While strong cash flow is a key indicator of stability, it doesn’t always translate to superior returns. Some cash-heavy businesses struggle with inefficient spending, slowing demand, or weak competitive positioning.
Luckily for you, we built StockStory to help you separate the good from the bad. Keeping that in mind, here are two cash-producing companies that excel at turning cash into shareholder value and one best left off your watchlist.
One Stock to Sell:
Upwork (UPWK)
Trailing 12-Month Free Cash Flow Margin: 22.3%
Formed through the 2013 merger of Elance and oDesk, Upwork (NASDAQ: UPWK) is an online platform where businesses and independent professionals connect to get work done.
Why Are We Hesitant About UPWK?
- 6.6% annual revenue growth over the last three years was slower than its consumer internet peers
- Sales are projected to tank by 8.6% over the next 12 months as demand evaporates
Upwork’s stock price of $8.63 implies a valuation ratio of 3.7x forward EV/EBITDA. Read our free research report to see why you should think twice about including UPWK in your portfolio.
Two Stocks to Watch:
W. R. Berkley (WRB)
Trailing 12-Month Free Cash Flow Margin: 24.2%
Founded in 1967 and operating through more than 50 specialized insurance units across the globe, W. R. Berkley (NYSE: WRB) underwrites commercial insurance and reinsurance through specialized subsidiaries serving industries from healthcare to construction to transportation.
Why Does WRB Catch Our Eye?
- Steady 11.3% annualized growth in net premiums earned over the last five years shows its insurance offerings are gaining traction
- Projected book value per share growth of 23.7% for the next 12 months is above its two-year trend, pointing to accelerating profitability
- Industry-leading 20% return on equity demonstrates management’s skill in finding high-return investments
W. R. Berkley is trading at $70.45 per share, or 2.5x forward P/B. Is now the right time to buy? Find out in our full research report, it’s free.
Tradeweb Markets (TW)
Trailing 12-Month Free Cash Flow Margin: 48.7%
Founded in 1996 as one of the pioneers in electronic bond trading, Tradeweb Markets (NASDAQ: TW) builds and operates electronic marketplaces that connect financial institutions for trading across rates, credit, equities, and money markets.
What Makes TW Stand Out?
- Impressive 20.8% annual revenue growth over the last two years indicates it’s winning market share this cycle
- Additional sales over the last five years increased its profitability as the 21% annual growth in its earnings per share outpaced its revenue
At $105.41 per share, Tradeweb Markets trades at 24.2x forward P/E. Is now a good time to buy? See for yourself in our in-depth research report, it’s free.
Stocks We Like Even More
ONE MORE THING: Top 5 Growth Stocks. The biggest stock winners almost always had one thing in common before they ran. Revenue growing like crazy. Meta. CrowdStrike. Broadcom. Our AI flagged all three. They returned 315%, 314%, and 455%, respectively.
Find out which 5 stocks it’s flagging this month — FREE. Get Our Top 5 Growth Stocks for Free HERE.
Stocks that made our list in 2020 include now familiar names such as Nvidia (+1,460% between June 2020 and June 2025) as well as under-the-radar businesses like the once-micro-cap company Kadant (+214% between June 2020 and June 2025). Find your next big winner with StockStory today.
