I installed QGIS (KyngChaos) after installing Miniconda. When I would open QGIS, I'd get an error about MetaSearch not started because requests couldn't be found. How I got things working again
Alias system Python 2.7 (This may be optional)
sudo alias python2=/usr/bin/python2.7
Get a copy of get-pip.py and use it to install pip
sudo /usr/bin/python2.7 /Users/maptastik/get-pip.py