On Wednesday, activist investor, Carl Icahn announced that he had raised his holdings on the online heath resource website, Web MD.  Mr. Icahn raised his particular stake to 13.12%, from 11.84%.  That is an additional $203.2 million worth of shares.

This is the not the first time the legendary investor has been adding to his Web MD position.  In fact, over the past four months or so, Icahn has been adding more and more to his position in the hopes of talking management into creating some shareholder value such as a buyback program.

Back in January, the activist investor began to increase his holdings once the company said that it was going to stop pursuing for an interested buyer.

Web MD has issued a $150 million stock buyback program which would take out 18 million shares at $26 apiece. However, Icahn was expecting more from the buyback program. The shareholder of Web MD was looking for a buyback of around $1 billion at a higher point like $30.

Carl Icahn has been busy this year.  He has stepped up his holdings and pressuring board members to enact his plans.  The funny thing is that Icahn usually gets his way.  He ends up with such large positions that management essentially has no choice but to follow Icahn’s plan, after some fighting back.

CVR Energy, Inc. (NYSE:CVI) is another great example of his management battles.  In this case, CVR Energy had decided they didn’t want to sell the company.  Icahn thought that a CVR sale would be the best for shareholders’ value. Icahn personally placed a bid to take over the company; however management is now trying to find another buyer because they do not want Icahn to be in control.  The important thing to note is that Icahn is able to eventually win what he wants because he owns such a large stake and he rallies the rest of the shareholders behind him.

Icahn had a good first quarter in 2012.  He increased a lot of holdings and pressure on company management to get his proposals passed.  Web MD should be no trouble for the activist investor after decades of experience.  That being said, $1 billion buyback program at $30 a share is pretty steep for a small company like Web MD.  I think it may take a little extra pressure on Icahn’s part to rally other Web MD investors and getting management to pass what they believe will increase shareholder value.