What if you'd held HIPO?
A $1,000 investment in Hippo Holdings Inc. (HIPO) at the month-end close of 2021-01 would be worth $114 at the close of 2026-08 — -88.6% total return, dividends reinvested. The same $1,000 in the S&P 500 would be worth $2,075.
Your scenario
Result
If you'd bought $1,000 at the start of each year
Value of $1,000 invested on January 1 of each year, held to 2026-08, dividends included.
Every year, $1,000 from 2021
| Year | Value of $1,000 | Year return |
|---|---|---|
| 2021 | $1,000 | — |
| 2022 | $192 | -80.8% |
| 2023 | $129 | -32.9% |
| 2024 | $378 | +193.5% |
| 2025 | $425 | +12.4% |
| 2026 | $461 | +8.5% |
Best and worst month-end to buy
The best single month-end close to have bought HIPO was 2023-10 ($7.20): $1,000 then is $4,533 today. The worst was 2021-02 ($291): $1,000 then is $112.
FAQ
What would $1,000 in HIPO be worth today?
A $1,000 investment in Hippo Holdings Inc. (HIPO) at the start of 2021 would be worth about $114 today, a total return of -88.6%. Dividends are reinvested in these figures.
What were the best and worst years for HIPO?
Hippo Holdings Inc. (HIPO)'s strongest calendar year since 2021 was 2024, a +193.5% return — $1,000 held through that year became about $2,935 by year-end. Its weakest year was 2022, at -80.8%.
Does the calculator include dividends and splits?
Yes where available. Prices are adjusted for both stock splits and reinvested dividends (total return), the same measure brokerages use.
How much would $100 per month in HIPO have grown?
Investing $100 at the end of every month since 2021-01 would have grown to about $9,641 on $6,800 invested.
Did HIPO beat the S&P 500?
Over the same period, $1,000 in the S&P 500 index would be worth $2,075. HIPO trailed the S&P 500 by +94.5% in total return.
Is this investment advice?
No. Wall Street Regrets is an entertainment and education tool. Every number is a historical calculation, not a prediction, and past performance never guarantees future results.
Methodology
Hippo Holdings Inc. (HIPO) historical total-return data from 2021-01 to 2026-08, reduced to month-end closes for the tables above.
Returns use adjusted close prices from Yahoo Finance historical data — adjusted for stock splits and reinvested dividends — the same convention used by major brokerages. A "year" scenario invests $1,000 at the prior December's month-end close and values it at the latest available month-end close. Non-USD amounts are converted at historical month-end exchange rates (Yahoo Finance): to USD on the buy date and back to your currency at the latest rate, so the return reflects the currency move as well as the asset.
Month-end resolution means intra-month extremes are not captured in tables; the calculator uses exact trading-day closes where daily data is available. Figures ignore taxes, fees, and the currency effects of non-USD listings. History is not a forecast. Wall Street Regrets is entertainment, not investment advice.
What if you'd held…
Data: adjusted close prices via Yahoo Finance. As of 2026-08. Not financial advice.