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Hippo Holdings Inc (HIPO) — wheel strategy suitability
Where HIPO sits as an underlying for selling cash-secured puts and covered calls, and what its own price history says about the risk of being assigned into a falling stock. Snapshot of 3 October 2026.
Hippo Holdings Inc (HIPO) scores 70 on the Wheel score, which puts it in the acceptable band — it passes the profitability and options filters but is not among the strongest candidates.
The score is carried by its quality (79/100) and held back by valuation (61/100). Growth is deliberately excluded from this score: fast growers tend to carry high implied volatility and gap risk, which is the opposite of what a wheel seller wants. It is not cheap, so assignment would leave you holding a fully priced stock.
It has monthly options only, which costs it a small liquidity haircut. Workable, but every roll commits you for a month.
1 accounting or quality flag knocked points off the score. Flags are not an accusation of anything — they mark filings worth reading before you sell a put that could hand you the shares.
Over the last 3.0 years it had 4 days with a fall of 10% or more (1.35 a year), a deepest drawdown of -39.6%, and a worst single session of -15.9%. That is worse than the median screened name (0.67 gap-downs a year, -44.9% typical worst drawdown).
Realised volatility runs about 64% annualised. That is high. More premium, and a materially higher chance of being assigned into a falling stock.
Ownership context: an activist 13D filing on the register (13D 5.2% '21). A 13D means someone has taken a stake with intent to influence the company. Read the recent news before selling puts here — that is the kind of situation that moves a stock on an announcement.
Entry timing currently reads as a dip within an uptrend — historically the better half of the cycle to sell puts into.
Score breakdown
| Wheel score | 70 | 0–100 suitability for options selling |
|---|---|---|
| Quality | 79 | ROIC, margins, leverage, accruals |
| Valuation | 61 | cheaper on fwd P/E, EV/EBITDA, FCF yield |
| Margin stability | — | steadier earnings score higher |
| Options listed | Monthly | weekly avoids the liquidity haircut |
| Accounting flags | 1 | −8 points each |
Realised tail risk
Computed from our own daily price history, 2023-10-04 to 2026-10-01 (749 sessions). The Wheel score is built from fundamentals, so these price-derived numbers are an independent check on it, not a restatement of it.
| Days falling 10%+ in one session | 4 | 1.35 a year |
|---|---|---|
| Deepest drawdown | -39.6% | peak to trough |
| Worst single session | -15.9% | |
| Realised volatility | 64% | annualised |
Flags on this name
- Low cash conversion (CFO/NI=0.16)
Fundamentals
| Revenue (ttm) | 469M USD |
|---|---|
| Revenue CAGR (3y) | 57.6% |
| Net margin | 12.3% |
| Return on equity | 13.2% |
| Share price | $31.51 |
| Days to earnings | 32 |
| Sector / industry | Financial Services · Insurance - Property & Casualty |
Open the HIPO options chain on Yahoo Finance to check live strikes and premium — this page deliberately carries no quotes, because a quote baked into a static page is stale before you read it.
Run the numbers on HIPO
Pre-filled with the snapshot price of $31.51 and 30-day realised volatility; add the strike and premium from the live option chain.