You can't press a button and buy that much stock. You'd likely have to buy from portfolios of hundreds of investor funds and family offices. Word gets around, and you'll have to jack up the bid with each successive call.
You'd also have to buy in large volumes on the public markets as well, so that'll bid up the price,providing a rationale for the board to reject the offer as undervalued.
But that doesn't seem any different to the process he would have to go through personally if he was allowed to obtain more than 15% himself without triggering the poison pill. I'm sure this makes it more difficult I'm just wondering, given the stakes involved, what is actually stopping this work around?
What's stopping the workaround you suggest is that the element of surprise is gone. Nobody knew that he was building up a 10% stake to take an activist investor stance, because he built up the stake slowly. But now we know.
And we know that for him to buy up enough shares to override the poison pill vote, he has to act much faster than he did the first time around. But the markets would be aware that he's looking to buy a much bigger stake, so existing holders can set whatever price they want.
You'd also have to buy in large volumes on the public markets as well, so that'll bid up the price,providing a rationale for the board to reject the offer as undervalued.