Trupanion [TRUP] vs Skyward Specialty [SKWD] Detailed Stock Comparison
Trupanion
NASDAQ
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Skyward Specialty
NASDAQ
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TLDR: Quick Comparison Summary
Based on 19 vital metrics comparison: Trupanion wins in 5 metrics, Skyward Specialty wins in 13 metrics, with 0 ties. Skyward Specialty appears stronger overall.
View Metrics Details
Vital Metrics Comparison
| Metric | Trupanion | Skyward Specialty | Better |
|---|---|---|---|
| P/E Ratio (TTM) | 174.00 | 14.58 | Skyward Specialty |
| Price-to-Book Ratio | 5.26 | 2.07 | Skyward Specialty |
| Debt-to-Equity Ratio | 32.20 | 13.29 | Skyward Specialty |
| PEG Ratio | -0.68 | 0.68 | Trupanion |
| EV/EBITDA | 67.54 | 9.18 | Skyward Specialty |
| Profit Margin (TTM) | 0.81% | 10.53% | Skyward Specialty |
| Operating Margin (TTM) | 0.65% | 16.15% | Skyward Specialty |
| EBITDA Margin (TTM) | 0.65% | 16.15% | Skyward Specialty |
| Return on Equity | 3.33% | 16.26% | Skyward Specialty |
| Return on Assets (TTM) | 0.65% | 2.81% | Skyward Specialty |
| Free Cash Flow (TTM) | $38.57M | $300.89M | Skyward Specialty |
| 1-Year Return | 3.90% | 15.85% | Skyward Specialty |
| Price-to-Sales Ratio (TTM) | 1.37 | 1.49 | Trupanion |
| Enterprise Value | $1.66B | $1.63B | Trupanion |
| EV/Revenue Ratio | 1.22 | 1.30 | Trupanion |
| Gross Profit Margin (TTM) | 15.51% | N/A | N/A |
| Revenue per Share (TTM) | $32 | $31 | Trupanion |
| Earnings per Share (Diluted) | $0.25 | $3.16 | Skyward Specialty |
| Beta (Stock Volatility) | 1.72 | 0.60 | Skyward Specialty |
Performance
News Sentiment
Key Stats
Valuation
Financials
Short Interest
Dividends
Trupanion vs Skyward Specialty Stock Performance Analysis
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Performance Comparison
Short-term Returns
| Stock | 1D | 1W | 1M | 3M | 6M | YTD |
|---|---|---|---|---|---|---|
| Trupanion | -0.58% | 4.05% | -8.48% | -15.92% | 23.19% | -7.74% |
| Skyward Specialty | 2.75% | -3.84% | -2.34% | -21.10% | -5.49% | -4.63% |
Long-term Returns
| Stock | 1Y | 3Y | 5Y | 10Y | 15Y | 20Y |
|---|---|---|---|---|---|---|
| Trupanion | 3.90% | -25.00% | -39.23% | 439.03% | 290.09% | 290.09% |
| Skyward Specialty | 15.85% | 143.65% | -9.34% | -9.34% | -9.34% | -9.34% |
News Based Sentiment: Trupanion vs Skyward Specialty
Trupanion
News based Sentiment: MIXED
Trupanion reported a strong Q2 2025, leading to analyst upgrades and positive investor reaction. However, the subsequent insider selling and a reduction in Goldman Sachs’ stake introduce uncertainty, creating a mixed investment narrative. The company's expansion into the Canadian market adds another layer to the story.
Skyward Specialty
News based Sentiment: MIXED
September was a pivotal month for Skyward Specialty, largely defined by the strategic acquisition of Apollo Group Holdings. While the market reacted favorably and analysts generally maintain a positive outlook, some divergence in price targets and a recent stock decline suggest caution regarding integration risks and short-term market volatility.
Performance & Financial Health Analysis: Trupanion vs Skyward Specialty
| Metric | TRUP | SKWD |
|---|---|---|
| Market Information | ||
| Market Cap | $1.87B | $1.87B |
| Market Cap Category | Small cap | Small cap |
| 10 Day Avg. Volume | 402,897 | 601,730 |
| 90 Day Avg. Volume | 522,722 | 454,650 |
| Last Close | $44.47 | $46.78 |
| 52 Week Range | $31.00 - $57.90 | $38.74 - $65.05 |
| % from 52W High | -23.20% | -28.09% |
| All-Time High | $158.25 (Dec 06, 2021) | $65.05 (Jun 02, 2025) |
| % from All-Time High | -71.90% | -28.09% |
| Growth Metrics | ||
| Quarterly Revenue Growth | 0.12% | 0.14% |
| Quarterly Earnings Growth | 0.12% | 0.25% |
| Financial Health | ||
| Profit Margin (TTM) | 0.01% | 0.11% |
| Operating Margin (TTM) | 0.01% | 0.16% |
| Return on Equity (TTM) | 0.03% | 0.16% |
| Debt to Equity (MRQ) | 32.20 | 13.29 |
| Cash & Liquidity | ||
| Book Value per Share (MRQ) | $8.27 | $22.23 |
| Cash per Share (MRQ) | $7.43 | $8.67 |
| Operating Cash Flow (TTM) | $69.99M | $374.84M |
| Levered Free Cash Flow (TTM) | $4.49M | $-68,535,872 |
| Dividends | ||
| Last 12-Month Dividend Yield | N/A | N/A |
| Last 12-Month Dividend | N/A | $0.00 |
Valuation & Enterprise Metrics Analysis: Trupanion vs Skyward Specialty
| Metric | TRUP | SKWD |
|---|---|---|
| Price Ratios | ||
| P/E Ratio (TTM) | 174.00 | 14.58 |
| Forward P/E | 725.00 | 14.09 |
| PEG Ratio | -0.68 | 0.68 |
| Price to Sales (TTM) | 1.37 | 1.49 |
| Price to Book (MRQ) | 5.26 | 2.07 |
| Market Capitalization | ||
| Market Capitalization | $1.87B | $1.87B |
| Enterprise Value | $1.66B | $1.63B |
| Enterprise Value Metrics | ||
| Enterprise to Revenue | 1.22 | 1.30 |
| Enterprise to EBITDA | 67.54 | 9.18 |
| Risk & Other Metrics | ||
| Beta | 1.72 | 0.60 |
| Book Value per Share (MRQ) | $8.27 | $22.23 |
Financial Statements Comparison: Trupanion vs Skyward Specialty
Financial Metrics
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Revenue
EBITDA
Operating Margin
Free Cash Flow
Long Term Debt
Profit Margin
Current Ratio
Operating Cash Flow
Income Statement (MRQ)
| Metric (MRQ) | TRUP | SKWD |
|---|---|---|
| Revenue/Sales | $353.56M | $320.80M |
| Cost of Goods Sold | $298.73M | N/A |
| Gross Profit | $54.83M | N/A |
| Research & Development | $8.59M | N/A |
| Operating Income (EBIT) | $22.16M | N/A |
| EBITDA | $38.03M | N/A |
| Pre-Tax Income | $10.55M | $49.80M |
| Income Tax | $1.13M | $10.96M |
| Net Income (Profit) | $9.41M | $38.84M |
Balance Sheet & Liquidity Metrics (MRQ)
| Metric (MRQ) | TRUP | SKWD |
|---|---|---|
| Cash & Equivalents | $166.31M | $112.92M |
| Total Current Assets | $628.34M | N/A |
| Total Current Liabilities | $369.34M | N/A |
| Long-Term Debt | $127.53M | $76.55M |
| Total Shareholders Equity | $333.67M | $850.72M |
| Retained Earnings | $-227.37M | $139.18M |
| Property, Plant & Equipment | N/A | N/A |
Cash Flow Statement Comparison (MRQ)
| Metric (MRQ) | TRUP | SKWD |
|---|---|---|
| Operating Cash Flow | $16.17M | $96.76M |
| Capital Expenditures | $-1.93M | $-202,000 |
| Free Cash Flow | $14.04M | $96.56M |
| Debt Repayment | $-338,000 | $0 |
| Common Stock Repurchase | $-915,000 | N/A |
Short Interest & Institutional Ownership Analysis
| Metric | TRUP | SKWD |
|---|---|---|
| Shares Short | 7.06M | 736,560 |
| Short Ratio | 12.58 | 1.78 |
| Short % of Float | 0.20% | 0.02% |
| Average Daily Volume (10 Day) | 402,897 | 601,730 |
| Average Daily Volume (90 Day) | 522,722 | 454,650 |
| Shares Outstanding | 42.49M | 40.13M |
| Float Shares | 33.44M | 37.43M |
| % Held by Insiders | 0.06% | 0.13% |
| % Held by Institutions | 0.98% | 0.94% |
Dividend Analysis & Yield Comparison: Trupanion vs Skyward Specialty
| Metric | TRUP | SKWD |
|---|---|---|
| Last 12-Month Dividend | N/A | $0.00 |
| Last 12-Month Dividend Yield | N/A | N/A |
| 3-Year Avg Annual Dividend | N/A | $0.00 |
| 3-Year Avg Dividend Yield | N/A | N/A |
| 3-Year Total Dividends | N/A | $0.00 |
| Ex-Dividend Date | N/A | N/A |