01
Never withdraw until the wheel closes.
Premium received is unearned income. Until the underlying gets called away or the put expires worthless, the cash is float, not profit.
About
Decision support for the people who actually run the wheel.
PremiumGuardHQ is the analytics platform for self-directed wheel traders who treat premiums as a real income source. The platform auto-detects every cycle across Schwab and Interactive Brokers, reconciles cost basis the way the broker doesn’t, and computes how much income is actually safe to withdraw, so the equity base stays intact through drawdowns.
Most wheel traders have no idea what their actual numbers are. They’re flying by the seat of their pants.
PremiumGuardHQ began as a private trading desk’s internal tool, built to solve a real, recurring problem on a real book. The methodology worked. The accounting, the cost-basis adjustments, and the question of how much is actually safe to withdraw did not.
Conversations with other operators surfaced the same gap. Wheel traders running serious capital still couldn’t answer three basic questions: What’s my real premium yield? What’s my equity P/L net of assignments? How much income is safely withdrawable without eroding the base? Most were guessing.
Existing tools required manual tagging or trade-by-trade data entry. That creates friction. Friction means the records don’t stay current, and the analysis breaks the moment the books drift from reality.
Other tools
- Tag every trade by hand
- Spreadsheet maintenance is the work
- Cost basis = whatever the broker says
- Drift & abandonment when it gets busy
PremiumGuardHQ
- Auto-detects every cycle from broker sync
- The platform does the maintenance
- Premium P/L, Equity P/L, Net Income, all reconciled
- The data shows up whether you remember or not
PremiumGuardHQ exists because too many wheel traders are flying blind.
I trade for income. I built this to protect it.
After my exit, I was running a fix and flip real estate business for income, but it was stealing weekends and stress that family time couldn’t pay back. After my daughter was born, I wanted income I could earn during market hours and be done. And be present.
The exit was Cave Tools, a barbecue e-commerce company I built and sold in 2021 for high seven figures. After the sale I needed income, not capital appreciation. The wheel turned out to be the most efficient income engine I’d tried. The process scales identically whether the account is $10K, $100K, or $1M, and the time-to-income ratio beats everything else I’d run.
I learned the methodology from a mentor who runs a multi-million-dollar covered-call fund. I still sit in monthly on their trades. The strategy worked. But two years in, I realized I couldn’t trust the numbers the broker was showing me. Wash-sale and premium-received adjustments were quietly bending my real P/L. I needed three numbers I could rely on: Premium P/L. Equity P/L. Net Income. Nobody was building that. So I built it.
Premium is unearned income until the wheel closes. PremiumGuardHQ is the dashboard that holds that line.
Michael “Medium Rare” O’Donnell
· founder
Four rules that run the playbook.
Verbatim from the founder’s desk. These run every position on the book. Yours can be different. PremiumGuard surfaces the data so you can write your own.
02
Start at 7% allocation. Double down once at most. No position over 15%.
Concentration risk gets you assigned at the worst possible moment. Sizing rules survive the weeks the strategy gets stress-tested.
03
Never sell a call below adjusted cost basis. If the stock is down, sell more time, farther out of the money.
Selling a call below cost locks in a loss on assignment. When a name is underwater, premium comes from time decay. Go further out, not closer in.
04
Only wheel stocks you would be okay owning through a correction.
Every cash-secured put can become a long position. The wheel only works on names you would hold through a 30% drawdown without flinching.
Built for traders who rely on premiums as an income source.
PremiumGuardHQ is opinionated about who the platform serves. Honest fit beats every feature list.
# Profile Fit Why
01 Weekly + monthly wheel traders Yes Cash-secured puts and covered calls are the core engine
02 Income-focused operators Yes Premium yield is the paycheck, not the bonus
03 Standalone call and put buyers Yes Single-leg long options track natively
04 Day traders No Broker sync runs every 24 hours, not in real time
05 Multi-leg and spread traders No Single-leg coverage today. Multi-leg roadmapped
06 Signal-shopping retail No PremiumGuard makes math visible, not picks
› Single-leg analytics today. Multi-leg coverage is on the roadmap.
An options analytics company, on the record.
Concrete facts beat marketing copy. Here’s what PremiumGuardHQ actually is, where it lives, and how the math gets to your screen.
Headquartered
Doylestown, PA
Bucks County · Greater Philadelphia
Parent entity
Medium Rare Enterprises
Pennsylvania · Established 2021
Broker integrations
Schwab · Interactive Brokers
Read-only OAuth · no write access
Methodology
Premium · Equity · Net Income
The three numbers that hold the line
Ready to see your real numbers?
Connect your broker. PremiumGuard does the cycle detection and the cost-basis math.
You decide what to withdraw.