Icahn has multiple investments. If he loses everything from Hertz, he is still remains one of the 25 richest people in the country. Secondly the VC issue isn'

Icahn has multiple investments. If he loses everything from Hertz, he is still remains one of the 25 richest people in the country. Secondly the VC issue isn't because VCs are not investors - they are. It is because VCs spread their money around and know very well that their investment returns depend on getting a home run or two. Gambling on high risk, high return strategies is therefore in the VCs interest, but not in the interest of people whose net worth is almost entirely in the company. This dynamic is widely understood and is a common source of conflict between VCs and founders. Thirdly related-party transactions are not necessarily a bad thing. I listed it as half in the company's interest. It is very good that when the company needs to do business they have someone to call who can make deals happen. But the activist investor isn't always acting in the company's best interests. That said, you are correct that Icahn was not the one who loaded Hertz with debt. (That restructuring happened in 2005 when Ford sold it to investment bankers.) But he has his own history of loading companies down with debt ever since he bought TWA back in the mid-80s. So the fact that he didn't do it to Hertz doesn't change the fact that he has proven willing to do so in the past.