Pineapple Financial (PAPL)
Market Price (12/4/2025): $3.23 | Market Cap: $2.1 MilSector: Financials | Industry: Commercial & Residential Mortgage Finance
Pineapple Financial (PAPL)
Market Price (12/4/2025): $3.23Market Cap: $2.1 MilSector: FinancialsIndustry: Commercial & Residential Mortgage Finance
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
| Valuation becoming less expensiveP/S 6M Chg %Price/Sales change over 6 months. Declining P/S indicates valuation has become less expensive. is -66% | Not profitable at operating income levelOp Inc LTMOperating Income, Last Twelve Months is -3.0 Mil, Op Mgn LTMOperating Margin = Operating Income / Revenue Reflects profitability before taxes and before impact of capital structure (interest payments). is -101% |
| Megatrend and thematic driversMegatrends include Artificial Intelligence, Fintech & Digital Payments, and AI in Financial Services. Themes include AI Software Platforms, Show more. | Debt is significantNet D/ENet Debt/Equity. Debt net of cash. Negative indicates net cash. Equity is taken as the Market Capitalization is 621% |
| Stock price has recently run up significantly6M Rtn6 month market price return is 3666%, 12M Rtn12 month market price return is 544% | |
| Not cash flow generativeCFO/Rev LTMCash Flow from Operations / Revenue (Sales), Last Twelve Months (LTM) is -24%, FCF/Rev LTMFree Cash Flow / Revenue (Sales), Last Twelve Months (LTM) is -58% | |
| 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 -6505% | |
| High stock price volatilityVol 12M is 3998% |
| Valuation becoming less expensiveP/S 6M Chg %Price/Sales change over 6 months. Declining P/S indicates valuation has become less expensive. is -66% |
| Megatrend and thematic driversMegatrends include Artificial Intelligence, Fintech & Digital Payments, and AI in Financial Services. Themes include AI Software Platforms, Show more. |
| Not profitable at operating income levelOp Inc LTMOperating Income, Last Twelve Months is -3.0 Mil, Op Mgn LTMOperating Margin = Operating Income / Revenue Reflects profitability before taxes and before impact of capital structure (interest payments). is -101% |
| Debt is significantNet D/ENet Debt/Equity. Debt net of cash. Negative indicates net cash. Equity is taken as the Market Capitalization is 621% |
| Stock price has recently run up significantly6M Rtn6 month market price return is 3666%, 12M Rtn12 month market price return is 544% |
| Not cash flow generativeCFO/Rev LTMCash Flow from Operations / Revenue (Sales), Last Twelve Months (LTM) is -24%, FCF/Rev LTMFree Cash Flow / Revenue (Sales), Last Twelve Months (LTM) is -58% |
| 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 -6505% |
| High stock price volatilityVol 12M is 3998% |
Valuation, Metrics & Events
PAPL Stock
Why The Stock Moved
Qualitative Assessment
AI Generated Analysis | Feedback
1. Delayed Annual Report Filing.
Pineapple Financial delayed the filing of its Form 10-K (Yearly Report) for the fiscal period ending August 31, 2025. This delay was attributed to the need for additional time to finalize the company's financial statements and for the independent public accounting firm to complete its audit. While no significant financial changes were expected, such delays can raise investor concerns.
2. Persistent Financial Instability and Unprofitability.
The company's financial performance has been consistently weak, marked by negative profit margins, ongoing liquidity challenges, and substantial operating losses. For the fiscal year ended August 31, 2025, Pineapple Financial reported an operating loss of $3.0 million, despite some reduction from the previous year.
Stock Movement Drivers
Return vs. Risk
Price Returns Compared
| 2020 | 2021 | 2022 | 2023 | 2024 | 2025 | Total [1] | |
|---|---|---|---|---|---|---|---|
| Returns | |||||||
| PAPL Return | - | - | - | - | -75% | 630% | 84% |
| Peers Return | 36% | 14% | -28% | 56% | 6% | 15% | 113% |
| S&P 500 Return | 16% | 27% | -19% | 24% | 23% | 16% | 112% |
Monthly Win Rates [3] | |||||||
| PAPL Win Rate | - | - | - | 100% | 8% | 30% | |
| Peers Win Rate | 58% | 65% | 38% | 55% | 53% | 48% | |
| S&P 500 Win Rate | 58% | 75% | 42% | 67% | 75% | 70% | |
Max Drawdowns [4] | |||||||
| PAPL Max Drawdown | - | - | - | - | -76% | -81% | |
| Peers Max Drawdown | -41% | -13% | -39% | -9% | -16% | -18% | |
| S&P 500 Max Drawdown | -31% | -1% | -25% | -1% | -2% | -15% | |
[1] Cumulative total returns since the beginning of 2020
[2] Peers: ESNT, WD, SNFCA, RKT, PFSI.
[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 12/3/2025 (YTD)
How Low Can It Go
PAPL has limited trading history. Below is the Financials sector ETF (XLF) in its place.
| Event | XLF | S&P 500 |
|---|---|---|
| 2022 Inflation Shock | ||
| % Loss | -26.9% | -25.4% |
| % Gain to Breakeven | 36.7% | 34.1% |
| Time to Breakeven | 525 days | 464 days |
| 2020 Covid Pandemic | ||
| % Loss | -43.3% | -33.9% |
| % Gain to Breakeven | 76.5% | 51.3% |
| Time to Breakeven | 295 days | 148 days |
| 2018 Correction | ||
| % Loss | -26.1% | -19.8% |
| % Gain to Breakeven | 35.2% | 24.7% |
| Time to Breakeven | 338 days | 120 days |
| 2008 Global Financial Crisis | ||
| % Loss | -83.7% | -56.8% |
| % Gain to Breakeven | 515.2% | 131.3% |
| Time to Breakeven | 4470 days | 1480 days |
Compare to
In The Past
SPDR Select Sector Fund's stock fell -26.9% during the 2022 Inflation Shock from a high on 1/12/2022. A -26.9% loss requires a 36.7% gain to breakeven.
Preserve Wealth
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Asset Allocation
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Latest Trefis Analyses
| Title | Topic | |
|---|---|---|
| DASHBOARDS | ||
| Is Pineapple Financial Stock Built to Withstand More Downside? | Return |
| Title | |
|---|---|
| ARTICLES |
Trade Ideas
Select past ideas related to PAPL. For more, see Trefis Trade Ideas.
| Date | Ticker | Company | Category | Trade Strategy | 6M Fwd Rtn | 12M Fwd Rtn | 12M Max DD |
|---|---|---|---|---|---|---|---|
| 11212025 | WU | Western Union | Dip Buy | DB | FCFY OPMDip Buy with High FCF Yield and High MarginBuying dips for companies with high FCF yield and meaningfully high operating margin | 3.4% | 3.4% | -0.4% |
| 11212025 | COIN | Coinbase Global | 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 | 9.5% | 9.5% | 0.0% |
| 11142025 | PYPL | PayPal | Dip Buy | DB | FCFY OPMDip Buy with High FCF Yield and High MarginBuying dips for companies with high FCF yield and meaningfully high operating margin | 0.1% | 0.1% | -7.5% |
| 11142025 | V | Visa | 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 | -0.1% | -0.1% | -2.7% |
| 11072025 | WD | Walker & Dunlop | Dip Buy | DB | P/E OPMDip Buy with Low PE and High MarginBuying dips for companies with tame PE and meaningfully high operating margin | -7.7% | -7.7% | -11.0% |
| Date | Ticker | Company | Category | Trade Strategy | 6M Fwd Rtn | 12M Fwd Rtn | 12M Max DD |
|---|---|---|---|---|---|---|---|
| 11212025 | WU | Western Union | Dip Buy | DB | FCFY OPMDip Buy with High FCF Yield and High MarginBuying dips for companies with high FCF yield and meaningfully high operating margin | 3.4% | 3.4% | -0.4% |
| 11212025 | COIN | Coinbase Global | 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 | 9.5% | 9.5% | 0.0% |
| 11142025 | PYPL | PayPal | Dip Buy | DB | FCFY OPMDip Buy with High FCF Yield and High MarginBuying dips for companies with high FCF yield and meaningfully high operating margin | 0.1% | 0.1% | -7.5% |
| 11142025 | V | Visa | 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 | -0.1% | -0.1% | -2.7% |
| 11072025 | WD | Walker & Dunlop | Dip Buy | DB | P/E OPMDip Buy with Low PE and High MarginBuying dips for companies with tame PE and meaningfully high operating margin | -7.7% | -7.7% | -11.0% |
Research & Analysis
Invest in Strategies
Wealth Management
Peer Comparisons for Pineapple Financial
| Peers to compare with: |
Financials
| Median | |
|---|---|
| Name | |
| Mkt Price | 40.80 |
| Mkt Cap | 4.1 |
| Rev LTM | 1,263 |
| Op Inc LTM | 134 |
| FCF LTM | -476 |
| FCF 3Y Avg | 22 |
| CFO LTM | -427 |
| CFO 3Y Avg | 24 |
Growth & Margins
| Median | |
|---|---|
| Name | |
| Rev Chg LTM | 14.0% |
| Rev Chg 3Y Avg | -0.3% |
| Rev Chg Q | 9.9% |
| QoQ Delta Rev Chg LTM | 2.4% |
| Op Mgn LTM | 10.8% |
| Op Mgn 3Y Avg | 11.4% |
| QoQ Delta Op Mgn LTM | 3.1% |
| CFO/Rev LTM | -19.6% |
| CFO/Rev 3Y Avg | -8.9% |
| FCF/Rev LTM | -38.7% |
| FCF/Rev 3Y Avg | -14.2% |
Valuation
| Median | |
|---|---|
| Name | |
| Mkt Cap | 4.1 |
| P/S | 2.0 |
| P/EBIT | 7.3 |
| P/E | 9.8 |
| P/CFO | -1.5 |
| Total Yield | 6.4% |
| Dividend Yield | 0.0% |
| FCF Yield 3Y Avg | 11.3% |
| D/E | 0.8 |
| Net D/E | 0.5 |
Returns
| Median | |
|---|---|
| Name | |
| 1M Rtn | 3.9% |
| 3M Rtn | 1.7% |
| 6M Rtn | 25.3% |
| 12M Rtn | 19.3% |
| 3Y Rtn | 66.3% |
| 1M Excs Rtn | 4.0% |
| 3M Excs Rtn | -5.1% |
| 6M Excs Rtn | 10.6% |
| 12M Excs Rtn | 4.6% |
| 3Y Excs Rtn | -2.5% |
Returns Analyses
SEC Filings
Expand for More| Report Date | Filing Date | Filing |
|---|---|---|
| 5312025 | 7142025 | 10-Q 5/31/2025 |
| 2282025 | 4142025 | 10-Q 2/28/2025 |
| 11302024 | 1212025 | 10-Q 11/30/2024 |
| 8312024 | 12202024 | 10-K 8/31/2024 |
| 5312024 | 7152024 | 10-Q 5/31/2024 |
| 2292024 | 4152024 | 10-Q 2/29/2024 |
| 11302023 | 1162024 | 10-Q 11/30/2023 |
| 8312023 | 12142023 | 10-K 8/31/2023 |
| 5312023 | 9152023 | S-1/A 5/31/2023 |
| 2282023 | 5162023 | S-1/A 2/28/2023 |
| 8312022 | 12012022 | S-1 8/31/2022 |
External Quote Links
| Y Finance | Barrons |
| TradingView | Morningstar |
| SeekingAlpha | ValueLine |
| Motley Fool | Robinhood |
| CNBC | Etrade |
| MarketWatch | Unusual Whales |
| YCharts | Perplexity Finance |
| FinViz |