What if you'd held TIPT?
A $1,000 investment in Tiptree Inc. (TIPT) at the month-end close of 2010-10 would be worth $5,620 at the close of 2026-09 — +462.0% total return, dividends reinvested. The same $1,000 in the S&P 500, dividends reinvested, would be worth $8,730.
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 2026-09, dividends included.
Every year, $1,000 from 2010
| Year | Value of $1,000 | Year return |
|---|---|---|
| 2010 | $1,000 | — |
| 2011 | $1,455 | +45.5% |
| 2012 | $1,818 | +24.9% |
| 2013 | $1,825 | +0.3% |
| 2014 | $2,012 | +10.3% |
| 2015 | $1,551 | -22.9% |
| 2016 | $1,582 | +2.0% |
| 2017 | $1,557 | -1.6% |
| 2018 | $1,495 | -4.0% |
| 2019 | $2,228 | +49.0% |
| 2020 | $1,415 | -36.5% |
| 2021 | $3,957 | +179.6% |
| 2022 | $4,012 | +1.4% |
| 2023 | $5,569 | +38.8% |
| 2024 | $6,280 | +12.8% |
| 2025 | $5,563 | -11.4% |
| 2026 | $5,689 | +2.3% |
Best and worst month-end to buy
The best single month-end close to have bought TIPT was 2010-11 ($3.01): $1,000 then is $6,143 today. The worst was 2025-03 ($23.63): $1,000 then is $782.
FAQ
What would $1,000 in TIPT be worth today?
A $1,000 investment in Tiptree Inc. (TIPT) at the start of 2010 would be worth about $5,620 today, a total return of +462.0%. Dividends are reinvested in these figures.
What were the best and worst years for TIPT?
Tiptree Inc. (TIPT)'s strongest calendar year since 2010 was 2021, a +179.6% return — $1,000 held through that year became about $2,796 by year-end. Its weakest year was 2020, at -36.5%.
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 TIPT have grown?
Investing $100 at the end of every month since 2010-10 would have grown to about $52,902 on $19,200 invested.
Did TIPT beat the S&P 500?
Over the same period, $1,000 in the S&P 500 with dividends reinvested (the S&P 500 Total Return index) would be worth $8,730. TIPT trailed the S&P 500 by +35.6% 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
Tiptree Inc. (TIPT) historical total-return data from 2010-10 to 2026-09, reduced to month-end closes for the tables above.
Returns use adjusted close prices — adjusted for stock splits and reinvested dividends, the same convention used by major brokerages. End-of-day and live prices come from EODHD; parts of the deep historical series are carried over from Yahoo Finance data. 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 (EODHD): 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 EODHD and Yahoo Finance. As of 2026-09-04. Not financial advice.