Scale Proportionally with anchor point

What I am looking to do is resize an object to match a second object. However, when I do it keeping to scale (holding shift) it moves all of the sides. What I want to do is line it up on the bottom and then resize it without it moving from the bottom, therefore making it easy to match the top. I attached a video to further explain. 

I have not been able to find anything like this in the questions. I don't really know how to word it so maybe that is the problem. 

Thanks