ETFOptimize | High-performance ETF-based Investment Strategies

Quantitative strategies, Wall Street-caliber research, and insightful market analysis since 1998.


ETFOptimize | HOME
Close Window

3 Unprofitable Stocks We Find Risky

FLYW Cover Image

Running at a loss can be a red flag. Many of these businesses face mounting challenges as competition increases and funding becomes harder to secure.

Finding the right unprofitable companies is difficult, which is why we started StockStory - to help you navigate the market. That said, here are three unprofitable companiesthat don’t make the cut and some better opportunities instead.

Flywire (FLYW)

Trailing 12-Month GAAP Operating Margin: -2.4%

Originally created to process international tuition payments for universities, Flywire (NASDAQ: FLYW) is a cross border payments processor and software platform focusing on complex, high-value transactions like education, healthcare and B2B payments.

Why Do We Think Twice About FLYW?

  1. Steep infrastructure costs and weaker unit economics for a software company are reflected in its low gross margin of 63.6%
  2. Competitive market means the company must spend more on sales and marketing to stand out even if the return on investment is low
  3. Rapid expansion strategy came at the expense of operating margin profitability

Flywire’s stock price of $11.89 implies a valuation ratio of 2.4x forward price-to-sales. If you’re considering FLYW for your portfolio, see our FREE research report to learn more.

Chegg (CHGG)

Trailing 12-Month GAAP Operating Margin: -135%

Started as a physical textbook rental service, Chegg (NYSE: CHGG) is now a digital platform addressing student pain points by providing study and academic assistance.

Why Do We Avoid CHGG?

  1. Services Subscribers have declined by 13.4% annually over the last two years, suggesting it may need to revamp its features or user experience to stay competitive
  2. EBITDA profits fell over the last few years as its sales dropped and it struggled to adjust its fixed costs
  3. Sales were less profitable over the last three years as its earnings per share fell by 30.8% annually, worse than its revenue declines

Chegg is trading at $1.50 per share, or 2.5x forward EV/EBITDA. Read our free research report to see why you should think twice about including CHGG in your portfolio.

Icahn Enterprises (IEP)

Trailing 12-Month GAAP Operating Margin: -6.6%

Founded in 1987, Icahn Enterprises (NASDAQ: IEP) is a diversified holding company primarily engaged in investment and asset management across various sectors.

Why Are We Cautious About IEP?

  1. Annual sales declines of 14.1% for the past two years show its products and services struggled to connect with the market during this cycle
  2. Waning returns on capital from an already weak starting point displays the inefficacy of management’s past and current investment decisions
  3. Negative earnings profile makes it challenging to secure favorable financing terms from lenders

At $9.19 per share, Icahn Enterprises trades at 0.5x forward price-to-sales. Dive into our free research report to see why there are better opportunities than IEP.

Stocks We Like More

When Trump unveiled his aggressive tariff plan in April 2025, markets tanked as investors feared a full-blown trade war. But those who panicked and sold missed the subsequent rebound that’s already erased most losses.

Don’t let fear keep you from great opportunities and take a look at Top 9 Market-Beating Stocks. This is a curated list of our High Quality stocks that have generated a market-beating return of 183% over the last five years (as of March 31st 2025).

Stocks that made our list in 2020 include now familiar names such as Nvidia (+1,545% between March 2020 and March 2025) as well as under-the-radar businesses like the once-small-cap company Exlservice (+354% five-year return). Find your next big winner with StockStory today for free.

StockStory is growing and hiring equity analyst and marketing roles. Are you a 0 to 1 builder passionate about the markets and AI? See the open roles here.

Stock Quote API & Stock News API supplied by www.cloudquote.io
Quotes delayed at least 20 minutes.
By accessing this page, you agree to the following
Privacy Policy and Terms Of Service.


 

IntelligentValue Home
Close Window

DISCLAIMER

All content herein is issued solely for informational purposes and is not to be construed as an offer to sell or the solicitation of an offer to buy, nor should it be interpreted as a recommendation to buy, hold or sell (short or otherwise) any security.  All opinions, analyses, and information included herein are based on sources believed to be reliable, but no representation or warranty of any kind, expressed or implied, is made including but not limited to any representation or warranty concerning accuracy, completeness, correctness, timeliness or appropriateness. We undertake no obligation to update such opinions, analysis or information. You should independently verify all information contained on this website. Some information is based on analysis of past performance or hypothetical performance results, which have inherent limitations. We make no representation that any particular equity or strategy will or is likely to achieve profits or losses similar to those shown. Shareholders, employees, writers, contractors, and affiliates associated with ETFOptimize.com may have ownership positions in the securities that are mentioned. If you are not sure if ETFs, algorithmic investing, or a particular investment is right for you, you are urged to consult with a Registered Investment Advisor (RIA). Neither this website nor anyone associated with producing its content are Registered Investment Advisors, and no attempt is made herein to substitute for personalized, professional investment advice. Neither ETFOptimize.com, Global Alpha Investments, Inc., nor its employees, service providers, associates, or affiliates are responsible for any investment losses you may incur as a result of using the information provided herein. Remember that past investment returns may not be indicative of future returns.

Copyright © 1998-2017 ETFOptimize.com, a publication of Optimized Investments, Inc. All rights reserved.