Shares with company value negative are something quite difficult to find in the markets, although not impossible. This article, which is a translation of the article “transaction costs and tax. It's not bad at all!
It seems that this strategy works much less for individual investors than it does for large institutional investors because most investment opportunities are micro caps with limited liquidity:
Profitability of companies with negative company value by market capitalization
Only about 3% of investment opportunities were in stocks with a market capitalization of $ 500 million or more. These opportunities appear with some regularity and provide attractive returns but have also lost money at times as well.
Profitability of companies with negative company value per year
In the top chart, the date axis shows the year of entry. Negative enterprise value stocks bought in 2.007 and held for 2.008 lost 35-45%, doing as badly or worse than the S&P 500 Index.
If these declines do not deter you, you should be able to improve your chances by looking at the countries in which companies have their headquarters:
Profitability of companies with negative enterprise value by country
Stocks with negative company value domiciled in Taiwan and especially in China have done much worse than average (although they still do quite well), mostly due to fraud. This effect can be magnified in small caps.
In short, stocks with negative enterprise value have had attractive returns for the past 40 years and are worth a look, provided you are able to handle their volatility.