MSTR vs TWLO

Comparison between Strategy Inc - Class A (MSTR, Company) and Twilio Inc Class A (TWLO, Company).

Both MSTR and TWLO are from the Technology sector.

5-Year PerformanceMSTR has outperformed TWLO, delivering a return of +12.4% compared to -11.2%

MSTR vs TWLO - Performance Comparison

Log

Key Characteristics

Financial metrics and valuation ratios

Metric	MSTR(COMPANY)	TWLO(COMPANY)
Market Cap	$33B	$32B
Max Drawdown	99.86%	90.36%
Sharpe Ratio	-1.74	1.20
5Y Beta	2.49	1.32
Industry	Software - Application	Software - Infrastructure
P/E Ratio	-12.49	190.32
Forward P/E	1.69	38.76
PEG Ratio	-0.11	N/A
Debt to Equity	22.36%	12.75%
Free Cash Flow Yield	-0.18%	2.99%

Market Cap

Winner

MSTR

$33B

TWLO

$32B

Max Drawdown

MSTR

99.86%

Winner

TWLO

90.36%

Sharpe Ratio

MSTR

-1.74

Winner

TWLO

1.20

5Y Beta

MSTR

2.49

Winner

TWLO

1.32

Industry

MSTR

Software - Application

TWLO

Software - Infrastructure

P/E Ratio

Winner

MSTR

-12.49

TWLO

190.32

Forward P/E

Winner

MSTR

1.69

TWLO

38.76

PEG Ratio

MSTR

-0.11

TWLO

N/A

Debt to Equity

MSTR

22.36%

Winner

TWLO

12.75%

Free Cash Flow Yield

MSTR

-0.18%

Winner

TWLO

2.99%

MSTR vs TWLO - Historical Returns

Returns include dividend reinvestment.

Period	MSTR	TWLO
1 month	-23.43%	+7.28%
3 months	-36.87%	+50.92%
6 months	-45.87%	+73.60%
1 year	-79.37%	+69.20%
5 years(CAGR)	+12.45%	-11.23%
10 years(CAGR)	+17.51%	+17.00%
Max(CAGR)	+2.48%	+21.64%

MSTR

-23.43%

Winner

TWLO

+7.28%

MSTR

-36.87%

Winner

TWLO

+50.92%

MSTR

-45.87%

Winner

TWLO

+73.60%

MSTR

-79.37%

Winner

TWLO

+69.20%

5Y(CAGR)

Winner

MSTR

+12.45%

TWLO

-11.23%

10Y(CAGR)

Winner

MSTR

+17.51%

TWLO

+17.00%

Max(CAGR)

MSTR

+2.48%

Winner

TWLO

+21.64%

MSTR vs TWLO - Annual Returns (1999 - 2026)

Returns include dividend reinvestment.

Year	MSTR	TWLO
2026	-40.17%	+49.39%
2025	-49.35%	+30.41%
2024	+322.71%	+51.95%
2023	+335.54%	+50.48%
2022	-74.64%	-81.33%
2021	+28.05%	-21.29%
2020	+169.25%	+228.16%
2019	+10.94%	+13.00%
2018	-3.07%	+255.78%
2017	-33.63%	-10.94%
2016	+15.35%	+0.21%
2015	+9.91%	N/A
2014	+31.47%	N/A
2013	+30.11%	N/A
2012	-16.09%	N/A
2011	+22.58%	N/A
2010	-11.12%	N/A
2009	+152.20%	N/A
2008	-58.78%	N/A
2007	-17.58%	N/A
2006	+31.03%	N/A
2005	+41.44%	N/A
2004	+16.43%	N/A
2003	+230.27%	N/A
2002	-61.18%	N/A
2001	-59.47%	N/A
2000	-90.89%	N/A
1999	+114.55%	N/A

MSTR vs TWLO Drawdown Comparison

The maximum drawdown for MSTR was -99.86%, occurring on Jul 26, 2002. Recovery took 6207 trading sessions.

The maximum drawdown for TWLO was -90.36%, occurring on Nov 4, 2022. This drawdown has not yet recovered.

The current MSTR drawdown is -80.16%. The current TWLO drawdown is -53.39%.

Rank	MSTR	TWLO
#1	-99.86% Mar 10, 2000 - Nov 11, 2024	-90.36% Feb 18, 2021 - Nov 4, 2022
#2	-82.63% Nov 20, 2024 - Jun 26, 2026	-66.41% Sep 28, 2016 - Aug 7, 2018
#3	-29.10% Dec 10, 1999 - Jan 10, 2000	-52.18% Jul 26, 2019 - May 7, 2020
#4	-20.42% Feb 16, 2000 - Mar 1, 2000	-27.05% Sep 25, 2018 - Nov 7, 2018
#5	-17.27% Nov 3, 1999 - Nov 22, 1999	-22.51% Aug 3, 2020 - Oct 2, 2020
#6	-14.35% Jan 28, 2000 - Feb 8, 2000	-21.81% Dec 12, 2018 - Jan 7, 2019
#7	-9.76% Nov 29, 1999 - Dec 3, 1999	-21.20% Oct 13, 2020 - Dec 11, 2020
#8	-9.65% Jan 10, 2000 - Jan 19, 2000	-21.10% Nov 7, 2018 - Dec 12, 2018
#9	-8.11% Nov 12, 2024 - Nov 18, 2024	-14.05% Jan 20, 2021 - Feb 4, 2021
#10	-7.59% Dec 6, 1999 - Dec 8, 1999	-12.52% May 16, 2019 - Jun 7, 2019
#11	-2.15% Nov 22, 1999 - Nov 24, 1999	-12.49% Aug 16, 2016 - Sep 21, 2016
#12	-2.12% Jan 21, 2000 - Jan 26, 2000	-11.79% Jul 15, 2016 - Aug 9, 2016
#13	-0.86% Mar 7, 2000 - Mar 9, 2000	-11.26% Dec 22, 2020 - Jan 12, 2021
#14	-0.71% Feb 8, 2000 - Feb 10, 2000	-10.03% Apr 30, 2019 - May 16, 2019
#15	N/A	-9.98% Mar 21, 2019 - Apr 29, 2019