For the latest business news and markets data, please visit CNN Business. How did he do it? He’s the first to admit that it’s a risky strategy. And it’s not for. He spends the entire trading day in front of a computer screen, in order to buy and sell stocks at the right time. He is sometimes in and out of stocks within minutes, and the longest he ever holds shares is a few days. So why trade penny stocks? Many of these companies are speculative because they are thinly traded, usually over the counter instead of on major exchanges like the New York Stock Exchange. The Securities and Exchange Commission warns tarding «investors in penny stocks should be prepared for the possibility that they may lose their whole investment.