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Side-by-side financial comparison of Skyward Specialty Insurance Group, Inc. (SKWD) and TripAdvisor, Inc. (TRIP). Click either name above to swap in a different company.

TripAdvisor, Inc. is the larger business by last-quarter revenue ($411.0M vs $385.6M, roughly 1.1× Skyward Specialty Insurance Group, Inc.). Skyward Specialty Insurance Group, Inc. runs the higher net margin — 11.2% vs -9.2%, a 20.5% gap on every dollar of revenue. On growth, Skyward Specialty Insurance Group, Inc. posted the faster year-over-year revenue change (26.7% vs 0.0%). Skyward Specialty Insurance Group, Inc. produced more free cash flow last quarter ($402.6M vs $-122.0M). Over the past eight quarters, Skyward Specialty Insurance Group, Inc.'s revenue compounded faster (20.6% CAGR vs 2.0%).

Skyward Specialty Insurance Group, Inc. is a specialty property and casualty insurance provider offering tailored coverage solutions including commercial auto, general liability, professional indemnity, and specialty property policies. It primarily serves small-to-medium enterprises and niche industry segments across the United States, focusing on underwriting complex, hard-to-place risks for underserved client groups.

Tripadvisor is an American company that operates online travel agencies, comparison shopping websites, and mobile apps with user-generated content.

SKWD vs TRIP — Head-to-Head

Bigger by revenue
TRIP
TRIP
1.1× larger
TRIP
$411.0M
$385.6M
SKWD
Growing faster (revenue YoY)
SKWD
SKWD
+26.7% gap
SKWD
26.7%
0.0%
TRIP
Higher net margin
SKWD
SKWD
20.5% more per $
SKWD
11.2%
-9.2%
TRIP
More free cash flow
SKWD
SKWD
$524.6M more FCF
SKWD
$402.6M
$-122.0M
TRIP
Faster 2-yr revenue CAGR
SKWD
SKWD
Annualised
SKWD
20.6%
2.0%
TRIP

Income Statement — Q4 FY2025 vs Q4 FY2025

Metric
SKWD
SKWD
TRIP
TRIP
Revenue
$385.6M
$411.0M
Net Profit
$43.2M
$-38.0M
Gross Margin
91.5%
Operating Margin
14.2%
-8.3%
Net Margin
11.2%
-9.2%
Revenue YoY
26.7%
0.0%
Net Profit YoY
200.1%
-3900.0%
EPS (diluted)
$1.03
$-0.32

Green = leading value per metric. Periods may differ when fiscal calendars don't align.

8-Quarter Revenue & Profit Trend

Side-by-side quarterly history. Quarters aligned by calendar period so offset fiscal years line up.

Revenue
SKWD
SKWD
TRIP
TRIP
Q4 25
$385.6M
$411.0M
Q3 25
$382.5M
$553.0M
Q2 25
$319.9M
$529.0M
Q1 25
$328.5M
$398.0M
Q4 24
$304.4M
$411.0M
Q3 24
$300.9M
$532.0M
Q2 24
$279.9M
$497.0M
Q1 24
$265.0M
$395.0M
Net Profit
SKWD
SKWD
TRIP
TRIP
Q4 25
$43.2M
$-38.0M
Q3 25
$45.9M
$53.0M
Q2 25
$38.8M
$36.0M
Q1 25
$42.1M
$-11.0M
Q4 24
$14.4M
$1.0M
Q3 24
$36.7M
$39.0M
Q2 24
$31.0M
$24.0M
Q1 24
$36.8M
$-59.0M
Gross Margin
SKWD
SKWD
TRIP
TRIP
Q4 25
91.5%
Q3 25
92.6%
Q2 25
92.1%
Q1 25
93.2%
Q4 24
93.4%
Q3 24
92.5%
Q2 24
92.8%
Q1 24
93.7%
Operating Margin
SKWD
SKWD
TRIP
TRIP
Q4 25
14.2%
-8.3%
Q3 25
15.8%
12.7%
Q2 25
15.6%
11.2%
Q1 25
15.7%
-3.8%
Q4 24
6.1%
0.2%
Q3 24
15.6%
13.2%
Q2 24
14.4%
7.2%
Q1 24
17.7%
-3.8%
Net Margin
SKWD
SKWD
TRIP
TRIP
Q4 25
11.2%
-9.2%
Q3 25
12.0%
9.6%
Q2 25
12.1%
6.8%
Q1 25
12.8%
-2.8%
Q4 24
4.7%
0.2%
Q3 24
12.2%
7.3%
Q2 24
11.1%
4.8%
Q1 24
13.9%
-14.9%
EPS (diluted)
SKWD
SKWD
TRIP
TRIP
Q4 25
$1.03
$-0.32
Q3 25
$1.10
$0.43
Q2 25
$0.93
$0.28
Q1 25
$1.01
$-0.08
Q4 24
$0.33
$0.03
Q3 24
$0.89
$0.27
Q2 24
$0.75
$0.17
Q1 24
$0.90
$-0.43

Balance Sheet & Financial Strength

Snapshot of each company's liquidity, leverage and book value from the latest quarter.

Metric
SKWD
SKWD
TRIP
TRIP
Cash + ST InvestmentsLiquidity on hand
$168.5M
$1.0B
Total DebtLower is stronger
$819.0M
Stockholders' EquityBook value
$1.0B
$645.0M
Total Assets
$4.8B
$2.6B
Debt / EquityLower = less leverage
1.27×

8-quarter trend — quarters aligned by calendar period.

Cash + ST Investments
SKWD
SKWD
TRIP
TRIP
Q4 25
$168.5M
$1.0B
Q3 25
$160.1M
$1.2B
Q2 25
$136.6M
$1.2B
Q1 25
$112.9M
$1.2B
Q4 24
$121.6M
$1.1B
Q3 24
$105.6M
$1.1B
Q2 24
$73.0M
$1.2B
Q1 24
$85.1M
$1.2B
Total Debt
SKWD
SKWD
TRIP
TRIP
Q4 25
$819.0M
Q3 25
$821.0M
Q2 25
$822.0M
Q1 25
$1.2B
Q4 24
$831.0M
Q3 24
$832.0M
Q2 24
Q1 24
Stockholders' Equity
SKWD
SKWD
TRIP
TRIP
Q4 25
$1.0B
$645.0M
Q3 25
$961.4M
$707.0M
Q2 25
$899.9M
$627.0M
Q1 25
$850.7M
$643.0M
Q4 24
$794.0M
$943.0M
Q3 24
$797.5M
$944.0M
Q2 24
$723.6M
$857.0M
Q1 24
$692.3M
$825.0M
Total Assets
SKWD
SKWD
TRIP
TRIP
Q4 25
$4.8B
$2.6B
Q3 25
$4.6B
$2.8B
Q2 25
$4.3B
$2.9B
Q1 25
$4.0B
$2.8B
Q4 24
$3.7B
$2.6B
Q3 24
$3.6B
$2.7B
Q2 24
$3.4B
$2.8B
Q1 24
$3.2B
$2.7B
Debt / Equity
SKWD
SKWD
TRIP
TRIP
Q4 25
1.27×
Q3 25
1.16×
Q2 25
1.31×
Q1 25
1.81×
Q4 24
0.88×
Q3 24
0.88×
Q2 24
Q1 24

Cash Flow & Capital Efficiency

How much cash each business actually produces after reinvestment. Cash flow is harder to manipulate than net income.

Metric
SKWD
SKWD
TRIP
TRIP
Operating Cash FlowLast quarter
$408.1M
$-103.0M
Free Cash FlowOCF − Capex
$402.6M
$-122.0M
FCF MarginFCF / Revenue
104.4%
-29.7%
Capex IntensityCapex / Revenue
1.4%
4.6%
Cash ConversionOCF / Net Profit
9.44×
TTM Free Cash FlowTrailing 4 quarters
$755.2M
$163.0M

8-quarter trend — quarters aligned by calendar period.

Operating Cash Flow
SKWD
SKWD
TRIP
TRIP
Q4 25
$408.1M
$-103.0M
Q3 25
$171.4M
$44.0M
Q2 25
$88.2M
$202.0M
Q1 25
$96.8M
$102.0M
Q4 24
$305.1M
$-3.0M
Q3 24
$168.0M
$-43.0M
Q2 24
$21.0M
$51.0M
Q1 24
$94.3M
$139.0M
Free Cash Flow
SKWD
SKWD
TRIP
TRIP
Q4 25
$402.6M
$-122.0M
Q3 25
$168.9M
$25.0M
Q2 25
$87.1M
$177.0M
Q1 25
$96.6M
$83.0M
Q4 24
$300.9M
$-26.0M
Q3 24
$167.6M
$-63.0M
Q2 24
$18.4M
$36.0M
Q1 24
$94.0M
$123.0M
FCF Margin
SKWD
SKWD
TRIP
TRIP
Q4 25
104.4%
-29.7%
Q3 25
44.2%
4.5%
Q2 25
27.2%
33.5%
Q1 25
29.4%
20.9%
Q4 24
98.8%
-6.3%
Q3 24
55.7%
-11.8%
Q2 24
6.6%
7.2%
Q1 24
35.5%
31.1%
Capex Intensity
SKWD
SKWD
TRIP
TRIP
Q4 25
1.4%
4.6%
Q3 25
0.6%
3.4%
Q2 25
0.3%
4.7%
Q1 25
0.1%
4.8%
Q4 24
1.4%
5.6%
Q3 24
0.1%
3.8%
Q2 24
0.9%
3.0%
Q1 24
0.1%
4.1%
Cash Conversion
SKWD
SKWD
TRIP
TRIP
Q4 25
9.44×
Q3 25
3.73×
0.83×
Q2 25
2.27×
5.61×
Q1 25
2.30×
Q4 24
21.18×
-3.00×
Q3 24
4.58×
-1.10×
Q2 24
0.68×
2.13×
Q1 24
2.56×

Financial Flow Comparison

Revenue → gross profit → operating profit → net profit for each company.

Revenue Breakdown by Segment

SKWD
SKWD

Segment breakdown not available.

TRIP
TRIP

Third Party$327.0M80%
The Fork$58.0M14%
Other$26.0M6%

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