7. 1967 E-Type Jaguar
In a Forbes video, Musk revealed that he received a book of classic cars when he was 17. Out of all classics, the E-Type Jaguar caught his eye, and he promised to himself that if the day came when he could afford it, he would buy this car.
This day came, and it was when Zip2 gave Musk his initial bonus check of $40,000. In the video, Musk said: “That one was like a bad girlfriend — it kept breaking down on me and causing me all sorts of trouble.” His expectations of this car must have been high, but the vehicle broke down on the way back from the dealer.