Chris Sacca built such deep conviction in Twitter that he created four separate funds to keep buying shares, ending up with affiliated funds owning nearly 18% of the company by its IPO, and he later showed the same hands-on approach with Uber by personally negotiating for the Uber.com domain. Beyond investing, he became known for running things from his Tahoe-area home—where founders like Travis Kalanick would spend long stretches working through ideas—and for a personal style so distinct, with his Western shirts and cowboy look, that it carried over into appearances as a guest shark on Shark Tank.