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Side-by-side financial comparison of OCTAVE SPECIALTY GROUP INC (OSG) and System1, Inc. (SST). Click either name above to swap in a different company.

OCTAVE SPECIALTY GROUP INC is the larger business by last-quarter revenue ($66.9M vs $51.9M, roughly 1.3× System1, Inc.). System1, Inc. runs the higher net margin — -26.0% vs -73.8%, a 47.8% gap on every dollar of revenue. On growth, OCTAVE SPECIALTY GROUP INC posted the faster year-over-year revenue change (2.6% vs -31.3%). Over the past eight quarters, OCTAVE SPECIALTY GROUP INC's revenue compounded faster (16.2% CAGR vs -21.8%).

Octave Specialty Group Inc. is a specialty insurance holding company that provides tailored property and casualty insurance products. Its core business focuses on excess and surplus lines, catering to commercial and individual clients across primary North American markets with customized risk coverage solutions.

System1 is an American Internet advertising company. Formerly known as OpenMail, it was founded in 2013. It describes itself as operating a "Responsive Acquisition Marketing Platform", and cites privacy as one of its principal foci, although it has been criticized for its influence on privacy-focused properties, including search engine Startpage.com. It is headquartered in Marina del Rey, California.

OSG vs SST — Head-to-Head

Bigger by revenue
OSG
OSG
1.3× larger
OSG
$66.9M
$51.9M
SST
Growing faster (revenue YoY)
OSG
OSG
+33.9% gap
OSG
2.6%
-31.3%
SST
Higher net margin
SST
SST
47.8% more per $
SST
-26.0%
-73.8%
OSG
Faster 2-yr revenue CAGR
OSG
OSG
Annualised
OSG
16.2%
-21.8%
SST

Income Statement — Q4 FY2025 vs Q4 FY2025

Metric
OSG
OSG
SST
SST
Revenue
$66.9M
$51.9M
Net Profit
$-29.7M
$-13.5M
Gross Margin
41.0%
Operating Margin
-76.7%
-33.6%
Net Margin
-73.8%
-26.0%
Revenue YoY
2.6%
-31.3%
Net Profit YoY
-41.7%
4.8%
EPS (diluted)
$-0.82
$-3.58

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
OSG
OSG
SST
SST
Q4 25
$66.9M
$51.9M
Q3 25
$66.6M
$61.6M
Q2 25
$55.0M
$78.1M
Q1 25
$62.8M
$74.5M
Q4 24
$65.2M
$75.6M
Q3 24
$70.0M
$88.8M
Q2 24
$51.0M
$94.6M
Q1 24
$49.6M
$84.9M
Net Profit
OSG
OSG
SST
SST
Q4 25
$-29.7M
$-13.5M
Q3 25
$-112.6M
$-18.5M
Q2 25
$-72.7M
$-17.5M
Q1 25
$-44.7M
$-15.9M
Q4 24
$-20.9M
$-14.2M
Q3 24
$-27.5M
$-23.6M
Q2 24
$-750.0K
$-26.4M
Q1 24
$20.8M
$-10.5M
Gross Margin
OSG
OSG
SST
SST
Q4 25
41.0%
Q3 25
36.9%
Q2 25
35.7%
Q1 25
38.2%
Q4 24
42.1%
Q3 24
28.0%
Q2 24
27.6%
Q1 24
21.9%
Operating Margin
OSG
OSG
SST
SST
Q4 25
-76.7%
-33.6%
Q3 25
-48.2%
-25.3%
Q2 25
-41.8%
-20.4%
Q1 25
-24.1%
-17.6%
Q4 24
-55.5%
-15.7%
Q3 24
-29.7%
-24.6%
Q2 24
-28.9%
-30.8%
Q1 24
-6.5%
-30.4%
Net Margin
OSG
OSG
SST
SST
Q4 25
-73.8%
-26.0%
Q3 25
-169.1%
-30.1%
Q2 25
-132.3%
-22.4%
Q1 25
-71.3%
-21.3%
Q4 24
-55.1%
-18.7%
Q3 24
-39.3%
-26.6%
Q2 24
-1.5%
-27.9%
Q1 24
41.9%
-12.4%
EPS (diluted)
OSG
OSG
SST
SST
Q4 25
$-0.82
$-3.58
Q3 25
$-2.35
$-2.30
Q2 25
$-1.54
$-2.23
Q1 25
$-1.22
$-0.21
Q4 24
$-11.75
$-3.41
Q3 24
$-0.63
$-3.37
Q2 24
$-0.02
$-3.80
Q1 24
$0.44
$-0.16

Balance Sheet & Financial Strength

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

Metric
OSG
OSG
SST
SST
Cash + ST InvestmentsLiquidity on hand
$146.4M
$86.9M
Total DebtLower is stronger
$117.6M
$305.1M
Stockholders' EquityBook value
$715.8M
$30.5M
Total Assets
$2.2B
$405.0M
Debt / EquityLower = less leverage
0.16×
10.01×

8-quarter trend — quarters aligned by calendar period.

Cash + ST Investments
OSG
OSG
SST
SST
Q4 25
$146.4M
$86.9M
Q3 25
$27.5M
$54.6M
Q2 25
$22.5M
$63.6M
Q1 25
$34.1M
$43.9M
Q4 24
$157.2M
$63.6M
Q3 24
$40.8M
$69.1M
Q2 24
$14.6M
$75.7M
Q1 24
$13.8M
$69.9M
Total Debt
OSG
OSG
SST
SST
Q4 25
$117.6M
$305.1M
Q3 25
$259.2M
Q2 25
$263.3M
Q1 25
$267.4M
Q4 24
$0
$255.1M
Q3 24
$518.0M
$259.2M
Q2 24
$515.0M
$263.3M
Q1 24
$512.0M
$268.6M
Stockholders' Equity
OSG
OSG
SST
SST
Q4 25
$715.8M
$30.5M
Q3 25
$843.4M
$42.7M
Q2 25
$859.8M
$58.2M
Q1 25
$852.2M
$67.2M
Q4 24
$798.4M
$80.3M
Q3 24
$1.5B
$90.3M
Q2 24
$1.4B
$109.4M
Q1 24
$1.4B
$131.7M
Total Assets
OSG
OSG
SST
SST
Q4 25
$2.2B
$405.0M
Q3 25
$2.1B
$385.2M
Q2 25
$8.5B
$429.2M
Q1 25
$8.3B
$419.2M
Q4 24
$8.1B
$459.1M
Q3 24
$9.3B
$479.3M
Q2 24
$8.2B
$511.3M
Q1 24
$8.4B
$521.1M
Debt / Equity
OSG
OSG
SST
SST
Q4 25
0.16×
10.01×
Q3 25
6.07×
Q2 25
4.53×
Q1 25
3.98×
Q4 24
0.00×
3.18×
Q3 24
0.35×
2.87×
Q2 24
0.38×
2.41×
Q1 24
0.38×
2.04×

Cash Flow & Capital Efficiency

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

Metric
OSG
OSG
SST
SST
Operating Cash FlowLast quarter
$-52.3M
$-10.6M
Free Cash FlowOCF − Capex
FCF MarginFCF / Revenue
Capex IntensityCapex / Revenue
0.0%
Cash ConversionOCF / Net Profit
TTM Free Cash FlowTrailing 4 quarters

8-quarter trend — quarters aligned by calendar period.

Operating Cash Flow
OSG
OSG
SST
SST
Q4 25
$-52.3M
$-10.6M
Q3 25
$-41.2M
$-2.1M
Q2 25
$2.1M
$24.5M
Q1 25
$-12.6M
$-15.9M
Q4 24
$762.0K
$772.0K
Q3 24
$48.9M
$-5.0K
Q2 24
$20.4M
$10.0M
Q1 24
$7.1M
$-16.0M
Free Cash Flow
OSG
OSG
SST
SST
Q4 25
Q3 25
Q2 25
Q1 25
$-16.0M
Q4 24
Q3 24
$-36.0K
Q2 24
Q1 24
FCF Margin
OSG
OSG
SST
SST
Q4 25
Q3 25
Q2 25
Q1 25
-21.5%
Q4 24
Q3 24
-0.0%
Q2 24
Q1 24
Capex Intensity
OSG
OSG
SST
SST
Q4 25
0.0%
Q3 25
0.0%
Q2 25
0.0%
Q1 25
0.1%
Q4 24
0.0%
Q3 24
0.0%
Q2 24
0.0%
Q1 24
0.0%
Cash Conversion
OSG
OSG
SST
SST
Q4 25
Q3 25
Q2 25
Q1 25
Q4 24
Q3 24
Q2 24
Q1 24
0.34×

Financial Flow Comparison

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

Revenue Breakdown by Segment

OSG
OSG

Other$28.7M43%
Specialty Property Casualty Program$23.1M34%
Accident Health$9.6M14%
Specialty Automobile$3.1M5%
Niche Specialty Risks$2.4M4%

SST
SST

Segment breakdown not available.

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