What if you'd held TRUP?
A $1,000 investment in Trupanion, Inc. (TRUP) at the month-end close of 2014-07 would be worth $3,110 at the close of 2026-08 — +211.0% total return, dividends reinvested. The same $1,000 in the S&P 500 would be worth $3,992.
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 2014
| Year | Value of $1,000 | Year return |
|---|---|---|
| 2014 | $1,000 | — |
| 2015 | $1,408 | +40.8% |
| 2016 | $2,240 | +59.0% |
| 2017 | $4,224 | +88.6% |
| 2018 | $3,674 | -13.0% |
| 2019 | $5,405 | +47.1% |
| 2020 | $17,274 | +219.6% |
| 2021 | $19,052 | +10.3% |
| 2022 | $6,859 | -64.0% |
| 2023 | $4,403 | -35.8% |
| 2024 | $6,955 | +58.0% |
| 2025 | $5,392 | -22.5% |
| 2026 | $4,488 | -16.8% |
Best and worst month-end to buy
The best single month-end close to have bought TRUP was 2014-11 ($6.07): $1,000 then is $5,124 today. The worst was 2021-12 ($132): $1,000 then is $236.
FAQ
What would $1,000 in TRUP be worth today?
A $1,000 investment in Trupanion, Inc. (TRUP) at the start of 2014 would be worth about $3,110 today, a total return of +211.0%. Dividends are reinvested in these figures.
What were the best and worst years for TRUP?
Trupanion, Inc. (TRUP)'s strongest calendar year since 2014 was 2020, a +219.6% return — $1,000 held through that year became about $3,196 by year-end. Its weakest year was 2022, at -64.0%.
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 TRUP have grown?
Investing $100 at the end of every month since 2014-07 would have grown to about $20,462 on $14,600 invested.
Did TRUP beat the S&P 500?
Over the same period, $1,000 in the S&P 500 index would be worth $3,992. TRUP trailed the S&P 500 by +22.1% 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
Trupanion, Inc. (TRUP) historical total-return data from 2014-07 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.