Value investing has produced some of the world’s most famous investing billionaires, including Warren Buffett, David Einhorn, and Seth Klarman, who built their fortunes by purchasing wonderful businesses at reasonable prices. But these hidden gems are few and far between - many stocks that appear cheap often stay that way because they face structural issues.

This distinction between true value and value traps can challenge even the most skilled investors. Luckily for you, we started StockStory to help you uncover exceptional companies. Keeping that in mind, here are three value stocks climbing an uphill battle and some other investments you should look into instead.

Flywire (FLYW)

Forward P/S Ratio: 2.2x

Initially created to solve the challenges of international student tuition payments, Flywire (NASDAQ: FLYW) provides specialized payment processing and software solutions that help educational institutions, healthcare systems, travel companies, and businesses manage complex payments.

Why Does FLYW Give Us Pause?

1. High servicing costs result in a relatively inferior gross margin of 60.1% that must be offset through increased usage
2. Long payback periods on sales and marketing expenses limit customer growth and signal the company operates in a highly competitive environment
3. Operating profits and efficiency rose over the last year as it benefited from some fixed cost leverage

Flywire’s stock price of $13.05 implies a valuation ratio of 2.2x forward price-to-sales. Dive into our free research report to see why there are better opportunities than FLYW.

Oshkosh (OSK)

Forward P/E Ratio: 13.5x

Oshkosh (NYSE: OSK) manufactures specialty vehicles for the defense, fire, emergency, and commercial industry, operating various brand subsidiaries within each industry.

Why Is OSK Not Exciting?

1. Annual sales growth of 3.9% over the last two years lagged behind its industrials peers as its large revenue base made it difficult to generate incremental demand
2. Competitive supply chain dynamics and steep production costs are reflected in its low gross margin of 16.5%
3. Earnings growth underperformed the sector average over the last two years as its EPS grew by just 4.5% annually

At $140.50 per share, Oshkosh trades at 13.5x forward P/E. Check out our free in-depth research report to learn more about why OSK doesn’t pass our bar.

Assured Guaranty (AGO)

Forward P/B Ratio: 0.6x

Serving as a financial safety net for over $11 trillion in debt service payments since its founding in 2003, Assured Guaranty (NYSE: AGO) provides credit protection products that guarantee scheduled payments on municipal bonds, infrastructure projects, and structured finance obligations.

Why Do We Think AGO Will Underperform?

1. Insurance policy sales contracted this cycle as net premiums earned decreased by 4.8% annually over the last five years
2. Sales are expected to decline once again over the next 12 months as it continues working through a challenging demand environment
3. Earnings per share have dipped by 8.7% annually over the past two years, which is concerning because stock prices follow EPS over the long term

Assured Guaranty is trading at $83.44 per share, or 0.6x forward P/B. Read our free research report to see why you should think twice about including AGO in your portfolio.

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Stocks that made our list in 2020 include now familiar names such as Nvidia (+1,326% between June 2020 and June 2025) as well as under-the-radar businesses like the once-micro-cap company Tecnoglass (+1,754% five-year return). Find your next big winner with StockStory today.