Twilio (TWLO)
Market Price (10/28/2025): $114.52 | Market Cap: $17.5 BilSector: Information Technology | Industry: Systems Software
Twilio (TWLO)
Market Price (10/28/2025): $114.52Market Cap: $17.5 BilSector: Information TechnologyIndustry: Systems Software
Investment Highlights
Why It Matters
Which of these 2 stories sounds closer for this stock?
1. Generates cash flow
The stock generated 4% or more of the share price (called cash flow yield), and shows moderate 10-15% or more growth.
2. Riding a trend
Think Tesla during the pandemic of 2020 when EVs were riding a cultural high, or Nvidia in the current AI boom, or even Figma. These companies don’t have enough yield, or, enough growth, or both - however - they are riding a trend. They have momentum. These can be more volatile - they don’t have the floor of strong cash flow
| Attractive cash flow generationCFO/Rev LTMCash Flow from Operations / Revenue (Sales), Last Twelve Months (LTM) is 17%, FCF/Rev LTMFree Cash Flow / Revenue (Sales), Last Twelve Months (LTM) is 15% | Weak multi-year price returns3Y Excs Rtn is -26% | Expensive valuation multiplesP/EBITPrice/EBIT or Price/(Operating Income) ratio is 242x, P/EPrice/Earnings or Price/(Net Income) is 867x |
| Yield minus risk free rate is negativeERPEquity Risk Premium (ERP) = Total Yield - Risk Free Rate, Reflects the premium above risk free assets offered by the investment. is -4.4% |
| Attractive cash flow generationCFO/Rev LTMCash Flow from Operations / Revenue (Sales), Last Twelve Months (LTM) is 17%, FCF/Rev LTMFree Cash Flow / Revenue (Sales), Last Twelve Months (LTM) is 15% |
| Weak multi-year price returns3Y Excs Rtn is -26% |
| Expensive valuation multiplesP/EBITPrice/EBIT or Price/(Operating Income) ratio is 242x, P/EPrice/Earnings or Price/(Net Income) is 867x |
| Yield minus risk free rate is negativeERPEquity Risk Premium (ERP) = Total Yield - Risk Free Rate, Reflects the premium above risk free assets offered by the investment. is -4.4% |
Market Valuation & Key Metrics
TWLO Stock
Return vs. Risk
Price Returns Compared
| 2020 | 2021 | 2022 | 2023 | 2024 | 2025 | Total [1] | |
|---|---|---|---|---|---|---|---|
| Returns | |||||||
| TWLO Return | 244% | -22% | -81% | 55% | 42% | 6% | 15% |
| Peers Return | 86% | 5% | -46% | 48% | -0% | 5% | 64% |
| S&P 500 Return | 16% | 27% | -19% | 24% | 23% | 17% | 110% |
Monthly Win Rates [3] | |||||||
| TWLO Win Rate | 67% | 33% | 17% | 50% | 58% | 44% | |
| Peers Win Rate | 63% | 62% | 37% | 60% | 48% | 53% | |
| S&P 500 Win Rate | 58% | 75% | 42% | 67% | 75% | 67% | |
Max Drawdowns [4] | |||||||
| TWLO Max Drawdown | -27% | -27% | -84% | -6% | -30% | -25% | |
| Peers Max Drawdown | -21% | -25% | -58% | -9% | -24% | -23% | |
| S&P 500 Max Drawdown | -31% | -1% | -25% | -1% | -2% | -15% | |
[1] Cumulative total returns since the beginning of 2020
[2] Peers: MDB, VRSN, OKTA, AKAM, WIX. See TWLO Returns vs. Peers.
[3] Win Rate = % of calendar months in which monthly returns were positive
[4] Max drawdown represents maximum peak-to-trough decline within a year
[5] 2025 data is for the year up to 10/27/2025 (YTD)
How Low Can It Go
| Event | TWLO | S&P 500 |
|---|---|---|
| 2022 Inflation Shock | ||
| % Loss | -90.4% | -25.4% |
| % Gain to Breakeven | 937.6% | 34.1% |
| Time to Breakeven | Not Fully Recovered days | 464 days |
| 2020 Covid Pandemic | ||
| % Loss | -45.6% | -33.9% |
| % Gain to Breakeven | 84.0% | 51.3% |
| Time to Breakeven | 52 days | 148 days |
| 2018 Correction | ||
| % Loss | -39.3% | -19.8% |
| % Gain to Breakeven | 64.7% | 24.7% |
| Time to Breakeven | 182 days | 120 days |
Compare to MDB, VRSN, OKTA, AKAM, WIX
In The Past
Twilio's stock fell -90.4% during the 2022 Inflation Shock from a high on 2/18/2021. A -90.4% loss requires a 937.6% gain to breakeven.
Preserve Wealth
Limiting losses and compounding gains is essential to preserving wealth over time.
Asset Allocation
Actively managed asset allocation strategies protect wealth. Learn more.
Latest Trefis Analyses
Trade Ideas
Select past ideas related to TWLO. For more, see Trefis Trade Ideas.
| Date | Ticker | Company | Category | Trade Strategy | 6M Fwd Rtn | 12M Fwd Rtn | 12M Max DD |
|---|---|---|---|---|---|---|---|
| 09302025 | ADBE | Adobe | Monopoly | MY | Getting CheaperMonopoly-Like with P/S DeclineLarge cap with monopoly-like margins or cash flow generation and getting cheaper based on P/S multiple | 1.4% | 1.4% | -6.7% |
| 09302025 | CRM | Salesforce | Monopoly | MY | Getting CheaperMonopoly-Like with P/S DeclineLarge cap with monopoly-like margins or cash flow generation and getting cheaper based on P/S multiple | 7.8% | 7.8% | -0.6% |
| 09302025 | MPWR | Monolithic Power Systems | Monopoly | MY | Getting CheaperMonopoly-Like with P/S DeclineLarge cap with monopoly-like margins or cash flow generation and getting cheaper based on P/S multiple | 20.0% | 20.0% | -1.8% |
| 09262025 | POWI | Power Integrations | Dip Buy | DB | CFO/Rev | Low D/EDip Buy with High Cash Flow MarginsBuying dips for companies with significant cash flows from operations and reasonable debt / market cap | 7.5% | 7.5% | -13.4% |
| 09262025 | ROP | Roper Technologies | Monopoly | MY | Getting CheaperMonopoly-Like with P/S DeclineLarge cap with monopoly-like margins or cash flow generation and getting cheaper based on P/S multiple | -7.0% | -7.0% | -7.0% |
| Date | Ticker | Company | Category | Trade Strategy | 6M Fwd Rtn | 12M Fwd Rtn | 12M Max DD |
|---|---|---|---|---|---|---|---|
| 09302025 | ADBE | Adobe | Monopoly | MY | Getting CheaperMonopoly-Like with P/S DeclineLarge cap with monopoly-like margins or cash flow generation and getting cheaper based on P/S multiple | 1.4% | 1.4% | -6.7% |
| 09302025 | CRM | Salesforce | Monopoly | MY | Getting CheaperMonopoly-Like with P/S DeclineLarge cap with monopoly-like margins or cash flow generation and getting cheaper based on P/S multiple | 7.8% | 7.8% | -0.6% |
| 09302025 | MPWR | Monolithic Power Systems | Monopoly | MY | Getting CheaperMonopoly-Like with P/S DeclineLarge cap with monopoly-like margins or cash flow generation and getting cheaper based on P/S multiple | 20.0% | 20.0% | -1.8% |
| 09262025 | POWI | Power Integrations | Dip Buy | DB | CFO/Rev | Low D/EDip Buy with High Cash Flow MarginsBuying dips for companies with significant cash flows from operations and reasonable debt / market cap | 7.5% | 7.5% | -13.4% |
| 09262025 | ROP | Roper Technologies | Monopoly | MY | Getting CheaperMonopoly-Like with P/S DeclineLarge cap with monopoly-like margins or cash flow generation and getting cheaper based on P/S multiple | -7.0% | -7.0% | -7.0% |
Research & Analysis
Invest in Strategies
Wealth Management
Peer Comparisons for Twilio
Financials
| Median | |
|---|---|
| Name | |
| Mkt Price | 126.92 |
| Mkt Cap | 16.7 |
| Rev LTM | 2,491 |
| Op Inc LTM | 113 |
| FCF LTM | 702 |
| FCF 3Y Avg | 490 |
| CFO LTM | 817 |
| CFO 3Y Avg | 530 |
Growth & Margins
| Median | |
|---|---|
| Name | |
| Rev Chg LTM | 12.1% |
| Rev Chg 3Y Avg | 11.8% |
| Rev Chg Q | 12.6% |
| QoQ Delta Rev Chg LTM | 3.0% |
| Op Mgn LTM | 5.3% |
| Op Mgn 3Y Avg | -3.0% |
| QoQ Delta Op Mgn LTM | 0.7% |
| CFO/Rev LTM | 30.4% |
| CFO/Rev 3Y Avg | 22.2% |
| FCF/Rev LTM | 23.0% |
| FCF/Rev 3Y Avg | 18.8% |
Valuation
| Median | |
|---|---|
| Name | |
| Mkt Cap | 16.7 |
| P/S | 4.9 |
| P/EBIT | 29.9 |
| P/E | 37.6 |
| P/CFO | 20.4 |
| Total Yield | 1.6% |
| Dividend Yield | 0.0% |
| FCF Yield 3Y Avg | 3.8% |
| D/E | 0.1 |
| Net D/E | -0.0 |
Returns
| Median | |
|---|---|
| Name | |
| 1M Rtn | -1.0% |
| 3M Rtn | -7.7% |
| 6M Rtn | -7.9% |
| 12M Rtn | 25.6% |
| 3Y Rtn | 54.3% |
| 1M Excs Rtn | -4.5% |
| 3M Excs Rtn | -15.5% |
| 6M Excs Rtn | -32.3% |
| 12M Excs Rtn | 9.0% |
| 3Y Excs Rtn | -24.0% |
Comparison Analyses
Segment Financials
Revenue by Segment
| $ Mil | 2024 | 2023 | 2022 | 2021 | 2020 |
|---|---|---|---|---|---|
| Twilio Communications (Communications) | 3,859 | 3,550 | 2,641 | 1,598 | |
| Twilio Segment (Segment) | 295 | 276 | 201 | ||
| Other | 65 | ||||
| Software | 98 | ||||
| Single segment | 1,134 | ||||
| Total | 4,154 | 3,826 | 2,842 | 1,762 | 1,134 |
| $ Mil | 2024 | 2023 | 2022 | 2021 | 2020 |
|---|---|---|---|---|---|
| Twilio Communications (Communications) | 842 | 319 | |||
| Acquisition and divestiture related expenses | -6 | -3 | |||
| Payroll taxes related to stock-based compensation | -13 | -24 | |||
| Charitable contributions | -17 | -10 | |||
| Loss on net assets divested | -32 | ||||
| Twilio Segment (Segment) | -72 | -30 | |||
| Restructuring costs | -166 | -77 | |||
| Amortization of acquired intangibles | -192 | -206 | |||
| Corporate costs not allocated to segments | -237 | -293 | |||
| Impairment of long-lived assets | -321 | -98 | |||
| Stock-based compensation | -663 | -784 | |||
| Total | -877 | -1,205 |
Returns Analyses
Earnings Returns History
Expand for More| Forward Returns | |||
|---|---|---|---|
| Earnings Date | 1D Returns | 5D Returns | 21D Returns |
| 8/7/2025 | -19.4% | -17.6% | -10.9% |
| 5/1/2025 | 2.3% | 7.5% | 22.2% |
| 1/23/2025 | 20.1% | 30.8% | 4.1% |
| 10/30/2024 | 14.3% | 28.0% | 48.1% |
| 8/1/2024 | 11.7% | 7.7% | 11.5% |
| 5/7/2024 | -7.5% | -1.8% | -9.5% |
| 2/14/2024 | -15.4% | -21.8% | -17.4% |
| 11/8/2023 | 0.3% | 11.4% | 26.5% |
| ... | |||
| SUMMARY STATS | |||
| # Positive | 10 | 8 | 9 |
| # Negative | 14 | 16 | 15 |
| Median Positive | 5.0% | 14.5% | 14.5% |
| Median Negative | -9.9% | -12.3% | -14.1% |
| Max Positive | 39.6% | 53.1% | 60.7% |
| Max Negative | -34.6% | -22.4% | -34.4% |
SEC Filings
Expand for More| Report Date | Filing Date | Filing |
|---|---|---|
| 6302025 | 8082025 | 10-Q 6/30/2025 |
| 3312025 | 5022025 | 10-Q 3/31/2025 |
| 12312024 | 2262025 | 10-K 12/31/2024 |
| 9302024 | 10312024 | 10-Q 9/30/2024 |
| 6302024 | 8012024 | 10-Q 6/30/2024 |
| 3312024 | 5082024 | 10-Q 3/31/2024 |
| 12312023 | 2272024 | 10-K 12/31/2023 |
| 9302023 | 11092023 | 10-Q 9/30/2023 |
| 6302023 | 8092023 | 10-Q 6/30/2023 |
| 3312023 | 5102023 | 10-Q 3/31/2023 |
| 12312022 | 2272023 | 10-K 12/31/2022 |
| 9302022 | 11042022 | 10-Q 9/30/2022 |
| 6302022 | 8052022 | 10-Q 6/30/2022 |
| 3312022 | 5052022 | 10-Q 3/31/2022 |
| 12312021 | 2222022 | 10-K 12/31/2021 |
| 9302021 | 10282021 | 10-Q 9/30/2021 |
Insider Activity
Expand for More| Owner | Title | Filing Date | Action | Price | Shares | TransactedValue | Value ofHeld Shares | Form | |
|---|---|---|---|---|---|---|---|---|---|
| 0 | Viggiano Aidan | Chief Financial Officer | 8192025 | Sell | 104.96 | 501 | 52,583 | 15,462,401 | Form |
| 1 | Viggiano Aidan | Chief Financial Officer | 7022025 | Sell | 124.33 | 7,964 | 990,137 | 19,409,869 | Form |
| 2 | Shipchandler Khozema | Chief Executive Officer | 7022025 | Sell | 124.51 | 13,008 | 1,619,582 | 33,315,601 | Form |
| 3 | ROTTENBERG ERIKA | 6042025 | Sell | 120.03 | 4,100 | 492,118 | 4,019,524 | Form | |
| 4 | Viggiano Aidan | Chief Financial Officer | 5222025 | Sell | 115.86 | 2,156 | 249,794 | 19,010,772 | Form |
External Quote Links
| Y Finance | Barrons |
| TradingView | Morningstar |
| SeekingAlpha | ValueLine |
| Motley Fool | Robinhood |
| CNBC | Etrade |
| MarketWatch | Unusual Whales |
| YCharts | Perplexity Finance |
| FinViz |