't name names, but let's say it was born to do one thing, and it sells that one thing for sixty bucks a month. A$$et signed up, loaded the page on his phone, and his phone respectfully declined to render it. Looked like it was built when George W. Bush was still in office and hadn't been updated since the second term. The desktop experience was marginally better in the way that a root canal is marginally better than two root canals.
The rest of the market was worse. Bloomberg-terminal-wannabes designed for people who think a six-monitor setup is "cozy." Options analytics tools that require a PhD to navigate and a therapist to recover from. Spreadsheet templates sold on Etsy — which, look, no judgment, but if you're buying financial tools from a marketplace that also sells crocheted plant hangers, you might want to ask some questions.
The checklist was simple:
- What's expiring? — Show me my expirations on a calendar, not buried in a table.
- Am I covered? — One screen. Color-coded. Sorted by what needs attention.
- Should I roll? — Compare strategies side by side. Show me the credits. Don't make me guess.
- How much have I made? — Real income. By month. By position. Exportable for tax time.
Four questions. That's it. If the tool couldn't answer all four in under ten seconds, it wasn't the right tool.
Now, A$$et is just a donkey. He knows covered calls, not code. He can calculate annualized return on a 30-DTE roll in his head, but he couldn't build a web app if his portfolio depended on it. So he did what any financially frustrated, technologically limited equine would do — he found people who could build it and told them exactly what he needed. Real traders. People who'd lived the spreadsheet nightmare. People who understood that if a 55-year-old retiree managing 12 positions can't figure out the screen in five seconds, you've already failed.
They called it Cover My Assets.
Because sometimes, you really do need to cover your a$$ets.
A$$et's still writing calls. Still collecting premiums. Still braying at red candles — old habits. But now he's got a system that answers the only four questions that matter, and his spreadsheet is retired. It sends a postcard sometimes. He doesn't open it.
If it works for this a$$, it'll probably work for you too.
A$$et Promises It's Easier Than a Spreadsheet
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