

Old Second vs Hippo
Old Second Bancorp operates community banking across Illinois with a reputation for disciplined underwriting, while Hippo Holdings tried to reinvent homeowners insurance through a tech-first direct model before burning through capital at an unsustainable rate. Both took very different bets on how to build financial services businesses, and only one has the balance sheet to show for it. Old Second vs Hippo contrasts earnings consistency, loss ratio trends, cash runway, and what each company needs to prove over the next twelve months.
Old Second Bancorp operates community banking across Illinois with a reputation for disciplined underwriting, while Hippo Holdings tried to reinvent homeowners insurance through a tech-first direct mo...
Investment Analysis

Old Second
OSBC
Pros
- Old Second Bancorp demonstrates strong profitability with a second-quarter 2025 return on average tangible common equity of 15.29% and a tax equivalent net interest margin of 4.85%.
- The company has a healthy balance sheet with a common equity tier 1 ratio of 13.77%, a loan-to-deposit ratio of 83%, and cash plus marketable securities exceeding 23% of total assets.
- Strategic growth through acquisitions, including Bancorp Financial and Evergreen Bank Group, has expanded operations and contributed to revenue increases, alongside a consistent dividend record with recent increases.
Considerations
- In Q3 2025, Old Second missed earnings per share expectations, posting $0.18 versus the forecasted $0.26, which led to a stock price decline.
- Despite revenue growth, net income was relatively modest at $9.9 million for Q3 2025, reflecting possible pressures on profitability or margin sustainability.
- The stock trades at a moderate price-to-earnings ratio (around 9.7x) which might reflect market concerns about future earnings growth or macroeconomic risks impacting the banking sector.

Hippo
HIPO
Pros
- Hippo Holdings operates in the insurance technology sector, targeting homeowners insurance with advanced data analytics, enhancing underwriting efficiency and customer experience.
- The company benefits from strong technological innovation in a growing insurtech market, positioning it well to capture market share from traditional insurers.
- Hippo has attracted significant venture capital investment, highlighting confidence in its growth potential and business model scalability.
Considerations
- Hippo faces substantial execution risks due to intense competition from both established insurers and newer insurtech entrants in a highly regulated market.
- The company has reported ongoing operating losses as it invests heavily in growth and customer acquisition, which may pressure near-term profitability.
- Exposure to property insurance claims volatility, including from natural disasters and climate risks, could negatively affect underwriting results and financial stability.
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